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.
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
10:00 AM – Depart from Florence
Begin your wine tour from Florence and leave the city behind as we drive through the rolling hills of Tuscany, where cypress-lined roads lead to charming medieval villages and world-class vineyards.
First Stop – Chianti Winery & Wine Tasting
Our first destination is a boutique Chianti winery surrounded by postcard-perfect vineyards. Meet passionate local winemakers, learn the secrets of Tuscan viticulture, and enjoy a guided Chianti wine tasting paired with regional specialties.
Second Stop – Family-Run Estate in the Heart of Chianti
Continue your journey to another authentic, family-run winery. Here, you’ll sample award-winning Tuscan wines while discovering the traditions that have made the Chianti Classico region famous worldwide.
3:00 PM – Arrival in San Gimignano
Explore the UNESCO World Heritage town of San Gimignano, celebrated for its striking skyline of medieval towers, winding cobblestone streets, and sweeping countryside views.
Overnight Stay Inside the Historic Center
Check into your accommodation right inside San Gimignano’s historic center – a rare privilege that allows you to experience the town after the day-trippers have gone. Wander the peaceful streets, admire the golden sunset over the Tuscan hills, and savor the magic of one of Italy’s most enchanting towns.
✨ Want more of a countryside vibe?
Upgrade to a cozy agriturismo stay surrounded by vineyards and olive trees. Think fresh air, local food, and rustic charm—basically, the perfect Tuscan Insta moment.
08:00 AM – Departure
Begin your unforgettable Tuscany day trip aboard a comfortable van, as we set off to discover some of the region’s most iconic and charming towns.
Siena – Medieval Splendor
Our first stop is Siena, home to the breathtaking Piazza del Campo and the magnificent Gothic cathedral. Stroll through its atmospheric streets, soaking up centuries of history and architectural beauty.
Cortona – Under the Tuscan Sun
Continue to the hilltop town of Cortona, made famous by the book and film Under the Tuscan Sun. Enjoy its panoramic views, artisan boutiques, and timeless Tuscan charm.
Light Lunch at a Local Farm
Savor a fresh, seasonal Tuscan lunch at a traditional countryside farm, surrounded by olive groves and vineyards.
Montepulciano – Wine & History
In the afternoon, visit Montepulciano, celebrated for its medieval streets and renowned Vino Nobile di Montepulcianowines. Take in the views over the Val d’Orcia and immerse yourself in the town’s unique blend of history and wine culture.
8:00 PM – Return to Chianti
Arrive back in Chianti with the evening free to relax and enjoy the peaceful Tuscan countryside.
You can arrive to Florence whenever it is best for you. Check in time is from 2:00pm, but if you arrive earlier feel free to store your bags in the accommodation. Tour will officially start in the afternoon (6:00pm approx).
All year round from Tuesday to Saturday
3* Hotel in Florence and San Gimignano, in the heart of the Tuscan Countryside.
Room Type:
Double Room for 2 people complete with an en-suite bathroom—ideal for couples or friends seeking extra comfort. Single Rooms available on request
Optional Upgrade: For a more countryside experience, choose a rustic agriturismo surrounded by vineyards and olive groves. Enjoy fresh local cuisine, tranquil scenery, and authentic Tuscan charm.
If you wish to extend your stay in Florence, make sure you select the extra nights.
The tour is ideal for:
