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Romantic 10-Day Italy Itinerary: From Venice to Lake Como

jonathan and sophie in lake como
From Lake Como to Tuscany and Florence to Venice, Italy is one of the most romantic destinations in the world. This dreamy itinerary will leave you swooning at every turn.

Trip Highlights

  • Dinner at a canal-side table in Venice
  • Private gondola ride through Venetian canals
  • Renting a boat on spectacular Lake Como 
  • Riding e-bikes through the rolling hills of Tuscany 
  • Gourmet dinner on the terrace of your Tuscan villa 
  • Sweeping views of Florence from Piazzale Michelangelo

This past May, my boyfriend and I took an extraordinary 10-day vacation to Italy. Since this would be our first international trip together, I knew it had to be special. I wanted him to fall in love with travel as much as I have and get him on board for a future full of adventure. Having already been to Italy several times, I knew that would be the place to win him over. I imagined the exact trip I wanted to take him on; it needed to be completely relaxing and totally breathtaking, with every single destination, meal, hotel, and activity romantic and almost ethereal in its perfection. High standards, I know. Luckily this trip delivered, and it ended up being the perfect fairy-tale backdrop to our love story. We decided on a tour of Northern Italy, and our destinations included Lake Como, Tuscany, Florence, and Venice. 

If you’re wondering how to plan a trip to Italy that’s certain to exceed your highest expectations, this is it. Read on to find the details of where we stayed, what we did, where we ate, important logistical information and more. 

Itinerary Overview

  • Day 1: Take the redeye from your starting city to Milan and arrive the next morning
  • Day 2 – 3: Lake Como 
  • Day 4 – 5:  Florence 
  • Day 6 – 7: Tuscany
  • Day 8 – 9:  Venice 
  • Day 10: Fly home

Also see: Italy Itinerary; Amalfi Coast Itinerary; Rome Itinerary; Venice Itinerary; Milan Itinerary; Florence Itinerary

Wine break in Greve, Tuscany
pizza in italy
The whole reason we came to Italy...PIZZA

Day 1: Take the Redeye and Arrive the Next Morning

With the time difference from the U.S., I think no matter where you’re flying from, taking the redeye to start your trip will allow you to maximize your vacation time by starting fresh the following morning. Otherwise, you’ll waste the whole first day of your trip on logistics and will likely be feeling the burnout from jet lag. 

Delta has direct flights from Atlanta to Milan, so we opted for a post-work flight on Friday to arrive in Italy Saturday morning.

Day 2 - 3: Lake Como

Beginning your trip in Lake Como packs an impressive punch. The sparkling blue waters against the striking backdrop of the Alps will leave you breathless, and you’ll quickly fall in love with the colorful towns dotting Lake Como’s shores. 

We stayed in the iconic lakeside town of Bellagio, which I would recommend for any first-timers to Lake Como.

Originally we planned to land at the airport in Milan, take a train to Milan’s central train station, take another train from there to the Lake Como town of Varenna, walk from the Varenna train station to the ferry port, take the ferry from Varenna to Bellagio, and then walk to our Bellagio hotel…buuut in the end we just hired a private taxi for $150 USD direct from the Milan airport to our Lake Como hotel. It took one and a half hours, compared to the probably two and a half hours our original route would have taken. Our flight from Atlanta was actually delayed by an entire day, so by the time we arrived in Italy we really just wanted to get there and opted for the simpler, but more expensive option to save time. 

If you choose to take the trains, however, it’s really not as complicated as it seems. Check out the Trenitalia and Trenord websites for the local train schedules and buy your tickets, which are inexpensive, ahead of time. It’s a five minute walk from the Varenna train station to the ferry port and you can buy your ferry ticket right there. Tickets are cheap and ferries run every half hour. If you’d rather make your home base in Varenna to make things easier and explore the rest of the lake from there, Varenna is also extremely charming and has plenty of great options for places to stay.

HOTEL BELLAGIO

Salita Grandi, 6, Bellagio, 22021, Italia

I cannot recommend this hotel enough, it is absolutely FABULOUS! Paying a bit extra for a room with a balcony overlooking the lake is essential, since this made the first leg of our trip feel really extravagant. Our room had strong Wi-Fi and great air conditioning which was crucial to combat the Italian summer heat. AC isn’t as common in Europe as it is in America, so you’ll want to check ahead of time to make sure all of your accommodations come with it. 

Hotel Bellagio is located right off Bellagio’s main street, which was the perfect location for exploring the area. Note that you’ll have to walk up a flight of stone steps to access it. 

10/10 would recommend bringing a bell boy with you to carry your bags!

