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Italy Biking: Tuscany

9 days  |  11 days with Florence extension  |  Loading prices

Physical activity
Equipment
Group size
6–16 travelers

A ride to remember through Tuscan wine country

Get ready to live out your Italian cycling fantasies on the ultimate trip through Tuscany. With five days of stunning rides—including sections of the historic Via Francigena, an ancient route that’s connected Canterbury to Rome for over 1,000 years—you know you’re in for quite the adventure. You’ll conquer tough—yet rewarding—climbs around San Gimignano, ride to wine tastings at vineyards in Chianti, and cruise through picturesque pastures and hillsides in the Val d’Orcia region. Along the way, medieval towns and castles await (you’ll even have the chance to dine in one!), as well as food so spectacular, it’s what put Tuscany on the map as a culinary hotspot. This is the land of pecorino cheese and pappa al pomodoro (Tuscan tomato and bread soup), after all. We’ve got all the gear and professional cyclist-curated routes waiting—all you need to do is take the plunge and jet over to Tuscany.

What's included

  • 7 nights in handpicked hotels
  • Private local transfers
  • Support van for bike rides
  • 7 breakfasts
  • 2 lunches
  • 4 dinners with beer or wine
  • 1 coffee tasting, 1 pasta tasting, 1 ricciarelli tasting, & 2 wine tastings
  • Two expert European Tour Directors/bike guides
  • Choice between performance road bike and e-touring bike (Road racing bike and e-road bike available for a fee)
  • Helmets, GPS tracking devices, and other biking equipment
  • 8 guided bike ride options through Tuscany
  • Select guided sightseeing tours

Why you'll love it

  • Pedal through Val d’Orcia’s wine country en route to a pasta factory for a tour and lunch
  • Conquer steep hills and descents on a scenic loop to Montalcino
  • Dine like a king or queen at a castle dinner and wine tasting in the Chianti region
  • Bike to Radda in Chianti, heart of the renowned Chianti Classico wine zone
  • Savor local cuisine at dinner in hilltop San Gimignano, where medieval meets magical
  • Tackle a challenging ride to the walled town of Monteriggioni

Itinerary

Overnight flight

Day 1: Fly to Florence

Your action-packed trip is about to kick off! Head to the airport and board your overnight flight to Italy.

Val d'Orcia region

Day 2: Arrival in Florence and transfer to Val d’Orcia region

Included meal: Welcome dinner

After landing in Florence, you’ll set off to your first region of the trip: Val d’Orcia, known for its characteristic green hillsides blanketed with vineyards and olive groves. Named after the Orcia river running throughout the region, Val d’Orcia is a heavily photographed stretch of Tuscany thanks to its typical medieval villages like Pienza and Montalcino. Try to get some sleep tonight—the adventure starts bright and early tomorrow.

Today’s highlights
  • Meet an EF representative at the airport.
  • Transfer 1–1.5 hours to your hotel in the Val d’Orcia region to check in and settle into Italian time.
  • Raise a glass of beer or wine during a meet-and-greet with your fellow bikers during a Welcome Orientation with your Tour Directors.
  • Get your first taste of Tuscan cuisine at a Welcome Dinner nearby.

Note: Airport transfers are included for travelers who book flights with EF Adventures. If you book your own flights, airport transfers may be available for a fee upon request.

Florence extension

Give your feet a break from pedaling and extend your adventure with a 2-night stay in Florence. The capital of Italy’s Tuscan region is a culinary and art mecca that’s home to masterpieces like Michelangelo's David sculpture. While the city can seem like a living museum, there’s plenty to do when you’re ready for an art break. From browsing the Mercato Centrale food hall to sampling the city’s best gelato and traditional Florentine desserts like zuccotto (a semi-frozen, dome-shaped cake), it’s not hard to fall head over heels for Florence.

Florence

Day 9: Travel to Florence & walking tour of Florence

Included meal: Breakfast

Considered the Cradle of the Renaissance, Tuscany’s capital, Florence, has inspired artists for centuries—this is where masters like Michelangelo once lived and worked. Leave the dates and names to your trusty local guide, who’ll whisk you around the city’s cobbled streets. Snap photos of the Florence Cathedral, known locally as the Duomo, and the freestanding Giotto’s Campanile, a bell tower with nearly 400 steps to the top, before continuing to Casa di Dante, a museum dedicated to the life and work of the Italian literary legend.

Today’s highlights
  • Travel from the San Gimignano region to Florence, starting your stay in the Tuscan capital with a guided city tour and tasting of some of the city’s finest gelato.
  • Step inside the famous Florence Cathedral to hear more about the Baptistery of San Giovanni, with its gilded bronze doors famously dubbed the “Gates of Paradise” by Michelangelo.
  • Enjoy the rest of the evening exploring the city on your own and having dinner or an aperitivo at a spot of your choosing.

