The verdict
Our pick
Chianti Wine Safari from Florence: Off-road Tastings in Vineyards★ 4.94 (5,738) · 6h–9h
Best value
Chianti Wine Tasting from Florence: 7 Wines & Vineyard Walk★ 4.58 (236) · 5h
Top rated
Chianti: Farm Cooking Class & Lunch with Vineyard Views★ 4.97 (187) · 4h
The 12 best-value of 18 options, side by side
✓ 2026-09-29Real price per person across the 18 options: € 25–€ 688 (median € 91). With 100+ reviews: 10 of 18.
Default order: real price per person — the group price divided by the seats it includes.
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Private experiences (3)
Chianti Wine Tour from Florence: Private Van & TastingsYou get hotel pickup, a private luxury van, and a driver who customizes the day to what you want to see and taste. Visit Greve village and taste at two working wineyards — one organic, one family-run — with optional lunch overlooking the vines. Eight hours total, return to your hotel by evening.Is it for me?Book this if you want to taste Chianti from people who make it, without arranging transport, timing yourself between wineries, or deciding which estates to visit — the driver handles all three, which is what makes a full day of tasting possible without the logistics.
Private Hot Air Balloon Flight over Chianti VineyardsA private hot air balloon flight departing from San Casciano in Val di Pesa in the Chianti region, about 20 minutes from Florence, takes you up at sunrise for an hour aloft over vineyards, olive groves and rolling hills. A pilot guides the flight while you float in silence above the landscape; the experience includes a safety briefing on the ground, prosecco and light refreshments after landing, and aviation insurance. The flight operates in English or Italian.Is it for me?The three-hour commitment—briefing, flight and celebration included—fits into a morning, leaving your afternoon free for wine tastings or exploring Florence. If you need a transfer from your hotel to the launch point at Bargino, arrange that separately before booking.
Florence: Chianti Wine Tasting & Vineyard Tour PrivateYou get picked up from your Florence hotel and spend the afternoon visiting two distinct Chianti wineries: a castle with 900-year-old cellars and a family-run operation. Along the way, you taste wines paired with Tuscan cheeses and cold cuts, see how wine is made using traditional methods, and drive through the vineyards and olive groves that define the region. The private guide handles all the logistics, so you just show up and taste.Is it for me?Book this if you want to taste real Chianti from two different producers without arranging transport, winery reservations, or figuring out the timing yourself—the private guide handles all of it, and you just show up at your hotel ready to taste.
Up to 2 hours (2)
Chianti: Casa Sola Vineyard Walk & Wine Tasting with SnacksYou’ll wander Casa Sola’s vineyards in Chianti with a local guide, taste three red wines plus Vin Santo, sample fresh olive oil on bread, and snack on Tuscan salumi and cheese. Expect laughter around the table, stories from winemakers, and quiet hillside views that linger long after you leave.
Florence: Horseback Riding Through Tuscan Vineyards & CountrysideYou arrive at the ranch, get fitted with a helmet, and spend 25 minutes in the field learning to ride. Then you're on a 60-minute guided horseback riding tour through Tuscan vineyards, olive groves, and cypress-lined countryside at a walking pace. A guide shares stories about the land as you go. You return for a group photo before heading back to Florence. No riding experience is required.Is it for me?Right for anyone who wants to ride through Tuscan countryside without arranging transport or finding a ranch on their own—the ranch handles the horses, the route, and the timing, so you just show up and ride.
2 to 5 hours (4)
Chianti Wine Tour from Florence: 2 Wineries, 3-4 TastingsYou travel by coach through forty minutes of Tuscan countryside to two family-run wine estates, walk the vineyards and cellars, and taste 3–4 wines at each stop paired with local cheese, salami, and olive oil. Pickup is included from central Florence, and you're back by early afternoon.Is it for me?Right for travelers based near Florence who want to taste real Chianti without arranging their own transport or navigating the region—the fixed pickup and return time means you're back in the city by early afternoon, leaving your evening open.
Florence E-Bike Ride to Fiesole & Chianti Vineyard TourYou collect an e-bike and helmet at the shop, follow a GPS route through Fiesole and Settignano's cypress forests, stop for Chianti wine and Tuscan snacks at a family-owned vineyard, then ride along the Arno back to Florence and up to Piazzale Michelangelo for the city views. The whole loop takes around five hours, and you're navigating it yourself — no guide, no group, just you and the route.Is it for me?Right for confident cyclists who want to explore the Tuscan hills on their own schedule without a guide keeping pace — the self-guided format and e-assist let you ride at your speed, but you need solid biking ability and moderate fitness to handle the route and the climbs.
Florence: Chianti Wine Tour & Lunch at 2 VineyardsYou're driven from Florence through Chianti to two family-run vineyards where you taste eight wines and eat a traditional Tuscan lunch with handmade pasta and local specialties. A sommelier and expert guide walk you through the estates' history and production, and you sample olive oil and balsamic at the second stop. Transport, tastings, and lunch are all included; the whole day takes around six to seven hours.Is it for me?This works well if you want to taste serious Chianti without driving yourself or worrying about who's drinking—the transport and guide handle the logistics, leaving you free to focus on the wine and the meal.
