The verdict
Our pick
Tuscany: Small-Group Wine Tasting Tour with 2 Wineries & Local Flavors★ 4.92 (8,421) · 4h 45m
Best value
Chianti Wine Tasting from Florence: 7 Wines & Vineyard Walk★ 4.58 (236) · 5h
Top rated
Tuscany: Vespa Tour in Chianti Hills with Lunch & Wine Tasting★ 4.99 (577) · 6h
The 12 best-value of 65 options, side by side
✓ 2026-09-29Real price per person across the 65 options: € 33–€ 595 (median € 120). With an extra fee to pay on site: 2 of 65. With 100+ reviews: 51 of 65.
Default order: real price per person — the group price divided by the seats it includes.
Sort
Private experiences (5)
Montalcino & Montepulciano: Brunello Wine Tour from FlorenceYou get picked up from your Florence hotel and driven through Val d'Orcia to Montalcino and Montepulciano, where you taste Brunello and Nobile wines directly from producers. The route includes Pienza for a Pecorino cheese tasting and a walk through its Renaissance streets. Lunch and all transport are included, and you return to Florence in the evening without arranging anything yourself.Is it for me?Book this if you want to taste Brunello and Nobile wines where they're made without arranging your own transport or winery contacts—the producer meetings and small-group format are what make a day in Montalcino and Montepulciano feel like an insider's visit instead of a standard wine route.
Tuscany: Private Wine Tour Chianti Classico & Food PairingYou’ll meet Tuscan winemakers in their own cellars, taste Chianti Classico and Supertuscan wines straight from the source, enjoy a private lunch with local food pairings, and travel through rolling hills with your sommelier guide—leaving you with memories of laughter, real stories, and flavors that linger long after you’re back home.
Florence: Siena & Chianti Wine Tasting Private Day TripYou're picked up at your Florence hotel and driven through Chianti wine country in a private Mercedes with an English-speaking driver who customizes the route to your interests. The day includes a stop in Greve in Chianti, a guided winery tour with wine and olive oil tasting, and a late-afternoon visit to Siena's cathedral and famous Piazza del Campo. You return to Florence in the evening, having seen the landscape and tasted the wine without arranging transport, tickets, or timing yourself.Is it for me?This suits travelers who want to see Chianti and Siena in one day without renting a car or coordinating their own transport and winery bookings — the driver handles the route and timing, which is what makes a full inland day possible from Florence.
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.
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)
Florence: Ponte Vecchio Wine Tasting & Tuscan SelectionsYou’ll sit right by Ponte Vecchio in Florence, tasting Chianti and Vermentino while a local guide shares simple tips for enjoying Tuscan wines. Expect laughter over tasting notes, a handy booklet for your own discoveries, and time to relax as Florence buzzes outside. It’s social, easygoing, and leaves you with new flavors (and memories) lingering long after.
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.
2 to 5 hours (20)
Florence: Sunset Food & Wine Tour with Historic Wine WindowsYou’ll wander Florence’s Oltrarno at sunset with a local guide, tasting Pecorino cheeses and bruschetta from historic wine windows, sipping Super Tuscan wines in an ancient cellar, learning about cucina povera over wild boar stew and pasta, then finishing with real artisan gelato under glowing streetlights. It’s more than just eating — you’ll feel part of Florence for an evening.
Florence: Pasta Class & Tuscan Wine Tasting with MuseumYou visit the Pasta Museum with an expert guide, then spend an hour learning to roll and shape fresh pasta by hand under instruction. Afterward you sit down and eat what you made, with dessert and a tasting of five organic Tuscan wines from the family farm. The full meal is included; you don't need to arrange food or transport separately. Book ahead, as groups are small and dates fill quickly.Is it for me?Pick this if you want to actually make pasta instead of just eating it, and you'd rather learn in a real palazzo near the Duomo than in a tourist kitchen — the museum visit first means you understand what you're doing with your hands, not just following steps.
