The verdict
Our pick
Tuscany Day Trip: Siena, San Gimignano, Pisa & Winery Lunch★ 4.86 (24,182) · 12h
Best value
Pisa & Leaning Tower: Half-Day Trip from Florence with Guide★ 4.56 (1,424) · 6h
Top rated
Florence: Siena & San Gimignano Private Tour with Chianti★ 5.00 (268) · 8h–9h
The 12 best-value of 38 options, side by side
✓ 2026-09-29Real price per person across the 38 options: € 38–€ 971 (median € 129). With 100+ reviews: 31 of 38.
Default order: real price per person — the group price divided by the seats it includes.
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Private experiences (11)
Private Siena, San Gimignano & Chianti Tour from FlorenceYou get picked up at your Florence hotel and driven through the Chianti wine region to Siena, where you see the Piazza del Campo and the cathedral, then either stop at Monteriggioni or take lunch at a farm with wine tasting, then finish at San Gimignano's medieval towers before returning in the evening. Everything is arranged — the route, the timing, the driver who knows the history — so you just show up and look out the window.Is it for me?Book this if you want to see three major Tuscan towns and the Chianti countryside in one day without renting a car or planning the route yourself — the private driver and fixed eight-hour schedule handle all the logistics, leaving you to focus on what you're looking at.
Cinque Terre from Florence: Private Day Trip & Boat TourYou get hotel pickup from Florence, private transport in an air-conditioned minivan, entry to three Cinque Terre villages with free time to eat and explore, and boat or train travel between stops. The route includes a pass through the Carrara Marble Quarries on the way down. The itinerary can be customized, and if you want to add Pisa, you can upgrade at booking. You're back at your hotel by evening.Is it for me?Book this if you want to see Cinque Terre without arranging your own transport, timing the boat or train connections, or navigating between villages—the private minivan and guide handle all of that, leaving you to focus on the villages themselves.
Livorno to Florence & Pisa: Private Day Trip with PickupYou’ll step right off your cruise into a private car bound for Pisa’s famous Leaning Tower before heading to Florence to wander its marble piazzas and cross Ponte Vecchio with a local guide. There’s time to pause at Santa Croce or gaze over rooftops from Piazzale Michelangelo — all with easy port pickup and drop-off so you won’t watch the clock too much.
Tuscany: Siena, San Gimignano & Chianti Private Day TripYou’ll wander Siena’s medieval streets with time to explore at your own pace before tasting real gelato under San Gimignano’s ancient towers. Enjoy flexible photo stops across Chianti’s vineyards and—if you want—sip local reds at a small winery before heading back to Florence with sunset views lingering behind you.
Tuscany Day Trip: Siena, Pisa & San Gimignano Private TourYou’ll cross Tuscany in comfort with your own driver, wandering Siena’s medieval lanes and marveling at its cathedral mosaics before tasting gelato in San Gimignano’s quiet squares. End your day beneath Pisa’s famous tower as sunset colors sweep across ancient stone — it’s less about checking boxes than soaking up moments you’ll replay long after you’re home.
Tuscany Day Trip: Siena, San Gimignano, Chianti & Pisa Private TourYou’ll start with hotel pickup in Florence and spend your day exploring Siena’s medieval charm, tasting Chianti wines at a local spot, wandering San Gimignano’s ancient towers, and snapping photos at Pisa’s Leaning Tower—all at your own pace with a friendly local driver guiding you along winding Tuscan roads.
Cinque Terre Day Trip from Florence: Private Guide & TrainYou're picked up from your Florence accommodation at 7am and driven to La Spezia, then guided through all five Cinque Terre villages by train and on foot. Lunch with local wine is included at a seaside restaurant, plus a boat ride between two villages so you see the coast from the water. Your guide handles the route, timing, and logistics all day, and you return to Florence by evening.Is it for me?This works well if you want to see all five Cinque Terre villages in one day without arranging your own transport, buying tickets at stations, or figuring out train schedules — the private guide and fixed itinerary remove those logistics so you can focus on walking, eating, and looking at the coast.
Pisa & Florence Day Trip from Livorno Port: Private TourYou’ll step into Pisa’s Piazza dei Miracoli for that first surreal look at the Leaning Tower before winding through Tuscany’s hills toward Florence. Expect stories from your local driver-guide, photo stops among vineyards, free time for shopping or lunch by Santa Croce, and enough small moments—like bells echoing over Ponte Vecchio—to linger long after you’re back at port.
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.
