Tuscany, Italy

This famous region of Italy should be on everyone’s bucket list. The food is fantastic, the wine is plentiful, and the landscapes are gorgeous. We spent nine days exploring Tuscany with a group of friends, and we’ve shared our itinerary in this post to help others plan a similar trip.

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Recommended Itinerary

Tuscany is huge and has attractions at every corner, so it can be difficult deciding where to stay and how to organize your trip. Florence is the major hub of the region, so your adventure will most likely start there. After you leave Florence though, you have so many options! We opted to rent a car and explore primarily the Siena region, followed by a few days at the beach on the island of Elba. The map below shows our route.

• Days 1-2: Florence
• Day 3: Florence to Montepulciano via Chianti Classico Region
• Day 4: Montepulciano and Montalcino
• Day 5: Montepulciano to Siena
• Day 6: Siena to Elba via San Gimignano
• Days 7-8: Elba Island
• Day 9: Leaving Elba

Because we flew in and out of Milan, we had to drive back from Elba to Milan after this portion of our trip, but the most common route will take you back to Florence instead for your flight home. This itinerary includes quite a bit of driving, but we enjoyed it because it allowed us to see a variety of areas, and day trips from a central home base would have required even more time in the car overall.

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Days 1 – 2: Florence

Whether you fly direct or come from one of Italy’s other major hubs (Rome or Milan), Florence is a great starting point for Tuscany. The city is filled with history and culture. You could easily spend more than two days exploring all that Florence has to offer, but below are some of the activities that we enjoyed.

• Cathedral of Santa Maria del Fiore: This massive church in the center of the city is incredible. The intricacies of the interior will take a couple hours to explore, but the real draw is the dome that sits atop the cathedral. You can even climb to the top of the dome for some extra time and a fee.

• Giotto’s Bell Tower: If you would rather look at the dome than climb up it, we recommend climbing Giotto’s Bell Tower. This tower sits directly across from the cathedral and therefore has a great view of the church. The walk is narrow and can be a bit strenuous, but there are floors for breaks along the way up.

• Baptistery of Saint John: While exploring the Cathedral and Bell Tower, we also recommend stopping at the Baptistery next door. The gates of paradise marking the exterior are beautiful and have a great story behind them. The Baptistery’s interior is also worth a stop, as the ceiling is incredibly intricate.

• Ponte Vecchio: This densely populated bridge is a bit of a tourist trap, but it is beautiful. The entire bridge is lined with vendors – some extremely upscale. Even if you don’t intend to buy anything, the bridge is well worth a visit.

• Accademia Gallery: Florence has many famous art museums. Perhaps the two most famous are the Uffizi and the Accademia Gallery. Because we had limited time, we opted to visit the smaller Accademia and head straight towards the Statue of David. It’s well worth a quick trip, but there is plenty to see if you can spend more time.

• Vivoli Gelato: Vivoli may have had our favorite gelato out of all the places we tried in Tuscany – and we tried A LOT of places. It was that good.

• Free Walking Tour: Walking tours are always a great way to get your bearings in a new, foreign city. While the tour we did in Florence wasn’t our favorite, it was still a good way to learn about the history of the city and some of the famous sites within it.

When choosing where to stay in Florence, consider that public transportation isn’t great in the old town. Being central to the main sites is key so that you can easily get everywhere on foot.

As far as dining is concerned, we actually didn’t try many restaurants since we were in part there for a wedding. One good spot we tried though was Gustarium. This counter-service pizza place doesn’t serve traditional pies or slices, but its focaccia-style pizza makes for a tasty, budget-friendly lunch.

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Day 3: Florence to Montepulciano via Chianti Classico Region

After a couple days in Florence, we opted to head south to Montepulciano. We did a decent amount of research before deciding on Montepulciano as a home base, as there are many beautiful towns in the region. Ultimately, we felt Montepulciano offered a good blend of dining options and proximity to nice vineyards.

To get to Montepulciano, we drove through the Chianti Classico Region. The drive is beautiful, and there are plenty of nice stops along the way. We broke up and made a day of the drive by making the below stops.

• San Donato: This small hilltop town has great views and a really charming atmosphere. We only spent an hour or so here, but we wish we could have stayed longer to enjoy a meal or visit some of the shops.

• Osteria Le Panzanelle: This delicious restaurant is a great lunch option on your way down from Florence. We recommend making a reservation if possible, as it can get quite busy. The pastas are all great, and there is a nice courtyard that will allow you to dine outdoors and enjoy the Tuscan weather.

• Badia a Coltibuono: The first vineyard we visited in Tuscany! This former monastery has a rich history, beautiful grounds, and many Chianti Classico wines. While the wine wasn’t our favorite on the trip, the tour and tour guide were great, and it was still a good tasting. It’s well worth a stop on the way to Montepulciano!