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: Evening Food Tour with Steak & Tuscan Wine TastingsYou’ll wander Florence’s lively streets at dusk with a local guide, tasting everything from peppery meats on Via dei Neri to rare Florentine steak paired with Tuscan wine in Oltrarno. Expect laughter over mispronounced Italian and stories behind every bite—including artisan gelato to end your night sweetly. It’s less about checking boxes and more about feeling part of Florence for an evening.
Florence: Vintage Fiat 500 Self-Drive & Tuscan Wine TastingYou’ll get behind the wheel of a vintage Fiat 500 in Florence and follow your local guide into Tuscany’s rolling hills. Enjoy stories along secluded roads, taste regional wines at a Renaissance villa with lunch included, and soak up those quiet countryside moments you can’t really plan for — just feel them as they happen.
Tuscany: Vespa Tour with Chianti Winery Lunch & Wine TastingYou’ll ride your own Vespa through winding Tuscan roads with a local guide, pausing for views across Chianti’s vineyards before settling into a family-run winery for lunch and wine tasting. Expect laughter over shared plates, olive oil tastings straight from the source, and small moments—like sunlight flickering through cypress—that stay with you long after you’ve returned to Florence.
Florence: Sant’Ambrogio Food Tour with Wine TastingsYou’ll wander Florence’s Sant’Ambrogio district with a local guide who knows every shortcut and story. Taste cecina fresh from the oven, sample wines you can’t pronounce yet, and swap smiles with real Florentines along the way. Expect laughter, drizzle on cobblestones, and flavors that linger longer than you’d guess.
Florence: Small-Group Pasta Class & Wine TastingYou arrive and help choose the day's menu with the group, then spend hours making two types of fresh pasta and two sauces from scratch under a professional chef's eye. You eat everything you've cooked together, with wine, and leave with printed recipes. Small groups mean real instruction, not a crowd.Is it for me?Right for anyone who wants to actually make pasta, not watch someone else make it, and doesn't mind a group setting where the menu gets decided together. The small size and hands-on format mean real instruction; the shared meal and wine make it social, not rushed.
Florence Food & Wine Tour: Tuscan Tastings & Gelato WalkYou’ll wander Florence’s lively piazzas with a local guide, tasting Chianti wine and classic Tuscan dishes like ribollita and lampredotto along the way. Enjoy creamy gelato near the Duomo, learn stories behind ancient wine windows, and end your day dipping cantucci cookies in sweet Vin Santo. Come hungry—you’ll leave with new friends and flavors stuck in your memory.
Florence Food Tour with Truffle Pasta, Steak & WineA 4-hour food and wine tour of Florence where you taste cheese, cured meats, aged balsamic, fresh truffle pasta, Florentine steak and gelato at locally loved restaurants, guided in English by a local expert. You choose the midday departure at noon or the evening tour at 5pm, and wine flows throughout the meal tastings.Is it for me?Choose the midday departure if you land in Florence in the morning and want to spend your first afternoon eating like a local; pick the evening tour if you'd rather explore the city earlier and come back hungry at 5pm.
Florence: Oltrarno Food & Wine Tour with Negroni ClassYou’ll wander Florence’s Oltrarno with a local guide, tasting Chianti wine, learning to mix your own Negroni cocktail, sharing plates of Tuscan pasta and Florentine steak in a cozy trattoria, and finishing with artisan gelato. Expect laughter, real stories behind ancient wine windows, and flavors you’ll remember long after you’ve left Florence.
Florence: Truffle Steak & Wine Dinner Tour with Cellar TastingYou’ll wander Florence by night with a local guide, tasting truffle pasta made before your eyes, sipping Chianti from centuries-old cellars, and sharing laughs over rare Florentine steak. Expect stories behind every bite — plus artisan gelato as you stroll past glowing palaces. This tour isn’t just about eating; it’s about feeling Florence come alive through its flavors.