Don't forget to bring a bell boy with you!
My boyfriend lugging my bags around Italy
The only reason I brought him along

Lake Como Day 1

Unfortunately, our flight from the U.S. was delayed and we missed the first official day of our trip. However this was our intended itinerary: 

  • Explore Bellagio. Check into your hotel and explore Bellagio. Pop into the charming shops, maybe grab lunch at a cute cafe along the lake, take in spectacular views, have some gelato, and buy silk souvenirs (Lake Como is known for high quality, inexpensive silk products). If you’re up for it, head to Bellagio’s iconic Villa Melzi, which is known for its stunning gardens and chapel.
  • Stroll through the villas of Tremezzo. Take the Centre Lake Shuttle Ferry or high-speed hydrofoil from Bellagio over to Tremezzo (also called Tremezzina when lumped together with its neighboring small towns), another colorful town with several famous historic villas. The main villas to explore here are Villa Carlotta, which is an eight minute walk from the town center, and Villa del Balbianello, which was the setting for films like Casino Royale and Star Wars Episode II: Attack of the Clones. Stroll through the stunning gardens and take in breathtaking views over the lake. You can also walk the Greenway del Lago di Como here, a gorgeous six-mile relaxing hike along the lake, which passes through ancient villages, beautiful villas and gardens, towns, restaurants, and fantastic views of Lake Como. 
  • Enjoy an aperitivo and dinner with a view. When you’re finished, take the ferry back to Bellagio and enjoy an aperitivo on the stunning rooftop terrace of Hotel Belvedere, Hotel Du Lac, or Hotel Florence. If you’re not in the mood to go out, indulge in wine and cheese on your hotel room balcony instead. Have dinner at a dreamy lakefront restaurant, or eat at Antico Pozzo, a romantic restaurant tucked away in one of the cobblestoned corners of Bellagio. 

Useful ferry information: Ferries between Varenna, Bellagio, Tremezzo and Mennagio only take about 15-20 minutes. Here is a map of the ferry routes, which will be useful for getting around.

Lake Como Day 2

Spend the day exploring Lake Como by boat. This was one of the highlights of our trip; it was such a unique experience to see the lake and its colorful towns from the water. Renting our own boat for the day was also relatively inexpensive and gave us the autonomy to spend the day how we wanted to and explore the lake at our leisure. Note that for smaller boat rentals you do NOT need a boaters license to book. 

  • Explore Lake Como by boat. Spend the day zipping across the lake, taking in phenomenal views, swimming and relaxing. Bring pizza and a bottle of wine with you and you’ll be golden. 
  • Temporarily dock your boat for lunch and explore another town. Depending on how long you rent your boat for, you can temporarily dock in several different towns so you can get off and explore for a few hours. Cernobbio (where George Clooney has a villa) and the larger town of Como are farther destinations if your home base is in Bellagio, but if you have the boat all day and are looking for some unique stops, these can be great places to break for lunch or exploring.

Lake Como temporary docking locations: Here are the locations of where you can temporarily dock in several towns along Lake Como. Note that there is a two-hour limit.

  • Have dinner in Varenna. Varenna is said to be one of Lake Como’s most romantic towns, and it certainly is. You don’t really need to make a reservation here unless you want to – all the lakeside restaurants along the main drag of this charming town are basically the same and very cute. Dinner with a view is unavoidable, and strolling around with some gelato afterwards isn’t a bad idea either. Just make sure you’re done in time to catch the last ferry back to Bellagio, or organize a water taxi ahead of time.
Captain Paul

Boat Logistics

We booked our boat through Get My Boat, which was very easy and had a ton of options to choose from. I would recommend booking well in advance, however, because day-of rentals are nearly impossible to get during the busy season in Lake Como. High season runs from mid-May through September. 

We picked up our boat in Menaggio, which was a 15 minute ferry ride from Bellagio where we were staying, and it ended up being kind of cool to check out another town. However, if you’d rather pick up and drop off your boat directly from the town you’re staying in, most towns offer their own boat rental options, too.

Lake Como Tips

  • Book everything in advance! Lake Como is a very popular summer destination for Italians and other Europeans, so you’ll want to make sure you book with enough time to ensure availability.
  • Stay in Bellagio. The lake is filled with cute towns, but trust me, Bellagio is where you’ll want to be based. It can be a bit of a pain to get to, but it’s totally worth it. 
  • Don’t overbook yourself here. Lake Como is the ultimate relaxing destination. The views themselves ARE the activity! So even if you just hole up on your balcony with some wine and cheese and don’t move for 3 days, you’ll still have done Lake Como right. Relax, read, write, eat, drink, stroll around, and just be present.
Uffizi Gallery
Ponte Vecchio

Day 4 - 5: Florence

It’s impossible not to fall in love with Florence. This city is all about shopping, eating, drinking, and visiting museums – do these things here! It’s also great to just wander aimlessly and lose yourself in the city, stopping into a cute wine bar for an aperitivo or strolling along the Arno River at your leisure. Florence isn’t very large, so nearly everywhere you would want to go is accessible within a 20-minute walk or less.

There are lots of ways to get to Florence, including by train, car or international airport. You can fly from America directly into Florence, which is nice if you plan to begin or end your trip here. Otherwise, most major Italian cities aren’t farther than a few hours by train, which is a common and inexpensive way to arrive in the city. 

For us, it made the most sense to rent a car in Milan and drive it down to Florence and Tuscany. Renting a car was easy and relatively inexpensive. We rented it ahead of time and picked it up at Milan’s central train station. If you do rent a car, however, you may need to get your international driver’s permit before you go, and make sure you’re comfortable navigating driving in a foreign country. Italy drives on the right-hand side of the road, same as in America. You’ll find more tips on renting a car in Italy below. 

