Tuscany & Umbria Family Bike Tour - Older Teens & 20s

The Land of the Renaissance from Rome to Florence

From $4,599 pp dbl. occ. | 6 days / 5 nights

(+$800 for sgl. occ.)

No doubt you'll arrive with certain expectations of Tuscany and Umbria. But somehow the sensory feast is still a wonderful surprise. The sheer beauty of olive groves and vineyards. The slow pace of life. The symphony of flavors in traditional dishes. And the rich passione of the locals. Expectations exceeded? Just another day in the heart of Italy with your family.

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Start Arezzo / End Florence

Tuscany and Umbria bike tour map


  • Discover the medieval ambience and ancient traditions in the streets and cafés of charming hilltop towns
  • Taste outstanding local wines, like Sagrantino, Montefalco Rosso and Vino Nobile di Montepulciano
  • Delight in hearty ribollita, panzanella, fresh pastas and delicious bruschetta—cornerstones of the regional cuisine
  • Connect with our friends and colorful locals, including at an exclusive agriturismo (working farm) dinner

Start Arezzo / End Florence

Tuscany and Umbria bike tour map


Days 1-2 Start your journey in Arezzo, where la vita è bella (life is beautiful) | Ride tranquil bike paths flanked by bright red poppies, cypress trees and undulating hills | After soaking up beautiful views from Montefalco, savor a farm-to-table lunch in the Valle Umbra | Ride to the timeless town of Spoleto to browse for ceramics, linens and olive wood pieces | Sample fine vintages of velvety Sagrantino, Umbria's prize vino rosso | Experience warm Umbrian hospitality and hearty cuisine at a dinner in the countryside.

Day 3 Discover the ancient village of Spello en route to the World Heritage site of Assisi, where we take time to enjoy lunch and explore the historic sites of St. Francis's famed home | Find your inner Italian royalty as you experience a night in a true Umbrian castle, Castello di Monterone | Enjoy sweeping views of the Perugian countryside where the produce for our gourmet meal is grown!

Days 4-5 Welcome to Tuscany! | Bike through the lush Val Niccone past tobacco fields, olive groves and sunflowers | Ride at your own pace through the hillsides of Montepulciano | Take time to explore Montepulciano's historic city center, revered for its 3,000-year-old Etruscan walls | Unwind at La Corte dei Papi, our enchanting hotel and a perennial favorite in the region | Visit historic hilltop Cortona, birthplace of many Renaissance artists and the setting for Under the Tuscan Sun |  Taste splendid Tuscan wines, like Vino Nobile di Montepulciano, Brunello di Montalcino and Cortona's very own rendition of Syrah. 

Day 6 Take a morning ride through the famous battlegrounds of Rome versus Carthage, biking through the colorful landscape of the border region between Tuscany and Umbria.

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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F Family Dates - Older Teens & 20s

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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 a large selection of dates for your group of 8 or more. Call us for date availability. If your party has fewer than 8 guests, or if your preferred date is not available, we'll create a departure just for you.

2019 Private Trip Pricing
  • 10 or more guests Guests: from $4,399 pp dbl occ
  • 8-9 Guests: from $5,099 pp dbl occ
  • 2-7 Guests: Give us a call or reach out here!

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

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    for 8 or more guests
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The sky’s the limit! Tell us what your dream trip would be and we'll make it happen! Whether you're looking for a honeymoon trip for 2, a 30-person family reunion or a 100-person corporate trip, we can do it all. A dedicated Custom Trip Consultant will work closely with you to bring your dreams to reality. Call us at 800-462-2848 to speak with your Custom Trip Consultant or click on the button below.



F Family Tours - Older Teens & 20s


From $4,599 pp dbl. occ.
6 days / 5 nights

(+$800 for sgl. occ.)

Traveling with Kids

Premiere Hotels*

Hotel Villa Zuccari

San Luca (2 nights)

* Casual Hotel
Castello di Monterone

Perugia (1 night)

Relais La Corte dei Papi
La Corte dei Papi

Cortona (2 nights)

Activity Level

This trip is rated Levels 1-3

What's Included

Services and equipment are included.

Why Backroads

Why Travel with Backroads in Tuscany and Umbria

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.

Hotel Villa Zuccari

San Luca (2 nights)
* Casual Hotel

In the Zuccari family since the 1500s, this gorgeous villa is surrounded by expansive rose-filled gardens and the vineyards of Montefalco. (pool)

Castello di Monterone

Perugia (1 night)

This 11th-century castle-turned-luxury hotel overlooks the vineyard-rich valley of Perugia and features bright airy rooms and Turkish baths. (pool, spa)

Relais La Corte dei Papi

La Corte dei Papi

Cortona (2 nights)

Feel welcomed like family by owner David Papi at this refined and superbly appointed 18th-century country home, rated one of the top hotels in Italy and a Backroads-exclusive property. (pool)

This Trip Is Rated Levels 1-3

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
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 11* 600 19 900 27 1700
2 19* 1100 24 1700 35 2300
3 12* 300 22* 1500 42 2700
4 25* 1200 30* 1400 42 2700
5 12* 700 20* 1700 34* 2400 45 2800
6 9* 700 16 1100


* 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 may give differing elevation figures due to different GPS and mapping technologies and other external factors.


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.

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)

Performance Road Bike (Included)

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)

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 and Umbria

A Variety of Routes Each Day

In Tuscany and Umbria 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.

More Leaders to Support You

On our Tuscany and Umbria 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.

Everyone at Their Own Pace

We design and support our Tuscany and Umbria 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.

Great Bikes Included

Our custom-designed titanium bikes are best in class. From avid cyclists to easygoing riders, we believe that everyone deserves a seriously great bike to match their riding style. Learn more about our bike fleet.

Kids Who Aren't Kids Anymore

Only Backroads offers active trips in Tuscany and Umbria designed for families with older teens and 20s. These trips are aimed at you and the amazingly grownup members of your clan—whether they're almost high school grads, already in college or further along. Find out more in this blog post.

Navigate Your Way in Tuscany and Umbria

Your ride comes equipped with a GPS device, preloaded with all the routes and route options for your trip. 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.

Your Trip Will Run. Period.

Under our Book with Confidence policy, your Backroads trip will run even for a single family of three or four people, 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.

A Second Van When You Need It

Backroads is the only active travel company providing two support vans in Tuscany and Umbria—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.

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

We Live in the Neighborhood

Our Trip Leaders in Tuscany and Umbria 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.

Quality You Can Measure

Since 1979, Backroads Founder and President Tom Hale has shown that staying #1 means constantly evaluating our performance using the best possible source of information: our guests. As we systematically analyze your feedback on our trip consultants, leaders, hotels, meals and on-trip activities, we never stop working to make a great company even better.