Bicycling and Walking Vacations Since 1971 Call a VBT Tour Consultant: (800) 245-3868

Italy: The Quiet Pathways of Tuscany

Experience the legendary landscapes of Tuscany on foot as well as sample the region’s celebrated wines and savor fresh, flavorful Tuscan cuisine while staying in converted monasteries in Pienza and Siena, two Tuscan jewels.

  • 10 Days
  • Activity Level: Easy / Moderate
  • Daily Mileage: 4 - 8 mi
  • Daily Walking: 2 - 5 hr
  • Small Groups: 20
  • Walking Activity
  • Ideal for those who walk for a morning or afternoon on a regular basis. Footing may be on a variety of surfaces. No extended ascents or descents, but some rewarding climbs.
  • Airfare Packages Available

Download Our Free Italy Travel Guide

Why You'll Love This Tour


Italy: The Quiet Pathways of Tuscany

Lush, rolling hills laced with verdant vineyards and cypress trees, fertile meadows awash with vibrant sunflowers and poppies, picturesque hilltop villages steeped in Renaissance history. Experience the legendary landscapes of Tuscany on foot with VBT. Join us as we explore the magnificent piazzas of Siena and Pienza, discover the thermal wonders of Bagno Vignoni, and admire the colorful frescoes of Monte Oliveto Maggiore. We’ll also sample the region’s celebrated Chianti and Brunello wines, and savor fresh, flavorful Tuscan cuisine during al fresco lunches in scenic San Guzme and the picturesque Starcia Valley.

Cultural Highlights

  • Rise early for a morning stroll and cappuccino with Sienese locals.
  • Taste Chianti classico in the cellars of a Relais & Châteaux agriturismo.
  • Walk the medieval city of Siena with a local expert.
  • Relax in a classic Renaissance garden in San Quirico d’Orcia.
  • Walk the historic Via Francigena pilgrimage route
  • Indulge in the natural hot springs of Bagno Vignoni.
  • Explore the UNESCO World Heritage Sites of Siena and Pienza.
  • Savor Tuscan picnics in San Gusmé and the Starcia Valley.
  • Walk the classic Tuscan landscape in the Crete Senesi.
  • See the frescoes at 14th-century Monte Oliveto Maggiore.
  • Sample soft Brunello wine in a Montalcino enoteca.

What To Expect

This tour features a combination of mostly unpaved footpaths, well-worn trails in the woods or in the countryside, and some very short stretches on paved road. In Chianti, you also walk on typical “white roads’ (well-traveled gravel roads shared by occasional auto traffic). Easy flat stretches alternate with some short hills. Optional, more moderate walks or hikes are often available. On rainy days, the footpaths can be wet and muddy. City walks are on paved and cobblestone roads. Our VBT support vehicle is available at specific meeting points for those who need assistance. Ideal for enthusiastic beginners and experienced walkers. Several of the walks require a transfer from our hotel to the start of the walk. Our Trip Leaders often use this time in the van for our morning route review, so we can enjoy a more leisurely morning at breakfast.

Average Daily Mileage: 4 – 8 miles (6.4–12.8 km)
Average Walking Time: 2 – 5 hours

Climate Information

Average High/Low Temperature (°F) – Florence
Apr  68º/46º  May  75º/53º  Jun  84º/58º  Sep 81º/58º  Oct 69º/51º

Average Precipitation (in.) – Florence
Apr 3  May 3  Jun 3  Sep  3.5  Oct 4

What’s Included:

Walking Vacatopm Only – without Air

  • 6 nights in historical 4-star hotels
  • 11 meals – 6 breakfasts, 2 lunches, 3 dinners

Air Package Plus

  • Roundtrip international airfare
  • 8 nights in historic 4-star hotels
  • 13 meals – 8 breakfasts, 2 lunches, 3 dinners
  • Transfers
  • AND the option to add our Low-Cost Trip Extension: Pre-trip: Florence– 2 nights for only $395 • Post-trip: Rome – 2 nights for only $395

Both Vacation Options Include

  • Service of two bilingual VBT Trip Leaders
  • On-tour vehicle support
  • FREE use of our custom VBT walking poles
  • Daily route directions and maps
  • Welcome reception
  • Sightseeing and cultural activities
  • Special Good Buy Discount
  • 5% Frequent Traveler Credit to use on your next VBT vacation. See details.

New! Reading List

Click here to download our Suggested Reading List.