• Castello di Brolio: This castle and its accompanying vineyard are massive. We spent a good chunk of time exploring the castle’s grounds and enjoying the views before visiting the gift shop across the street for a tasting. The wines here are really good. We still preferred the wine from the next region (Montepulciano and Montalcino), but Castello had our favorite Chiantis on the trip.

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Day 4: Montepulciano and Montalcino

Once you arrive in Montepulciano, you’ll realize your car won’t help you much. The hilltop town is not vehicle friendly and is better suited to exploring on foot. It really is beautiful though and has fantastic views. We opted to rent an apartment in the middle of town, and we were very happy with our choice. It was easy to walk to all the shops and restaurants, and the dedicated parking was just a short walk down the hill.

While staying in Montepulciano, we highly recommend dinner at La Grotta. The tasting menu here was fantastic – especially with the wine pairing. We also ate at Ristorante Godimento Divino, but that restaurant wasn’t as great.

From Montepulciano we took a day trip to the Banfi winery. The grounds here are beautiful, and we highly recommend booking a tour (in advance). You’ll also have the option of reserving a lavish lunch for after your tour that is accompanied by a tasting. It is pricey but worth it.

On the way back from Banfi we stopped in the town of Montalcino and drove through Val d’Orcia. The countryside here is incredibly picturesque, so we stopped at Chapel Vitaleta for a quick walk and some photos.

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Day 5: Montepulciano to Siena

After Montepulciano we made our way to Siena. While also a beautiful town, the vibes are very different. Where Montepulciano is charming and scenic, Siena feels larger and more historic.

One commonality between the towns is that they are not vehicle friendly. The drive between the two wasn’t bad, but we decided to book a room just outside Siena instead of braving its streets. Luckily, it is a short walk into the city, and it’s not difficult at all to get around on foot once you’re through the city’s walls.

Siena has a ton of attractions. Below are those we recommend based on our own visit.

• Tuscan Cooking Class: You shouldn’t visit Tuscany without doing a cooking class! The region is so famous for its food, it’s only right to learn how to make some of it for when you go back home. Our favorite part of the class we did was hand-rolling the pasta. While the end result was delicious, we do wish our class allowed everyone to make their own dishes, rather than contributing pieces to a meal largely made by the instructor.

• Duomo di Siena: You would think we’d be tired of visiting churches at this point of our trip, but they continued to impress. The Siena cathedral isn’t as massive as the one in Milan or Florence, but the Gothic architecture and black and white interior are striking. Give yourself at least an hour to wander around and explore the building. If you go over the summer, you may also be lucky enough to see the mosaic floors unveiled – which are only uncovered and visible 6-10 weeks each year.

• Piazza del Campo: This public space in the center of Siena is surrounded by bars and restaurants. It is a great place to enjoy an aperitivo before dinner. Depending on the time of year you visit Siena, you may also get to experience the Palio, which is a famous horse race that takes place in the Piazza each year. It is supposedly a huge spectacle and incredibly crowded, but a great way to experience the culture of the region.

• Santa Maria della Scala: This museum right next to the Duomo has a number of exhibits, but we visited for the rooftop views. It is very hot and exposed to the sun, but you can get a nice look at the countryside, cathedral, and piazza below.

For a quick bite to eat, we also recommend stopping at Pizzeria Gurgu, Kebab. It’s a hole in the wall, but it hit the spot for a cheap eat. You can even get a kebab pizza! And for dessert, check out La Vecchia Latteria.

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Day 6: Siena to Elba via San Gimignano

Time for another travel day! You could easily spend more than a day in Siena, but we were ready to get out of the heat and enjoy the Tuscan coast.

The car ferry to Elba departs from Piombino, which is a few hours from Siena. Because we had some time to kill, we took the scenic route and passed through San Gimignano on our way to Piombino.

This picturesque hilltop town is really beautiful and definitely worth a visit. If the views from one of the iconic towers aren’t enough to entice you, consider the world famous gelato sold at Gelateria Dondoli. This delicious shop located in the main Piazza del Duomo was a very pleasant surprise – if we were in San Gimignano for more than a few hours, we absolutely would have indulged there multiple times.

Another shop worth visiting if you have time is Balducci Ceramica. The handmade pottery here is really nice and makes for an excellent souvenir or gift! We purchased a few olive oil dispensers that we now use all the time.

Once we left San Gimignano, we had about two hours of driving to Piombino. The car ferry port was easy to find in this coastal town, but we do recommend arriving early to avoid any added stress while boarding. Parking the car on the boat can be a bit snug. Luckily, the ride itself was nice and gave us time to relax and play some cards.

The ferry dropped us off at Portoferraio, which is the main town on Elba. We recommend staying here for your island adventures, as there are some really good bars and restaurants in the town, and some great beaches are only a short drive away.

