Visit two boutique estates in the heart of Tuscany’s most celebrated wine region. Learn about the art of Chianti blending, stroll through vineyards, and enjoy guided tastings of signature reds.
Recommended duration: 2 hours
Included: Yes, all tours

Just 45 minutes from Florence, the Chianti wine region is the perfect escape for a half-day or full-day adventure. Rolling hills, historic villages, and world-class vineyards make it a must-see for food and wine lovers. Easy AC bus transfers and guided tastings mean you can soak in the Tuscan charm stress-free.
Chianti lies just an hour from Florence. Sit back and enjoy scenic views of rolling vineyards, olive groves, and medieval villages as you travel in an air-conditioned coach.
Licensed tour escorts and local winemakers share Chianti’s history, tasting techniques, and winemaking secrets, perfect for both first-time tasters and wine enthusiasts.
Visit family-run estates for guided cellar tours, vineyard walks, and tastings of world-renowned red wines straight from the source paired with local snacks and olive oil.
Enjoy free time to wander through charming hill towns, browse small shops, or simply soak up the countryside views.
Some tours include Tuscan lunches or stops in nearby towns like Siena, giving you the flexibility to tailor your Chianti experience.
Duration & timing
Transport options
Booking & reservations
Guides & extras
Wine, food & olive oil
Cost & group size
Age restrictions
Sit back on a scenic drive through Tuscany, no need to plan routes, book tastings, or drive after wine. Our expert-led tours include transfers, winery visits, and curated tastings for a seamless countryside escape.
| Tour | Duration | Inclusions | Transfers | Group size | Food | Best suited for | Quick links |
|---|---|---|---|---|---|---|---|
Chianti Wine Tasting Tour | Half-day (~4–6 hrs) | Licensed English-speaking escort, visits to 2 family-run wineries, guided cellar & vineyard tours, 2 wine tastings, regional snacks, free time to explore | AC coach | Small to medium groups | Wine tastings, regional snacks, olive oil samples | Wine lovers, short on time, first-time visitors to Chianti | Book now |
Siena & Chianti Day Trip with Dinner | Afternoon to evening (~5–6 hrs) | Licensed escort, independent time in Siena, visit to 1 Chianti winery with guided tasting, countryside dinner | AC coach | Small groups | Wine tasting + Tuscan countryside dinner | Travelers wanting cultural + culinary experience, sunset dinner, relaxed pace | Book now |
Morning:
Depart from Florence aboard a comfortable, AC coach and head south along the scenic Via Chiantigiana, Tuscany’s famous wine route. Watch the cityscape fade into rolling vineyards, olive groves, and hilltop villages. Your guide shares insights about the Chianti Classico region as you approach your first estate.
Afternoon:
Arrive at a family-run winery and enjoy a guided tour of the vineyards and cellars. Learn about traditional winemaking methods before sampling signature Chianti wines paired with regional snacks and extra virgin olive oil. Depending on your tour, continue to a second estate or enjoy free time to browse countryside shops and soak in the panoramic views.
Evening:
If you’ve chosen a Siena & Chianti dinner tour, continue toward Siena’s medieval old town for an independent stroll through its UNESCO-listed center before heading to a countryside estate. Dine on fresh Tuscan dishes paired with local wines as the sun sets over the vineyards. All tours include return transfers to Florence, ensuring a relaxed and scenic ride back to the city.
When exploring Chianti, you’ll hear both vineyards and wineries mentioned often, and while they’re closely linked, they aren’t the same thing.
Weather:
Spring (April–June) and autumn (September–October) offer the best conditions, with warm days, cool evenings, and lush vineyards at their most vibrant. Summer (July–August) can be hot, especially midday, while winter (November–February) is quieter but cooler, with some wineries operating on shorter hours.
Events:
Visit in September or early October to experience the Chianti grape harvest (vendemmia), a highlight for wine lovers, often celebrated with local festivals. The Radda nel Bicchiere wine festival in June and Chianti Classico Expo in September are great chances to sample top vintages and meet local producers.
Crowds:
May to early October is the peak tourist window, especially weekends when day trips from Florence are most popular. For a more relaxed pace and easier winery bookings, aim for shoulder months (April, early June, or late September) when the scenery is just as stunning but less crowded.


The distance between Florence and the Chianti region is approximately 35 kilometers (21 miles) by road. It's a 45 minutes - 1 hour drive.
Most Chianti tours last 5 to 11 hours, depending on the itinerary. Half-day tours focus on wine tastings and estate visits, while full-day options include stops in Siena, San Gimignano, or Pisa. All experiences include round-trip transfers, so you’ll return to Florence the same day.
Chianti isn’t directly connected by train, and local buses don’t stop near most vineyards. You can self-drive (about 45 minutes each way) or book a guided coach tour, which is the easiest and safest option for wine tastings. Guided tours handle transport, reservations, and language assistance, you just sit back and enjoy the ride.
Yes. Several full-day tours combine Chianti with Siena, San Gimignano, or Pisa, giving you a balanced Tuscan experience. Check our Tuscany Day Trips from Florence for combo options that include scenic hill towns and iconic landmarks.
It's recommended to book your Chianti tour at least two weeks in advance during peak season (June to August) to ensure availability, especially for popular tours that include wine tastings and visits to multiple towns. During other seasons, booking 3 days to one week in advance is fine.
While the core itinerary is standardized to ensure you experience the best of Chianti, we offer a variety of permutations and combinations to suit your preferences. You can choose from top experiences like visiting specific wineries, exploring historic towns such as Siena and San Gimignano, or even adding a traditional Tuscan lunch. This flexibility allows you to tailor your day while still benefiting from a well-planned tour.
The Chianti region is known for its laid-back, family-oriented culture, making it a comfortable environment for families to enjoy wine tasting and local cuisine together. Although, do note that guests under 18 must be accompanied by an adult to book our tours. Many wineries in Chianti are family-friendly, offering activities like scavenger hunts, outdoor play areas, and educational components about winemaking. It is generally recommended that children be at least 5 years old to enjoy the experience.
It’s possible by renting a car, but parking can be limited, and many wineries require advance bookings for tastings. A guided tour offers better access, guaranteed tastings, and no need to drive after wine sampling, making it the preferred choice for most travelers.
Most tours depart from central Florence, usually near Santa Maria Novella train station or designated city meeting points. Exact details will be mentioned in your booking confirmation email.
Chianti tours operate year-round, and light rain rarely affects the experience, most tastings and cellar tours are indoors. In case of extreme weather, tour operators offer rescheduling or refunds as per their policy.
Half-day trip from Florence to two Chianti Classico wineries with guided tastings & transfers.
Inclusions
Assistance at the meeting point
Transport by air conditioned bus with Wi-Fi on board
Licensed tour escort
Wine tasting
Explore Siena’s medieval charm and savor Chianti wines over a Tuscan countryside dinner.
Inclusions
Half-day trip around Siena and Chianti
Expert local guide in English or Spanish
Pick up from Florence
Round-trip AC bus transfer
Vineyard visit, wine tasting, and dinner in Chianti
Exclusions
You can cancel these tickets up to 48 hours before the experience begins and get a full refund.
Book now without paying anything. Cancel for free if your plans change.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Book now without paying anything. Cancel for free if your plans change.