Dates & Prices
Refine Your Tour Results
  • Select Airport
  • Select Months

Departure &
Return Dates

Now Showing:


Air Package Plus 10 Days Includes round-trip international airfare


Air Package Plus 10 Days Includes round-trip international airfare


Air Package Plus 10 Days Includes round-trip international airfare

Land Only

Air Not Included,
Departs after Air Package Plus.
Tue, Sep 26
to Thu, Oct 5

Departure: Tuesday, September 26
Return: Thu, Oct 5

From $4,495 $3,995
  • From $3,995
  • Tue, Sep 26
    to Thu, Oct 5
  • (800) 245-3868
From $4,845 $4,345
  • From $4,345
  • Tue, Sep 26
    to Thu, Oct 5
  • (800) 245-3868
From $4,595 $4,095
  • From $4,095
  • Tue, Sep 26
    to Thu, Oct 5
  • (800) 245-3868
Thu, Sep 28
to Wed, Oct 4

Departure: Thursday, September 28
Return: Wednesday, October 4

From $3,445 $2,945
  • From $2,945
  • (800) 245-3868
Tue, Oct 10
to Thu, Oct 19

Departure: Tuesday, October 10
Return: Thu, Oct 19

From $4,045
  • From $4,045
  • Tue, Oct 10
    to Thu, Oct 19
  • (800) 245-3868
From $4,395
  • From $4,395
  • Tue, Oct 10
    to Thu, Oct 19
  • (800) 245-3868
From $4,145
  • From $4,145
  • Tue, Oct 10
    to Thu, Oct 19
  • (800) 245-3868
Thu, Oct 12
to Wed, Oct 18

Departure: Thursday, October 12
Return: Wednesday, October 18

From $2,995
  • From $2,995
  • (800) 245-3868

Air Package Plus Single Supplement: $595 | 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. 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.

2007399E-LOGO AFKLM QStar Alliance


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

Depart from home 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 p.m. 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  347 85 74 265. 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 Florence with your City Information as a guide. In the evening, relax in one of the city’s many fine restaurants and savor the local cuisine.

Hotel: Hotel Tornabuoni Beacci

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 a.m. in the main lobby on the fourth floor of Hotel Tornabuoni Beacci (Via de’ Tornabuoni 3, Firenze; tel: +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 a.m., 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 a.m, when your group departs for Siena, you must take a taxi (approximately one hour) at your own expense (approximately 100 euros) 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 a.m. 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 one hour. After the meeting, board a private motorcoach to Siena (approximately one hour). Your 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. You will stay here for the next 3 nights.

Later this afternoon you are met by our local city expert, who will help us explore Siena during a private, guided walk through the historic center, a UNESCO World Heritage Site. You will see the city’s main monuments as you tour one of the contrade (small, distinctive neighborhoods) and learn about the famous horse race, Il Palio, which occurs twice every year and is conducted by teams from each of the city’s commune.

Siena is the sublime embodiment of a medieval city. Its inhabitants pursued their rivalry with Florence right into the Renaissance, but then lacked the funds to keep up. Rather than demolish the original structures in favor of newer buildings, the urban plan of Siena retained its beautiful Romanesque-Gothic appearance. The entire city was built around the shell-shaped Piazza del Campo, and many of its buildings (especially the Cathedral with its green, red and black marble exterior) complement the surrounding landscape.

This evening you will 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.

Hotel: Hotel Athena
Meals: B (included for Air Package guests only), D
Daily Options: Morning: 2 miles (3.2 km) on flat paved and cobblestone streets.
Afternoon: 1-mile (1.6-km) city walk on paved and cobblestone streets with some ascents in the city center.

DAY 4: Chianti / Borgo San Felice Winery

After breakfast, you’ll shuttle about 30 minutes outside Siena to medieval San Gusmé, one of the oldest and best-preserved castle-villages in the Chianti region. From here, you’ll start your walking loop in the scenic wine region, passing by the beautiful manicured grounds of Villa Arceno. For lunch, enjoy a picnic in San Gusmé with Tuscan specialties. In the afternoon our walking option starts at the foot of the famous Castello di Brolio. You’ll visit this 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 you can walk an easy stretch to ancient San Felice, a former Chianti pieve (hamlet) that is now a 5-star Relais & Chateux agriturismo resort. Here, our hosts will take us to the underground winery for a wine tour and tasting. Later this afternoon, you’ll shuttle back to Siena to relax and dine on your own.