Florence: Leaning Tower of Pisa & San Gimignano Private Day TripYou're driven from your Florence hotel through Tuscan countryside to the Leaning Tower of Pisa, where you can visit the 12th-century basilica and climb the tower if you've reserved ahead; then on to San Gimignano, a walled medieval town with 14 surviving towers and the Basilica of Santa Maria Assunta. Hotel pickup and drop-off are included, and the whole day runs on your schedule, not a group's.Is it for me?Book this if you want to see the Leaning Tower and a genuine medieval town in one day without arranging a rental car or timing yourself around a group schedule — the private vehicle and hotel pickup mean you're moving on your own pace, not waiting for others to finish.
Florence: Pisa Leaning Tower & San Gimignano Private Day TripYou're picked up from your Florence hotel and driven to Pisa, where you climb the Leaning Tower for views across the cathedral square; then continue to San Gimignano to walk the medieval streets, visit the 13th-century Duomo, and see the fourteen towers that define the skyline. Hotel drop-off closes the day, with no additional transport to arrange.Is it for me?Right for travelers based in Florence who want to see Pisa's Leaning Tower and a UNESCO medieval town in one day without arranging their own transport or managing multiple entry bookings—the private format means you set the pace at each stop.
2 to 5 hours (1)
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.
Half day and longer (22)
Cinque Terre Day Trip from Florence with Hiking & Pisa OptionYou travel by coach and train through five coastal villages, with the option to hike the cliffside trails between them or take the train instead. Free time in each village lets you swim, eat local food, and explore narrow streets. A scenic boat ride to the final village runs April through October if weather permits. The Pisa add-on swaps your return journey for a stop at the famous tower and cathedral before heading back to Florence.Is it for me?Right for travelers with moderate fitness who want all five villages in one day without arranging their own transport and park tickets. Plan for a full day out—roughly 12 hours from pickup to return—and bring proper walking shoes; the uneven village streets and optional hiking require them, and the pace doesn't slow for casual footwear.
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.
Florence: Pisa, San Gimignano & Siena Day Trip with LunchYou travel by coach from Florence through the Tuscan countryside, spending time at the Leaning Tower and cathedral complex in Pisa, eating a traditional lunch with wine in San Gimignano, and walking the medieval streets of Siena with a local guide. The tour includes transport, lunch with four wine pairings, and optional cathedral entry in Siena. You return to Florence in the evening.Is it for me?Book this if you want to see Pisa's Leaning Tower, two UNESCO medieval villages, and Siena's cathedral all in one day without renting a car or buying separate tickets — the fixed itinerary and included transport are what make four towns fit into a single departure from Florence.
Florence: Siena & San Gimignano Day Trip with Winery LunchYou depart Florence in a small group of no more than a dozen people, guided through Siena's cathedral and main piazza, pause at the fortified village of Monteriggioni, then sit down to a seasonal Tuscan lunch with wine pairing at a working estate. The afternoon is yours to explore San Gimignano's medieval towers and streets before returning to Florence around 6pm. Transport, guide, and lunch are included; the Siena Cathedral entrance (€15) is optional and paid on the day.Is it for me?Book this if you want to see Siena, San Gimignano, and a working winery in one day without arranging your own transport or timing—the small-group format and fixed schedule handle the logistics, leaving you to focus on the places themselves.
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.
Cinque Terre Day Trip from Florence: Train, Boat & 3 VillagesYou travel by air-conditioned coach from Florence to the Cinque Terre gateway, then move between three UNESCO villages by train and seasonal boat ride, with a local guide for the walks and free time in each village to swim, eat, or explore. Transport, inter-village tickets, and the boat ride are all included; lunch in Monterosso is optional. Plan for a full day out—you leave Florence early and return in the evening.Is it for me?A good fit if you want the iconic Cinque Terre villages in one day without arranging your own trains, boats, and timing—the coach pickup and included tickets mean you just show up in Florence and the day unfolds. Expect moderate walking through narrow streets and some steps to harbors, which is what lets you reach three villages and still have free time to swim or eat.
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.
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 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.
Cinque Terre day trip from Florence: Train, boat & villagesA full-day tour from Florence to Cinque Terre, a UNESCO-protected stretch of five villages clinging to the Ligurian coast, with a multilingual guide, train tickets between villages, and a ferry boat ride along the shoreline. You travel by bus from Florence in the early morning, spend free time in each village to eat and explore, and return to the city center by evening. Choose between a guided tour with street food tastings or a transfer-only option where you move through the villages at your own pace.Is it for me?Book the guided tour if you want the villages explained and the timing arranged so you see all five in a single day without building the schedule yourself. Choose transfer only if you prefer to move through the villages at your own pace and decide which ones to linger in—you'll need to buy train tickets separately, but the freedom to skip stops or stay longer is yours.