Florence: San Lorenzo Market Food Tour & Wine TastingYou taste nine local foods and six drinks at San Lorenzo Market's family-run stalls, then move to a 1944 wine shop for a sommelier-led tasting with food pairing. The guide introduces you to the vendors who've been there for decades, teaches you how to spot real gelato, and shows you how locals actually finish a meal. Dietary needs are accommodated with advance notice.Is it for me?Book this if you want to eat what Florentines actually eat, not what's on a tourist menu — the guide's connections to the market vendors and the sommelier's knowledge of the wine shop's own farm wines are what make the difference between tasting and understanding.
Chianti Wine Tasting & Sunset Tour from FlorenceYou spend an afternoon driving through Chianti's vineyard landscape, stopping at two family-run wineries for tastings paired with Tuscan food, visiting hilltop villages like Greve in Chianti and Montefioralle, and watching the sunset from the countryside instead of the city. Hotel pickup is included if you book the private option, and the group stays small — maximum eight people — so the pace feels personal rather than herded.Is it for me?Book this if you want to taste real Chianti at the source without spending a full day on logistics — the fixed five-hour schedule, included transport, and two confirmed winery visits mean you're not arranging anything yourself, and the late-afternoon timing lets you catch the sunset light that makes the landscape worth seeing in the first place.
Florence: Pasta Cooking Class with Singing & Wine TastingYou’ll roll fresh pasta dough by hand in Florence’s lively center, guided by real Italian chefs who’ll have you laughing (and maybe singing). Taste local red and white wines as your sauce simmers nearby. Share stories—and dinner—with fellow travelers around the table. Expect flour on your sleeves and a song or two stuck in your head.
Tuscany: Pasta Making & Wine Tasting in Castle CellarsYou’ll roll out fresh pasta dough in a Tuscan castle kitchen, taste local wines straight from ancient cellars, and share a homemade lunch with new friends. Expect warm guidance from your chef, laughter over pronunciation attempts, and moments where time feels slower than usual.
Florence: Chianti Wine Tasting & Tuscan Lunch Small GroupYou taste seven Chianti wines with a sommelier at a private 12th-century villa, eat traditional Tuscan lunch on the property with wine included, and travel by air-conditioned van from central Florence with a bi-lingual guide. Small groups keep the pace intimate and the conversation real. The whole day runs from 10am departure through afternoon return, with no transport or entry logistics to arrange yourself.Is it for me?Book this if you want to taste serious Chianti wines without renting a car or navigating the region yourself — the guide, transport, and fixed itinerary mean you show up at 10am and everything else is arranged.
Florence E-Bike Tour: Tuscan Countryside & Local Wine Tasting, Max 4You ride 30–40 km on e-bikes through Etruscan countryside starting from Fiesole, stopping at a monastery, Michelangelo's childhood home, or panoramic viewpoints depending on the day's conditions. The group never exceeds four people. Midway through, you pick fresh produce at a farm, then prepare and share a traditional meal with local wine and olive oil at a family estate. Everything — bikes, helmet, food, wine, guide — is included. You return to Florence by public bus in under 20 minutes.Is it for me?This is for people who want to see real Tuscan countryside and eat real Tuscan food without joining a bus tour, and who can ride a bike confidently on mixed terrain including steep downhill sections. The small group (max 4) and e-motor support are what make it possible to cover distance, stop for a proper meal, and still feel like you're exploring on your own terms rather than following a script.
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 (35)
Tuscany Day Trip: Siena, San Gimignano & Pisa with Lunch & WineYou leave Florence early by coach, spend a guided hour in Siena learning about the city's medieval squares and cathedral, then drive through the countryside to a family-owned winery for a three-course Tuscan lunch with wine pairing. After that, you have free time to explore the medieval towers of San Gimignano and the white marble monuments of Pisa, including the Leaning Tower. The coach returns you to Florence the same evening, with all transport, the Siena guide, and lunch included.Is it for me?Pick this if you want to see three of Tuscany's most famous medieval towns in a single day without arranging your own transport, hiring separate guides, or figuring out timing—the fixed schedule and included lunch mean you show up and the day unfolds around you.
