Travel Guides: Italy Travel Guide: Overview
In Southern Europe—right in the heart of the Mediterranean—lies a boot-shaped country stuffed to the brim with culture, history and fine cuisine.
Biking
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Tuscany Bike Tour
A Taste of Italy from Pienza to Siena & Chianti
Couples, Friends & Solos
6 days 5 nights
Activity Level: 2-5
Casual & Casual Plus Hotels
From: $4,199 - $4,749 pp dbl occ
($600 for sgl occ)
Bike from one unbelievable view to the next. Marvel at extraordinary Renaissance art and architecture. And savor delicious pecorino cheese, homemade pasta, fruity olive oils and celebrated Chianti and Brunello di Montalcino wines. Few things in this world live up to the hype. We're happy to report that everything you've heard about Tuscany is true.
Italy Tuscany Biking Tour
Italy
Start Arezzo / End Florence
Start/End locations may vary. Do not book flights until your trip details are confirmed.
Highlights
- Capture a quintessential Tuscan experience, biking from south to north through a beautiful rolling landscape
- Sample fine wines in charming enotecas and dine on handmade pastas, bruschetta and other local specialties
- Explore some of the region's most iconic towns, including Pienza, Montalcino, Siena and Radda in Chianti
- Pedal peaceful roads and green hills past picturesque Brunello, Chianti Classico and Sangiovese vineyards
Videos
Itinerary
Accommodations may vary based on departure date.
6 Days Casual & Casual Plus Hotels
Accommodations may vary based on departure.
Days 1-2
Description
Experience some of the region's must-see highlights, including Pienza, a World Heritage site famous for pecorino cheese, exquisite ceramics and Renaissance architecture | After a nourishing spread of Tuscan specialties, ride cypress-lined roads through southern Tuscany's open undulating terrain into the Val d'Orcia | Montepulciano, with its winding streets and hidden squares, invites a stroll | Enjoy post-ride poolside lounging at our welcoming hotel.
Accommodations
Albergo le Terme
Bagno Vignoni
| Casual Hotel This enchanting family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)
Day 3
Description
Climb by bike through a sea of vineyards to the wine village of Montalcino, where enoteche pour samples and remarkable views reach as far as Siena on a clear day | Leave Val d'Orcia behind as you climb up the ridgeline to enter Crete Senesi area, where we reach an agriturismo with farm fresh Tuscan food | Our hotel's terrace provides an idyllic venue for a sunset aperitivo.
Accommodations
Borgo Casabianca
Asciano
| Casual Plus Hotel An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool)
Days 4-6
Description
Engage in a fascinating Q&A session with a renowned local author | Bike past the exposed chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine and Sienese paintings | Sun-drenched pastures dotted with sheep and crumbling stone farmhouses give way to oak woodland and olive groves | Take some time to explore Siena on your own | Ride rolling hills alongside Chianti Classico and Sangiovese vineyards | Get to know ridgetop Radda, the center of Chianti wine production | Looking for a gift? Family-owned Ceramiche Rampini offers ceramics hand-painted in the Renaissance tradition.
Accommodations
Villa Curina Resort
Curina
| Casual Plus Hotel A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool)
Dates & Prices
The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind — you won't be charged to transfer to a different trip before your final payment is due. View cancellation policy.
Click on dates for pricing, itinerary variations and to book your trip. Price is per person, double occupancy.
May 2023
May 28 - Jun 2
Sold out
July 2023
August 2023
September 2023
Looks like you’re traveling with a smaller group
Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.
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From our Guests
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#MyBackroadsTrip
Share your adventure #MyBackroadsTrip
Activity Level: 2-5
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.
Daily Route Options
What's Included
Available Bike Options
The key to a stellar day's ride is a bike that's perfectly in tune with your cycling style… Backroads has you covered with the best bike fleet in the world! Please note that bike requests are subject to availability and prioritized based on the date they're submitted.
Click the arrow to see all bike options.
Backroads Performance Road Bike
Performance Road Bike
Included in your trip price
This custom-designed titanium bike is lightweight and responsive, featuring Shimano Ultegra Di2 electronic shifting, 11-speed compact gearing, a premium Mavic Ksyrium Pro wheelset and a full carbon fork.
Backroads Touring Bike
Touring Bike
Included in your trip price
A proven classic, this custom-designed titanium bike is suited for a wide range of cyclists. It features a comfortable ergonomic seat and a long wheel base that add to the bike’s control and stability.
Backroads Electric-Assist Bike
Electric-Assist Bike
Included in your trip price
Keep pace or zip ahead, pedaling with an electric boost. This bike provides plenty of power to flatten the hills and more than enough battery range to cover the distance.
Min. age to ride e-bike: 16+
Cannondale Synapse Pro Carbon Bike
Carbon Bike
Ride like a pro with the top-of-the-line carbon Cannondale Synapse Hi-Mod Red ETAP AXS. Delivering phenomenal acceleration and handling in a light and powerful package.
$650 rental fee; subject to availability
Co-Motion Torpedo Tandem Bike
Tandem Bike
This hand-built frame features Co-Motion's custom-designed cro-moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train, and a custom, upgraded wheelset. For experienced tandem riders.
$400 rental fee
Also Included
- All breakfasts, 4 lunches, 4 dinners
- Expertise and services of our experienced Trip Leaders
- Snacks and beverages between meals
- Additional guides and experts from the region on many trips
- Van shuttles to support a variety of route options
- Comprehensive Travel Planner with detailed pre-trip information
- Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
- All gratuities at hotels and restaurants
- Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
- On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
- Trailercycles, carriers, and kid-sized helmets for Family Trips
- Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
- Park and other entry fees
- Fares for trains, ferries and other modes of travel as listed in the Travel Planner
- Select coach transfers
- Baggage transfers and porterage
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