Escape to the peaceful beauty of the Tuscan countryside on a 3-day, 2-night getaway where rolling hills, vineyards, and timeless charm set the scene for pure relaxation. Savor world-renowned Chianti wines, discover hidden corners of the countryside, and let the warmth of Tuscany slow your pace. You’ll stay within the walls of San Gimignano, the region’s most enchanting medieval hill town, with easy access from both Florence and Siena. For an extra touch of rustic luxury, you can even choose to stay in a countryside agriturismo surrounded by olive groves and vines.
If you’re looking for a long tour in Italy, please explore our other Multi-Day Tour Packages in Italy.
Spend 3 unforgettable days in Tuscany, surrounded by rolling hills and postcard-perfect landscapes. Discover the iconic hilltop town of San Gimignano, set in the heart of the Chianti region, famous for its medieval tower skyline, charming cobblestone streets, and breathtaking countryside views.
You’ll stay within the historic center, giving you the freedom to explore during the day and soak in the quiet, magical atmosphere of San Gimignano once the day-trippers have gone.
✨ Want more of a countryside vibe?
Upgrade to a welcoming agriturismo, ideal for travelers with their own car, nestled among vineyards and olive groves. Enjoy fresh air, authentic local cuisine, and rustic elegance—your perfect Tuscan stay, scenic, peaceful, and effortlessly accessible.”
Depart in the morning by shared minivan in a small group and travel through the rolling Chianti hills, passing vineyards, cypress-lined roads, and medieval villages. With your local guide, visit three different wineries—from a family-owned estate to a small producer and a boutique winery—each offering a unique take on Tuscan winemaking.
At each stop, enjoy tastings of local Tuscan wines including Chianti Classico, Vernaccia, Super Tuscans and more…. and learn about the traditions and techniques behind them, with time to explore the vineyards or cellars depending on the winery.
Spend the afternoon of the day at leisure: enjoy dinner at a local trattoria, stroll through San Gimignano, or take a short bus ride to Siena for an evening visit.
Wake up to another serene morning in Chianti, feeling refreshed and fully immersed in the Tuscan rhythm. After breakfast, check out of your accommodation—but the experience doesn’t have to end just yet!
We’ll be happy to arrange a little “farewell treat” before your departure. Choose from a variety of relaxing or active add-ons to make your weekend last a little longer—perhaps a cooking class on a local farm, a horseback ride through the vineyards, or a rejuvenating spa morning complete with heated pools, sauna, Turkish bath, and herbal tea lounge.
Optional activities:
– 4-hour Tuscan cooking class
– 1 hour horseback ride
– Half-day Vespa rental
– Spa & beauty treatments
Get in touch with our team for more details
This is a flexible holiday and if you are interested in adding extra nights or departing on a different day please get in touch with our team!
3* Hotel in 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: Upgrade to a welcoming agriturismo, ideal for travelers with their own car, nestled among vineyards and olive groves.
Tour Type: Partially Guided
This tour offers a balanced mix of organized activities, giving you the chance to meet fellow travelers while also providing ample free time for independent exploration.
Transport: San Gimignano can be easily reached by bus or train from Florence. Take the train or bus to Poggibonsi central station (1 h ) and from there take the local bus to San Gimignano ( 20 m ). If you have your own car, you’ll find convenient parking available just outside the historic center.
Check-in info: Check-in usually starts at 2:00 pm, but if you arrive earlier, you’re welcome to leave your bags at reception and start exploring right away.
The tour is ideal for:
