While we’ve been to Rome and the surrounding areas, we had never been to northern Italy and decided to plan an entire trip around just this spectacular region. From wine to history to hiking, this trip really showcased the best that Italy has to offer (except for beaches!). While there is tons more to explore in northern Italy that we did not get to on this trip, we are determined to return and finish exploring this amazing country.
Over 10 days we saw Florence, Venice, and 2 different parts of the Dolomites. In Florence we took day trips to Tuscany, Chianti, and indulged in the food and wine, while in Venice we were transfixed by the stunning architecture and culture. In the Dolomites we completed gorgeous hikes that ended with spectacular views and saw a different side of Italy that not everyone gets to. This was a truly incredible trip and we hope it will help you plan your dream vacation!
Table of Contents
Day 1 – Arrive in Italy
We arrived in Milan at 11 AM, and picked up our rental car through RentalPlus Italy. The company will pick you up at departure door 16, and then it is just a quick 5-7 minute ride to the rental location. We didn’t plan on spending any time in Milan as the main reason we were flying in there was because of the cheaper and more convenient flights. Instead, we made our way down to Florence.
While we drove the 3.5 hours from Milan to Florence, we highly recommend training instead. The train system in Italy is outstanding, and the drive was definitely longer than a train would have been (and more frustrating thanks to the traffic!). However, if you do end up driving, there are many service areas to stop for food, gas, coffee, and bathrooms that are much, much nicer than any rest stop in the US.
Once we arrived in Florence, we dropped our car off at a parking structure recommended by our hotel and walked a few blocks to where we’d be staying. Our hotel in Florence was the B&B Le Stanze del Duomo, a charming venue just a block away from the Duomo. Breakfast was included at Konnubio restaurant, just 2 blocks away. The hotel can be hard to find, so look for the pharmacy’s green cross and the door just to the right of it. There is a sign next to the door that says B&B Le Stanza del Duomo.
Day 2 – Tuscany in a Day
Our first full day in Florence we decided to head out and experience the Tuscan countryside in all its glory! We booked a Tuscany in One Day Sight Seeing Tour, which took us to 3 iconic Tuscan cities and a lovely farm for a traditional Italian meal.
The tour began at 8am in front of the Santa Maria Novella train station where we boarded a coach for our day trip. Our first stop was Siena, where we met a local guide who gave us a walking tour of the charming medieval town. Siena is a glorious city, steeped in tradition including the world famous Palio! If you happen to be in Siena at the right time, this is an experience you won’t want to miss (just be prepared with water!).
Siena is a truly beautiful town, and the tour of the city was great. Our only complaint was that, after seeing the city and the impressive Duomo, we had just 30 minutes of free time in the city. We highly recommend buying any ceramics you are looking for in Siena, as there are numerous shops with very good prices compared with Florence and other towns.
After Siena, we were shuttled on to Fattoria Poggio Alloro, a beautiful farm in the Tuscan countryside. The view is stunning, and the food and wine are incredible. We highly recommend visiting even if you do not book this tour. All of their products are available for purchase, including their wine, olive oil, honey, and even saffron! The best part is you can even order from here online and ship it to the US!
After lunch we continued on to San Gimignano, a well-preserved medieval town that still consists of many preserved towers and city walls. In the city we were given free time to wander, get gelato (a must!), see the architecture, and even shop. In the main square there is a gelato shop that will have a very long line, but if you keep walking along the main street you will come to Gelateria Artigianale, a much less popular but no less excellent option that we rather enjoyed!
After some time, we made our way to our last stop – Pisa. We were given an hour to explore Pisa, though we felt we did not need nearly that much. Unlike Siena and San Gimignano, there is only just the main picturesque square to explore and not much else. While that was very beautiful, the rest of Pisa left a lot to be desired. You can climb the Leaning Tower of Pisa, or just wander around the main medieval area as we did.
With that, our tour came to an end with a bus trip back to Florence. You will do a lot of walking this day, so wear proper shoes and bring water!
