Over 43 years of leadership in international
active vacations at unsurpassed value
Travel & Leisure's 2013 World's Best Award

Walking Vacation Italy: Quiet Pathways of Tuscany​

Activity Level: Easy / Moderate  |  Daily Mileage: 4 – 8 mi  |  Daily Walking: 2 – 5 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*

Pin It

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. and travel to 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 (approximately 30 minutes) 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 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 Florence with your City Information included in your Final Travel Booklet. 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 Siena / City Walk / Welcome reception

VBT No-Air Package guests: Meet your VBT Trip Leaders at 9:00 am in the lobby of Hotel Tornabuoni Beacci, via de' Tornabuoni 3, Firenze, phone + 39 055 212645. Your VBT Trip Leaders will be wearing VBT staff garments. Please come to the meeting in your walking clothes. If your arrival at the hotel is scheduled later than 9:00 am, or if you are delayed, please contact the hotel and the staff will pass your message along to your VBT Trip Leaders. If you arrive later than 10:00 am, when guests leave for Siena, you must take a taxi (approximately 1 hour) at your own expense (approximately 100 euros/$150 USD) or a bus to your Siena hotel. VBT highly recommends flying to Italy at least one day before the tour begins; this allows you to rest and recover from jet lag before you begin sightseeing and walking.

VBT Air Package and Pre-Extension guests: Meet your VBT Trip Leaders at 9:00 am in the main lobby; they will be wearing VBT staff garments. Please come to the meeting in your walking clothes.

At the hotel our VBT Trip Leaders will hold an introductory and safety talk lasting about 1 hour. After the meeting, board a private motorcoach to Siena (approximately 1 hour). Our walk starts outside the medieval walls of Siena and ends inside the city. Afterward, you'll have time to enjoy lunch and to explore a bit more on your own.

After lunch, settle in to your hotel in the city center of Siena. We will stay here for the next 3 nights.

Later this afternoon we are met by our local city expert, who will help us explore Siena during a private, guided walk. We will see the city's main monuments as we tour one of the contrade and learn about the famous horse race, Il Palio, which occurs twice every year here.

Siena is the embodiment of a medieval city. Its inhabitants pursued their rivalry with Florence right into the area of urban planning. Throughout the centuries, they preserved their city's Gothic appearance. The entire city of Siena, built around the Piazza del Campo, was created artfully, so as to complement the surrounding landscape.

This evening we gather for a welcome reception, followed by a dinner of regional specialties served in a typical Sienese Osteria, full of pictures of Il Palio and snapshots of local culture.

Day 4 - Chianti / Borgo San Felice Winery

After breakfast today we shuttle about 30 minutes outside Siena to the medieval village of San Gusmé, one of the oldest and best preserved castle-villages in the Chianti region. From here we start our loop in the scenic wine region, passing by the beautiful manicured grounds of Villa Arceno. For lunch we'll enjoy a picnic in San Gusmé, where our walking afternoon options start. All options take us to the foot of the famous Castello di Brolio, the imposing castle of the Ricasoli family. Bettino Ricasoli, a famous 19th-century politician has been credited with the development of the celebrated Chianti wine varietal.  From here, we can walk an easy stretch to the ancient village of San Felice. This former Chianti village is now a Relais & Chateux hotel. Here, our hosts will take us to the underground winery for a wine tour and tasting. Later this afternoon, we shuttle back to Siena to relax and dine on our own.

Day 5 - Siena / Monteriggioni

Take an early morning stroll around Siena and get a genuine feel for life in the city as locals begin their day with a cappuccino or two. Walk the quiet cobblestone streets back to our district, Contrada Della Chiocciola, and have breakfast at our hotel. Later choose to spend the morning shopping and exploring on your own or to join our walk from Colle Val D'Elsa to Strove. This stroll follows a stretch of the ancient pilgrimage route ‘Via Francigena' connecting Canterbury in England to Rome. We walk gentle, downhill and flat country paths in the Elsa Valley over iron-rich, sienna-hued soil.

Have lunch on your own and then choose to spend the afternoon in Siena or walking from Strove to the walled city of Monteriggioni through open sunflower fields and macchia shrub. Built in 1213, the Castle of Monteriggioni could not be conquered by the Florentines in spite of their frequent attacks. It fell only when the captain of the troops betrayed the Sienese. Stepping inside, we glimpse life as it was 800 years ago. A short shuttle will take us back to our hotel. Dinner is on our own tonight.

