Day Trips from Tuscany to Siena

Discover the enchanting Chianti wine region and its picturesque rolling hills on this full-day tour from Florence. Explore the medieval village of San Gimignano, climb its tallest tower for panoramic views, and capture photos among the vineyards. Savor a homemade pasta lunch and taste five Tuscan wines, including Chianti and Super Tuscan, at a family-run farm in Badesse to complete your Tuscan journey.

See more of Tuscany in less time on this expertly curated small-group tour from Florence. Travel through the region’s most iconic destinations—Pisa, Siena, and San Gimignano—without the hassle of organizing transport or logistics. Capture unforgettable photos of the Leaning Tower in Pisa, enjoy a traditional Tuscan lunch and wine tasting at a local winery, and explore Siena’s historic center with a guided visit. Finally, wander through the medieval streets of San Gimignano, famous for its skyline of towers and award-winning gelato. Combining culture, scenery, and authentic flavors, this tour offers a complete Tuscan experience—ideal for first-time visitors and those short on time. Note:Wine tastings take place in English, with your tour leader providing translation support when needed. A moderate amount of stairs and walking is involved During special events, opening times can change The tour itinerary may change, but all tour stops will be visited

Escape far from the crowds and traffic—and enjoy an immersive way to explore the iconic Chianti countryside that few other visitors get to experience—on this small-group, full-day hiking tour from Florence. Ramble for 4 miles (7 kilometers) on trails through vineyards and olive groves to really soak up the scenery. Along the way, visit three wineries to sample up to 10 wines, and enjoy Tuscan specialties for lunch.

Get a personal introduction to Siena and Chianti with a full-day, private tour from Florence in a luxurious van. Stroll Siena’s gothic streets with a local guide, and discover the art and black-and-white architecture of its UNESCO-listed historic center. Explore rolling vineyards and olive groves then taste your way through famous wineries, family cellars, local olive oils and aged balsamic vinegar.

Get ankle deep in Tuscan tradition on a half-day grape stomping tour from Florence. You’ll explore the history and modern practices of winemaking. After tromping on the locally grown grapes, replenish your strength with a homemade lunch and wine tasting, and explore the hamlet of Castellina in Chianti before returning to your accommodation.

Private excursion aboard classic Tuscan gozzo boats with lunch or aperitif. A day dedicated to you and what you prefer to do. Discovering the best beaches of Scarlino and Punta Ala, between sun, sea, relaxation, aperitifs at sunset and the scent of salt! The best way to enjoy the Maremma! To guarantee you the best experience, the program may vary according to sea conditions and your preferences.

Discover two of Tuscany's most beautiful cities, Montepulciano and Siena, in just one day on this private trip. From Florence, journey in an air-conditioned vehicle to Montepulciano, with time to take in hilltop views from the Torre di Pulcinella. Next, visit Siena, where you can explore a medieval square and the local Gothic cathedral—climb to the top for views over the city.

Experience the treasures of Tuscany on a private day trip from Florence. Travel by luxury minivan through countryside full of historic vineyards, medieval villages, and olive groves. Visit the charming medieval city of Siena and the town of Montalcino. Your professional, English-speaking driver shares local history and can recommend the best places to visit, shop, and dine for a customized experience.

- Very knowledgeable drivers with explanation about wine, food and general history of Tuscany. - Visit the town of Siena a Unesco World Heritage Site. - Lunch in a typical Trattoria or a wine Estate in the Chianti area. - Visit San Gimignano, the medieval "Manhattan" frozen in time.

Embark on a private excursion from Florence to Siena, to experience the historic towers, pointed arches, and narrow streets of this important Tuscan city. Take in the sights and sounds of Siena and its stunning architecture, plus make a stop for photos in Monteriggioni. Led by an expert local guide, receive a detailed description of the highlights, enjoy exclusive access to the Cathedral, and indulge in the local cuisine.

Discover the art, history, and culture of Siena, Monteriggioni, and San Gimignano on a private tour. Listen to in-depth commentary from your driver, then explore each location on your own. Because it’s a private tour, you get to travel in comfortable transportation and enjoy a completely immersive experience without spending a moment waiting on other people.

Spend a full day exploring a trio of Tuscany’s best-preserved medieval cities on a private day trip from Florence. Skip the stress of renting a car and let a personal chauffeur take your group directly from your hotel door through the Tuscan countryside and into the historic centers of Siena, San Gimignano, and Pisa. Explore the cities at your own pace, with the help of tips and local guidance from your driver.

