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Tuscany's Chianti Bike Tour

A Journey through Hilltop Towns

From $4,798 - $5,148 pp dbl. occ. | 6 days / 5 nights

(+$1,660 for sgl. occ.)

Tuscany is not a destination. It's a sublime experience. Cypress-lined roads overlooking the vineyards will stop you on your bike. And no view will compare to that view. Until you round the next bend and see another. It's a wonder anyone ever finishes the rides. And that's only what you'll see. Imagine the wines, flavors and luxuries you'll discover. 

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Italy

Start Arezzo / End Florence

Tuscany Italy Map

Highlights

  • Pedal our favorite Tuscan roads—with ample van support, of course—as we wind our way from breathtaking Florence to glorious Siena
  • Luxuriate at handpicked hotels that represent Tuscany's finest, such as Castello del Nero, which houses a Michelin-starred restaurant
  • Taste Chianti and vernaccia, among other critically acclaimed regional wines that have been cultivated in the region for millennia
  • Discover idyllic hilltop towns brimming with stunning examples of medieval and Renaissance architecture
Italy

Start Arezzo / End Florence

Tuscany Italy Map

Itinerary

Day 1 Embark on a quintessential Tuscan journey on scenic routes in the Florentine countryside | Sample Tuscan specialties at an agriturismo before biking past olive orchards and vineyards | The sette ponti (seven bridges) road through well-kept villages leads us to our historic hotel.

Days 2-3 Descend into the Arno River Valley as you pedal toward the heart of the Chianti, passing through legendary wine villages like Gaiole in Chianti | Ride into the Crete Senesi, an area known for its lunar landscape | Explore Siena's medieval back streets and stunning piazza del campo, home to Italy's most important horse race, Il Palio | Learn the nuances of Tuscany's renowned red wines at an exclusive sommelier-led tasting.

Day 4 Cruise the ridge to ancient hilltop Radda, former capital of the Antica Lega del Chianti (Old Chianti League) | Visit the picturesque neighboring village of Castellina | Celebrate Tuscan-style with a Michelin-starred dinner at La Torre, our hotel's superb restaurant.

Days 5-6 Bike to Colli Fiorentini, northern Tuscany's slice of Chianti wine production | Pedal the verdant Elsa River Valley to the spectacular World Heritage town of San Gimignano, crowned by 13 towers | Celebrate la dolce vita over a glass of refreshing vernaccia, a Tuscan white wine, before heading to Florence.

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.

Please click on a date below for specific pricing and possible itinerary variations.

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C Classic Dates

2018 April
2018 August

View Private Dates

Gather your favorite people to share a Backroads adventure on a ready-to-book Private Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities. You can pick from the selection of dates below for your group; some dates are only available for 16 or more guests while other dates are available for 8 or more guests. If your party has fewer than 8 guests, or your preferred date is not available, we'll create a departure just for you. Call or email us to reserve your date.

2018 Private Trip Pricing
  • 10 or more guests: from $4,798 pp dbl occ
  • 8 - 9 guests: from $5,298 pp dbl occ
  • 6 - 7 guests: from $6,798 pp dbl occ
  • 4 - 5 guests: from $7,398 pp dbl occ
  • 2 - 3 guests: from $8,598 pp dbl occ

Please click on a date below for specific pricing and possible itinerary variations.

Don't see your ideal travel date? Make a Date

  • 8 AVAILABLE TO BOOK
    for 8 or more guests
  • 16 AVAILABLE TO BOOK
    for 16 or more guests
  • Reserved

C Classic Tours

2018 May
2018 June
2018 August

View Scheduled Dates

Prices

From $4,798 - $5,148 pp dbl. occ.
6 days / 5 nights

(+$1,660 for sgl. occ.)

Premiere Hotels

Il Borro
Il Borro

San Giustino Valdarno (1 night)

Borgo San Felice
Borgo San Felice

San Felice (2 nights)

Castello del Nero
Castello del Nero

Tavarnelle Val di Pesa (2 nights)

Activity Level

This trip is rated Levels 2-4

What's Included

Services and equipment are included.