We returned to Florence around 8pm and stopped at Ciro & Sons for dinner. We had excellent pizza, mussels, and delicious wine (including Chianti Classico Ruffino!) and was just a few blocks from both our hotel and the train station.
Day 3 – One Day in Chianti
You can’t go to Florence and not visit the world famous wineries that Tuscany has to offer! With that in mind, we booked a winery tour to the Chianti wine region to see the best that Italy has to offer! We absolutely loved this tour and would highly recommend it to anyone who enjoys wine. It was just fantastic from start to finish!
The tour consists of 3 wineries and a stop in the town of Greve for ~30 minutes. We particularly enjoyed Casa Emma and Luiano, two stunning wineries with excellent wine, so good in fact that we could not help but buy a few bottles (even though it was somewhat expensive for Italy, we felt it was very worth it!).
Lunch is included at the second winery, Casa Emma. We had several courses, including gnocchi, each of which was delicious and was accompanied by some of their own tasty wine.
We also had a quick ~30 minute stop in Greve, a cute Italian town with a small main square to walk around, shop, or grab a quick coffee or espresso.
We then made our way back to Florence and were dropped off around 5pm. After dropping our wine off in the hotel room, we walked across the Ponte Vecchio, one of the most famous bridges in Europe. While all of the other bridges in Florence were destroyed by the retreating German Army in 1944, the Ponte Vecchio was spared – legend has it that the bridge was saved on the personal orders of Hitler, who had met Mussolini on the bridge in 1938 to form the “Pact of Steel.”
On the other side of the Ponte Vecchio we made our way to Beccafico to try the world-famous Florentine Bistecca. This is a classic and hearty meal that you must try while in Florence! The star of the dish consists of a greater than 2 pound steak from a local Tuscan breed of cow. The steak is cooked on the rare side and can easily be split between two people! Beccafico was a great place to try it and had a really good price and atmosphere.
After dinner we walked back to the Duomo and made our way to View on Art Rooftop Cocktail Bar for a night cap. This restaurant has an excellent view of the Duomo, but you must arrive early or make reservations in order to have one of the few seats facing it.
Day 4 – Tuscan Cooking Class and Florence
One of our favorite things to do in any country, but especially Italy, is take a cooking class. Naturally, while we were in Florence we made sure to book one that took us out of the city and into the countryside, specifically to a San Gimignano Winery for a cooking class and wine tasting combination!
The day started with a pickup near the train station once again at 9am. From there we made our way to Tenuta Toriano Winery, the site of the class and wine tasting. This was a small group tour, so there ended up only being 5 of us.
The class consisted of making 3 different pastas – a ravioli, a thick pasta, and a thin spaghetti-like pasta. We did not make the sauce, but we did make the pasta and the filling for the ravioli.
After we made the pasta, we were taken to a different area of the winery for a wine tasting while our final pasta dishes were prepared. We tried 8 total wines paired with charcuterie, and while the wine was very good, it is also very, very expensive for Italy.
We also walked through the gardens and the vineyards, which were very beautiful. The winery even has some animals like peacocks that we were able to admire before heading back to Florence. Overall, while we did enjoy this class and wine tasting, we felt it was on the pricey side and would probably look for other options the next time we are in Florence.
We returned in the afternoon and made our way to the Leather Markets which Florence is famous for. It’s important to look for genuine leather using these 4 tips from Italy Magazine, as some of the shops may not be selling real leather.
From there we walked to Piazza Michelangelo for the best view of the city of Florence. Note: this is the most famous and popular spot to see sunset over Florence (for good reason), but if that’s something you are looking for you must get there early to secure a good view.
For dinner we made our way to Santa Felicita Ristorante which had excellent pizza, Greek salad, and mussels. They even provided an on the house limoncello shot to finish the meal off!