Note: If you’re planning to use this exact 10-day Italy itinerary, we took an early morning ferry from Bellagio to Varenna, walked five minutes from the ferry port to the Varenna train station then took the train from Varenna to the Milano Centrale train station. From there, we rented a car and drove to Tuscany. I would recommend going from Lake Como straight to Florence, however, and in that case it would make more sense just to board another train from Milano Centrale directly to Florence. Trains all over Italy are cheap and run frequently.  

I won’t even share where we stayed because it wasn’t great! Solid location, but that was about it. Instead, I would recommend choosing a hotel either near the Duomo (full name is the Santa Maria del Fiore Cathedral) or the Ponte Vecchio. These are both central locations to anything you’ll want to see and do in Florence, so if you’re nearby one of these you’ll be good to go. 

Duomo di Firenze

Florence Day 1

If you’ve only got a couple days in Florence, you’ll want to hit the ground running by seeing the city’s most iconic sights right off the bat. Luckily, everything in Florence is within walking distance so you’ll be able to see a lot quickly and easily get your bearings. 

  • See the Duomo. First thing’s first, head to the symbol of Firenze, the Duomo. Its full name is the Santa Maria del Fiore Cathedral, and it’s situated in an enormous, centrally located plaza. Walk around, take your pictures, maybe even wait in line to enter and take a tour of this spectacular cathedral. If you’re traveling in summer, this site is likely to be extremely crowded and chaotic, so don’t plan to spend too much time here. If you want to climb to the top of the dome, consider buying skip the line tickets because trust me, you’ll want them. 
  • Stroll along the Ponte Vecchio. Another classic tourist destination in Florence, the Ponte Vecchio is an iconic bridge over the Arno River. It’s filled with cute shops and vendors and is the place for the quintessential “Florence” photo. This site is also really chaotic, but there are a bunch of other calmer bridges parallel to this one you can check out later for a more relaxing promenade. 
  • Go shopping. Florence is known for incredible shopping. Take your time walking from the Duomo to the Ponte Vecchio and make sure you cut over to the Via por Santa Maria (the street the Ponte Vecchio is on) early, for everything from designer shops to local street vendors, cute boutiques, and name-brand retailers. This is a great way to experience the hustle and bustle of the city, and you’re likely to find a variety of talented street performers playing live music. 
  • Eat lunch in the Piazza Santo Spirito. Once you’ve crossed over the Ponte Vecchio, you’ll be in Florence’s Santo Spirito neighborhood. This area is (slightly) less touristy and a little more local, though it’s still home to some of the city’s top tourist sights. Eat at Gustapizza, Osteria Santo Spirito, or any of the charming outdoor patio restaurants in the square. If you’re up for it, head to Gelateria della Passera for gelato afterwards. It’s right in the neighborhood and has been ranked as the best gelato in Italy several times in a row, yet there likely won’t be much of a line. It’s fabulous!

Tip: Gustapizza will probably have an extremely long line to sit down at a table. Consider ordering a pizza to go (which is much quicker) and find a spot in the square to sit and people watch instead.

  • Head to the Boboli Gardens. About a three-minute walk from the Piazza Santo Spirito are the Pitti Palace and the Boboli Gardens. By the end of your Florence visit you might be all museum’d out, so I’d recommend skipping the Pitti Palace and heading right to the gardens. Bring a bottle of wine, a picnic blanket (and some water, it can get really hot), and spend the afternoon strolling around the gardens and relaxing.
  • Have dinner at La Giostra. After you’ve had some time to recharge, head to La Giostra for dinner. This is a super romantic Italian restaurant with twinkle lights, candles, and all the vibes. The food is also fantastic; we loved the pear ravioli, pasta bolognese, lamb chops, and tiramisu, and any regional bottle of Chianti Classico will do just fine.
  • Check out a rooftop bar. Florence has fantastic nightlife, but by the end of this jam-packed day, you might be more in the mood for a casual nightcap rather than a big night out on the town. Check out La Terraza rooftop bar inside Hotel Continentale for spectacular views of the Ponte Vecchio and a trendy upscale vibe.
Arno River, Florence
Boboli Gardens, Florence

Florence Day 2

Now that you’ve had a chance to get a feel for the city, you can dive into its more cultural and historic features. 

