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Biking Vacation Tuscan Hill Towns by Bike​

Activity Level: Moderate/Advanced  |  Daily Mileage: 30 – 60 mi  |  Daily Biking: 3 – 6 hr
Air package plus
10 days from only
Price includes roundtrip airfare.
Land only
7 days from only
Pre-trip Extension:
Florence · 2 nights $345

Post-trip Extension:
Rome · 2 nights $345
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Detailed Itinerary

Please note: For those traveling in 2015, your itinerary may vary slightly from what is presented below. 

Day 1 - Depart U.S. / Fly overnight to Florence

Depart the U.S. 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 have airport staff page our driver with your last name so they may be notified of your delay. You may also contact our One Call travel assistance to advise of your delay and they will contact our transfer service. Our drivers are only able to wait for up to 45 minutes from the time your flight lands after which you would be responsible for your own transfer.

You have the rest of the day free to explore the city with VBT's City Information included in your Final Travel Booklet as your guide. In the evening, relax in one of the city's restaurants and sample the local cuisine.

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 (transfer time 1½ hours). This hotel, located just outside the charming town of San Gimignano, was once a monastery, 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 before 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. Then pause for dinner with regional specialties in the hotel's impressive restaurant, once the church of the monastery.

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 bristled 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, where you can stroll and look for a trattoria for dinner on your own.

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. After lunch, shuttle or continue biking to our next accommodations in Siena. If you opt to cycle, you'll ride through several charming towns, including Abbadia Isola and Staggia Senese, past fields of red poppies and rolling hills.

Your hotel in Siena is a restored monastery in the complex of San Niccolo' Church, in the quietest part of the city. Located in the “contrada della Chiocciola” (the Snail district), it is only a few steps from a typical “Chiesa del cavallo” (horse church). You can only find them here: Churches where horses are received and blessed before the Palio race. This evening, attend a presentation on the Italian Renaissance, the history of Siena and of the Palio by a local art historian, who will then join the group for dinner in a local restaurant.

Day 6 - Explore the Chianti region and Siena

Early this morning, start your day with a short self-guided walk to stretch out and 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 sleepy 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 their rivalry with Florence right into the area of 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 was to influence the course of 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 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, when 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. It is run to celebrate the miraculous apparition of the Virgin Mary and 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, starting 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.

Day 7 - Cycle 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 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.

Day 8 - Ride into the Orcia Valley to Montepulciano

Today's reel follows a rolling scenic road unfolding in the scenic Orcia valley, a UNESCO World Heritage Site. Our destination is the medieval hilltop village of Monticchiello, surrounded by city walls. Then pedal toward Montepulciano, where you can spend some time browsing wine shops and cobbled alleyways before lunch on your own.  

In the afternoon, cycle longer miles and 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.

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

After breakfast transfer to Rome.

VBT No-Air Package guests: Your trip ends in Rome around 12:00 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 1:00 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 Baroque Rome. Our VBT City Information included in your Final Travel Booklet has recommendations for restaurants, museums and transportation in Rome to help you explore on your own.

Day 10 - 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 ready in the hotel reception area at the designated transfer time**.

*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.

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