Tuscany Active Culinary Walking & Hiking Tour

Food Adventure in Italy from Chianti to Florence

From $4,149 - $4,299 pp dbl. occ. | 6 days / 5 nights

Call for single supplement pricing

Discover the joys of the Tuscan table as you learn the secrets of Italian cooking from our charming local friends. Celebrate fresh seasonal ingredients prepared with passion, yet minimal manipulation. Slow down and let food be the focal point of the day. And savor this journey that nurtures both body and spirit.

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Start Arezzo / End Florence

Start/End locations may vary. Do not book flights until your trip details are confirmed.

Tuscany Italy Map


  • Walk through brimming vineyards and be welcomed by nonne (grandmothers) in old-world villages
  • Prepare and savor farm-to-table recipes passed down through generations—buon appetito!
  • Hike the cypress-lined white roads of southern Tuscany and hunt for the region’s prized truffles
  • Relish handmade cuisine, from your first plate of pasta to your final bowl-scraping spoonful of tiramisu

Start Arezzo / End Florence

Start/End locations may vary. Do not book flights until your trip details are confirmed.

Tuscany Italy Map


Days 1-2 Meander through vineyards, woodland and Renaissance hill towns | Get a taste of the region’s undulating terrain as you walk from Castellina to Vèscine | Homer once called olive oil “liquid gold”—you’ll call it “delicious” during our exclusive degustazione (tasting) | Explore Panzano, home to numerous fine Chianti wineries | High ridges and peaceful forests lead the way to our lunch spot in the home of a local friend—a one-of-a-kind experience! | Join pizzaiolo and Backroads’ friend Mario to learn how to let the pizza dough fly.

Day 3 From the tiny hamlet of Vertine, hike from one unbelievable vista to the next, stopping for lunch at a local home for an alfresco feast among the grapevines | In Radda, enjoy a private wine talk and pour—and balsamic vinegar tasting—with our friend Fabrizio | Prepare a home-style Italian meal alongside locals in the cucina of their cooking school.

Days 4-6 Follow the strade bianche (white roads) of southern Tuscany’s Val d’Orcia | Head south to the crete senesi (chalk hills) to hunt for truffles | Wander in Renaissance-style Pienza, Pope Pius II’s utopian village | Lunch takes place at an agriturismo (working farm) and dinner is a hands-on affair as we prepare piatti tipici, typical Tuscan dishes | Say arrivederci to Tuscany with a leisurely hike in the countryside surrounding Bagno Vignoni.

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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  • Private Trip
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C Classic 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. Call or email us to reserve your date.

Private Trip Pricing
  • 10 or more Guests: from $3,999 pp dbl occ
  • 9 Guests: from $4,499 pp dbl occ
  • 8 Guests: from $4,699 pp dbl occ
  • 2-7 Guests: Give us a call or reach out here!

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

View Scheduled Dates

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.



C Couples, Friends & Solos Tours


From $4,149 - $4,299 pp dbl. occ.
6 days / 5 nights

Call for single supplement pricing

Casual Plus Hotels*

Relais Vescine
Il Borgo di Vèscine

Radda in Chianti (2 nights)

* Casual Plus
Palazzo Leopoldo
Palazzo Leopoldo

Radda in Chianti (1 night)

* Casual Plus
Albergo Le Terme
Albergo le Terme

Bagno Vignoni (2 nights)

* Casual Plus

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

Reviews by Power Reviews ®

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Casual Plus 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.

Relais Vescine

Il Borgo di Vèscine

Radda in Chianti (2 nights)
* Casual Plus

A 13th-century hamlet handsomely restored as a welcoming hotel with unsurpassed views of the Tuscan countryside. (pool)

Palazzo Leopoldo

Palazzo Leopoldo

Radda in Chianti (1 night)
* Casual Plus

Located in the heart of the Chianti region, this elegant 14th-century manor house features spacious guest rooms with original frescoes. (pool, spa) 

Albergo Le Terme

Albergo le Terme

Bagno Vignoni (2 nights)
* Casual Plus

This charming family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa) 

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 4 600
Tutti a Tavola Cooking School (4 Hours)
2 5* 500 6* 500 8* 1000
Chianti Classico Winery Visit & Lunch (1.5 Hours)
Pizza Making Demonstration (1 Hour)
3 5* 600 6* 800 7* 1300
Wine & Balsamic Vinegar Tasting (1 Hour)
4 3* 400 4* 700 9* 1200
Truffle Talk with Lunch (1.5 Hours)
5 3* 500 5* 700 9* 1400
Cooking Demonstration & Dinner (4 Hours)
6 2* 600

Note: The terrain on this trip includes a mix of rolling vineyard paths, gravel roads and wooded trails.

* 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, 5 lunches, 4 dinners

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

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.

More Leaders to Support You

On our Tuscany trips we have an extra leader supporting you along the trail—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.

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.

The Right Local Pairings

Our Trip Leaders combine deep local expertise with a firm grasp of North American expectations around quality of service. By the same token, we pair experienced Backroads leaders with local guides who know how to cater to your needs while cracking open the culture or natural history in ways that are meaningful, memorable and often magical.

The Value of Casual Hotels

In addition to the ideal balance of comfort and hospitality in our choice of lodgings, this trip featuring Casual Hotels includes nearly all of your meals, plus everything from cocktail receptions to the best snacks along the road. So there's rarely a need to reach for your wallet – we've got you covered.

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.

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.