The true spirit of Tuscany is distilled in its majestic hill towns. This popular VBT itinerary sets out to experience that spirit to its fullest with awe-inspiring reels through the stunning countryside. Its two medieval gems—San Gimignano and Siena—stand at the center of this cycling adventure. But oh … there’s so much more to discover! From the magical Chianti region to the perfect Renaissance town of Pienza, we’ll cycle into Tuscany’s very heart, staying in converted monasteries, visiting with a local art historian, admiring the finely wrought frescoes at a 14th-century abbey, and—of course!—sampling famed red wines.
Enjoy time to explore two medieval gems of Tuscany: San Gimignano and Siena
Learn some Italian at a language lesson
See where medieval and modern Tuscany come together in Colle Val d'Elsa
Enjoy a Renaissance lecture by a local art historian
Gain an appreciation for the local wine on a ride through the scenic Chianti region
Explore the 14th-century Benedictine abbey of Monte Oliveto Maggiore
Savor a picnic lunch in the lunar-like landscape of the Crete region of Siena
Attend a wine tasting and lecture at an enoteca
Cycle through the Orcia valley, 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
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
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
Air Package Plus Single Supplement: $545 | Land Only Single Supplement: $395
Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. 2015 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.
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 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 would 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 Colle Val d'Elsa and Siena
After breakfast, we ride to Colle Val d'Elsa, a picturesque town famous for its fine handcrafted crystal and medieval architecture. Entering the borough via the monumental Porta Nuova, we wind our way past numerous 16th- and 17th-century noble houses to the magnificent Palazzo Campana, which marks the entrance to the castle and the oldest part of Colle Val d'Elsa. We continue 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 walled city of Monteriggioni, an ideal stop for lunch. After lunch, shuttle or continue biking to our next accommodations in Siena. Your hotel in Siena is located in the quietest part of the city, the contrada della Chiocciola, or the Snail district, it is only a few steps from a typical chiesa del cavallo, or horse church. You can only find these unique places of worship here: Churches where horses are received and blessed before the Palio race. This evening, a local art historian provides insight into the Italian Renaissance, the history of Siena and the Palio, then joins the group for dinner in a local restaurant. Hotel: Il Chiostro Del Carmine Alternate Hotel: Hotel Athena Meals: B, D Daily Options: 31.9 or 41.9 miles ( 51. 6 or 67 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: Il Chiostro Del Carmine Alternate Hotel: Hotel Athena Meals: B Daily Options: 28.7 or 42.2 miles (46 or 67.6 km)
DAY 7: Cycle to Pienza and the Sienese Crete
This morning, we shuttle to the 14th-century Benedictine abbey of Monte Oliveto Maggiore. In the cloister, we admire many frescoes painted by some of the most famous artists of the Sienese school. Then we pedal into the Crete, a lunar-like region of clay hummocks and treeless gullies. On our way we stop near the picturesque village of Trequanda for an included picnic lunch prepared by our Trip Leaders. 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 before finding a restaurant for lunch on our own. Late in the afternoon, 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, L Daily Options: 14.3 or 26.4 miles (22.9 or 42.3 km)
DAY 8: Ride into the Orcia Valley to Montepulciano
Today's reel follows a rolling scenic road through the Orcia Valley, a UNESCO World Heritage Site. Our destination is the medieval hilltop village of Monticchiello, surrounded by city walls. Then pedal toward another great walled city, Montepulciano, where you can spend browse wine shops and cobbled alleyways before lunch on your own. In the afternoon, you can opt for a longer route over more rolling hills to Torrita di Siena in Val di Chiana. Or bike or shuttle back to Pienza on a different route. A local trattoria hosts our farewell dinner featuring typical pici pasta. Hotel: Il Chiostro di Pienza Meals: B, D Daily Options: 13.7, 22.5 or 31.1 miles (22, 36 or 50 km)
DAY 9: Transfer to Rome / Free time / VBT No-Air Package ends
VBT No-Air Package guests: Your trip ends in Rome around 12 pm 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. **VBT recommends that you check your transfer time in your “Transfer Reminder.” Please note: 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
The Athena, a four-star hotel in Siena, stands in the heart of the old town center 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.
Located just outside San Gimignano, the hotel was in the old times (1587) a monastery of the Cappuccini monks. It was turned in the late eighties into an elegant and deluxe hotel of 21 rooms and 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 built in the ancient church, a bar on the terrace with great views of San Gimignano medieval towers. The hotel is fully air conditioned and equipped with WiFi connection. Each room has a Jacuzzi bathtub.
Located in two Renaissance palaces on one of Florence’s most elegant shopping streets, the Palazzo Minerbetti and the Palazzo Strozzi del Poeta are close to all the important monuments of the city. Featuring a rooftop garden with panoramic views of Florence, the hotel welcomes guests in its elegant 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-19th centuries and elegant chandeliers in Murano glass are definitely part of the charm.
Located in the heart of the city, a few steps from Piazza Del Popolo and the wonderful 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 at bar and reception. VBT has reserved only superior rooms, larger than the otherwise very small standard bedrooms. It’s a great spot from which to discover the Eternal City. WiFi is free throughout and an Internet point is also available in the lobby.