Day 5 – Florence to Venice
After 4 fantastic days in Florence, it was time to head to our next destination – Venice! We ate breakfast one more time in Florence, took a few last photos of the Duomo, then began the drive to Venice at 10am.
After about 2 hours of much easier driving, we arrived at the Tronchetto Parking Garage and hopped on Water Taxi 2 towards Piazza San Marco. The boat ride took a little over 30 minutes, and we disembarked in San Marco and walked a few minutes to Domus Superior to check in. This is a lovely hotel in the absolute perfect location, just a few blocks from the most popular parts of Venice. It’s a modern hotel but with the old Venetian charm, and while it doesn’t include breakfast there are plenty of restaurants near by!
After exploring for a few hours, we walked to the Rialto Bridge to meet our guide for our Venetian Walking Food tour at 5pm. We just cannot recommend this tour enough! You’ll get “off the beaten path” and wind your way through Venice’s iconic canals, stopping at restaurants that are relatively unknown to tourists and which offer a more realistic tasting experience!
The best part of this tour is trying food that is out of your comfort zone and authentic, with our absolute favorite being the fried mozzarella with prosciutto. This was probably our favorite food we had all trip, and the best we had were at Rosticceria Gislon on the tour. We liked it so much we retraced the tour the next day to find the restaurant and have them again!
The walking food tour ended in a quieter, more local part of Venice which was perfect for us to grab another drink and then a small bite for dinner. We found the perfect restaurant, Oficina Ormesini, right along a nice canal featuring plenty of less-touristy restaurants.
After dinner we walked back towards our hotel and stopped by the Rio Lounge for a nice drink right along the Grand Canal. This was an incredible experience as the ambiance and the view of the Grand Canal were top notch, however the drinks (though good) are very expensive.
One quick note about Venice – while in Venice, you absolutely must try pistachio desserts. The Veneto region is well known for pistachios, and the two desserts we loved more than any others were the pistachio cannoli and gelato!
You also must get as many Aperol spritz as possible! Be sure to try the “Select” Spritz which is local to Venice. Venetians drink all day (literally, we saw a worker grab a red wine at 10am), so grab one whenever!
Day 6 – Venice
To begin our full day in Venice we went to Caffe Florian in Piazza San Marco, the second oldest coffee shop in the world. Stepping inside feels like you’ve been transported back to the 17th Century, and it’s easy to imagine the intellectuals of the past drinking tea and discussing the most important matters of the day inside the extravagant interior.
While it is definitely pricey, the tea and coffee are worth it (and they serve breakfast if you so desire!). In fact, this was potentially Matt’s favorite experience he’s ever had on a trip. The elegance and classical charm of Caffe Florian cannot be missed on any trip to Venice.
After enjoying our tea and coffee, we caught the #7 Water Taxi to Murano, an island known for its beautiful glass art. From San Marco the taxi takes about 30 minutes to reach Murano.
Murano is much less crowded than Venice itself, and there are tons of shops to explore, with many of them specializing in glass products! As soon as we stepped off the taxi we were offered a free glass blowing demonstration, which was incredible. We saw the expert create a beautiful glass horse from nothing but a glowing ball of glass. Definitely something worth seeing in person!
For lunch we ate at Ristorante Dalla Mora right along the “Grand Canal” of Murano. The portions here are huge, and we were able to split the one person seafood spaghetti with both of us feeling full afterwards! The dish had plenty of seafood and the placement of the restaurant allowed both of us to have great views up and down the canal. We highly recommend eating here if you go to Murano!
After lunch we took the water taxi back to Venice and found a side canal to do the most touristy thing in Venice – take a Gondola ride. While very touristy and even cliche, we just felt we would have regretted not doing it and it ended up being really fun! Seeing Venice from this angle also left even more of an impression on us and showed how magnificent the city really is. Definitely try to do it before 6pm as rates go up after 7, and it is already pricey enough without the increase!