Why Backroads

Why Travel with Backroads in Tuscany

More On This Trip

Reviews by Power Reviews ®

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Premiere Hotels

Accommodations may vary based on departure date. Any difference from what is listed below can be found by clicking on your desired date on the View Scheduled Dates or Private Dates tabs.

Il Borro

Il Borro

San Giustino Valdarno (1 night)

This family-owned hotel resides in a stunning setting atop a narrow ridge and features an acclaimed winery. A Relais & Châteaux member. (pool, spa)

Borgo San Felice

Borgo San Felice

San Felice (2 nights)

Described by the Hideaway Report as an "enchanting resort enclave set within a restored medieval hamlet fringed by olive groves and vineyards in the Chianti Classico region." A Relais & Châteaux member. (pool, spa)

Castello del Nero

Castello del Nero

Tavarnelle Val di Pesa (2 nights)

A castle with a Michelin-starred restaurant steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)  

This Trip Is Rated Levels 2-4

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next—and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do.

Daily Route Options (drag to see full )

Daily Route Options
Day EASYGOING ACTIVE AVID
Level 1 Level 2 Level 3 Level 4 Level 5
miles feet gain miles feet gain miles feet gain miles feet gain miles feet gain
1 21 1100 25 2000
2 23* 2200 33* 3200 41 4000
3 25* 1900 31* 2200 41 3300
4 24* 2100 36 2800 42 3900
5 15* 1600 36 3300 45 4300
6 15 1200
 

Note:

* Includes shuttle.

Learn more about how we determine our activity level and fully support a range of abilities and interests.

Please note that our distance and elevation figures come from Ride with GPS. Other sources (such as Map My Ride and Garmin devices) may give differing elevation figures due to different GPS and mapping technologies. Readings from a Garmin or a smart phone are influenced by other factors such as air pressure.

Meals

All breakfasts, 4 lunches, 4 dinners

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! Read on for your available bike options for this trip or view our full bike fleet in further detail.

Backroads Titanium Bikes (Included in your trip price)

Our custom-built titanium bikes are specially designed for you—and we offer different models for varied terrain so your bike is ideally suited to the region. Our custom-made bikes are included in your trip price.

Touring Bike (Included)

Road Bike (Included)

For trips departing before 4/15/18, please see available bike options here.

Backroads Custom Electric-Assist Bike (Included in your trip price)

Wishing for a little extra assistance up those hills? Our custom Backroads Electric-Assist Bike lets you experience the thrill of exploring on two wheels while providing a boost when you want it. We've modified a selection of our great Titanium Bikes with the intuitive BionX "pedal-assist" system.

Backroads Custom Electric-Assist Bike (Included)

Specialized S-Works Roubaix & Ruby ($400 rental fee)

Ride like a pro with the new top-of-the-line S-Works bike featuring ultrasmooth Shimano Di2 electronic shifting. Faster and smoother than any other bike out there, this race-ready carbon machine delivers phenomenal acceleration and handling in an ultralight, ultrapowerful package—perfect for experienced riders. The Specialized S-Works Ruby is a light, agile speed machine precisely designed for women. You can upgrade to a Specialized S-Works Roubaix or Ruby on your trip.

Specialized S-Works Roubaix (Upgrade)

Specialized S-Works Ruby (Upgrade)

Co-Motion Torpedo Tandem ($400 rental fee)

Do you prefer to spin in tandem with your partner? You'll love the Co-Motion Periscope Torpedo tandem on your Backroads trip. You can upgrade to a Co-Motion Torpedo Tandem on your trip.

Co-Motion Torpedo Tandem (Upgrade)

Also Included

  • 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

Get the Straight Talk about This Trip

We want to make sure you're on the right trip and that you have the best experience possible. Every Backroads trip is unique and this one is no exception.

Why Travel with Backroads in Tuscany

You Get the Most out of Tuscany

Our perfectly planned routes and legendary on-trip support free you to focus on enjoying your rides through stunning Tuscan landscapes, following cypress-lined roads as they wind among sunbaked hilltop villas. No other biking company covers as much of Tuscany as we do. But just as importantly, we've figured out how to ensure the experience is captivating, not grueling – with three leaders and two vans always there to back you up.