Chianti Wine Safari from Florence: Off-road Tastings in VineyardsYou’ll roll through Tuscany’s countryside by 4x4 with a small group, tasting Chianti wines straight from historic cellars and savoring local cheeses and salumi. Enjoy a leisurely Tuscan lunch paired with regional reds while learning from an expert sommelier guide. Expect laughter, real flavors, and moments that stick with you long after you’ve left those vineyard hills behind.
Siena, San Gimignano & Chianti Wine Tour from FlorenceYou travel by luxury coach from Florence to three medieval towns—Monteriggioni, Siena, and San Gimignano—with free time to explore each one. A professional guide leads a one-hour walking tour in Siena (Classic option) or you roam for 2.5 hours on your own (Semi-Independent). The day ends with Chianti wine tasting and regional snacks at a local estate before returning to Florence in the evening.Is it for me?Book this if you want to see three of Tuscany's most famous medieval towns and taste Chianti wine in a single day without driving yourself or piecing together separate tickets and transport—the fixed schedule and included coach handle all the logistics, leaving you free to walk, explore, and eat at your own pace.
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 to Chianti: Small Group Wine Tour & Tuscan LunchYou’ll ride from Florence into Chianti’s rolling hills with a small group, tasting wines at three different estates and sampling olive oil straight from the source. Stroll through Greve’s lively piazza, share laughs over homemade pasta at lunch, and end your day gazing over Florence from a quiet villa garden—letting Tuscany linger just a little longer.
Val d'Orcia: Wine Tasting Day Trip & Gladiator FieldsYou’ll taste Brunello wines in Montalcino cellars, climb fortress walls for sweeping views of Val d’Orcia’s hills, sample pecorino cheese in sunlit Pienza streets, and walk through real-life Gladiator fields with your guide sharing stories along the way. Expect laughter over shared snacks and quiet moments where Tuscany just sinks in.
Florence: Chianti Bike Tour with Wine Tasting & LunchYou’ll pedal through the Chianti hills with a local guide, pass vineyards and castles, and pause for wine and olive oil tasting at a Tuscan villa. A traditional lunch is included—think simple dishes full of flavor—and there’s time to soak up the scenery before heading back to Florence. Expect laughter, good company, and those small moments that stick with you.
Tuscany Wine Tour: 2 Wineries & San Gimignano from FlorenceYou meet your guide at Piazza della Calza at 9:45am and spend seven hours visiting two family-run wineries in the Chianti region, tasting eight wines plus olive oils and balsamic vinegar with local snacks. You'll walk through San Gimignano's medieval streets and towers, then return to Florence by 5:00pm. The minivan holds eight people, so groups stay manageable, and an English-speaking guide handles all the driving and commentary.Is it for me?Book this if you want to taste real Tuscan wines at family-run estates and see San Gimignano's medieval towers without arranging your own transport, timing, or winery bookings — the fixed schedule and small group size mean you get a full day of Tuscany without the logistics.
Florence: Chianti Wine & Olive Oil Tour with Tuscan LunchYou spend the day in a Mercedes minivan with a certified sommelier, moving between three estates in the Chianti Classico region. You taste olive oil at a historic mill, learn to evaluate wine in a boutique winery's cellars, wander a medieval village, and eat a three-course Tuscan lunch paired with estate wines. Transport from Florence, all tastings, and the meal are included; the semi-private upgrade (max 8 guests) adds deeper cellar access and a focus on Supertuscan wines if you want it.Is it for me?Right for travelers who want to understand Chianti wine and Tuscan food culture in one day without arranging their own transport or timing—the fixed schedule and expert guide handle all three. Plan for a full day out, which is exactly what makes fitting three estates, a village, and a proper lunch possible.
Chianti & San Gimignano: Wineries Tour, Tuscan Lunch & GelatoYou’ll wander Chianti’s vineyards with a local guide, taste fresh olive oil and wines straight from the source, explore San Gimignano’s medieval charm (and world-famous gelato), then share an easygoing Tuscan lunch at another winery before catching sunset views over Florence. Expect laughter, good food, and small surprises along the way.
