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Tuscan Hill Towns by Bike

Medieval masterpieces like San Gimignano and Siena await you on this delightful cycling adventure in the Tuscan hills that produce some of Italy’s most famous red wines.

  • 10 Days
  • Activity Level: Moderate / Challenging
  • Daily Mileage: 30 - 60 mi
  • Daily Biking: 3 - 6 hr
  • Small Groups: 20
  • Biking
  • Moderate / Challenging
  • Plane

2016 departure dates now available below!

Why You'll Love This Tour


Tuscan Hill Towns by Bike

Experienced cyclists thrill to Tuscany’s famous hills—but you don’t have to be a cyclist at all to fall under the spell of this enchanting region. Here, you’ll find a countryside whose beauty is rivaled only by the fabulous paintings and frescoes that abound in villas, churches, and museums … ancient cities that helped shape the course of civilization … and a hearty cuisine coupled with world-class wines. From San Gimignano, bristling with medieval towers, to Gothic Siena, a model of early urban planning, you’ll explore the heart of this region, enjoying special touches like wine tastings and a lecture by a local historian along the way.

Cultural Highlights

  • Marvel at stunning views of the Tuscan countryside
  • View the remarkable towers of medieval San Gimignano
  • Sip the local vintage at the Vernaccia Wine Museum
  • Master some Italian phrases, courtesy of your Trip Leaders
  • Gain insights into the Renaissance from a local art historian
  • Admire the Gothic beauty of Siena
  • Discover why horse racing is integral to Sienese culture
  • Enjoy a picnic lunch in beautiful Tuscan countryside
  • Learn about Tuscan wines and enjoy a tasting
  • See why the Orcia valley is a UNESCO World Heritage Site

What to Expect

This tour offers the full range of easy terrain mixed with moderate and challenging hills. Our VBT van support shuttle is always available for those who need assistance with the hills. Ideal for more experienced cyclists.

Average Daily Mileage: 15-45 miles
Average Cycling Time: 3-5 hours

Climate Information

Average Daily Temperature (°F) – Florence May 75°  Jun 84°  Jul 89°  Aug 88°  Sep 81°  Oct 69°

Average Rainfall (in.) – Florence May 3  Jun 2.7  Jul 1.5  Aug 1.9  Sep 3.3  Oct 4

What’s Included:

Bicycle Tour Only – without Air

  • 6 nights in 4-star historic hotels and one country villa
  • 10 meals – 6 breakfasts, 1 lunch, 3 dinners

Air Package Plus

  • Roundtrip international airfare
  • 8 nights in 4-star historic hotels and one country villa
  • 12 meals – 8 breakfasts, 1 lunch, 3 dinners
  • Airport transfers
  • And the option to add our Low-Cost Trip Extensions: Pre-trip: Florence – 2 nights for only $345 • Post-trip: Rome – 2 nights for only $345

Both Vacation Options Include

Dates & Prices

2016 departure dates are available! Click on 2016 under "Departure & Return Dates" and start planning your 2016 vacation today!

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Air Package Plus 10 Days Includes round-trip international airfare


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Air Package Plus 10 Days Includes round-trip international airfare

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Fri, Oct 9
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Departure: Friday, October 16
Return: Sun, Oct 25
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From $4,195
  • From $4,195
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From $3,895
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  • Fri, Oct 16
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From $2,645
  • From $2,645
  • (800) 245-3868

2015 Air Package Plus Single Supplement: $545 | 2015 Land Only Single Supplement: $395 |2016 Air Package Plus Single Supplement: $645 | 2016 Land Only Single Supplement: $495

Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. 2015/2016 Prices include all airline surcharges and Government taxes and fees. Ask our Tour Consultants for details. Every effort has been made to produce this information accurately. We reserve the right to correct errors. Prices are based on preferences selected above, including meals and sightseeing as specified in What’s Included. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only.

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Itinerary & Map
Or, Expand All Days
DAY 1: Depart from home / Fly overnight to Florence

Depart from home for Italy. The particulars of your arrival overseas are detailed with your flight itinerary.

DAY 2: Arrive in Florence

Upon your arrival at the Florence airport, a VBT local representative meets you outside the customs area and helps you transfer to your hotel (approximately 30 minutes). The representative will be holding a VBT sign. If you arrive early, your room may not be ready until 2:00 pm. You may store your luggage with the reception desk.