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.
Set in the heart of medieval Pienza, the 4-star Il Chiostro di Pienza is housed in a former 15th-century Franciscan convent. As you relax in your comfortable accommodations, you will find its central location enables you to explore this Renaissance city, so well-preserved and rich in history. Hotel amenities include a terraced garden offering sweeping views of the Orcia and Asso valleys, an outdoor swimming pool and a refined restaurant serving Tuscan specialties. Though its air-conditioned rooms vary in layout and décor, all feature cable/satellite television, a minibar, and private bath with shower and hair dryer. Complimentary WiFi is available in the lobby.
Enjoy Your Vacation Longer With LOw-Cost Trip Extensions
Pre-Trip Extension - Florence
2 nights for only $345
Two nights at the Hotel Tornabuoni Beacci
Begin your Italian bicycling vacation with two magical days in Florence, the art lover’s paradise. The Italian province of Tuscany boasts more classified historical monuments than any other region in the world, and the most dazzling are in Florence. The Renaissance began here, and the period’s great works of art are on display throughout the city. Florence also has delightful cafés for relaxing and people-watching. A city that is fun to explore on foot, Florence has many attractions concentrated in the relatively small historic center stretching from Piazza del Duomo south to the Arno River. Only available with the Air Inclusive Package. Single supplement: $145
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 / Begin your Trip Extension
Upon arrival at the Florence airport, a VBT local representative meets you outside the customs area and helps you transfer to your hotel. 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 would 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. At the hotel our local expert will be available at 5:00 pm to answer your questions and offer an optional private guided walk to make the most of the city. You have the rest of the day free to explore the city. Please note: to visit the Uffizi Gallery, you must make reservations in advance. To reserve online, go to www.florence-museum.com. For information on all Florence museums, go to www.italy-museum.com. Please note: Italian museums are closed on Mondays.
DAY 3: Independent exploration of Florence
After breakfast, you may wish to explore the city's most famous museum, the Uffizi Gallery (advance tickets required). Or stroll along the shop-lined promenades of the Via Tornabuoni, then cross the River Arno in search of antiques or handicrafts in the Piazza del Duomo. Hotel: Hotel Tornabuoni Beacci Meals: B
DAY 4: Independent exploration of Florence / Join VBT Air Package guests
You have the day free to explore the historic city of Florence and enjoy its Renaissance architecture and famous museums. In the evening, relax in one of the city's restaurants and sample the local cuisine. VBT Air Package guests arrive throughout the day. Hotel: Hotel Tornabuoni Beacci Meals: B
Post-Trip Extension - Rome
2 nights for only $345
Two nights at the Hotel River Palace
Discover the Eternal City at your leisure as you spend two nights in Italy’s timeless capital. History, art and architecture abound, from Greek sculpture to Roman ruins. Marvel at the grandeur of the Vatican, where St. Peter’s Basilica and the Sistine Chapel await. Stroll through the ancient ruins of the Roman Forum and the Coliseum. Take time to walk up the Spanish Steps, toss a coin in the Trevi fountain to ensure your return to Rome, or just spend a relaxing afternoon at a quiet outdoor café. Many attractions are within walking distance of your centrally located hotel. Only available with the Air Inclusive package. Single supplement: $245
DAY 1: Independent exploration of Rome
Continue your exploration in Rome for an additional two nights and spend today exploring the city. This is an independent extension—there is no VBT representative or Trip Leader. Today's opportunities are endless. You might visit the Forum, the political and commercial center of ancient Rome when the empire was at its greatest power. Various emperors constructed temples, monuments and other buildings here over a period of nine centuries. Today you can still see the Curia where the Roman Senate met. Take a walk up the Palatine Hill, where tradition says the first settlers of Rome built their huts under the direction of Romulus, and which was the later home of Caligula, Nero, Tiberius and Domitian. Hotel: River Palace Hotel Meals: B
DAY 2: Independent exploration of Rome
Today, perhaps you'll step out of Italy while you're still in Rome with a visit to the Vatican, an independent state. The Vatican museums are filled with magnificent art that goes far beyond such well-known pieces as the Pieta and Michelangelo's Sistine Chapel ceiling. Tour Rome's famous Catacombs, located in tunnels carved out of rock along the Via Appia (Appian Way). We offer an optional guided tour that you can book through the hospitality desk on your arrival. Spend an idyllic afternoon in the gardens of the Villa Borghese, one of Europe's most elegant parks. And by all means, do as the Romans do—sip espresso, savor Italian wine and, even in the middle of the rush of modern European life, take the time to enjoy la dolce vita. After a full day of independent exploration, retire to your hotel or perhaps enjoy one of Rome's fine restaurants. Please note: Italian museums are closed on Mondays. Vatican museums are closed on Sundays, since they are in Vatican State. Hotel: River Palace Hotel Meals: B
DAY 3: Rome extension concludes / Depart for U.S.
After breakfast* this morning, transfer to the Rome airport (approximately 40-60 minutes, depending upon traffic) for your departing flight**. Please ensure you are waiting in the hotel reception area at the designated time. *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. **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 are 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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