Day 6 - The Abbey of Monte Oliveto / Pienza

This morning a 45-minute shuttle takes us to San Giovanni d'Asso, in the Asso river valley. From here we start our walk to the tiny stone village of Chiusure, making our way along a spectacular lunar-like region of ‘Crete Senesi'. Lunch is on your own in Chiusure before we continue walking on the crest with amazing views of the valley and abbey of Monte Oliveto. The 14th-century Olivetan abbey of Monte Oliveto Maggiore is our final destination today. In the Great Cloister, we admire the frescos painted by some of the most famous artists of the Sienese school.

Later shuttle to nearby Pienza and settle in at our historic hotel, located in the ancient cloister of the San Francesco church. Before dinner, follow our Trip Leaders in an orientation walk of this elegant, small 15th-century town, hailed for its Renaissance layout. Just outside of town, discover the peaceful Pieve di Corsignano before gathering for a group dinner at a local trattoria. Taste the famous, local ‘pici all'aglione'.

Day 7 - Montalcino / Sant'Antimo Abbey / Pienza

This morning we shuttle to the hilltop village of Montalcino, famous for its Brunello wine. Ascend to its topmost “fortezza” for spectacular countryside views of the Orcia Valley, a UNESCO World Heritage Site. Then, visit one of the many enoteca or wine cellars.

Leaving Montalcino, we hike country paths and sidle along vineyards of Sangiovese grapes, olive groves and lovely hamlets. Our route descends gradually into the Starcia Valley, where we find a picturesque spot for our Tuscan picnic lunch. We continue to the Romanesque Abbey of Sant'Antimo, whose luminescent, alabaster interior shimmers with the day's changing light. From here, we shuttle back to Pienza. Stroll the small town for some wood or pottery souvenirs or enjoy the hotel swimming pool and sunny terrace.

Dinner is on our own tonight.

Day 8 - San Quirico / Bagno Vignoni

This morning a short shuttle takes us to our next starting point, San Quirico d'Orcia. This fortified, little town on the northern edge of the Orcia Valley is on the ancient pilgrimage route of Via Francigena, which brought fame and wealth to the city. We admire the Romanesque church, Collegiata, with three doorways featuring fine stone carvings. We then regroup in the Leonini Gardens for a stretching class before starting our walk. Enclosed within the ancient ramparts of the city, the gardens are a particularly lovely spot. They retain the original Renaissance structure and prove to be a well-preserved example of the traditional Italian-style garden.

Our walk leads us to Bagno Vignoni. This is a tiny spa town founded by the Romans, who discovered its thermal waters 2,000 years ago. The Medici later built a huge pool in the town's main square, where the hot water bubbles up. Have lunch at one of the cafes around the picturesque pool, or picnic just outside town near the natural waterfall.

In the afternoon, you can choose to remain in Bagno Vignoni and opt to enjoy the waters at the nearby Hotel Le Terme or in the natural springs or you can continue walking on an optional, more challenging route.

Later, we drive back to Pienza. Get ready for a festive farewell dinner in a local ristorante in the nearby hilltop village of Monticchiello, where we take in our last views of the Orcia Valley at sunset.

Day 9 - Pienza / Transfer to Rome

After breakfast transfer to Rome, arriving at about 12:00 pm. 

VBT No-Air Package guests: Your trip finishes at Hotel River Palace, via Flaminia 33, phone +39 06 830011, around 12:00 pm.

VBT Air Package guests: Arrive at our Rome hotel at approximately 12:00 pm and have the rest of the day at your leisure.

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 make the most of the “Eternal City”. You can also refer to your VBT City Information in your Final Travel Booklet, which includes maps and recommendations for restaurants, museums and transportation in Rome.

Day 10 - Depart for U.S.

After breakfast* this morning, you will transfer to the Rome airport (approximately 40-60 minutes, depending on traffic) for your departing flight. Please be sure 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.” 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.

Tour Search
Date Range
Request a
Find your next vacation
with over 145 pages
of tour information
...yours FREE!
Call now to speak
to one of our
Tour Consultants
Sign up for our newsletter and receive special offers!
E-Mail :
Facebook VBT Bicycle Tours
Pay Your Invoice