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Travel with Maddy and Max

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Tuscany Travel Guide

Our time in Tuscany was a highlight of our unforgettable Italian summer adventure. We loved the freedom of exploring the medieval towns and the rolling hills with our small Italian car, tasting incredible wine, and exploring areas off the beaten path. We loved the slow pace and authentic experience in Tuscany compared to the crowded areas in larger Italian cities. If you are looking for a more authentic Italian experience or romantic getaway, we hope our Tuscany travel guide will help you plan the ultimate trip.


Stunning landscape of San Gimignano, Tuscany, Italy

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 oil. 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. Our time at Fattoria Di Pancole was amazing and offered a relaxing and romantic retreat in the heart of Tuscany. Whether we were exploring nearby towns or relaxing by the pool, it provided the perfect home base during our time in Tuscany.



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.