If you are going to be delayed meeting our transfer representative for more than 15 minutes due to delayed or lost luggage, please let our Airport staff know by calling or sending a text message to +39 351 20 49 571. Our drivers are generally able to wait for up to 45 minutes from the time your flight lands, after which you will be responsible for your own transfer. However, they might be able to reschedule your transfer if they are aware of the delay. You may also contact our One Call travel assistance to advise of your delay, and they will contact our transfer service.

You have the rest of the day free to explore the city, using VBT’s City Information as your guide. In the evening, relax in one of the city’s restaurants and sample the local cuisine.

Hotel: Hotel Tornabuoni Beacci

DAY 3: All guests meet in Florence / Transfer to San Gimignano

VBT No-Air Package guests: Your tour starts at 12:30 pm at the Florence hotel (Hotel Tornabuoni Beacci, via de’ Tornabuoni 3, Firenze, phone +39 055 212645). Please have lunch on your own before meeting your VBT Trip Leaders, who will be in the lobby wearing VBT staff garments. If your arrival at the Florence hotel is scheduled later than 12:30 pm, or if you are delayed, you must take a taxi (approximately 1 hour) at your own expense (approximately 100 euros/$150 USD) to Hotel La Collegiata. Contact Hotel La Collegiata to advise the staff of any travel delays or changes, and they will pass the message on to your VBT Trip Leaders.

VBT Air Package guests & Pre-Trip Extension guests: Explore Florence after breakfast, then meet your Trip Leaders at the hotel in Florence at 12:30 pm. They will be wearing VBT staff garments. Please plan to have lunch on your own before meeting your Trip Leaders.

Once the group has assembled, we transfer by motorcoach to our first hotel, Hotel La Collegiata (approximately 1½ hours). This hotel, located just outside the charming town of San Gimignano, was once a monastery, and was transformed in the late 1980s into a 20-room deluxe hotel. It features a large park and Italian-style garden with a swimming pool. After settling in, meet for a safety and bike-fitting session, followed by a short warm-up ride through the countryside. Later, gather with the group for a welcome reception on the terrace, enjoying the view of San Gimignano’s medieval towers. Dinner tonight features regional specialties in the hotel’s impressive restaurant, once the church of the monastery.

Hotel: Hotel La Collegiata
Meals: B, D
Daily Options: 3.7 miles (5.7 km)

DAY 4: Explore San Gimignano

This morning, cycle past silvery olive groves and old fattorie (farm villas) with stunning open views of the Tuscan countryside. Our ride takes us to San Gimignano, known for its characteristic skyline visible from miles away. It’s hard to believe that such a small medieval center once brimmed with 76 towers, erected in a 14th-century building frenzy by competing families. Today, only 13 remain. You have free time to explore on your own and eat lunch. Or choose an optional and challenging ride to Ulignano and San Benedetto.

Later, participate in an included language workshop with your native Italian VBT Trip Leaders. For dinner tonight, we head into San Gimignano first at the Wine museum for a glass of Vernaccia and a toast from its spectacular balcony, and then for a stroll and stop in at a trattoria for dinner on your own.

Hotel: Hotel La Collegiata
Meals: B
Daily Options: 15, 24.3 or 40.1 miles (24, 39 or 64.2 km)

DAY 5: Cycle to Monteriggioni and Siena

After breakfast, we ride through several charming little towns like Strove and Abbadia Isola in the sleepy countryside of Siena, past fields of red poppies and rolling fields, before entering the medieval walled city of Monteriggioni, an ideal stop for lunch. After lunch, shuttle or continue biking to our next accommodations, in the heart of Siena.

Your hotel in Siena is located in the quietest part of the city, the contrada della Pantera, or the Panther district—only a few steps from a typical chiesa del cavallo, or horse church. You can find these unique places of worship only here: Churches where horses are received and blessed before the Palio race. This evening, a local art historian provides insight into the Italian Renaissance and the history of Siena and the Palio, leading you in a walking tour of the city. We then dine in a local restaurant.