Pisa, San Gimignano & Siena: Chianti Wine Tasting Day TripYou leave Florence at dawn, spend the morning exploring Pisa's cathedral complex and Leaning Tower, then drive through Chianti vineyards to a working winery for lunch and wine tasting. Afternoon takes you through the medieval streets of San Gimignano, followed by a guided walk through Siena's most important squares and the Cathedral. You return to Florence in the evening with a professional guide, air-conditioned bus, and all transport included.Is it for me?This works well if you want to see four major Tuscan destinations in a single day without renting a car or coordinating your own schedule — the fixed itinerary and included transport are what make it possible to move between Pisa, the Chianti hills, San Gimignano, and Siena all in one morning-to-evening loop.
Florence to Tuscany: Vespa Tour, Medieval Town & Wine LunchYou’ll ride a Vespa through Tuscany’s countryside from Florence with a local guide leading the way, pause for gelato in a medieval hilltop village, and share lunch with Chianti wine at a family-run winery. Expect laughter over wobbly starts and unforgettable views—this day trip is all about soaking up real Tuscan moments.
Florence: Horseback Ride San Gimignano & Chianti Wine TastingYou ride through vineyards and hills for just over an hour with no experience required, visit the medieval town of San Gimignano with free time to explore, and finish with an authentic Tuscan lunch and guided wine tasting at a local winery. Pickup and drop-off in Florence are included, along with your helmet, insurance, and a multilingual guide who handles all the logistics so you just show up.Is it for me?Book this if you want to ride through the Tuscan countryside without worrying about experience, logistics, or arranging your own transport to San Gimignano and a winery—the fixed itinerary and included lunch mean you show up at 9 am and everything else is handled.
Val d'Orcia: Brunello & Montepulciano Wine Day TripYou’ll wind through Val d’Orcia’s rolling hills with a small group, sipping Brunello in Montalcino, tasting Pecorino cheese over lunch in Pienza’s garden (or cozy indoors), and exploring Montepulciano’s ancient cellars with local stories along the way. Expect laughter, earthy scents, good wine—and maybe a view you’ll keep thinking about long after you’re home.
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 to Chianti & Siena: Wine Tasting & Medieval TownsYou get picked up in Florence, driven through the Chianti hills to a family farm for a wine-paired lunch, then have free time in the medieval villages of San Gimignano and Siena before returning to the city. Transport, the farm experience, and lunch are all included; groups stay under 15 people, and the minivans let you skip the parking lots and walk straight into the old towns.Is it for me?Right for travelers based in Florence who want a full Tuscan day without arranging transport, vineyard access, or lunch logistics themselves. Plan for moderate walking through medieval towns with steep streets—that's what gives you the authentic village experience instead of a bus-window view.
Chianti Day Trip: 2 Wineries & Dario Cecchini LunchYou’ll taste Chianti wines straight from two organic wineries with a local guide who actually knows their stuff (and jokes). Lunch is a loud, joyful feast at Dario Cecchini’s famous butcher shop—with steak you’ll remember for ages. Expect laughter, real Tuscan flavors, and moments that stick with you long after you’re back in Florence.
Florence: Tuscan Farmhouse Pasta & Gelato Cooking ClassYou’ll roll fresh pasta by hand in a Tuscan farmhouse kitchen near Florence, guided by local chefs who treat you like family. Taste your own creations—ravioli, pappardelle—and learn to make real Italian gelato using garden ingredients. With plenty of wine and countryside views included, it’s less a class than a memory you’ll carry home.
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.
San Gimignano: Tuscany Vespa Tour, Lunch & Wine TastingYou’ll zip through Tuscany’s Chianti hills on your own Vespa (or as a passenger), guided by locals who share stories along winding roads lined with cypress trees. Taste three local wines and fresh olive oil during lunch at a family-run winery—expect laughter over mispronounced Italian words and time to soak up those vineyard views before heading home.
