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Beautiful scenery in Tuscany

Exploring the charming towns of Tuscany easily became the highlight of our unforgettable Italian summer adventure. Each town offered unique charm, delicious food, authentic local experiences, and breathtaking views of the rolling Tuscan hills. Tuscany unquestionably captured our hearts, inspiring us to create this perfect one-week Tuscany itinerary, so you can also experience why we fell in love with this beautiful destination.

How to Get to Tuscany

When it comes to reaching Tuscany from various parts of Italy, the most convenient option is to take the train. We traveled from Monte Isola to Florence by train to start our journey in Tuscany. From Florence, another train took us to the charming town of San Gimignano. If you're flying into Italy, it's best to arrive in Florence and then either rent a car or take a train to your final destination in Tuscany.

Getting Around Tuscany

For the ultimate Tuscany experience, renting a car is the way to go. Once we arrived in San Gimignano, we secured a car from the local car rental company, Bellucci Rent. Mr. Bellucci, an aficionado of cars and photography, treated us to a tour of his personal car museum, a copy of his Tuscany guidebook featuring his photography, and set us up with our car. It's important to note that most cars in Europe are manual, so if you require an automatic like we did, be prepared for a potentially more challenging search and higher costs.

Maddy and Max exploring Mr. Bellucci's car museum

How Much Time to Spend in Tuscany

We dedicated five days for our Tuscan getaway, relaxing at our farm stay and discovering the charming small towns of Tuscany. We believe that 5 to 7 days is the perfect amount of time to experience Tuscany at a leisurely pace.

Where to Stay in Tuscany

Our home base was Fattoria Di Pancole, located just outside the town of San Gimignano. This vineyard offers private apartments, a pool with breathtaking panoramic views of the Tuscan countryside, and complimentary parking on its extensive 60-hectare vineyards and olive groves. The apartments came equipped with everything we needed, including kitchenettes and private gardens.

Fattoria Di Pancole is a fully functioning vineyard renowned for its exceptional white wine and high-quality olive. Situated only a 5-minute drive from San Gimignano, it was the ideal location for exploring the region's small towns. We highly recommend participating in a wine tasting or tour for a personal, local experience during your stay.

Rosewood Castiglion del Bosco is a 5-star hotel within a 900 year-old Italian estate set on 5,000-acres located in Montalcino, Tuscany. This luxury hotel offers Italy's only private golf club, a winery, cooking school, spa, outdoor heated pool, and much more.

This luxury Marriott resort is located outside the walled medieval city of Lucca, which offers an ideal location in the heart of Tuscany. The hotel offers a spa, pool, bar, and cooking classes.

Things to Do in Tuscany

Italian Cooking Class

During our stay in Tuscany, we had the opportunity to take our first-ever cooking class, an experience that left us hooked on culinary adventures. We booked this class through Cesarine, which offers authentic culinary experiences throughout Italy. Lucia Casagli hosted our class at her home in San Gimignano, with her neighbor translating since she didn't speak English. During this 4-hour class, Lucia taught us how to prepare fresh pasta, pork ragu, Tuscan chicken, and delicious tarts for dessert. This immersive experience taught us so much about the local culture and cuisine of Tuscany. We truly recommend booking a cooking class through Cesarine, which costs around $165/per person including food and wine.

Our stay at Fattoria Di Pancole gave us the chance to participate in a one-on-one wine tasting, allowing us to sample their award-winning wines alongside local charcuterie. The tasting lasted for an hour and cost €25.00 per person. We would have loved to do the guided tour of the vineyard, cellar, and tasting of all wines, but unfortunately, this was already booked during our stay. If you want to partake in a full tour, be sure to book ahead of time to avoid missing out like we did!