Hotel: Hotel Athena
Meals: B, D
Daily Options: 24 or 37 miles (39 or 60 km)

DAY 6: Explore the Chianti region and Siena

Early this morning, start your day with a short self-guided walk to absorb the city as it wakes from its slumber. Students head to the nearby university. Kids clutch their mothers’ hands on their way to school. Sip a cappuccino in a typical bar, take it all in, and try your Italian with some locals!

Later today, ride through the Chianti region on Via Chiantigiana, a panoramic road that runs north-to-south across the vineyards and through hilltop villages like Radda and Castellina. Back in Siena, discover the city at your own pace during your free time.

Siena is the embodiment of a medieval city. Its inhabitants pursued an intense rivalry with Florence, even with their careful attention to urban planning. Throughout history, they preserved their city’s Gothic appearance, which was developed between the 12th and 15th centuries. During this period, the work of Duccio, the Lorenzetti brothers and Simone Martini set the stage for developments in Italian and, more broadly, European art. The whole city of Siena, built around the Piazza del Campo, was created as a work of art that blends gracefully into the surrounding landscape.

Tonight, dinner is on your own in one of the many local trattorias in the heart of the city. After dinner, after all the tourists have gone, take a stroll through the various rioni (the territories of each contrada) or in the quiet Duomo district.

The Palio horse race, which takes place every year on July 2 and August 16, is one of Italy’s most famous and popular events. A celebration of the miraculous apparition of the Virgin Mary, it first took place on August 16, 1656. From 1701, it was run in honor of the Madonna dell’Assunta, the patroness of Siena. The race’s history is strictly connected with the origins of Siena’s contradas, or districts. Each contrada is an institution in itself, with its own headquarters, government, oratory, coat of arms, appellations, titles of nobility, emblems and colors, official representatives, festivities, patron saints, district sculptures, delimited territories, and population. Today only 17 contradas exist, 10 of which participate in the race. The preparations for the race are like liturgical ceremonies, from the transformation of the Campo square into a race track to the blessing of each contrada horse. During the month of July, we are likely to see some of the festivities and decorations surrounding this famous local event.

Hotel: Hotel Athena
Meals: B
Daily Options: 28.7 or 42.2 miles (46 or 67.6 km)

DAY 7: Montalcino / Cycle to Pienza and the Sienese Crete

This morning, we shuttle to Montalcino to start out ride into the ‘Crete Senesi’ park.Set within a full circle of fortified walls and watched over by a mighty castle of medieval perfection, Montalcino is a beautiful village immersed in the breathtaking Val d’Orcia Natural Park, renowned all over the world for the production of its precious Brunello red wine. From there we pedal into the Crete, a lunar-like region of clay hummocks and treeless gullies.

Later this afternoon we arrive in Pienza, a charming town set on a hill in Tuscany’s Val d’Orcia. This is a perfect example of Renaissance town planning as dictated by Pope Pius II. We have free time to relax in the piazza or explore the town. This evening, enjoy an included wine tasting and talk on Tuscan wines at one of the most famous enotecas in Italy. Tonight, dinner is on your own.

Hotel: Il Chiostro di Pienza
Meals: B,
Daily Options: 19 or 42.5 miles (31 or 68 km)

DAY 8: Ride into the Orcia Valley to Montepulciano / Picnic lunch

Today’s reel follows a rolling scenic road through the Orcia Valley, a UNESCO World Heritage Natural Site. We stop for lunch to enjoy a picnic lunch with a beautiful panoramic view. You then have the option to continue toward another great walled city, Montepulciano, where you can spend time to browse wine shops and cobbled alleyways before looping or shuttling back to Pienza.

A local trattoria hosts our farewell dinner featuring typical pici pasta, fresh hand made by our host Lucio’s father..

Hotel: Il Chiostro di Pienza
Meals: B, L, D
Daily Options: 18, 26.5, or 47.5 miles (28.5, 42.5, or 76 km)

DAY 9: Transfer to Rome / Free time / VBT No-Air Package ends

VBT No-Air Package guests: Your trip ends in Rome around noon at the River Palace Hotel (Via Flaminia 33, phone +39 06 830011). You are responsible for your own transfer to the airport for your flight home.

