A 10days-long road trip through Tuscany is a fantastic way to explore the region's picturesque landscapes, charming towns, and delicious cuisine. The trip can be tailor made accordingly to the season (summer is quite hot), the number of days you can stay and the number of hotels you are available to change. Experiences/Extras can be added to enrich the journey with special memories. Here is a first suggested itinerary to start, changing the hotel everyday!
Upon arrival, collect your rental car and make your way to the iconic leaning Tower of Pisa. Afterward, head to the charming town of Lucca, wander through its picturesque historic center, and visit landmarks such as the Cathedral of St. Martin. For a unique experience, rent a bike and enjoy a leisurely ride along the scenic, tree-lined fortified walls.
10:00 - 18:00
Begin your journey by driving through the picturesque Tuscan countryside. Make a stop in Volterra, a town with Etruscan origins, offering breathtaking views, ancient ruins, and charming medieval streets. Continue on to San Gimignano, a UNESCO World Heritage Site, often referred to as the "Manhattan of the Middle Ages" due to its impressive skyline of 14 surviving towers. End your day with a visit to a local winery, where you can enjoy a glass of Vernaccia di San Gimignano.
9:00 - 18:00
Drive toward Siena, pausing at the charming medieval village of Monteriggioni. Wander its ancient walls before continuing to Siena’s historic center. Climb the Torre del Mangia for breathtaking panoramic views over Piazza del Campo. Marvel at the intricate beauty of the Cathedral, and finish with a stroll through the city's winding medieval streets, soaking in its timeless atmosphere.
9:00 - 18:00
Embark on a scenic drive through the Tuscan hills of Val d’Orcia, known for its breathtaking landscapes. Avoid main roads and visit Montalcino, San Quirico d’Orcia, Bagno Vignoni, and Pienza. Relax in the hot spring baths in Bagni di San Filippo before reaching the off-the-beaten-path villages in the Southern part of the region: Sorano, Sovana, and Pitigliano. Consider a visit to the Tarot Garden in Capalbio.
9:00 - 18:00
Drive to the hilltop town of Orvieto and explore its magnificent cathedral, a masterpiece of Gothic architecture, before delving into its fascinating underground city. Continue to Montepulciano, famed for its exquisite wines and elegant Renaissance palaces. End your day at a local winery, savoring a glass of the celebrated Nobile wine while soaking in the Tuscan countryside.
9:00 - 18:00
Drive toward Florence along the scenic Chianti valley, winding through charming villages like Gaiole, Radda, Castellina, and Greve. Pause at a renowned winery for a tasting, or immerse yourself in Tuscan flavors with a hands-on cooking class. Upon reaching Florence, explore its iconic landmarks—the majestic Cathedral, Giotto’s Bell Tower, the world-class Uffizi Gallery, Piazza della Signoria, and the timeless Ponte Vecchio. Treat yourself to exquisite leather bags, shoes, and gloves before savoring a farewell dinner in one of Florence’s enchanting trattorias.
9:00 - 18:00
Take the last shots in Florence and head to the airport for your return flight.
9:00 - 10:00
Hi Barbara - On behalf of my wife and I, I want to thank you for planning an incredible honeymoon for us. We had the absolute time of our lives and could not have done it without you. Here are just a few pictures that we took to commemorate the trip but every part of the trip from start to finish was an absolute dream. We are already thinking about planning our next trip so we will certainly stay in touch! If you are ever in New York please feel free to reach out for recommendations we would be happy to help.
Hi Barbara! We are sitting down having lunch before our tour of Pompei and wanted to tell you how much we are enjoying our trip so far.The hotel in Rome was perfectly located and such a lovely spot! Our first dinner in Rome was at Restaurant MonteCarlo was really good and we loved our tour with Edwardo. Julia and Clara’s fav spot was the trevi fountain. We lucked out at the Pantheon and got a really good tour guide (and skipped the lines). We managed to get to the basillica without much of a wait (about 30 min - maybe less).I am so happy that you recommended Herculeum. So impressive! We are having pizza every meal and loving it!
Hello Barbara! Now that we have settled in at home, I wanted to once again thank you for your help in planning an amazing trip to Italy. We had the absolute best time and only wish we could have stayed longer. Everyone we met along the way could not have been nicer. We felt like we were among lifelong friends! We did get to travel to to meet my ancestors’ family and visit the home where my great-grandfather lived-it was amazing! We actually met a woman from our hometown who moved back to Italy 25 years ago! She graduated from high school with my husband’s brother!! What a coincidence! Anyhow, thank you again for all of your help in planning an amazing trip! It could not have been more perfect. Here are a few pictures from our reunion with my Italian family