Only the Best Hotels

On this trip featuring Premiere Hotels, you can count on the best lodgings Tuscany has to offer. In fact, the hotels we've chosen in this region have higher retail room rates than those offered by any other active travel company—even when their trips cost more.

Great Bikes Included (or Upgrade)

Choose a Backroads Custom Titanium or Custom Electric Assist bike—included in your trip price. Maybe a Specialized carbon-fiber pro model is more your speed or go for double fun on a tandem. Our fleet is the best in active travel, so you don't have to roll the dice on this vital trip component. Learn more about our bike fleet.

Navigate Your Way in Tuscany

Your ride comes equipped with a Garmin Edge Explore 1000, the best bike-touring GPS device on the market. This is a Backroads exclusive, and it's included with your bike in Tuscany. If you prefer to bring your own device, we also have downloadable GPS files and of course, our good old paper directions are always available. Read more on why our navigation options are the best.

We Live in the Neighborhood

Our Trip Leaders in Tuscany live in the area and are deeply engaged in their communities, giving them unique inside knowledge they're happy to share in making your experience that much richer. They'll introduce you to people, customs and parts of town you'd likely never encounter on your own—and teach you a few local phrases to help break the ice.

Everyone at Their Own Pace

We design and support our Tuscany trips to suit mixed abilities and varied interests—so you can set your own pace, then change things up as the day unfolds. And all guests are free to do the same, traveling together or apart, with no one cramping anyone else's style. Which sounds easy in theory, but it's hard to pull off. Here's more on how we do it.

A Variety of Routes Each Day

In Tuscany you head off each morning after choosing among several expertly designed routes—all with detailed directions, mileage and shuttle options. Unlike trips with one fixed daily route (or worse, one guide that everyone's obliged to follow), you're free to enjoy the best of the region at your pace, stopping wherever you want to explore further.

Our Cultural Roots Run Deep

Thanks to our extensive connections in Tuscany, Backroads takes you off the beaten track and deep into the region's culture in ways that traditional travel can never hope to do. We know the people and their customs, the legacy of art and architecture, the complex history and politic—and if we're not sure, our amazing local experts can fill in the blanks.

A Second Van When You Need It

Backroads is the only active travel company providing two support vans in Tuscany—because we know it's essential to ensure a truly great travel experience. It doubles our ability to be there when you need us to offer hydration, lighten your load or give you a lift if it's time to take a break. Read more on why two vans make all the difference.

More Leaders to Support You

On our Tuscany trips we have an extra leader supporting you along the road—for a total of three, compared to the industry standard two. So we can be in more places at once, giving personal attention to guests traveling at their own pace. Here's more on our Trip Leaders.

In Europe Since 1988

Backroads has been welcoming active travelers to Europe since before the Berlin Wall came down. Today it's virtually our second home. We know the perfect roads and trails, the most scenic valleys and hilltop towns, the hidden churches and gem-like museums, the up-and-coming vintners and celebrated chefs—and, of course, all the best places to stay.

We've Set the Standard

For nearly four decades we've worked to earn and maintain our right to call Backroads the world's #1 active travel company. In pursuing that vision on behalf of our guests, we believe we've set the standard for our industry—captured in the Backroads Quality Guide, which clearly sets out the benchmarks of excellence, choice and support that we live by

Your Trip Will Run. Period.

Under our Book with Confidence policy, your Backroads trip will run even for one or two people (or a family of three or four), subject to a nominal extra fee. Or transfer to another trip, and we'll give you a credit. It's all part of our trademark commitment to treating guests with integrity, transparency and total accountability. Read all the details.

We Know Where We're Going

Tom Hale has been keeping Backroads on track, with one eye on the horizon, since 1979. His passion for active travel, and for ensuring the highest-quality travel experience, is evident in every detail we add to make a guest's trip unforgettable—and the fact he's right there in the office, making it happen. To hear Tom describe his vision, watch our video.  

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