VBT Air Package guests: Arrive at our Rome hotel around noon and enjoy the rest of the day at leisure. Your room may not be ready until 1 pm, but you can store your luggage with the reception desk.

If you have chosen the independent Post-Trip Extension to Rome, you will remain at this hotel for three nights. When you arrive today, VBT’s Rome representative can answer your questions and offer an optional city walk to help you make the most of the Eternal City. Our VBT City Information has recommendations for restaurants, museums, and transportation in Rome to help you explore on your own.

Hotel: River Palace Hotel
Meals: B

DAY 10: Depart for home

After breakfast* this morning, transfer to the Rome airport (approximately 40-60 minutes, depending upon traffic) for your departing flight. Please ensure you are ready in the hotel reception area at the designated transfer time**.

*Please note: For guests with early-morning departures, breakfast at the hotel may not be available. Please check with the front desk to verify the times that breakfast is served.

** Please note: VBT recommends that you check your transfer time in your “Transfer Reminder.” VBT transfer times and departure points are finalized in advance and cannot be modified for individual guests. If you extend your stay beyond the scheduled program dates, return transportation to the airport will be at your own expense.

Meals: B

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Hotel Athena

The Athena, a four-star hotel in Siena, stands in the heart of the old town centre inside the ancient city walls. It is ideally located for reaching Piazza del Campo and the Cathedral, just a few minutes’ walk away. The Hotel offers a wide range of 4-star hotel services and a splendid view of the surrounding countryside characterized by its gently rolling hills and the profile of cypress trees and old farmhouses which add touches of color to the skyline.
Free WiFi Included

Hotel La Collegiata

Located just outside San Gimignano, the Hotel La Collegiata is a refurbished 16th-century monastery of the Cappuccini monks. In the 1980s, it was transformed into an elegant and deluxe hotel of 21 rooms. Until very recently, it was part of the Relais & Chateaux chain. It features a park and an Italian-style garden with a swimming pool, a rose garden, an impressive restaurant inside the sanctuary of the ancient church, and a terrace bar with stunning views of San Gimignano’s medieval towers. The hotel is fully air conditioned and equipped with WiFi connection. Each room has a Jacuzzi bathtub.
Free WiFi Included

Hotel Tornabuoni Beacci

Located in two former Renaissance palaces, the Palazzo Minerbetti and the Palazzo Strozzi del Poeta, and located on one of Florence’s most elegant shopping streets, Hotel Tornabuoni Beacci is close to all the important monuments of the city. Featuring a rooftop garden with panoramic views of Florence, the hotel offers guests  rooms decorated with frescos and antique furniture. Typical of historical Italian palaces, each room is different in layout and size. The historic paintings, antique pieces from the 17th to 19th centuries, and elegant chandeliers in Murano glass are all part of the charm.
Free WiFi Included

River Palace Hotel

Located in the heart of the city, a few steps from Piazza Del Popolo and the beautiful Santa Maria del Popolo Church (with paintings by Caravaggio), this charming property is intimate and refined. It features a very good restaurant called Caravaggio, a nice breakfast room, and friendly staff. VBT has reserved only superior rooms, larger than the otherwise rather small, standard bedrooms. WiFi is available throughout.
Free WiFi Included

Il Chiostro del Carmine

Located in the heart of Siena, far from the city noise and near the city walls, this historic property was once a 14th-century Carmelite monastery and is now classified as a holiday resort. It features 17 comfortable rooms overlooking either the internal cloister or the valley south of Siena. The atmosphere is very peaceful and familiar. Breakfast is served in the ancient “barrel room” where monks used to press and store wine in big barrels. The cloister offers seating and relaxation.
Free WiFi Included

Il Chiostro di Pienza

Set in the heart of medieval Pienza, the 4-star Il Chiostro di Pienza is housed in a former 15th-century Franciscan convent. You’ll find that its central location enables you to explore all directions of this Renaissance city. Hotel amenities include a terraced garden offering sweeping views of the Orcia and Asso Valleys, an outdoor swimming pool and a restaurant serving Tuscan specialties. Its air-conditioned rooms vary in layout and décor, and all feature cable/satellite TV, a minibar, and private bath with shower and hair dryer. Please note: Free WiFi is available in the lobby, but not available in your room.

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Post-Trip Extension - Rome

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