  • See the David at the Accademia Gallery. Start your day at the Accademia Gallery where you’ll have the chance to see Michelangelo’s remarkable David statue. There are a few other interesting things to see in this gallery, but David is really the main event. I would recommend purchasing skip the line tickets for this to save time and headaches. By the time we arrived, the line was already around the corner of the museum and it was 90 degrees…get the skip the line tickets! 
  • Explore the leather market. Walk over to the leather market and buy some incredibly inexpensive and high quality leather products. Florence is known for its leather, so this is the place to get a fun keepsake from your trip. We bought leather jackets, wallets, tote bags, sunglasses cases and other trinkets…we really went all out here, but we’ll have a lot of this stuff forever!
  • Have a bite at the Central Market. Florence’s Central Market is located right next to the leather market, so it’s a great place to stop for lunch or a snack. The bottom floor of the market is filled with local vendors selling things like flowers, meat, fruits and vegetables, spices, and other local products. The top floor is home to a variety of gourmet food stalls selling everything from pasta and bruschetta to dumplings and chocolate.
  • Check out the Uffizi Gallery. Another of Florence’s must-see museums, the Uffizi Gallery is home to works by famous artists like Boticelli and Michelangelo. You may recognize famous pieces like The Birth of Venus and La Primavera. This is another museum where it’s essential to purchase skip the line tickets ahead of time. This can save you countless hours of waiting in line and it doesn’t cost too much more than the regular ticket price.
  • Watch the sunset at Piazzale Michelangelo. One of the most memorable moments of your trip will definitely be watching the sunset from Piazzale Michelangelo. It’s a bit of a climb to get to the top, but it is 100% worth it. Come here for unmatched views over the entire city. Bring a bottle (or two) of wine and enjoy the sunset to the tune of talented street musicians and appreciative onlookers. This area is usually crowded with both local and study abroad students gathering and relaxing, and is the perfect way to unwind after a long but fulfilling day. 
  • Have dinner at a charming local haunt. You’ve got endless fantastic options to choose from, but check out the list below for a few of my top picks.
  • Spend a night out on the town. Florence is known for its epic nightlife scene, so whether you head to a chic rooftop bar, nightclub, “American” dive bar, or have a drink out on a patio for something more low key, you should definitely experience at least one night out in Florence.
  • Try to find a secret bakery. If you make it out late enough, you can try to find one of Florence’s notorious “secret bakeries”. Every night at around 2 or 3AM, the bakeries that make all the baked goods for the entire city start baking for the next day. If you quietly knock on the door, they’ll illegally sell you wholesale pastries for 1 euro right out of the oven. Rumor has it there are five secret bakeries in the city, and you’ll have to use your nose to find them!
Ponte Vecchio evening stroll
Maverick enjoying the Florence leather market

How to Book a Day Trip or Half-Day Trip from Florence to Tuscany

While for a romantic trip I would definitely suggest spending at least one night in Tuscany, if you don’t have the time, you can easily take just a half or full-day tour from Florence to Tuscany. Viator.com has tons of excellent and affordable options that will pick you up from your hotel, take you on a wine and olive oil tasting tour of Tuscany (or a cooking class, market tour, e-bike tour, or anything else), and then will deposit you back at your hotel at the end of the day. I’ve taken several of these tours and they never disappoint.

Pizza

  • Gustapizza – Consider ordering takeout and eating somewhere scenic to avoid the long lines for a table.
 

Dinner

Lunch

  • All’Antico Vinaio – Outrageous paninis (located near the Uffizi Gallery)
  • Antico Noe – Outrageous paninis (located near the Uffizi Gallery)

Gelato

Nothing in Florence is really farther than a 20-minute walk, so getting around on foot is the best way to explore the city. There are taxis, but especially in high season when it’s crowded it’s often faster just to walk than to take one. Note, too, that most taxis only take cash.

  • Day trip to Parma. On our drive from Milan to Florence, we stopped in the city of Parma, where, you guessed it, parmesan cheese was invented! We couldn’t help ourselves, so we bought an enormous brick of parmesan cheese. Being too impatient to wait for a knife to cut it, I took a massive bite directly from the brick of parm. You’ll never really understand how intense the flavor of parmesan cheese is until you take an enormous bite from a literal brick of cheese. Needless to say, I think I’ve had my parmesan cheese fill for the rest of my life and I never need to eat it again. My boyfriend was less of an animal about it, though, and remains a fan of parm from Parma.
A meal I clearly hated
gelato in Florence
Gelateria della Passera – best gelato in Italy

Florence Tips

  • BUY SKIP THE LINE TICKETS. I cannot emphasize this enough. There is absolutely nothing worse than waiting outside for hours in the heat of summer, wasting precious hours of your vacation, just to get into a museum you already bought tickets for. Buying a skip the line ticket will literally let you walk right in, and it’s not much more expensive than the original ticket cost, either. It’s totally worth it. Here is the link for skip the line tickets for the Uffizi Gallery and for the Accademia Gallery (The David). You might also consider buying a skip the line ticket for the Duomo in Florence if you’re interested in going inside or climbing to the top.
  • It’s worth it to wait in line for epic gelato. There actually IS a difference between great gelato and meh gelato. We didn’t believe that any “famous” gelato shop could really be any better than the countless other gelato shops on every street corner of Florence, so we opted not to wait in the line that was already wrapped around the block at Gelateria dei Neri. We popped into another random gelato shop along our way and it really wasn’t very good. The next day, we went to another famed gelato shop to compare and let me tell you, COMPLETE difference. Day and night. Best gelato I’ve ever had in my life, hands down. Wait in the line, it’s worth it. You’re welcome.
Tuscany
Chianti, Tuscany

Day 6 - 7: Tuscany

Tuscany (and the whole trip really) was right out of a movie. Tuscany is utter bliss. The backdrops were magnificently scenic and we were totally relaxed and completely present the entire time. Tuscany somehow makes you forget about absolutely everything else and simply exist in the moment. 

Riding electric bikes through the Chianti wine region genuinely took my breath away. Photos can’t describe the depth of the landscape or the intensity of the colors that characterized the seemingly endless rolling hills. To feel the wind in your hair and look on as the purest beauty on the planet is sprawled out before you – it’s completely exhilarating. I feel so grateful to have been able to share this place and experience with my best friend and partner in life, and I would certainly recommend everyone who is able not to skimp out on Tuscany.