Hotel: Hotel Athena
Meals: B, L
Daily Options: Morning: 3.8 miles (6.1 km) on flat to lightly rolling gravel road.
Afternoon: 1.8 miles (2.8 km) on flat to lightly rolling gravel road.

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 Pantera, and have breakfast at your hotel. Later, choose to spend the morning shopping and exploring on your own, or join our walk from Strove to the walled city of Monteriggioni through open sunflower fields and macchia shrub. This stroll follows a stretch of the ancient pilgrimage route “Via Francigena” connecting Canterbury in England to Rome.

Have lunch on your own in Monteriggioni. 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, you’ll glimpse life as it was 800 years ago. A short shuttle will take us back to Siena and our hotel. The rest of the day is free. Dinner is on your own tonight.

Hotel: Hotel Athena
Meals: B
Daily Options: Morning: 5.6 miles (9 km) on flat to rolling gravel road, dirt path, and paved country roads, with a last ascent on steps.
Early morning or afternoon: 1.5 miles (2.4 km), optional self-guided city walk in Siena.

DAY 6: The Abbey of Monte Oliveto / Pienza

This morning, a 45-minute shuttle ride brings you to San Giovanni d’Asso in the Asso river valley. From here you’ll start your walk to the tiny stone village of Chiusure, making our way along a spectacular lunar-like region of Crete Senesi, which literally means “Sienese clay.” These undulating hills, dotted with olive groves and vineyards, present the distinctive rolling landscapes we associate with Tuscany. Lunch is on your own in Chiusure before you continue walking on the crest with amazing views of the valley and the 14th-century abbey of Monte Oliveto Maggiore, our final destination today. In the Great Cloister, you’ll admire 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 your Trip Leaders in an orientation walk of this elegant, small 15th-century town, hailed for its Renaissance design. Just outside of town, you’ll discover the peaceful Pieve di Corsignano before gathering for a group dinner at a local trattoria. Here is a great opportunity to taste the famous, local pici all’aglione (Tuscan pasta with tomato-garlic sauce).

Hotel: Il Chiostro di Pienza
Meals: B, D
Daily Options: Morning: 3.2 or 4.4 miles (5.1 or 7 km) on rolling dirt roads.
Evening: 1.2 miles (1.9 km) on paved roads with some cobblestones.

DAY 7: Montalcino / Sant'Antimo Abbey / Pienza

This morning, you’ll shuttle to the hilltop village of Montalcino, famous for its Brunello wine. Explore this fascinating village on your own, perhaps ascending its topmost fortezza (stronghold) for spectacular countryside views of the Orcia Valley, a UNESCO World Heritage Site, and maybe visiting one of the many enoteca, or wine cellars. Your Trip Leaders will also offer an optional morning walk.

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

Dinner is on our own tonight.

Hotel: Il Chiostro di Pienza
Meals: B, L
Daily Options: Morning: 1.6 to 4.5 miles (2.5 to 7.2 km) on rolling dirt roads and paths, including ‘white’ gravel roads, typical of Tuscany.
Afternoon: 1.9 miles (3 km) on gradually descending paths. Some rocks in the last stretch

DAY 8: San Quirico / Bagno Vignoni

This morning, a short shuttle ride takes you to our next starting point, San Quirico d’Orcia. This small fortified 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. You’ll admire the Romanesque church, Collegiata, with three doorways featuring fine stone carvings. You’ll 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 whose Renaissance design is a well-preserved example of the traditional Italian-style garden.

Your walk leads to Bagno Vignoni, 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 to enjoy the waters at the nearby Hotel Le Terme or in the natural springs; continue walking on an optional, more challenging route; or shuttle back to relax at the hotel swimming pool.

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

Hotel: Il Chiostro di Pienza
Meals: B, D
Daily Options: Morning: 3.2 miles (5.1 km) of gradual climb, then gradual descent on gravel roads.
Afternoon: 2 miles (3.21 km) on lightly rolling gravel roads.

DAY 9: Pienza / Transfer to Rome

After breakfast transfer to Rome, arriving at about noon.

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

VBT Air Package guests: Arrive at our Rome hotel about noon 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, which includes maps and recommendations for restaurants, museums and transportation in Rome.

Hotel: River Palace Hotel
Meals: B

DAY 10: Depart for home

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.

