A TASTE OF TUSCANY
Days: 4 D | 3N Group Size: 2 - 8 Start: Chianti Ends: Chianti Tour Type: Partially Guided
Escape the hustle and bustle with this exclusive 3-day tour, designed for friends and couples seeking a personalized adventure through the heart of Tuscany. This is not a group tour but a carefully crafted journey that allows you to immerse yourself in the region's beauty at your own pace.
Enjoy stunning landscapes, charming hilltop villages, and exceptional wines as you explore Tuscany's treasures with your travel companions. Whether it's a romantic getaway or a shared adventure with friends, this tour offers the perfect blend of relaxation, culture, and authentic Tuscan experiences.
Places You'll See
Highlights:
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Discover the Chianti Wine Region: Wander through the rolling hills and vineyards of one of the most famous wine regions in the world.
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Enjoy Picture-Perfect Views: Capture unforgettable moments with breathtaking panoramas of Tuscany’s iconic landscapes.
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Sample Local Wines and Flavors: Indulge in authentic wine tastings and savor traditional Tuscan cuisine.
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Visit San Gimignano: Explore one of Tuscany's most beautiful medieval towns, filled with charm, history, and stunning architecture.
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Flexible Itinerary: Relax by the pool or customize your stay with optional activities like cooking classes, horseback riding, or a rejuvenating SPA experience.
Itinerary
Day 1
Arrival
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.
Day 2
Chianti Wine Tour & free evening
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.
Day 3
Departure
Spend your morning relaxing by the pool or choose from optional activities to enhance your stay. Learn to cook authentic Tuscan dishes, ride through vineyards on horseback, or rejuvenate at a luxurious SPA. Check out feeling refreshed and inspired by your Tuscan adventure.
What's Included
Accommodation: 2-night stay in a carefully selected Tuscan hotel in San Gimignano.
Transportation: Comfortable travel between locations on Day 2
Meals: Daily breakfast
Local tour leader with information about the area and places visited
Wine Tasting: Visits 3 esteemed wineries with guided tastings of wines, balsamic vinegar, and olive oil.
Optional Add-Ons: Personalized activities to enhance your stay, such as cooking classes, Vespa rentals, or SPA treatments.
Additional info
Accommodation
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
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Chech 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.
Optional Upgrade: Optional Upgrade: Upgrade to a welcoming agriturismo, ideal for travelers with their own car, nestled among vineyards and olive groves.
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.
Tour Type
The tour is ideal for:
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Discerning travelers who appreciate a balance of guided sightseeing and free time to explore independently
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Anyone looking for a curated but flexible itinerary — combining iconic landmarks and hidden gems
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First-time visitors to Tuscany who want to experience a bit of everything — art, wine country, countryside, and history
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Couples, friends, or small groups looking for a well-organized semi private tour with personal attention