If you plan to stay overnight in Tuscany, renting a car will likely be your best option. Having your own car will give you the most freedom to explore the area at your convenience, and most accommodations in Tuscany offer free overnight parking. The best places in the region are remote and hard to get to without a car, so unless you hire a taxi or private driver from Florence to Tuscany, renting a car will be your best bet. If you want to hire a private transfer instead of renting a car, however, I recommend using Connecto Tranfers, which we really liked in Lake Como. It’s reliable and might end up being less expensive than renting a car depending on the distance.

Though it’s a bit farther from Florence than Siena or San Gimignano, Chianti is known to be the most scenic region of Tuscany and it’s definitely worth the schlep. Once you’re there, you can drive yourself to different towns, wineries and markets or ask your hotel if they can organize a taxi or transfer service for you. This is an especially good choice if you’re planning to drink wine and don’t want to worry about driving once you get there.

Castello la Leccia

Località La Leccia, 53011 Castellina in Chianti SI, Italy.

THIS HOTEL. Wow. Definitely one of the most impressive places I’ve ever stayed. Situated in the hills of Chianti, this gorgeous villa is more than just a hotel. It’s also an organic winery with its own wine cellar, vineyards and extra virgin olive oil. This boutique wine resort features stunning gardens, a pool, spa, and a gourmet restaurant with fantastic views overlooking the entire region. The hotel is expensive, but not unmanageably so if you’re looking to stay at a luxury property. We spent about $330 USD per night.

Even if you don’t choose this specific hotel, I would definitely recommend staying in the Chianti Classico wine region of Tuscany. All of Tuscany is beautiful but Chianti is the absolute most scenic area, which will elevate your experience tenfold.

tuscany hotel
Castello La Leccia hotel, Chianti, Tuscany

Tuscany Day 1

Tuscany is all about relaxing, so don’t overbook yourself here. Choose an accommodation with stunning views and great wine so you can simply unwind and take it all in. 

  • Arrive at your charming Tuscan villa in the heart of the Chianti wine region. Spend some time exploring the grounds, then sit outside in the garden or somewhere with a stellar view to enjoy a bottle of local wine.
  • Take a cooking class or try another local activity. We organized a cooking class directly with the hotel so we wouldn’t have to leave the grounds (since Chianti is kind of remote), but there are plenty of pasta, pizza, and gelato making classes available throughout the Tuscany region. Some even include market visits beforehand to pick the freshest ingredients. If a cooking class isn’t your thing, consider horseback riding, a vineyard tour and wine tasting, renting vespas or a classic car, heading to the spa, or relaxing by the pool instead. Depending on where you stay, your Tuscany hotel will likely offer most of these activities.
  • Dinner al fresco on the terrace. In the evening, sit outside on the hotel restaurant’s rooftop terrace overlooking all that lies below. If you’ve taken a cooking class earlier in the day, your chef will serve you your handmade pasta paired with wine sourced from the hotel’s own vineyard. Enjoy great conversation, delicious food, fantastic views, and the warmth of each other’s company in a simply perfect location.
tuscany hotel
The garden at our Tuscan hotel
tuscany garden
Views from our Tuscany hotel

Tuscany Day 2

Today you’ll get the real Tuscany experience when you explore the Chianti Classico wine region by electric bicycle. 

  • Breakfast in the garden. Enjoy breakfast in the hotel garden with views overlooking the gorgeous Tuscan landscape.
  • Head to the charming town of Greve to pick up your e-bikes. Be sure to organize a transfer with your hotel ahead of time so you won’t have to drive yourselves there and back after a long day of visiting wineries! Consider grabbing a snack or an espresso in Greve because it’s just too cute not to.

We rented our bikes from BikeSquare in Greve in Chianti which was easy and inexpensive, and the shop was about a 30-minute drive from our hotel. 

You can book your e-bikes and select your route ahead of time so everything is ready for you when you arrive. When you get there they will show you how to use and charge your e-bike (you shouldn’t have to charge it during the day, but you never know), and they set you up with an app on your phone that offers a route through the region with GPS. From there you’re on your own to follow the route and stop off at different wineries and towns along the way. The self-guided route gives you a lot of freedom and allows you to take your time and explore the region at your leisure. 

We selected the Volpaia Ring route ahead of time, so we were able to make some reservations for wine tastings and vineyard tours before we went. I would 100% recommend making reservations for all the places you plan to stop at (even if you don’t end up making it to all of them) because they do tend to book up. 

For us, this self-guided e-bike tour was incredibly romantic because it was really just us riding through the peaceful, rolling hills of Tuscany together. We were awestruck by the raw natural beauty of the landscape and the overall experience just felt so magical and really special.  

*Note: I would ONLY recommend renting an e-bike (NOT a regular bike) for exploring Tuscany. It is ALL hills! You will not make it all day long unless you’re on an electric bike (or if you do, it won’t be nearly as pleasant or relaxing!).

