Day Trips from Tuscany to Siena

Immerse yourself in Tuscany’s charm with a tour from Florence! Begin your adventure in Pisa, where you’ll marvel at the Piazza dei Miracoli, Duomo, Baptistery, and the Leaning Tower of Pisa. Next, visit a Chianti Classico estate for a sommelier-guided wine tasting and a delicious lunch featuring local specialties. Continue to Siena for a guided walk through its historic gems like the Duomo and Piazza del Campo. End your day with a stop at Monteriggioni Castle before returning to Florence.

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.

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.

One full day of a beautiful guided sightseeing tour driving through symmetrical vineyards, olive trees, wooded groves, stone farm houses, late Renaissance villas and old villages, castles and medieval hamlets.

Visit one of Tuscany’s most respected wine regions on this tour from Florence to Brunello di Montalcino. In a private, air-conditioned car with a guide, drive first to Montalcino, a hilltop medieval walled city to explore the ancient town. Next, visit family-owned wineries in the Brunello countryside like Poggio Rubino and Capanna. Your guide will also take you to see the beautiful Abbey of Sant’Antimo, which is thought to date back to the sixth century.

Escape the hustle and bustle of Florence for a private tour of Tuscany’s medieval towns. Visit San Gimignano, known as the “Town of Fine Towers,” explore Monteriggioni’s perfectly preserved castle, and immerse yourself in the historic charm of Siena, a UNESCO World Heritage Site. From breathtaking views to centuries-old architecture, this tour provides a glimpse into the region’s rich past.

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.

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s simple use as a vehicle. Ideal both on city’s tiny alleys and on the famous country-side windy roads. We will be visiting typical medieval villages, get in touch with local wine and food producers as well as artisans, and stop along the way to take some picturesque photos that will become indelible memories. An experienced tour guide will lead you around and show you the way as only a local can. The tour ends in a local farm where we will be hosted by a family that has been living there since centuries, producing their own wine, Chianti Classico. We will have the chance to visit the property including the cellar and then relax where a traditional Tuscan lunch will be served, all accompanied by their wines. Pick up and drop off from your accomodation in Siena included.

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.

Take off your shoes and - literally - immerse yourself into ancient Tuscan culture on a grape stomping excursion to the Chianti hills.  In addition to grinding grapes into juice with your bare feet, you’ll also get an up close look at life at a Tuscan winery. A visit to the wine cellar and tasting is also included. After you’ve stomped to your heart’s content, replenish your strength with a homemade lunch.

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.

Discover the Tuscan countryside and cuisine on a private bike tour from Florence. After a transfer from your hotel, follow your guide as you pedal through the world-famous Tuscan landscape on an electric bike, to avoid becoming fatigued on the famous hills. The scenic journey takes you to a family farm where you enjoy a gourmet lunch prepared using local ingredients. The culinary experience continues with wine and olive oil tastings, before a leisurely ride back to the starting point.

Explore the landscape of Tuscany on a private, full-day cycling tour from Siena. With the full attention of your guide, follow a route along the Via Francigena, an ancient pilgrimage route that once linked Canterbury to Rome and a popular destination for photographers. Rest and refuel after a day of activity with a three-course lunch and wine pairings at a Tuscan vineyard. Hotel pickup and drop-off is included.

Experience the hidden beauty of Tuscany like never before—aboard a Land Rover Defender, journey through the region’s legendary "strade bianche" (white roads), the secret gravel paths winding through vineyards, olive groves, and deep forests. Your journey includes three winery visits, each offering a unique perspective on Chianti Classico and its appellations. The experience culminates in a traditional Tuscan lunch, where authentic flavors meet world-class wines, creating a true taste of Tuscany.

Explore Chianti’s backroads and beautiful vistas while traveling in a private 4WD on this tour with hotel pickup. Soak up the scenery while a driver handles the country roads, stopping at off-the-beaten-track cellars and cantinas to taste several Chianti Classico wines along with Tuscan olive oil, honey, and other specialty products. Balance out all that wine with a traditional Tuscan lunch at a scenic family estate.

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.

In Chianti, wine is more than a business—it’s a way of life. Indulge in the good life when you book this private wine tour from Florence. This tour unveils the history, traditions, and unique qualities of the wine culture, rooted in Etruscan origins and enhanced by mineral-rich soil. Learn about the characteristics of Chianti Classico as you visit three distinct wineries for tastings of their exceptional wines.

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.

Departing from Montecatini Terme with roundtrip hotel transfer, this full-day escorted tour immerses you in the heart of Tuscany. Explore Siena, with its medieval streets, Gothic cathedral, and charming squares. Wander its historic alleys, admire centuries-old palaces, and soak in the vibrant local atmosphere. Then visit a charming estate at the foot of Monteriggioni Castle. Discover the estate’s history, and enjoy a guided wine tasting along with fragrant olive oils and artisanal vinegars, paired with traditional Tuscan cold cuts, cheeses, and bruschette. Continue to Monteriggioni, a walled medieval village frozen in time, before concluding in San Gimignano, the “Town of Towers,” with its artisan shops, narrow streets, and panoramic views over the Tuscan hills. Return to Montecatini Terme with unforgettable memories of Tuscany’s history, flavors, and charm.

We will spend an entire day crossing the most characteristic and beautiful part of the Tuscan countryside: the Chianti. Here we will visit small villages and admire unique landscapes ... without forgetting to taste some good wine!

This tour includes a car at your disposal during the tour and a transfer to San Gimignano, where you’ll have free time to explore the beautiful medieval village of San Gimignano. Then transfer to a winery in the countryside where you’ll have a guided tour of the estate, a winery lunch in the cellar with local products (Lasagna or Tuscan Ribollita + Roasted meat with roasted potatoes and vegetables + Dessert with Cantuccini and Vinsanto) and a Wine & Olive Oil Tasting of 8 wines and oils with Appetizers (Tuscan cheeses and salami, Bruschetta and snack). After Lunch, 2 hrs free tour of Siena: its soaring skyline is its pride, dominated by the gothic cathedral (Duomo is one of the most spectacular in Italy and one of the few to have been built south of the Alps in full Gothic style) and the taut needle of the Torre del Mangia and yet the shell-shaped Piazza del Campo, probably captures the most attention and fame.

Experience the best Tuscany has to offer in just one day, with a private tour taking in Pisa, Siena, Diborrato Waterfall, and a wine tasting of local Chianti wines. After being picked up from your accommodation in Florence, explore historic Pisa and get those all-important pictures with the famous Leaning Tower. Discover beautiful San Gimignano and Diborrato Waterfall, before arriving at Siena. Here, your private guide explains the local history and enjoy a tasting of Chianti wine in a traditional bar or restaurant.

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.

Spend a day uncovering the charm of Siena, San Gimignano, and the Chianti region with a private tour from Florence. Enjoy an intimate experience exploring Siena's vibrant main square, the picturesque hilltop town of San Gimignano, and the historic town of Castellina in Chianti. Complete your adventure with a visit to a local winery for a taste of Chianti wines, including rosè and Supertuscan, and insight into how sangiovese grapes are cultivated.