Day 10: Optional visit to Pitti Palace & the Boboli Gardens & free time in Florence

Included meal: Breakfast

Within walking distance from your hotel, you can join an optional excursion to the Pitti Palace and Boboli Gardens, where you’ll stroll through the Grand Dukes’ former living quarters and the Medici’s private collection of art before soaking up sweeping views of Florence from the hilltop gardens. And if you’re looking to fill a day in Florence, there’s plenty to do. Art fans should check out the world-famous Uffizi Gallery, known for its impressive collection of sculptures and paintings from the Middle Ages to modern day, while Regina Bistecca is must-try for foodies looking to sample what’s said to be the city’s top bistecca alla Fiorentina (Florentine steak).

Today’s highlights
  • Admire the Pitti Palace’s Modern Art Gallery, home to more than 30 rooms of works spanning the 18th to 20th centuries, on an optional excursion that includes a stop at the Boboli Gardens. 
  • Enjoy a day continuing to explore Florence’s landmarks like the city’s symbolic Ponte Vecchio, a medieval stone bridge lined with shops.

Flight home

Day 11: Fly home

Included meal: Breakfast (excluding early morning departures)

Now it’s really time to say arrivederci, or until next time, to Tuscany and pack your bags for your short transfer (about 30-60 minutes) to the Florence airport to catch your international flight home.

Handpicked accommodations

From boutique hotels to 5-star luxury retreats, our accommodations are curated with the expert eye and attention to detail that come from 60 years of travel experience, always prioritizing authenticity. We select high-quality properties that balance comfort, location, sustainability, and local charm. From bustling city centers to serene countryside and picturesque small towns, each hotel is chosen to complement your adventure’s unique style. While the specific accommodations may vary based on your travel dates, you can always count on staying at fantastic properties that meet our standards for quality and character.

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Historic stone buildings with lit windows reflecting in a calm river under a deep blue evening sky.

Val d'Orcia region - Albergo le Terme

Tradition meets modern comfort in the heart of Val d'Orcia. Albergo le Terme occupies a 15th-century palace with a remarkable history and overlooks Bagno Vignoni's famous Piazza delle Sorgenti, a thermal pool dating back to...

Rustic spa room with stone walls, lounge chairs, and a large window overlooking a lush garden. Soft lighting creates a tranquil atmosphere.

Chianti region - Villa Campomaggio

Nestled among Chianti's rolling hills lies Villa Campomaggio, an 18th-century aristocratic residence turned enchanting retreat. Whether you've spent the day cycling through Chianti's vineyards or exploring nearby towns, Villa...

Outdoor pool area with a central fire pit surrounded by red chairs. Lush greenery and umbrellas in the background create a serene atmosphere.

San Gimignano region - Borgo San Luigi

Spread across 60,000 square meters of Tuscan countryside, Borgo San Luigi is more than just a hotel—it's a sanctuary for relaxation. This oasis offers rooms that blend medieval village charm with modern comforts. Lounge by the...

Elegant hotel room with a large bed, warm lighting, abstract wall art, desk, and window with heavy curtains. A robe and towels are on the bed.

Florence - Grand Hotel Adriatico (Extension)

Steps from Florence's iconic sights, Grand Hotel Adriatico welcomes you with its comfortable rooms, on-site restaurant, and garden bar (a quiet retreat from the city buzz). Unique perks include a 24/7 gym and in-room massages....

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Equipment

We've partnered with EF Pro Cycling and Cannondale to offer four exceptional Cannondale bikes for you to choose from. You'll be able to select your preferred bike in your online account after you book.

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Flights

Round-trip flights are one more thing we handle to make your journey as smooth as possible. Our team of travel experts will find the best flight itinerary for you at a competitive rate, thanks to our partnerships with top airlines.

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Weather

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Monteriggioni, Italy

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48°51°57°64°70°81°88°88°78°68°57°50°35°36°39°44°50°58°64°64°57°51°44°38°48°51°57°64°70°81°88°88°78°68°57°50°35°36°39°44°50°58°64°64°57°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Greve, Italy

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48°51°57°64°71°81°87°88°78°68°58°50°35°36°40°45°50°58°63°64°58°51°44°38°48°51°57°64°71°81°87°88°78°68°58°50°35°36°40°45°50°58°63°64°58°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Siena, Italy

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48°51°57°64°70°81°88°88°78°68°57°50°35°36°39°44°50°58°64°64°57°51°44°38°48°51°57°64°70°81°88°88°78°68°57°50°35°36°39°44°50°58°64°64°57°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Montalcino, Italy

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46°49°54°61°67°78°85°85°75°66°56°49°34°35°38°42°48°57°62°63°56°50°43°37°46°49°54°61°67°78°85°85°75°66°56°49°34°35°38°42°48°57°62°63°56°50°43°37°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

San Gimignano, Italy

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48°52°58°65°71°81°88°88°78°68°57°49°35°37°40°46°51°59°65°65°58°51°44°38°48°52°58°65°71°81°88°88°78°68°57°49°35°37°40°46°51°59°65°65°58°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Florence, Italy

Weather averages

Temperature scale

48°51°57°64°71°81°87°88°78°68°58°50°35°36°40°45°50°58°63°64°58°51°44°38°48°51°57°64°71°81°87°88°78°68°58°50°35°36°40°45°50°58°63°64°58°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND
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Round-trip flights are one more thing we can handle to make your journey as smooth as possible. Our team of travel experts will find the best flight itinerary for you at a competitive rate. Rates shown in cart.