Tuscany Wine Tasting & Vineyard Tour from FlorenceYou're picked up in an air-conditioned van and driven 25 minutes into Tuscan vineyards, where you walk the rows and learn which grapes become which wines. Back at the winery, a sommelier guides you through a tasting of wines made on-site, then you sit down to a traditional Tuscan lunch with wine pairings and a tour of the cellar. The whole day is small-group, which means you're not herded through with thirty other people.Is it for me?Pick this if you want to understand Tuscan wine without spending a full day on it — the small group and fixed itinerary mean you taste, eat and learn without the logistics of finding a winery yourself or waiting in a queue.
Half day and longer (6)
Florence Chianti Vespa Tour: Ride through vineyards & winery lunchYou ride an original Piaggio Vespa or choose a lighter scooter or e-car through Chianti's vineyard roads, stopping in quiet medieval villages and ending at a working winery for wine tasting, olive oil tasting, and a 3-course Tuscan lunch. A professional escort leads the route with a support vehicle following, so you're guided but not herded. The whole day takes about six hours from Florence pickup to return, and includes roundtrip minivan transport to the countryside starting point.Is it for me?Right for riders and passengers who want to experience Chianti's countryside without arranging their own transport or navigation, and who prefer a structured itinerary that includes both the ride and a proper meal at a working estate — the escort and support vehicle are what make it safe to focus on the road and the views instead of logistics.
Florence: 2 Chianti Wineries & Vineyard Dinner with TastingYou meet your guide at Piazzale Montelungo near Florence's main train station and travel by coach through the Chianti countryside to two working wine estates. At the first, you tour the winery and taste regional wines; at the second, you sit among the vineyards for a 4-course Tuscan dinner with wine pairings, including Chianti Classico, as the sun sets. Transport, all tastings, dinner, and a professional guide are included; you return to Florence in the early evening.Is it for me?Book this if you want to taste Chianti wines where they're made and eat dinner in the vineyard without arranging your own transport or timing—the fixed schedule handles the logistics so you can focus on the experience.
Florence: Tuscany Wine Tour Siena & San Gimignano LunchYou travel by coach from Florence through Siena's medieval center, stop at a family-run Chianti winery for a guided cellar tour and six-wine tasting paired with a three-course Tuscan lunch, then finish in the hilltop town of San Gimignano with free time to explore. Round-trip transport, an English-speaking guide, and all meals are included; the full day runs 10+ hours and involves sustained walking on uneven terrain in two towns.Is it for me?Book this if you want the main Tuscan highlights—wine, medieval towns, and a proper lunch—without arranging transport, timing stops, or figuring out which winery to visit; the fixed itinerary and English guide handle all three, and the coach means you can relax between towns instead of navigating roads yourself.
Tuscany: Farm Cooking Class, Wine Tasting & Pasta Day TripYou’ll walk among ancient olive trees in Tuscany, taste five local organic wines straight from the cellar, learn to make fresh pasta with a chef, then share your meal at a big family-style table overlooking vineyards. It’s not just about food or wine—it’s about slowing down and feeling what life is like here for an afternoon.
Florence: Chianti Wine Tour & Tuscan Dinner in VineyardsYou're picked up in Florence and driven to two Chianti wineries where you tour cellars, taste wines paired with local snacks, and browse the medieval village of Greve. As the sun sets, you sit down to a four-course Tuscan dinner among the vineyard rows, with each dish paired to wines made on the estate. Transport, both tastings, dinner and appetizers are included; you return to Florence after dark.Is it for me?Book this if you want the full Chianti experience — two wineries, a cellar tour, tastings and a proper dinner — without arranging transport, timing the stops yourself or navigating between estates. The fixed itinerary and included dinner mean you show up and the day unfolds; the small group size keeps it intimate instead of crowded.
Florence & Chianti E-Bike Tour: Self-Guided Vineyard RouteYou rent an e-bike or regular bike with GPS navigation, helmet, and a water bottle you keep. Follow a self-guided digital map through the Florentine hills and Chianti vineyards at your own pace, stopping at a traditional wine and oil maker and the town of San Casciano. The full-day option covers more ground and more wine country; the half-day stays in the hills around Florence. Check in by 10:45 am with a charged phone and downloaded map.Is it for me?Right for riders who want to explore Chianti and the Florentine hills at their own pace without a guide or group schedule, and who have a moderate level of fitness and a charged phone to navigate by GPS.
Frequently asked questions
Can I book with free cancellation?
Yes: 18 of the 18 options offer free cancellation, so you can book now and confirm your plans later.
How long do these experiences last?
Most options last half a day or longer. There are also shorter and longer formats to fit your itinerary.
Which one is the travelers' favorite?
Chianti Wine Safari from Florence: Off-road Tastings in Vineyards is the travelers' favorite, rated 4.94 out of 5 across 5,738 reviews.
Are private options available?
Yes, 3 private experiences are available if you prefer a closed group.
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