Maddy and Max enjoying a wine tasting at Fattoria Di Pancole in Tuscany

Olive Oil Tasting

Just outside of San Gimignano, we enjoyed sampling local olive oil at Cesani Winery. We had never participated in an olive oil tasting before and it was such a fun and unique experience for us. Cesani Winery not only produces olive oil but also wine and saffron. During our tasting, our host guided us through this fun and informative tasting where we learned about differences in Italian olive oil depending on the region, and taught us the proper way to taste olive oil, all with a stunning panoramic view from their terrace. You can even stay at Cesani, where they offer traditional rooms, an outdoor pool, wine and olive oil tastings, cooking classes, and more.

Explore Medieval Towns

Exploring the charming Tuscan medieval towns by car was such a fun adventure. Learning about the history, architecture, and cuisine of each village taught us so much about Tuscany.

San Gimignano

San Gimignano is one of the most popular small towns in Tuscany and its known for its medieval architecture and iconic towers. San Gimignano is one of the best preserved wall towns in Tuscany and is full of ancient stone buildings to explore. There's something for everyone with plenty of shops, restaurants, gelato, museums, and many more!


Siena is a Tuscan city with a perfectly preserved medieval center with a cathedral, the famous Piazza del Campo, and amazing views of Tuscany.


Certaldo is another well-preserved medieval walled town in Tuscany and a great place to explore and admire medieval architecture. This quaint town is full of charming streets, shops, and authentic restaurants like Osteria da Chichibio.

Where to Eat in Tuscany

This charming restaurant in San Gimignano offers amazing wine and authentic Italian cuisine, making it an excellent spot for a casual and delicious meal. We loved the truffle pizza, anchovy and caper pizza, and the house wine.

Truffle pizza and house wine at Osteria Baccano in San Gimignano

Osteria da Chichibio is a restaurant serving delicious and authentic Tuscan dishes in Certaldo. Their charcuterie board is a must-try, and the pici all'aglione with garlic and hot chili peppers was my personal favorite.

Located in Siena, this traditional Italian restaurant serves delicious pasta and authentic Tuscan entrees. Their fresh pasta was amazing and we loved their cacio e pepe.

Cacio e pepe and wine at La Vecchia Taverna di Bacco in Siena

The Perfect 1-Week Tuscany Itinerary

Day 1:
  • Arrive in Florence.

  • Head to San Gimignano by train.

  • Check into Fattoria Di Pancole.

  • Take the evening to explore San Gimignano and enjoy dinner at a local restaurant.

Day 2:
  • Breakfast at Fattoria Di Pancole.

  • Take a guided tour of Fattoria Di Pancole and participate in a wine tasting.

  • Dinner at a local restaurant in San Gimignano.

Day 3:
  • Relax at Fattoria Di Pancole and enjoy the panoramic views.

  • Enjoy lunch at Osteria Baccano in San Gimignano

  • Join a cooking class and enjoy the dinner you created.

Day 4:
  • Head to Cesani Winery for an olive oil tasting and explore their grounds.

  • Relax by the pool at Fattoria Di Pancole

Day 5:
  • Day trip by car to explore medieval towns.

  • Visit Certaldo and explore its medieval architecture.

  • Lunch at Osteria da Chichibio in Certaldo.

  • Continue to Siena to explore the medieval center.

  • Dinner at La Vecchia Taverna di Bacco in Siena.

Day 6:
  • Drive to Montalcino and explore the town.

  • Check into Rosewood Castiglion del Bosco in the afternoon.

  • Enjoy the amenities of the 5-star hotel, such as the spa and outdoor pool.

Day 7:
  • Relax with coffee and pastries at Rosewood Castiglion del Bosco.

  • Consider participating in activities offered by the hotel, such as a cooking class or a visit to the private golf club.

  • Afternoon departure from Tuscany, either by train or rental car depending on your plans.


After our two weeks in Italy, our time in Tuscany stood out as our absolute favorite, and it's the place we're wanting to return to the most. Tuscany offers an incredible blend of history and breathtaking scenery that makes you feel like you've been transported to another time or right in a rom-com movie. If you're considering a trip to Italy, we wholeheartedly recommend including Tuscany in your itinerary, and using our perfect one-week Tuscany itinerary as your guide!

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