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Days 7 – 8: Elba Island

Elba is beautiful. It is a completely different vibe than the rest of Tuscany, but it was exactly what we needed after venturing through the countryside in the June heat for a week.

While Elba won’t blow you away with its food like the rest of Tuscany, there are still plenty of good restaurants and bars in Portoferraio:

• La Cisterna: The pizza here is fantastic. We got a few pies for the table and loved them all. Relative to the rest of the options on Elba, this restaurant is also pretty affordable. We didn’t have any issues getting a table for a late dinner without a reservation.

• C’era una volta: This small, family-run restaurant has some truly delicious seafood. The one menu item we consider a must get is the seafood sampler appetizer. It is a great way to try a number of local specialties and fresh-caught selections. The seafood pastas here are also delicious.

• Teatro Bistro & Wine Bar: If you’re interested in dinner with a view, we recommend making a reservation at Teatro. This restaurant has a large terrace atop the hill in Portoferraio that is perfect for watching sunset. The food isn’t half bad either. All of the pastas and appetizers we got for the table were delicious.

• Da Nory Street Food Piadineria e Creperia: For dessert or a quick bite, we recommend swinging by this creperie. It was surprisingly delicious and some of the cheapest, quickest food we had on Elba.

• La Tonnina: This bar is awesome. It is located right on the water with outdoor seating, and they have really nice cocktails. The snacks they bring to the table with your drinks are also delicious. We just had to go here twice!

The real reason you should come to Elba though is to enjoy the weather and water. There are a number of great beaches on the island, but below are those we visited that we would recommend:

• Spiaggia di Sansone: This secluded cliffside beach a short drive from Portoferraio is stunning. It is a short walk downhill from the street parking, but at the bottom you’ll find a beautiful pebble beach with crystal clear water and chairs and umbrellas available for a cash rental. We highly recommend paying up for the rentals, as it will be much more comfortable than laying a towel on the pebbles. While the water here is great for swimming, this beach is also known to have jellyfish, so be mindful if you choose to go for a dip.

• Spiaggia di Cavoli: If you’re looking for more of sandy beach, Spiaggia di Cavoli is a great option. It is a bit further from Portoferraio (30 minutes) and doesn’t have the same views, but it is great for swimming with fewer jellyfish. There is minimal shade on this beach though, so bring plenty of sunscreen.

• Spiaggia delle Ghiaie: If convenience is all you care about, consider making a trip to this beach. It is right in Portoferraio and a short walk from many of the hotels and apartment rentals. The beach is relatively small though, gets crowded, and doesn’t have any shade. If you’re up for a drive, we’d recommend only walking here for sunset after you’ve spent the day at a nicer beach.

Getting around Elba without a car is next to impossible. To make your life easier, we recommend booking a rental car for the entirety of the Tuscany road trip, then taking the car ferry as we did. There is plenty of parking available in Portoferraio – we managed to find a free lot a block behind our apartment rental.

One last note – if you’re a fan of candles and scents, you should check out Acqua dell’Elba. We first saw this store’s locations in Milan but figured we should wait until getting to the namesake for a visit. Their products make great souvenirs or gifts for family back home!

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Day 9: Leaving Elba

Last day in Tuscany! You will need to take the car ferry again from Portoferraio as you’re leaving the island. Use your journey to Elba as an indicator of how early you need to get in line. We stayed right next to the port, so we were able to stroll up very close to the departure time.

After leaving Elba, you have a number of options depending on your travel itinerary. Because we got to Italy via a round trip to Milan, we had to make our way north. Rather than returning the car in Tuscany and taking the train, we opted to drive through the Emilia-Romagna region to stop at a balsamic vinegar farm, the Ferrari museum, and the city of Parma. We’ll have a post coming soon on this mini-trip!

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Other Tips & Tricks

• Getting Around: For the itinerary we outlined, you will need a rental car. In general we recommend getting your own car (rather than taking a pre-planned tour) so that you have the freedom to explore the various regions of Tuscany. If cost is no concern, you can also hire a driver. Regardless, make sure you budget extra time for all drives in your trip, as the roads are windy, and you will want to stop and take photos of the beautiful scenery.

• Cash vs Card: Make sure you have cash on hand for some of the smaller shops and for areas without great cell service (like Elba). Even stands that typically accepted credit card ended up requiring cash since their card reader could not connect to the internet.

• What to Pack: Tuscany gets really hot in the summer. Dress light, and bring a change of clothes for each day if you plan to go exploring in the sun. You will also want comfortable walking shoes for the hill towns, sunglasses, and water shoes for the pebble beaches (if you choose to go to Elba). If you plan to bring wine home from your trip, we also recommend investing in a reusable wine bottle protector or two to safely transport the wine in your luggage.

Happy traveling!

Kitrina & Jordan