In the evening we made our way back to Caffe Florian for a drink. This time we sat outside and were serenaded by a live string quartet – magical doesn’t even begin to describe how it incredible of an experience this was. You know the music is amazing when they charge 6 euros just to sit at the table and listen to it! In our opinion this is the top thing to do in Venice!
We stayed in San Marco Plaza through the evening, when the lights flick on and its charm comes to life.
For dinner, we walked around and got small plates (cicchetti) at various bacaros rather than a sit down meal. This was also a really fun experience and allowed us to have a bit of all of our favorites from the walking food tour one more time!
Day 7 – Venice – The Dolomites
On our last morning in Venice we got food and coffee at a bacaro near the boat port in Plaza San Marco. Then we headed back to Tronchetto to pick up our car and drive to Cortina D’Approuza in the Dolomites. Depending on the route you take, some of the roads can be a bit sketchy if you aren’t used to tight mountain roads. Most were typical 2 lane roads with plenty of room by mountain standards.
Weather in the Dolomites can be very unpredictable and change quickly. You will likely see a chance of rain forecast for every day while you are there (depending on the season). However, rain is typically just a short storm that passes, so don’t let it ruin all your plans!
When we arrived it looked like it would storm in an hour or two, so we didn’t want to risk being caught on a big hike. Instead, we drove to Lago di Marsupia, a charming lake ~1.5 miles in circumference with a walking path following the shore line. There are several small shops and restaurants around the lake, but be prepared that most of them will not open until 5:30 or later for dinner.
We stopped in one of the restaurants and got a drink until they began serving dinner, then ate and headed to Cortina to wander it’s streets. In early June the town is just coming to life, so it was about 50-50 in terms of businesses being open. Then we headed back to our hotel for the evening.
We stayed at the B&B Hotel Passo tre Croci Cortina. It is a very nice, updated, and clean mountain hotel located less than 10 miles from Cortina. One of the best hikes in the region, Lago di Sorapis, leaves directly from the hotel. It is also less than 30 minutes from Tre Cime di Laverado, and only 45 minutes to Lago di Braies, two of the top must see destinations in the entire Dolomites. Buy the breakfast, it is a buffet and very worth it. We can’t recommend this hotel enough!
Day 8 – Tre Cime di Lavaredo and Lago di Braies
This morning we had breakfast at the hotel and then got an early start heading to Tre Cime di Lavaredo as storms were expected around 1pm. The entrance fee to the area is 30 euros per car, but it is well worth to see this iconic landscape.
The Tre Cime de Lavaredo hike is around 7 miles. We started our hike at 8:20am and finished just after 11:30am, walking at a steady but unhurried pace. From the refugio where you park, if you go right the path is relatively flat and wide, with stunning views of the mountains and the valley below. When you pass some old WWI fortifications, you will come right up to the base of Tre Cime de Lavaredo.
Yes, WWI was, in fact, fought in this unforgiving environment. High on these slopes Italian and Austrian forces clashed for more than 3 years, sometimes advancing only a mile or two in a year while slogging it out. Seeing the ruins of a fortification more than 100 years old in this terrain was quite the experience!
At this point you can either turn around and go back, or continue for the whole loop. If you continue, the path gets a bit hillier and harder as you descend then climb back to the car. We had to traverse some snow patches, but nothing overly difficult in early June. We can’t recommend this hike enough as it is one of the most beautiful places we have ever been to, and the WWI history is unlike any other hike.
We then decided to head to Lago di Braies, a stunning mountain lake that is so picturesque the Nazis made Hotel di Braies along its shores one of their command headquarters during WWII. Parking is only 8 euros for 3 hours. As you walk to the lake from the parking lot you are treated to increasingly spectacular views before the whole lake opens up in front of you.
We first stopped at Emmas Bistro for a chocolate cake and cappuccino for our midday pick-me-up and, of course, an Aperol Spritz. After a storm passed, we decided to walk around the lake a bit for better views of the hotel and to see the lake from a different angle.