  • Take a self-guided e-bike ride through the picturesque landscapes of Chianti. We didn’t realize how far the distances were between the wineries and towns on the route I selected, so we only ended up making it to one winery and two medieval towns, which took the entire afternoon. Even if that happens, biking really is the main event because the views are so spectacular (and it’s a really easy ride since you’re on an electric bike). Make sure to start your tour first thing in the morning, though, so you have all day to explore the region. 
  • Stop at local vineyards for wine tastings and views. BikeSquare offers lots of interesting bike routes to choose from in the Chianti region, but we chose the Volpaia Ring because it included a little bit of everything we wanted – wineries, vineyards, and medieval towns. I was able to make reservations at the wineries along the route for wine tastings ahead of time, and one winery, Lamole di Lamole, even offered a “picnic in the vineyards” option, where they set you up with a picnic basket full of food and wine and send you out into their vineyard for a romantic picnic. Unfortunately they don’t start offering that until June and we were there in May. The regular wine tasting was still lovely and inexpensive, though.
  • Have lunch or gelato in a medieval town in the countryside. These tiny, ancient towns add even more character to this enchanting region. The final stop on our bike tour was Radda in Chianti, which is a super charming historic village with well-preserved medieval pubs alongside more modern restaurants and shops. We sat down for wine and cheese in a cute local shop where we chatted with the owner and took in beautiful views of the countryside before heading back to Greve to drop off the bikes.
  • Head back to your hotel for a relaxing dinner on the terrace, or order room service instead! This is the perfect way to end an incredible day in Tuscany.

 

Dinner al fresco
Restaurant terrace at our Tuscany hotel

Other Activities You Can Do in Tuscany

  • Local markets
  • Rent a vespa or a classic car
  • Horseback riding 
  • Spa 
  • Pool 
  • Explore nearby towns 
  • Cooking classes

Special note for those with allergies –

When considering how to plan a trip to Italy, you may want to avoid heading to Tuscany in the early spring and opt to go later in the summer or even in the fall instead. My boyfriend is incredibly sensitive to pollen and we must have been there just as everything was starting to bloom because his allergies were absolutely horrible! His face swelled up so huge he could barely breathe, even with allergy medication. 

His face was extremely swollen and he couldn’t stop sneezing, but once we started drinking wine, his face instantly went back down to normal and he was completely fine. Our theory is that since alcohol suppresses the immune system, the wine simply calmed his allergies down. Obviously once we realized that we got completely carried away and got belligerently drunk, but for those with better self control, we found that moderate drinking can be a decent solution!

Ironically, despite his allergies Tuscany was still my boyfriend’s favorite part of the entire trip because the views were that sensational and the experience was that unique, go figure!

Venice
Venice, Italy

Day 8 - 9: Venice

When originally planning this trip, I had forgotten how incredible Venice is. Now after returning, I remember that it truly is one of the most unique places in the world; it has so much character and is so dreamy. We only planned for one day in Venice and immediately regretted it, wishing we had at least one or even two more days there. 

Venice offers plenty to do, from gondola rides and classic opera to museums and world-class shopping. Even just wandering aimlessly through the maze of canals or finding a picturesque patio for a glass of wine is a great experience in Venice. It’s a really special destination and merely existing there is all you need.

The best way to get to Venice is by train. Most northern Italian cities have direct trains that run frequently in and out of Venice. There is also an international airport in the city which is extremely convenient, and has direct flights from several major U.S. airports. We took the train from Florence to Venice which was easy and relaxing.

Once you arrive in Venice, however, getting to your hotel can prove a bit more complicated. Keep in mind that this is an unusual city, and the “roads” are mostly canals which you can only access by boat. Vaporettos, or water taxis, can be good options for getting around but can be quite expensive. There are ferry routes which are more accessible for getting around, but don’t expect to find many regular taxis or cars anywhere on the island. Once you’re settled into your hotel, you’ll find that walking will be the easiest and most convenient way for getting around in Venice.

UNAHOTELS Ala Venezia

San Marco 2494, 30124, Venice, Italy 

This was a lovely hotel situated perfectly near the Piazza San Marco and the Teatro La Fenice opera house. It’s a short walk to most of the touristy places you’d want to check out in Venice, besides the Murano and Burano islands which you’d need to access by ferry. 

This hotel was gorgeous and featured a stellar rooftop patio overlooking canals and scenic Venetian rooftops. The rooms were spacious, comfortable, and well-appointed, and the hotel has a cute little bar attached which also serves a fabulous complimentary breakfast for hotel guests. We chose a room with a canal view (you might consider upgrading to a room with a balcony overlooking a canal instead), and the lobby opened up directly onto a canal so when our water taxi picked us up to take us to the airport, we stepped directly out of the lobby and onto the boat. It was a very interesting and unique experience, to say the least!