Chianti wine country is known for its magical scenery, but exploring the area can be tricky for out-of-town travelers. Leave traffic and navigation to your private driver as you sit back and enjoy the ride on this half-day wine-tasting tour. Savor both red (Chianti Classico) and white (Vernaccia) wines, capped off by the chance to explore the beautiful medieval town of San Gimignano.

Brunello di Montalcino is one of Italy's most prestigious wines, but navigating to the rural wineries outside of Montalcino on your own can be stressful. On this private wine tour, let your driver take the wheel and focus on vineyard views as you make your way to the top wine estates and cellars for exclusive tasting experiences. Explore stunning vineyards, learn about traditional winemaking techniques, and savor the rich flavors of Tuscany with guided tastings and a traditional lunch.

Sip wine and go back to medieval times during this small-group guided tour that includes an authentic Tuscan lunch. Wander the streets of the ancient, hilltop town of Montalcino known for its wine before touring the Brunello di Montalcino winery. Learn how biodynamic wines are made and sample varieties straight from the barrel. After lunch, visit a second winery to sip samples and eat Tuscan fare.

Cruise through Tuscan wine county in true Italian style — behind the wheel of a vintage Fiat 500. Learn how to drive the classic Italian car with a brief lesson, then hit the road with a private guide for a joy ride along scenic country roads. Stop at a typical Chianti village, a medieval hamlet, and an antique farmhouse, where you'll be treated to a homemade lunch and tasting of wine, grappa, and olive oil.

Go beyond Florence and see more of Tuscany with this private day trip to Siena, San Gimignano, and Pisa. Tour these old towns with a guide, discovering their histories and taking in their highlights. Enjoy a balanced itinerary that includes a guided tour of Siena and the Piazza del Campo, along with free time to explore all the towns included in the trip. Don't worry about trying to find something to eat on the go, with lunch, and wine, at a farmhouse included.

Discover the essence of Tuscany on this immersive tour that combines history, stunning landscapes, and exquisite flavors. Departing from Villa Costanza, journey to Monteriggioni, a medieval fortress town where cobbled streets and artisan shops await. After exploring its historical charm, indulge in a guided wine tasting at a picturesque Chianti winery, savoring local varietals and regional delicacies. Continue to a renowned family-run winery in San Gimignano for another rich tasting experience that reflects the region's winemaking passion. This tour promises a blend of cultural immersion and culinary delight, perfect for history buffs and wine enthusiasts alike. - Depart from Villa Costanza at 14:45 for a half-day adventure - Explore the medieval fortress-town of Monteriggioni with free time - Enjoy guided wine tastings and cellar tours at two charming wineries - Experience the richness of Tuscan terroir with local cuisine pairings

Bus tours of Tuscany can feel out of touch with the beautiful, rolling countryside that travelers love. This tour allows you to get out of the bus and into the landscapes of the Tuscan countryside on a bike, following routes designed for casual cyclists or professionals. It’s a small-group affair and finishes with a lunch of Tuscan dishes and wine.

Visit two of Tuscany's beautiful hilltop towns, plus enjoy tours and tastings at boutique wineries in Chianti and Montalcino on this small-group tour from Siena. All transport is included for a hassle-free experience, with free time to explore Pienza. Sample top Chianti, Brunello, and Super Tuscan wines, and relax over a Tuscan lunch featuring local specialties.

Explore the charming towns of Siena and San Gimignano on this full-day minivan tour from Florence, with a photo stop at Monteriggioni. Discover the medieval and Gothic architecture of the towns and learn their histories from your informative guide. Visit the main attractions of each city and sample their delicious cuisine—at your own expense—while walking around and absorbing the atmosphere of the cities.

Discover Siena, Monteriggioni, and San Gimignano on a day trip from Florence, and indulge in a Tuscan wine tasting, too. The day-long tour starts with a guided walk around Siena’s historical center with admission to Siena Cathedral, the city’s Gothic masterpiece. In the afternoon, you’ll visit Monteriggioni for photos, stop at a Tuscan estate for lunch and wine, then amble the streets of San Gimignano at your own pace.

Discover the history of the Chianti region, visit Montalcino's medieval fortress, and enjoy a scenic drive through Val d'Orcia on this small-group tour from Siena. Taste Chianti Classico and Brunello wines paired with Pecorino cheese, bruschetta, salame, and extra virgin olive oil. Explore the historic cellar and learn about the wine production process in a boutique family-owned winery.

Pedal through the Tuscan countryside during this half-day e-bike tour through Brunello. Bike along unpaved roads with ease on your electric bike towards local Tuscan vineyards. Enjoy a wine tasting at the Abbey of Sant’Antimo and learn about the ancient winemaking process. Sample three glasses of wines, including the Brunello di Montalcino, before heading to the medieval town of Montalcino to explore.