Things to do in Tuscany
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Greve in Chianti: Organic Winery Tour & Wine TastingYou walk the vineyard, learn how Chianti Classico is produced from cellar floor to barrel, then taste the wine paired with local cheese and salami. The group stays small — no more than 15 — and the whole experience moves at a pace that lets you actually absorb what you're seeing instead of rushing through a checklist.Is it for me?Right for wine drinkers who want to understand how Chianti is actually made, not just taste it. The small group size and family-run setting mean you get real conversation with the people who made the wine, and the cellar tour is hands-on enough that you'll remember the process when you drink it later.
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.
Montalcino Brunello Wine Tasting & Lunch in a CastleMontalcino wine tasting and lunch combines three local wines — including Brunello di Montalcino — with a three-course Tuscan meal served in a medieval castle. A professional sommelier leads you through the vineyard, explains the winemaking methods, and guides the tasting; the experience runs about 90 minutes and includes a tour of the property. English and Italian options are available, and vegetarian lunch is an option at checkout.Is it for me?Book this if you want to taste Brunello where it is made and understand how, rather than just sample wines in a tasting room — the sommelier's walk through the vineyard and the castle grounds is what sets this apart from a standard wine bar visit.
Florence: Medici Chapels Private Tour & Michelangelo ArtYou’ll walk through centuries-old halls in Florence’s Medici Chapels on this private tour—with tickets included—guided by someone who knows every corner and story. Touch cool marble, hear tales of rivalry and art in Michelangelo’s New Sacristy, and pause where history feels close enough to breathe in. There’s something quietly powerful about being there with a local guide.
Florence: Design Custom Sneakers with Italian Artisan & WineYou’ll step inside a Florentine atelier and work side by side with Italian artisans to design your own custom sneakers—choosing every material and color yourself. Sip Tuscan wine, snack on local cheese, and watch as your ideas become real right there in the workshop. Your finished sneakers are delivered straight to your hotel—a piece of Florence you can walk away with.
Florence Photoshoot: Professional Photos & City TourYou meet a photographer in central Florence and walk the main attractions — Cathedral, Ponte Vecchio, Uffizi Gallery and quieter streets — while they capture candid and posed shots. Choose 30 minutes with 20 photos, 60 minutes with 50, or 90 minutes with 75 and an outfit change. All images download from a secure gallery within 48 hours, and you can order prints or framed sets afterward.Is it for me?Book this if you want professional photos of yourself in Florence without arranging a separate photographer or worrying about framing and angles — the guide handles the route and the shots, so you just walk and look natural.
Cinque Terre Day Trip from Pisa: Train & Ferry with Small GroupYou travel from Pisa by minivan to the Cinque Terre villages, moving between Riomaggiore or Manarola, Vernazzo, and Monterosso by train or ferry depending on weather. A tour leader stays with your small group all day, handling the route and timing so you can focus on the villages, the views, and the free afternoon in Monterosso for swimming or lunch. Transport, park entry, and ferry or train tickets are included; you just need to show up with walking shoes and a willingness to move at a steady, unhurried pace.Is it for me?Right for travelers based in or near Pisa who want to see the Cinque Terre villages without arranging their own transport and tickets. Plan for a full day out — that's what makes visiting three villages and having real free time in Monterosso possible in one trip.
Montepulciano: Tuscan Cooking Class & Wine PairingYou spend a morning in a seven-generation Tuscan kitchen learning to make gnocchi, pappardelle, Chianina beef and tiramisu from a chef who grew up cooking these exact dishes with his grandmother. Four local wines are paired as you cook and taste each course. You leave knowing both the recipes and the reasoning behind them — how to choose ingredients, why flavors work together, how tradition adapts without disappearing.Is it for me?Book this if you want to learn recipes that actually matter — ones with real history behind them — and understand the thinking that makes them work, rather than just follow steps. The small group format and Giacomo's background as both chef and sommelier mean you're getting genuine knowledge, not a performance.
Tuscany: Farm Vineyard Wine Tasting & Lunch with PickupYou’ll get picked up right at your Montecatini hotel for a relaxed day trip into the Tuscan countryside—think vineyard walks, homemade pasta lunch, and generous pours of local wine. Taste grappa if you’re brave (it’s strong!), meet locals who actually live on the farm, and leave feeling like you’ve been let in on something special.