Venice Day 1

  • Arrive in Venice. Once you’ve arrived at your hotel, you’ll likely want to stroll around and get your bearings – maybe stop for lunch at a charming canal-side restaurant or have an espresso and people watch in Piazza San Marco. 
  • Explore the city on foot. You’ll want to acquaint yourselves with the main tourist attractions of the city during your first day, and luckily everything is accessible on foot. Head to the central square, the Piazza San Marco, where you’ll find the city’s duomo (main cathedral), Saint Mark’s Basilica, and the iconic Palazzo Ducale (Doges’ Palace). Walk along the waterfront then head to the famed Rialto Bridge and the Grand Canal. As you walk, pop into carnival-themed shops lined with intricate masquerade masks and trinkets. You’ll also find numerous high-end stores and boutiques if you’re in the mood to go shopping. 
  • Take a classic gondola ride. Unsurprisingly, one of the best ways to really get a feel for Venice is by boat. There are gondoliers advertising private gondola rides everywhere throughout the city, so I would recommend just taking a half an hour ride with one of those guys rather than booking a private ride ahead of time. The local gondoliers are available at any time of day or night and are very easy to find. It’s about 80 euros (cash) for a private 30 minute ride, which may seem steep, but it’s worth it for the unforgettable and utterly romantic experience. We had actually booked a private gondola ride ahead of time, which cost twice as much for the exact same ride, but we got caught up wandering around and didn’t make it to the pick up point across the city in time, and they wouldn’t rebook us. We ended up just finding a local gondolier to take us which ended up being much more convenient and cost efficient. 
  • Enjoy dinner at an enchanting canal-side table. Experience an evening you’ll never forget when you dine canal-side at Ristorante ai Barbacani. Make sure to make a reservation at the romantic canal-facing table well in advance, as it requires a special reservation and fills up quickly. Besides the fact that this is absolutely a once in a lifetime experience and will likely be one of the most unique moments of your trip, all of the food at Barbacani is also solidly delicious. Order the house wine (which I always recommend doing in Italy, as it’s typically cheap and very good), and anything on the menu is sure to be excellent. The fish is extremely fresh, as with all seafood in Venice, and the tiramisu is to die for.
  • Explore Venice by night. After dinner, stroll through the dreamy streets of Venice. Whether you stop to listen to live music in Piazza San Marco or wander into a bustling local bar for a nightcap, you won’t want to miss the fairytale feeling a warm summer night in Venice elicits.
Venice canals
Venice

Venice Day 2

Unfortunately we only had one full day in Venice and had to leave the next morning. However, if we had had another day (and I would recommend at least one more to anyone else), this is how we would have spent it: 

  • Take a tour of Dodges’ Palace and St. Mark’s Basilica. These gorgeous and historic buildings are certainly worth exploring if you have time. As some of the most famous and important sites in the city, you’ll be happy you took a tour.
  • Head to the glass-blowing islands of Murano and Burano by boat. Take the ferry over to these unique islands known for glass blowing. These charming and colorful islands are definitely worth a visit if you’re interested in the renowned Venetian art of glassmaking. We bought stunning glass-blown drinking glasses, but you might also consider bringing home mirrors, figurines, beads, jewelry and more as keepsakes from your trip.
  • Relax and wander freely. Wandering through the charming streets of Venice really never gets old. You’ll want to soak up the unique character of your surroundings as much as you can.
  • See an opera. If you’re looking for a totally authentic and unique experience in Venice, head to the famed Teatro La Fenice for an opera. This stunning historic opera house played a fundamental role in the development of Italian opera.

 

Head to the airport: The final morning of our trip we took a private water taxi directly from our hotel to the airport, rather than taking the public ferry. The ferry would have taken two hours and been much cheaper, and the water taxi was quite expensive, some 140 euros I believe, but only took half an hour. We had so much luggage by the end of our trip that we decided the water taxi was worth it, and it ended up being a heck of a way to get to the airport! 

The water taxi was an experience in itself, and we absolutely loved it. The vaporettos (water taxis) in Venice are actually really gorgeous boats, so you’re basically zipping around the canals in the boat equivalent of a limo. For us it was a really fun (and extremely convenient) way to finish up the trip and quickly get to the airport.

dinner on the venice canal
Dinner at Ristorante ai Barbacani

Other Activities You Can Do in Venice

  • Murano and Burano glass blowing islands 
  • Shopping! There are tons of high end and antique stores
  • Jewish Ghetto 
  • Food or walking tours
  • St. Mark’s Basilica
  • Doge’s Palace
  • See an opera

Venice Tips

  • Venice is known for seafood, so be sure to indulge in some fresh fare.
  • While this is probably my favorite city overall, basically all of the people we met in Venice were a little rude. This is likely just because there are SO many tourists in Venice (overtourism has been a major problem there, actually), so everyone who lives and works in the city is kind of just over it. Of course we still had a nice time, but you can definitely expect Italians to be much nicer everywhere else!
Our hotel in Chianti

Day 10: Fly home

Now it’s time to figure out how to pack all your souvenirs into your luggage, look through all your photos and cry the whole way home! Surprisingly, Venice has direct flights to a number of major U.S. airports, so we were able to fly directly from Venice back home to Atlanta. 

I like to use Google Flights to find and book the best flight options for my dates, but Scott’s Cheap Flights can also be a great tool for finding the cheapest airfare if you’re more flexible with your dates. For this trip, we actually had an idea of the exact flights we wanted to get, and then I got an email from Scott’s Cheap Flights tipping me off that flights to Italy for May would be cheap during the next two days. I was able to book the round trip flights we wanted for $600 each, which is a steal for direct flights to Europe.

