Day Trips from Tuscany to Siena

Trade the busy streets of Florence for the ancient vineyards, medieval villages, and scenic landscapes of the Chianti wine region on this half-day tour. Let a knowledgeable local driver take you to some of the area’s best family-run wineries, where you can learn about traditional production methods and taste the local bounty like extra-virgin olive oil and renowned wine varietals like Chianti Classico. The private tour can be customized to suit your interests, such as a stop for an authentic Tuscan lunch at a local farm.

Cross the Tuscan hills in search of fine wine, local food, and unforgettable views. This small group tour from Florence takes in UNESCO heritage sites, charming medieval towns, and a landscape that captivated Renaissance painters. Stop in Montalcino for a lunch of local fare and a tasting of some of the best wines in the world. And head to Montepulciano to wander its picturesque palazzos and visit the historical wine cellars.

Traverse Tuscany in search of architecture, landscapes, and local flavors—without needing to self-drive—on a small-group tour departing from Florence. See the iconic Leaning Tower of Pisa, admire the Siena Duomo, and stroll through the medieval streets of San Gimignano and Monteriggioni. Plus, relax with lunch and a Chianti wine tasting to complete your Tuscan adventure.

Experience the allure of Tuscany without the hassle of tricky logistics with this all-inclusive day trip from Rome. Save time with a high-speed train to Florence, where you’ll hop on a minibus with your tour leader and small group to visit Monteriggioni, Siena, and San Gimignano. End your Tuscan adventure with a wine and olive oil tasting in Chianti before heading back to Florence for the return train to Rome.

Ideal for travelers looking for off-the-beaten-path adventures, Italian-style, this tour pairs an all-terrain vehicle (ATV) off-road session with wine tastings and medieval village visits. After a quick lesson, explore the Chianti countryside riding your own ATV or on the back of someone else's. Then, hop on the tour minivan and head to the Tuscan hill towns of Montefioralle and Piazza Matteotti for exploring and shopping. Finish the day with a generous lunch and six wine tastings at a classic Tuscan winery.

Visit three of the most captivating towns in Tuscany in a single day with this tour that includes time-saving transportation directly from Florence. Enjoy a guided tour of Siena to take in the Piazza del Campo and Duomo, then relax over a traditional Tuscan lunch with wine at a local cellar. Spend your afternoon exploring first San Gimignano and then Pisa—including the iconic Leaning Tower—at your own pace. Hassle-free transport from Florence to see Siena, San Gimignano, and Pisa Delve into the history and architecture of Siena with a guided walking tour Sample tagliatelle pasta, salami, cheeses, and local wines at lunch Free time to explore San Gimignano and Pisa’s Piazza dei Miracoli

When visiting Florence (or Siena), spend a delicious day winery hopping in the renowned Chianti wine region. Visit two of the best estates for tastings of Chianti Classico and other top varietals, and enjoy a gourmet lunch of Tuscan specialties. There's also time to soak up countryside culture and history with a stop in San Gimignano or Monteriggioni, two of the best-preserved medieval towns in Tuscany.

Discover Tuscany at its finest in one day, with historical towns, breathtaking views, and stunning art. Avoid transport hassle with a private driver, who will whisk you through beautiful countryside to the historic towns of Pisa, San Gimignano, and Chianti. Learn about the area's culture and see the famous Leaning Tower of Pisa. Experience wine being produced in the renowned Chianti region, with the option for lunch and a tasting of six wines (own expense).

Soak up the Tuscan sun, and delve into Chianti's cuisine, without the hassle of navigating on this open-top minivan tour. Enjoy a scenic drive through the countryside, stopping for a tour and tasting at a local cellar. Take a stroll through the villages of Montefioralle and Greve in Chianti before sitting down to a Tuscan lunch at a second cellar featuring a multi-course meal with wine pairing.

Getting around Tuscany by public transport can be daunting. Skip the hassle of coordinating train and bus schedules and cover two top Tuscan towns in a single day with this San Gimignano and Siena tour. Explore the medieval old town of San Gimignano and enjoy a wine tasting before continuing on to Siena. Skip the line to enter the magnificent cathedral and explore the sights, shops, and eateries at your own pace.

Enjoy personalized attention as you explore Siena and San Gimignano on this 6-hour private day trip from Florence. Skip the hassle of renting a car, as this tour provides round-trip transportation to both locations. Hotel pickup and drop-off is included.

Siena and San Gimignano are two of the most stunning locations in Tuscany, but a driver is essential for visiting them in a single day. Discover both during this full-day private tour, which includes round-trip transportation offered from either Florence or Livorno Port. Travel through rolling hills, vineyards, and villas. Tours include a Tuscan lunch and wine tasting at a hand-picked estate.

Break from the hustle and bustle of Florence for a tour into the heart of the Tuscan countryside. On this small-group excursion, visit the villages of Certaldo and Monteriggioni, learn to make authentic Tuscan dishes during a cooking class, and sample several Chianti wines during a guided tasting and lunch. This tour includes a balanced mix of guided exploration with free time at each destination.

Explore the beautiful Tuscan countryside like a real Italian on the back of an authentic Vespa scooter. Zip along hillside roads past historic villas, medieval villages, olive groves, and vineyards. Stop at a local farm and winery for a fresh Tuscan lunch and a tasting of Chianti wines. Drive your own Vespa, or ride with an experienced guide if you prefer.

Get a taster of Tuscany on this private tour that features a selection of the region's highlights. Visit Siena, the Chianti countryside, and San Gimignano all in the same day, without having to hire your own car. Enjoy an itinerary that includes historic sightseeing and regional wineries, with the option to try local varietals (extra cost). Ideal for travellers who are only in the area for a short time.

Explore the best of Tuscany in a single day on this private tour from Florence. Travel along scenic countryside roads to reach iconic destinations, including Siena, Pisa, and the UNESCO-listed hilltop town of San Gimignano. See famous landmarks such as the Leaning Tower of Pisa and Piazza del Campo without the hassle of planning your route. Enjoy private transportation and accommodation pickup upon request for added comfort.

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 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.

Discover the beauty of Tuscany on this evening tour from Florence, featuring a visit to the Chianti countryside and a 4-course dinner. Head to a charming farmhouse winery to sample up to three glasses of Tuscan wine. Then head to a second estate to enjoy a relaxing evening of wine, dinner, and stunning views before returning to Florence.

Treat your senses to a memorable day in the world-famous Chianti wine region on this private tour from Florence. Travel in a luxury minivan through a landscape of historic vineyards, rolling hills and medieval villages, with a private driver at your disposal throughout the day. Taste renowned Chianti wines and authentic Tuscan cuisine at estates of your choosing, or let your local driver make suggestions for the best places to wine, dine and explore.

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.

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.

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.

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.