Day Trips from Florence to Siena

Discover Tuscany on this private day tour to San Gimignano and Siena from Florence. Explore the hillside town of San Gimignano, known for its many towers, with a guide and enjoy free time for shopping. After lunch with wine tastings near San Gimignano (own expense), visit Siena and discover one of Italy’s finest Gothic churches, the Cathedral of Siena (Duomo di Siena). Hotel pickup is included for added convenience.

Avoid the hassle of trying to navigate your way around the Tuscan countryside and visit two top wineries in a single day with this small-group Chianti wine tour. Leave the driving to a professional and sip worry-free as you stop to sample local reds and whites at traditional cellars in the hills of Tuscany. Learn more about the area's wine-producing history and culture, plus enjoy tasty snacks while taking in views over the Chianti countryside.

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.

- 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.

Swap the busy streets of Florence for the tranquility of rural Tuscany on a private day trip to San Gimignano. A private tour means you can customize your itinerary according to your interests while also receiving the undivided attention of your guide. Plus, letting someone else drive means that you’ll be able to spend less time navigating and more time focusing on the rolling vineyards of Tuscany.

Explore the enchanting Tuscan countryside on this self-drive adventure with an electric Vespa. With a dedicated guided app, drive through Chianti’s winding roads, surrounded by vineyards, olive groves, and cypress trees. Discover charming medieval towns like Montefioralle and Greve in Chianti, and stop to feast on a delicious Tuscan lunch in a typical trattoria.

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.

The mountainous Tuscan region of Chianti is home to vineyards and wineries that produce some of Italy’s most popular vintages, but they can be difficult to reach without a car. On this full-day private tour, your driver transports you to several dispersed towns and villages in the region, all with a unique attachment to winemaking. Opt to join wine tastings (own expense) and explore each location on short walks.

Set out on a hunt for the elusive truffle on this private tour from Florence. Traverse the forest with an official truffle hunter and his dog to learn everything there is to know about this delicacy. After you work up an appetite, sit down to a delicious 3-course truffle lunch accompanied by wine from a local farm.

Visit the charming Tuscan towns of Siena and San Gimignano without the hassle of organizing the trip yourself on this full-day private tour from Florence. Your driver-guide provides insight and recommendations while on the road, but then leaves you with free time to explore, shop, and dine at your own pace. In San Gimignano, enjoy stunning panoramic views of the area.

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.

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.

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.

Taste the famous flavors of Tuscany's wines and olive oils on this private tour from Florence. Travel through the Chianti region in a luxury tour vehicle, taking in the sights of the rolling hillsides covered with groves of olives and grapes. Take tours of several vineyards and learn about their production through guided commentary. Enjoy tastings of Chianti varietals and tuck into a tasty 3-course lunch with more wine.

Explore the medieval town of San Gimignano before heading into the scenic Chianti hills on this private Tuscan experience, which includes lunch and wine tasting. Walk through cobblestone streets, enjoy a gelato or glass of Vernaccia, then travel to local wineries for a traditional Tuscan lunch and guided wine tastings. This tour blends cultural heritage with countryside charm and regional flavors for a well-rounded day in Tuscany with hotel pickup included.

Immerse yourself in Italian wine culture on this half-day tour around the revered Chianti Classico wine region. There’s no crowding into cellar doors on this small-group tour of the region. Instead, spend your afternoon exploring the cellars and sampling the products of some of the region’s vineyards. All transport is provided, so you can fully enjoy your tastings.

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.

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.

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.

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.

Nothing says wine like Tuscany’s Chianti region, but it takes local knowledge to find the best wineries. Enjoy two exclusive wine tastings, topped off by a Tuscan lunch, during this private day trip from Florence. Learn the secrets behind the winemaking process as you go, and tour vineyards, cellars, and more. You’ll have time to browse traditional artisan workshops, too.

Chianti is not well-served by trains and buses, so exploring by public transportation can be a chore. Navigate around the Tuscan countryside with ease on this full-day private tour to the Chianti wine region from Florence. Enjoy convenient pickup from your hotel and travel by minivan along an itinerary customized to your interests. Admire views of the rolling, vineyard-covered landscape, stop to visit medieval villages, and opt to visit a winery for lunch and a wine tasting (own expense).

Immerse yourself in Italian wines on this small-group tour and experience the best of Florence and Chianti from a sidecar. Meet winemakers and visit a working winery to explore its production processes. Then, enjoy wine tastings and even a Tuscan lunch complete with local products. As you explore the vineyards on this sidecar adventure, snap great photos and videos of timeless countryside views.

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.