Florence to Siena & San Gimignano: Medieval Towns & Chianti ViewsYou travel by private coach from Florence through the Chianti countryside to Siena, where you have 2.5 hours to explore Piazza del Campo and the Duomo on your own. Then it's another scenic drive to San Gimignano, where you spend another 2.5 hours wandering medieval piazzas and tower-lined streets before returning to Florence in the evening. An English-speaking guide handles transport and timing; you handle the rest. Optional audio guide in Siena and wine tasting available at booking.Is it for me?Book this if you want to see two of Tuscany's most famous medieval towns in a single day without renting a car or arranging your own transport — the fixed schedule and small group size mean you get both towns and the Chianti drive without the logistics.
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: 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.
Cinque Terre & Pisa Day Trip from Florence with Boat RideYou travel by coach from Florence to Manarola, walk through seaside vineyards, then take a scenic boat (or train, weather permitting) to Vernazzo for free time in the village. After Cinque Terre, you stop in Pisa to see the Leaning Tower and Piazza dei Miracoli before returning to Florence. The tour includes park entry, transport, and an English-speaking guide, so you skip the train-schedule puzzle and get both destinations in one day.Is it for me?Book this if you want both Cinque Terre and Pisa in a single day without arranging your own transport, park tickets and train schedules — the fixed itinerary and included guide handle all three, leaving you free to walk, look, and eat.
Florence to Tuscany: Siena, San Gimignano, Pisa Day Trip & LunchYou’ll join a small group for an easygoing day trip from Florence through Tuscany’s most iconic towns: stroll medieval Siena with a local guide, sample sweet treats and regional wines, wander San Gimignano’s ancient streets at your own pace, sit down for a relaxed Tuscan lunch in Chianti countryside, and end with free time beneath Pisa’s famous Leaning Tower—returning home with more than just pictures.
Tuscany: Truffle Hunting Day Trip & Lunch from FlorenceYou’ll follow a local hunter and his dog through San Miniato’s woods searching for white truffles, then sit down for fresh tagliolini al tartufo with Chianti wine. Expect laughter, muddy boots, real stories from your guide — plus transport from Florence so you can just relax into it all.
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: San Gimignano & Siena Day Trip with Free TimeYou spend 2.5 hours exploring San Gimignano's medieval towers and narrow streets, then another 2.5 hours in Siena's Gothic center, including time at Piazza del Campo. Transport, audioguide, and a multilingual guide are included; you return to Florence at sunset. Plan for a full day out — that's what fits both towns in one trip.Is it for me?Right for travelers based in Florence who want to see two major Tuscan towns in a single day without arranging separate transport or guides. The free time in each town means you set the pace, and the fixed schedule gets you back by evening — expect a full day out, which is what makes both stops possible.
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.
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.
Cinque Terre Day Trip: Coastal Villages by Train & BoatA full-day guided tour from Florence to Cinque Terre takes you through five UNESCO-listed coastal villages—Manarola, Vernazzo, Monterosso and Riomaggiore—by bus, train and boat, with a professional English-speaking guide and a group kept under 25 people. The boat service runs April through mid-October, weather permitting; when boats are not operating, trains connect the villages instead. A moderate fitness level helps, as the villages sit on steep terrain and involve walking narrow streets and stairs.Is it for me?Book this if you want to visit all five villages in a single day using local trains and boats—your guide coordinates the connections so you move seamlessly between each stop.
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.
More options (1)
Florence: Pisa, San Gimignano & Siena Day Trip with LunchYou visit Pisa's Leaning Tower, walk the medieval towers of San Gimignano, and explore Siena's Cathedral and historic center, with a winery lunch and wine tasting included. Transport, guide, and most entry fees are arranged; you just show up at the Florence meeting point in the morning and return by evening. The fixed schedule means you see the highlights without planning the route or managing three separate tickets.Is it for me?Book this if you want to see three major Tuscan towns in one day without arranging transport, tickets, or timing yourself — the coach and fixed schedule handle the logistics, leaving you free to walk, photograph, and eat.
Frequently asked questions
Can I book with free cancellation?
Yes: 36 of the 38 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 Day Trip: Siena, San Gimignano, Pisa & Winery Lunch is the travelers' favorite, rated 4.86 out of 5 across 24,182 reviews.
Are private options available?
Yes, 11 private experiences are available if you prefer a closed group.
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