Gorgeous Tuscany sunset
bike riding in tuscany
Renting e-bikes in Tuscany

Want to stay in Italy longer? Here are some other fantastic Italian destinations to add on to your trip:

Other places in Italy I’d suggest checking out if you have more time include:

  • The Amalfi Coast 
  • Puglia/Sicily
  • Portofino 
  • The Dolomites
  • Sardinia
  • Lake Garda (which is supposed to be even more beautiful than Lake Como, but I can’t confirm!)
venice restaurant
spaghetti in italy

IMPORTANT: Tips for Renting a Car in Italy

  • Get your international driver’s permit beforehand. You may need an international driver’s permit in order to rent a car in Italy (and in most places abroad, actually). You can get this for $20 at your local AAA (even if you don’t have AAA, but it may cost you a bit more). You have to go in person to get the permit, and bring a passport-sized photo. If you don’t have one, they can take it for you there. It’s super easy to get the permit, and all you do is show it to the rental company when you go to pick up the car, then keep it in the car with you while you’re driving. Not all rental car companies will ask for it but some will. Also, if you get pulled over, you may be fined for not having an international driver’s permit, so better to be safe than sorry.
  • Rent automatic. Double check that the car you’re planning to rent is automatic and not manual! Most cars in Europe default to manual, so if you don’t know how to drive a stick, you’re screwed!

What Are the COVID, Visa and Vaccination Requirements?

At the time of writing (July 2022), Italy does NOT require tourists traveling from the U.S. to take a Covid test for entry. However, you’ll need to show that you’re fully vaccinated for this to be the case. Once there, you don’t really have to wear masks anywhere except for on the trains between cities, and honestly we were never asked to show our Covid vaccination card anywhere during the trip, including in museums, restaurants, bars, etc. That said, I would still bring your vax card, or at least a picture of your card, with you when you’re out and about, just in case. 

American citizens do not need a visa or any special vaccinations (besides the Covid-19 vaccine) to enter the country.

varenna lake como
Varenna, Lake Como
menaggio lake como
Menaggio, Lake Como

Using Your Cell Phone in Italy

Many cell service companies offer some type of daily plan that allows you to use data while traveling abroad. I have AT&T which lets you have unlimited data for $10/day. All you need to do is turn on your phone normally when traveling and you’ll automatically be charged. If you don’t want to use the data one of the days or at all, simply keep your phone on airplane mode. 

If you’re traveling with other people who don’t have a data plan but you do, or vice versa, they can connect to your Wi-Fi hotspot at any time to get connected as needed. My boyfriend has Verizon which also offers an international data plan, and I believe Sprint also offers its own plan as well. If you’d prefer not to have data abroad, there are plenty of places in Italy (and all over Europe) that offer free Wi-Fi.

A Note About Organizing Your Itinerary: City First, Countryside Second

If you choose to change the order of this 10-day Italy itinerary or omit some destinations in favor of others, I would suggest starting your trip in a major city and then moving on to a calmer destination, rather than doing what we did which was start with two very calm locations (Lake Como then Tuscany) and then heading to Florence third. By the time we got to Florence, we were in such a relaxed mindset and had grown so used to the calm that when we arrived in Florence (hungover from too much wine in Tuscany) it was like a shock to our systems. It was only the end of May, but it was already extremely hot and the city was insanely crowded with tourists. We just didn’t feel prepared or mentally fresh enough to tackle the city our first day there, which is a bummer because Florence is one of the best cities in Italy. So when you make your itinerary, do it with that in mind. 

Start with a busier city, then move on to a more relaxing destination so it’ll feel more like a vacation and a relaxing break. In this itinerary, I switched the order of Tuscany and Florence so that Florence comes first for future trips. Lastly, I would always recommend ending your trip with a bang. Wherever you choose as your final destination (we chose Venice and it was perfect), make sure it’s somewhere really special so you can finish your vacation with a positive outlook on your trip overall. You’ll definitely leave feeling happy that you came and looking forward to returning.

Tuscany
Volpaia, Tuscany

Italy Tips

Here are a few useful tips before heading to Italy:

  1. Don’t plan to use Uber. Outside of Milan and Rome, Uber isn’t huge in Italy. Be prepared to take taxis, and know that while some will accept credit cards, most prefer or only allow cash. 
  2. Don’t rely solely on an American Express credit card. American Express isn’t widely accepted in Italy, so make sure to bring another credit card just in case. Visa and Mastercard are good basically everywhere. You may also want to check to make sure your credit card doesn’t charge foreign transaction fees, as those can quickly add up on a vacation.
  3. Bring your own water bottle. You CAN drink the water everywhere in Italy so bring a reusable water bottle.
  4. Make sure your hotel has AC. Double and triple check that the hotel you book has air conditioning! Most places in Europe do NOT have AC, so if you’re staying in an Airbnb it can be pretty miserable, especially in the heart of summer. Even just at the end of May it was sweltering hot, so I was grateful all the places we stayed at had working AC. 
  5. Make sure you can take out cash. Always be prepared to take out more cash than you think you’ll need. We needed it for tons of random things we didn’t think we would, like water taxis, regular taxis, small purchases like water bottles or a quick snack, the private driver to Bellagio, the gondola ride etc. I like using the Charles Schwab debit card when I travel internationally because it lets you take out cash at any ATM all over the world and doesn’t charge any international transaction fees. The only downside is that you’ll need to make sure you have enough money available in your account several days before you go, because if it turns out you want to take out more than you have, it will take a few days for the money to transfer over. Either way, you should still bring your regular debit card with you to Italy in case of emergency. 
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2 thoughts on “Romantic 10-Day Italy Itinerary: From Venice to Lake Como”

  1. Terri Mazer

    Your trip sounds incredible! I am sending this on to my sibs as we are planning to go …hopefully next year. Thanks for being so thorough and planning a wonderful adventure.

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