Explore the historic streets of Florence, sip wine in the rolling hills of Chianti, and visit iconic towns like San Gimignano, Siena, and Cortona. Enjoy two exclusive wine tastings, a hands-on Tuscan cooking class, and plenty of free time to immerse yourself in the local culture.

Perfect for small groups and solo travelers, this tour blends guided experiences with flexibility to explore at your own pace.

Any questions about this tour of Italy? Please get in touch. If you’re looking for a shorter tour experience in Italy, please browse our Day Tours in Italy.  

• A Perfect Blend of Guided Experiences and Free Time

• Enjoy Florence and 4 Tuscany’s iconic towns like San Gimignano, Siena, and Cortona

• Unforgettable Scenery and History

• Savor the best of Tuscany with two wine tastings at renowned Chianti wineries and a hands-on Tuscan cooking class, giving you a true taste of local traditions.

• Small-Group Experience

Arrive in Florence and check in to your accommodation from 2:00 PM. After check-in, join your guide for a welcome walk through the historic center. Admire landmarks such as the Duomo, Piazza della Signoria, and the Ponte Vecchio as Florence’s timeless beauty unfolds before you.

Spend the evening discovering Florence at your own pace. Whether it’s dining in a traditional trattoria, sipping wine in a cozy café, or exploring hidden corners of the city, Florence offers endless charm

Optional Activity: Enjoy a traditional Florentine Aperitivo with spritz and local food

Immerse yourself in the beauty and history of Florence with a full day to explore at your leisure. Discover the city’s iconic landmarks, charming streets, and vibrant atmosphere at your own rhythm.

Contact us to learn more about all available optional experiences and tailor your perfect day in Florence!

Depart Florence in the morning, set off on a full-day journey through some of Tuscany’s most iconic towns in a comfortable van. Your first stop is Siena, a city of medieval splendor. Stroll through the atmospheric streets to reach the breathtaking Piazza del Campo and admire the magnificent Gothic cathedral, soaking in centuries of history and architectural beauty.

From Siena, continue to the hilltop town of Cortona, made famous by Under the Tuscan Sun. Here, enjoy sweeping views of the surrounding valleys, browse artisan boutiques, and experience the timeless charm of a traditional Tuscan town. Pause for a local food tasting at a local countryside farm, where seasonal ingredients and rustic dishes highlight the flavors of the region.

In the afternoon, visit Montepulciano, celebrated for its medieval streets and the renowned Vino Nobile di Montepulciano. Explore the town at a leisurely pace, taking in the views over the Val d’Orcia while learning about its rich history and wine culture.

By the evening, arrive in the UNESCO-listed town of San Gimignano. Wander its winding cobbled streets, admire the striking medieval towers, and take in sweeping views of the surrounding countryside.

Spend the night inside the historic center, giving you a rare chance to experience the town after the day-trippers have gone. Meander through the quiet streets, watch the Tuscan sunset, and savor the magic of this enchanting town.

Leave the town behind as you drive through the rolling hills of Tuscany, where cypress-lined roads lead to charming medieval villages and picturesque vineyards.

Your first stop is a boutique Chianti winery, set amid postcard-perfect scenery. Here, you’ll meet passionate local winemakers, learn about the region’s viticulture, and enjoy a guided tasting of Chianti wines paired with delicious regional specialties.

Next, continue to a family-run estate in the heart of Chianti, where you’ll sample award-winning wines while hearing stories about the traditions that have made this area world-renowned.

In the afternoon return to San Gimignano, leaving time to relax and enjoy the serene beauty of the Tuscan countryside.

Take part in a hands-on Tuscan cooking class, learning authentic recipes from a local chef. Sit down to enjoy the meal you’ve prepared, accompanied by a glass of local wine.

Return to Florence by 5:00 PM, marking the conclusion of your Tuscan adventure.