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
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
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
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
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
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
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
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