Florence: Chianti Wine Tasting & San Gimignano with LunchYou get hotel pickup, a panoramic stop at Piazzale Michelangelo, an hour in San Gimignano's medieval streets, lunch with wine at a Tuscan farmhouse, and tastings at two separate wineries—all in one afternoon without arranging transport, timing stops, or choosing which wines to try. The fixed itinerary and small-group format mean you're not negotiating logistics; you're just moving through the day.Is it for me?Book this if you want the main Chianti wine experience and San Gimignano in one afternoon without arranging your own transport, choosing which wineries to visit, or timing the day yourself—the fixed schedule and small-group van mean you show up and move through it all.
Florence: Chianti Wine Tour with 3 Tastings & Tuscan LunchYou’ll taste Chianti wines straight from Tuscan vineyards, learn about Supertuscans from local experts, enjoy a slow lunch with regional flavors, and wander an iconic village near Florence. With transport included and an English-speaking wine guide by your side, you’ll feel both welcomed and quietly wowed by simple pleasures.
Florence to Chianti: Vespa Tour, San Gimignano Views & Winery LunchYou’ll ride your own Vespa from Florence into Chianti’s rolling hills with a small group and local guide, stopping for views of San Gimignano’s skyline and photo breaks among cypress trees. Taste home-cooked Tuscan food and wines at a family-run winery before cruising back through golden fields — it’s more than sightseeing; it feels like living here for an afternoon.
Tuscany Day Trip: Siena, Cortona & Montepulciano with Wine TastingYou’ll walk medieval streets in Cortona, taste fresh farm food under Tuscan sun, sip wine deep inside Montepulciano’s ancient cellars, and end your day wandering Siena’s glowing piazzas—all with stories from your local guide and time to just soak it in.
Florence: Chianti Wineries & San Gimignano with Lunch & TastingsYou visit two family-run Chianti wineries with cellar tours and tastings, stop in the medieval towers of San Gimignano with free time for gelato and exploring, eat an authentic Tuscan lunch with wine and olive oil tasting at the second farm, and finish at Piazzale Michelangelo for the classic Florence view. Small group (up to 8), air-conditioned transport, and a licensed guide who knows the route.Is it for me?Book this if you want to taste real Chianti wine from the people who make it, eat a proper Tuscan lunch, and see a medieval village — all without renting a car or figuring out the route yourself. Small groups mean you're not lost in a crowd, and the fixed itinerary is what lets a full day fit between breakfast in Florence and dinner back in the city.
Siena & San Gimignano: Chianti Wine Tasting & Tuscan LunchYou travel by minivan through four medieval towns — Monteriggioni, Siena, San Gimignano — with a guided walk in Siena and free time to explore each village. Lunch and wine tasting happen at a working Chianti winery, where you taste seven wines, oils, and vinegars alongside a traditional Tuscan meal. Hotel pickup is not included, but you meet at Porta Romana in Florence at 8:45am and return by 6pm the same day.Is it for me?Book this if you want to see the best of Tuscany in a single day without arranging transport, tickets, or timing yourself — the small-group format and fixed schedule mean you move through four towns and a winery without the chaos of a large tour bus.
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 to Chianti: E-Bike Tour with Lunch & 2 Wine TastingsYou’ll pedal through olive groves and vineyards from Florence into Chianti on an e-bike with a local guide leading the way. Taste wines at a family-run winery paired with classic Tuscan lunch—think fresh cheese and handmade pasta—and finish with another tasting back in Florence. Expect laughter, real stories, good food, and views you might not forget soon.
Val d'Orcia Wine Tour: Brunello & Montepulciano from FlorenceYou'll taste two major Tuscan wines in their cellars, walk through a UNESCO-protected landscape, eat lunch at a winery, and spend free time in medieval towns — all without arranging transport, tickets, or timing yourself. Hotel pickup from Florence and return in the evening are included, along with an expert multilingual guide.Is it for me?Book this if you want to taste serious Tuscan wines in the cellars where they're made without arranging your own transport, cellar visits, or lunch — the fixed itinerary and included guide handle all of that, leaving you free to focus on the wine and the landscape.