We then got another Aperol Spritz to enjoy in peace right on the edge of the lake. Hands down one of the best experiences of the trip!
If you want, you can rent a small paddle boat and go out on the lake. We did not, but be prepared that it can be very busy and the wait can be long.
After enjoying the lake for as long as possible, we headed back to our hotel where we ate dinner for 25 euros per person. It was an incredible deal as it was a great buffet plus water and 2 glasses of wine each included. This evening we experienced one of the most incredible mountain thunderstorms we’ve ever seen!
Day 9 – Lago di Sorapis and Ortisei
We again got breakfast at our hotel, then set off for our next hike – Lago di Sorapis. The best part of this hike was that it left directly from the hotel, so it was extremely easy to find the trailhead.
The first few miles of the hike are fairly flat, though it quickly becomes much steeper and narrower on the edge of cliffs (careful if it is wet, it can be very slippery!). The total distance to the lake is just about 4 miles, but the lake surrounded on 3 sides was an absolutely stunning reward.
While we highly, highly recommend this hike thanks to the stunning reward of the mountain lake, we discourage doing it if the weather forecast calls for rain or if it has recently rained heavily as the trail will be slippery and parts of it are very exposed.
After finishing the hike, we went back to Lago di Braies for one more Aperol Spritz and gorgeous view before heading to our last stop on the trip, Ortisei. Ortisei is about 2 hours by car from Cortina, and it is a very cute little town situated in a valley with dramatic mountain peaks on each side. We stayed at the Classic Hotel AM Stettinick. This is a cute hotel with a heavily German influence. It has a prime location in town, and offers a great breakfast as well!
There are plenty of shops and restaurants in town, with our favorite being Mauriz Keller Restaurant Pizzeria. We stopped there for dinner on our first night and had an appetizer of mussels and clams (huge portion!), and two different types of great pasta. For dessert, we had the creme brule which was absolutely amazing. They also give you a limoncello to end the evening! If you have time, there is a wine bar next door named Vinotheque. We did not go, but it seemed very lively and fun.
Day 10 – Seceda
On our last morning of the trip we headed up to Seceda. You can hike to the top, but we recommend taking the gondola as the hike is 6 miles of very steep uphill. On our way down we passed just a couple people doing the uphill hike, and let’s just say they were struggling! If you are arriving in peak season the gondola can be very crowded so arrive early or buy your tickets in advance! We were there by 9:30am and a line was just beginning to form, but we were not in peak season. You will need to get the all the way to the top Seceda ticket (there is a transfer halfway).
Once to the very top we were treated to one of the most spectacular and unique landscapes we’ve ever seen. We explored the area, walking as close to Seceda as we were allowed. We also explored the Twin Peaks of Pieralongia, a rock formation that looks eerily similar to a shipwreck.
Near the top you will find Baita Troier Hutto. This cafe has wonderful food and drinks, good prices, and perhaps the best restaurant view imaginable. We could have spent all day there, and we almost did. This is an absolute must and is not to be missed! We have already decided that we will be going back one day soon for this experience alone.
After spending as much time as possible at Baita Troier Hutto, we began the long descent back to town. The hike down isn’t overly strenuous, but it can be hard on the knees in various points. While we enjoyed the experience, we both decided that next time we would just take the gondola down to allow more time at the top. We did get to see St. Jakobs church on our hike down and it was stunning, though it can also be reached with just a short walk from town.
Once we arrived back in Ortesei we stopped at Turonda for a late lunch/early dinner. This had absolutely delicious pizza and was the perfect way to refuel after our hike.
Unfortunately, we then had to head back to Milan for our flight early the next morning. We stayed at the MOOM Hotel, a modern hotel very close to the airport which was perfect for our early morning departure.
That concludes our magical 10 day trip to Northern Italy! This trip had some of our all-time favorite experiences including coffee at Caffe Florian, Aperol Spritz at Seceda, and cake at Lago di Braies. We hope this will inspire your next Italian dream vacation!