Tuscany Active Culinary Women's Hiking & Walking Tour

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

30s & 40s Adults 30-49

Families with Young Adults 20s & Beyond Best for ages 20+ (min. age 18)

Families with Teens & 20s Best for ages 16+ (min. age 14)

Families with Kids & Teens Best for ages 7-17 (min. age 4)

6 days

5 nights

Activity Levels 1-3

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We rate our trips based on a range of activity levels from 1-5.

Activity Levels None (Black)

See this trip's Activity Options & Terrain for more details.

Deluxe Hotels

4 nights, Deluxe Hotels
1 night, Casual Hotel

Learn more about where you'll stay.

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Tuscany Active Culinary Women's Hiking & Walking Tour

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

30s & 40s Adults 30-49

Families with Young Adults 20s & Beyond Best for ages 20+ (min. age 18)

Families with Teens & 20s Best for ages 16+ (min. age 14)

Families with Kids & Teens Best for ages 7-17 (min. age 4)

6 days

5 nights

Activity Levels 1-3

Tooltip Desktop

We rate our trips based on a range of activity levels from 1-5.

Activity Levels None (White)

See this trip's Activity Options & Terrain for more details.

Deluxe Hotels

4 nights, Deluxe Hotels
1 night, Casual Hotel

Learn more about where you'll stay.

2026: Sep-Oct 2027: May, Sep-Oct

From $4,599 - $4,749/person

Gourmet Adventure in Italy from Chianti to Val d'Orcia

Tuscany’s greatest pleasures are simple: beautiful walks, exceptional food and good company. Discover all three across vineyard-clad hills, medieval villages and unforgettable farm-to-table experiences.

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Highlights

  • Stroll through lush vineyards and old-world villages like Radda in Chianti and Pienza
  • Cook with locals, learning farm-to-table recipes passed down through generations—buon appetito!
  • Hike the cypress-lined white roads of southern Tuscany and sip Chianti Classico in the hills where it was born
  • Share in Italy's culinary traditions, from your first plate of handmade pasta to the last bowl-scraping spoonful of tiramisu
  • Retreat to inviting Tuscan estates and boutique hotels that pair authentic local heritage with refined modern style
Italy Tuscany Active Culinary Walking & Hiking Tour map

Italy

Start Arezzo

End Florence

Airports & Travel details*

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

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Itinerary

Close-up of guests at cooking class.

Days 1-2

Description

Get a taste of Tuscany’s rolling countryside as you trek from just outside the village of Castellina to our hotel • Explore the famed wine-growing area around Radda • Hike from one stunning vista to the next, pausing for lunch at a favorite local agriturismo • Learn to prepare a homestyle Italian meal in a hands-on cooking class led by an engaging local chef • Sip Chianti Classico and discover the traditions behind regional recipes • Relax at our beautiful hotel in the heart of the Chianti Valley.

Accommodations

Nights 1-2

Hotel Villa Campomaggio Resort & Spa
Radda in Chianti
*Deluxe Hotel

Beautiful vineyards surround this elegant retreat in the Chianti countryside—fit with a spa and wellness center housed in an ancient wine cellar. (pool, spa)

Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.

Day 3

Description

Hike from the village of Gaiole through vineyard-crowned hills and along panoramic ridgelines with sweeping views of the Chianti countryside • Learn to make traditional dishes with local hosts and enjoy an exclusive tasting of Traditional Modena Balsamic Vinegar at a favorite agriturismo • Trek past charming villages and manicured vineyards on the way to the hill town of Radda in Chianti • Join a hands-on cooking class in a converted monastery • Sip locally produced Chianti Classico wines and learn the secrets of authentic Tuscan recipes before enjoying a memorable dinner.

Accommodations
Palazzo Leopoldo

(1 night, Casual Hotel)

Night 3

Palazzo Leopoldo
Radda in Chianti
Casual Hotel

Housed in a 14th-century building in the center of Radda in Chianti, Palazzo Leopoldo reflects the character of a historic Tuscan residence. The property offers easy walking access to the town's shops and restaurants, while a spa and pool provide relaxed spaces to unwind. (pool, spa) 
 

Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.

Local cheese and wine market.

Days 4-6

Description

Journey into southern Tuscany’s Crete Senesi, famed for its moonlike landscape • Walk through the vineyards and woodlands of Montalcino, birthplace of renowned Brunello wines • Follow the strade bianche (white roads) of UNESCO-listed Val d’Orcia, home to celebrated pecorino cheese • Savor regional specialties like truffles during memorable meals showcasing local culinary traditions • Stroll through Renaissance-era Pienza, Pope Pius II’s visionary ideal city • Enjoy lunch at a friend’s gourmet trattoria, complete with a dessert-making demonstration • Soak in our hotel’s restorative thermal pools or unwind with a spa treatment • Say arrivederci to Tuscany with a leisurely hike through the countryside surrounding Bagno Vignoni.

Accommodations
Hotel La Posta

(2 nights, Deluxe Hotel)

Nights 4-5

Hotel La Posta
Bagno Vignoni
*Deluxe Hotel

Set in the medieval village of Bagno Vignoni, La Posta is an elegant boutique hotel centered around a tranquil garden courtyard. Thermal waters from the area's natural underground springs feed the hotel's pools and spa, continuing the village's long tradition as a historic spa destination. Stylish rooms, a lively bar and peaceful outdoor spaces create a relaxing place to unwind at the end of the day. (pool, spa)

Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.

Want to learn more about this trip?

Request a Detailed Itinerary! Complete with descriptions of each day, tips on travel arrangements, regional highlights and more, it’s the perfect tool to help you choose. You can easily share it with friends too!

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What's Included

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From $4,599/person

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Dates & Prices

Click on dates to see pricing, hotel or itinerary variations and to book your trip. Price is per person, double occupancy, in USD. 

Unplugged

Unplugged dates are perfect for guests who want to ride an acoustic bike.
E-bikes are available to travel companions by request only.

Solo Room Savings

We’ve made it even easier to go solo or enjoy your own space on select dates with reduced private room fees.

Your guest & room selections

1 adult

1 room, 1 bed

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Please Select a Group Size

Group size is required to show per-person pricing. Your group size can be approximate and can change.

Want to learn more about this trip?

Request a Detailed Itinerary! Complete with descriptions of each day, tips on travel arrangements, regional highlights and more, it’s the perfect tool to help you choose. You can easily share it with friends too!

Download & Share

Book with Confidence

Backroads provides flexible booking policies so that you can plan your vacation with complete peace of mind.

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From $4,599/person

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