Chianti: Open-Top Van Wine Safari & Tuscan Lunch TourYou’ll ride through Chianti’s hills in an open-top van, taste local wines at two family-run vineyards, stroll Montefioralle’s medieval lanes, and share a traditional Tuscan lunch overlooking vineyards. Expect laughter over new flavors, time to explore Greve’s artisan shops, and moments of quiet beauty you might not see coming.
Tuscany: Brunello & Montepulciano Wine Safari Day TripYou’ll ride offroad through Tuscany’s Val d’Orcia with a local guide, tasting Brunello in Montalcino cellars and Vino Nobile in Montepulciano’s family-run winery. Enjoy lunch by ancient thermal springs in Bagno Vignoni and free time wandering Pienza’s artisan shops. It’s less about rushing between sights than soaking up flavors, stories, and landscapes you’ll remember long after you leave.
Tuscany: Chianti Wine Tour & San Gimignano with 2 TastingsYou’ll taste up to nine Tuscan wines at two family-run wineries in Chianti, sample truffle oil and aged balsamic vinegar, and wander medieval San Gimignano’s streets with time for gelato or quiet moments by the basilica. With roundtrip transport and an English-speaking guide handling all the details, you can just relax into the rhythm of Tuscany—and maybe discover your new favorite wine along the way.
Florence to Chianti: Wine Roads, San Gimignano & Lunch TourYou’ll ride from Florence into classic Chianti villages with a local guide, taste Tuscan wines straight from family cellars, wander medieval San Gimignano on your own time, then share lunch at a working farmhouse. Expect laughter over bruschetta, stories from winemakers, and moments where Tuscany just feels close—you might not want to leave.
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 Wine Tasting & Montalcino Day TripYou're picked up from your Florence hotel and driven through Chianti vineyards for a morning wine and oil tasting, then to a working farmhouse near Montalcino for a guided lunch with local wines and regional food, followed by walks through the medieval villages of Montalcino and Montepulciano, with return to Florence by evening. The minivan holds eight people maximum and includes WiFi, so you're not crammed in, and the driver handles all the navigation and timing.Is it for me?Best for travelers based in Florence who want to see the main Tuscan wine villages and taste wines at source without renting a car or arranging their own transport and timing—the fixed schedule and included lunch mean you show up at your hotel and the rest is handled.
Frequently asked questions
Can I book with free cancellation?
Yes: 63 of the 65 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?
Tuscany: Small-Group Wine Tasting Tour with 2 Wineries & Local Flavors is the travelers' favorite, rated 4.92 out of 5 across 8,421 reviews.
Are private options available?
Yes, 5 private experiences are available if you prefer a closed group.
More things to do in Florence
Day Trips from Florence38 optionsFlorence Walking Tour43 optionsFlorence Museum Tours8 optionsFlorence Vineyard Tours18 optionsFlorence City Tour11 optionsFood Tours in Florence84 optionsCooking Classes in Florence40 optionsFlorence Vespa Tour8 optionsPitti Palace Tickets10 optionsFlorence Bike Tours14 optionsBoboli Gardens Tickets8 optionsPalazzo Vecchio Tickets10 optionsVasari Corridor Tours6 optionsArt Tours in Florence54 optionsFlorence Airport Taxi16 optionsFlorence Street Food9 optionsMedici Chapels: Tours & Activities9 optionsFlorence Hot Air Balloon Ride7 optionsMichelangelo's Statue of David14 optionsGolf Cart Tours in Florence9 optionsBoat Tour Florence6 optionsPiazzale Michelangelo Tours13 optionsFlorence Pizza Making Class5 optionsPonte Vecchio Tours10 optionsSkip-the-Line Tickets in Florence32 optionsClimbing in Florence7 optionsSelf-Guided Tour of Florence6 optionsPonte Vecchio Walking Tour5 options