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.
Pisa to Marina di Pisa: Bike Tour on Trammino Cycle PathYou cycle 20 kilometers round trip from central Pisa to the Tuscan coast on a flat, dedicated path through countryside and pine forests. The self-guided app navigates you past the Arno delta and traditional fishing nets to Marina di Pisa, where you swim, eat, or rest before riding back at your own pace. Bike, repair kit, and locker are all included.Is it for me?A good fit if you want to see Pisa beyond the tower without booking a guided tour or arranging transport — the flat path and included app mean you just show up and ride. Plan for a half-day out; the round trip is about 20 kilometers, which is manageable for families and casual cyclists, and the pace is entirely yours.
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.
Lucca: Tuscan Vineyard Wine Tasting & Pickup from TownYou're picked up at your Lucca hotel and driven through the Tuscan hills to a family-run vineyard. Walk the vines with the owner, tour the cellar, then taste wines paired with local cheese and cured meat. The driver brings you back to town at the end of the afternoon, so you skip the logistics of finding the place or arranging your own transport.Is it for me?Book this if you want to taste real Tuscan wine without spending the morning researching wineries or figuring out how to get there — the pickup and the small-group format mean you show up and the farmer does the rest.
Florence: Drawing & Watercolor Workshop Outdoor or TerraceYou’ll sit (or stand) right in Florence’s heart with a brush in hand while Betty guides you through drawing & watercolor techniques—no experience needed. Materials are included and if it rains, you’ll move to a terrace overlooking the Dome. Expect laughter over wobbly lines and small discoveries as you see Florence differently.
Lucca: Wine Tasting & Lunch at Family Winery in MonasteryYou tour a working Tuscan winery in a 1700s monastery with the owners as your guides, walk through the cellar to see how they make wine using organic methods, then sit down to a light lunch and wine tasting. Groups are small and shared, so expect other guests; if you want privacy, you can arrange a private session when you book.Is it for me?Right for travelers in Lucca who want to understand how wine actually gets made, not just taste it—the owners hosting it themselves means you learn from people who chose this life, not from staff reading a script. Plan for a shared group experience; if you prefer to be alone, arrange a private tour when you contact them.
Florence: 4-Course Italian Dinner Cooking Class & WineYou arrive at 5pm and spend three hours cooking an appetizer, fresh pasta, a meat dish and dessert alongside a chef in a Florence kitchen. The group is capped at twelve, so you're actually cooking, not watching. You eat everything you made, drink Tuscany wine, and leave with the recipes. The whole thing takes about three hours and includes the meal, water and wine.Is it for me?Book this if you want to learn to cook Italian food you can actually make at home, and you'd rather spend an evening doing it than watching a video — the small group and the chef's attention are what make the learning stick, and eating what you cooked is the reward.
San Gimignano: Private Wine & Olive Oil Tasting LunchYou’ll join a Tuscan family just outside San Gimignano for an easygoing day: walk through vineyards, taste organic wines and six types of olive oil, and enjoy a homemade lunch under the sun. Expect laughter over local cheeses and real stories behind every glass—and maybe find yourself wishing you could stay longer.
Florence: Pasta & Dessert Cooking Class with Tuscan WineYou’ll step into a real Florentine kitchen to make fresh pasta and tiramisù with local chefs guiding you every step. Taste herbs from the garden, sip Tuscan wine as you cook, then share your creations over a relaxed family-style lunch. It’s not just about recipes — it’s about laughter, new friends, and feeling at home in Florence.
Siena: Private Walking Tour of Medieval Alleys & Quiet ChurchesYou’ll start in Siena’s famous main square with your private guide, then slip into quieter medieval alleys most visitors miss. Step inside peaceful churches and climb toward panoramic city views from an old basilica. Expect small surprises, gentle conversation, and moments where Siena feels like it belongs just to you.
Florence: Tuscan Cooking Class with Homemade Pasta & WineYou’ll join locals in a real Tuscan kitchen near Florence, rolling out homemade pasta and sharing laughs over appetizers and wine. Expect hands-on cooking with guidance, plenty of Chianti, and classic desserts like tiramisu—all followed by relaxed conversation at the table. You’ll leave full but also feeling oddly connected to everyone around you.