Meals: B

Tuscan Walking Tour Map

Download Itinerary PDF

Download Now

Hotel Athena

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 services, as well as splendid views of the surrounding countryside from its rooftop San Marco terrace. Relax a while here with a glass of wine, and admire the gently rolling hills, cypress trees and old farmhouses that add touches of color to the skyline. All rooms have air conditioning, a private bath with hairdryer, safe and flat-screen TV.
Free WiFi Included

Hotel Tornabuoni Beacci

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

River Palace Hotel

Located in the heart of Rome, 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 pleasant breakfast room, a stately bar and a friendly staff. VBT has reserved only superior rooms, which are larger than the otherwise rather small standard bedrooms. All guest rooms have a private bath, air conditioning, an LCD-screen satellite TV, minibar and safe. You’re sure to find this a great spot from which to discover the “Eternal City,” with the Vatican just a ten-minute walk away and a metro stop only 300 feet (91.4 meters) from the front door. WiFi is available throughout, and an Internet terminal is also available in the lobby.
Free WiFi Included

Il Chiostro di Pienza

Set in the heart of medieval Pienza, the four-star Il Chiostro di Pienza is housed in a former 15th-century Franciscan convent. 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 Italian specialties. Though its air-conditioned rooms vary in layout and décor, all feature cable/satellite television, a minibar and private bath with shower and hairdryer.
Free WiFi Included

Italy Walking Tour Photo Gallery


Enjoy Your Vacation Longer With LOw-Cost Trip Extensions

Tuscan Bike Tour Pretrip in Florence

Pre-Trip Extension - Florence

2 nights for only $395

Post-Trip Extension - Rome

2 nights for only $395

Get The Most Value With VBT

Travel Protection Plan

  • VBT takes pride in making sure every step is taken to ensure your perfect vacation, but unexpected events can arise.
  • Our exclusive Preferred Vacation Protection Plan provides extra peace of mind.
  • What could be more precious to protect than you and your loved ones?

Air Advantage

Secure, easy, pay at your own pace...
VBT is committed to providing unsurpassed value to our travelers, including airfare. Fly aboard world-class airlines, enjoy extended stays, and even choose your departure times and routes with Customized Air and save even more on your vacation.

Refer a Friend

When you introduce new travelers to VBT, you’ll receive $150 in travel credits toward your next VBT vacation when the person you refer to us returns from her or his first trip. You can also get cash bonuses when you make additional referrals. Your friends benefit, too, with a $100 discount on their first VBT trip.

Request A
Free Catalog

Find your next vacation with over 130 pages of tour information
… yours FREE!

Get Yours Now

Talk to a VBT Tour Consultant

(800) 245-3868

Mon – Fri 8:30am – 6:30pm EST
Saturday 10:00am – 3:00pm EST

Search Tours Request a Reservation

Related Tours You Might Be Interested In

Spain: A Walking Tour of Basque Country

Spain: A Walking Tour of Basque Country

From only $3,595

Spanning the border between two nations, framed by the soaring Pyrenees and the Bay of Biscay, the autonomous region of Spain known simply as Basque Country offers spellbinding landscapes, superlative cuisine and warm, welcoming—and intensely proud—people.

10 Days
Take Me There
Beautiful Amalfi Coast Walking Vacation

The Amalfi Coast & Capri

From only $3,995

Few places can rival the dramatic beauty of the Amalfi Coast and Capri, an enchanting region where walking trails like the iconic Path of the Gods give way to panoramic views of rugged mountains plunging into the Mediterranean Sea. Off the trail we’ll visit the ruins of Pompeii and visit scenic seaside towns like Positano and Ravello.

10 Days
Take Me There
Lake Como on Walking Tour

Walking the Italian Lakes

From only $3,995

Stroll the scenic shores of Italy’s Lake District including Como, Maggiore and Orta and explore their opulent Renaissance villas. Along the way we’ll pause to savor the acclaimed wines and cuisine of Piedmont and Lombardy.

10 Days
Take Me There

© 2017 VBT. All Rights Reserved.
VBT Bicycling and Walking Vacations, 426 Industrial Ave, Suite 120 Williston, VT 05495
Talk to a VBT Tour Consultant: (800) 245-3868

Travel+Leisure® and World’s Best Awards are trademarks of Time Inc. Affluent Media Group and are used under license. From Travel+Leisure Magazine, August 2017 ©2017 Time Inc. Affluent Media Group. Used under license. Travel+Leisure and Time Inc. Affluent Media Group are not affiliated with, and do not endorse products or services of VBT Bicycling and Walking Vacations.