Tuscan Hilltowns Women's Adventure

Trip Length 7 Days
Group Size 4-14
Activity level
Starting from
$3,799 for REI Members
$4,199 for non-members

Departure dates will be announced soon.

We can let you know as soon as they are.

Immerse yourself in the Tuscan way of life on this seven-day ramble through friendly villages, ancient cities and the timeless countryside.

Suitable for anyone who wants to truly experience this region of Italy, this trip blends hiking with history, cultural experiences and to-die-for food and wine, all within the storybook loveliness of the Tuscan landscape. From Florence, we set out to see Tuscany by foot. Each day brings a new trail and new scenery. We walk through vineyards and olive groves, follow a Middle Ages pilgrim’s path past medieval fortresses and Renaissance villas, explore villages like San Gimignano and Colle di Val d’Elsa, and stroll cypress-lined country lanes with the steeples of ancient Volterra beckoning us across the valley.

A sampler of quintessential Italian experiences add flavor to our journey. We spend two nights in a Tuscan villa, tour a traditional alabaster workshop and marvel at 3,000-year-old Etruscan artifacts. Our trip ends in beautiful Siena, city of the Medicis, where you can sip one more perfect cappuccino under the Italian sun.

Open trip gallery
See all trip photos

Trip Highlights

  • Explore Tuscany's postcard-perfect countryside and medieval hill towns
  • Hike to Volterra, San Gimignano, Siena and Chianti
  • Enjoy an Italian cooking class, private wine tasting, and spa visit
  • Walk past olive groves, vineyards, and stone farmhouses
  • REI Women’s Adventure—designed for women, guided by women


This trip is rated Moderate [3]. The daily hikes range from 4-9 miles and are over varied terrain - from grassy lanes to rocky, gravel pathways.

Since some of the trails we hike can be steep and/or hilly, a conditioning regimen beginning at least 2-3 months prior to departure is highly recommended. Walking/hiking, running and biking are all great ways to physically prepare for this adventure. The better shape you are in, the more you'll be able to enjoy all that Tuscany has to offer!

  • Hiking

What's Included

Hotel accommodations with private bathrooms; meals as noted in the daily itinerary; guide/leadership; luggage transfers; private in-country transportation; special wine tasting; local city guides in Volterra and Siena; spa entrance fee on Day 4.


Small hotels, 6 nights

Your Adventure Itinerary

Day 1

Meet in Florence and hike through olive groves to the Tuscan town of Volterra.

Our trip begins in Florence, Italy. We meet at a centrally-located hotel this morning and transfer to the outskirts of Volterra. We begin our first hike to this historic Tuscan town, situated on a plateau overlooking the countryside. Our walk takes us up through olive groves and vineyards, past stone farmhouses, and to the imposing city walls. We have lunch at a local trattoria followed by a guided walking tour of Volterra, whose history spans Etruscan, Roman, Medieval and Renaissance periods. We visit the Etruscan Museum, with a guided tour focusing on objects used by women during the Etruscan civilization. From atop the city's medieval walls we look down on the Roman Theater and out across the landscape of Tuscany to the sea. The rest of the afternoon is free until we meet for an aperitivo and a brief orientation, followed by dinner. Overnight in Volterra the next two nights. Lunch and dinner included.

Hiking: 4 miles; Terrain: Dirt and paved pathways; Elevation gain: 700'. Driving: 1.5 hours.

Day 2

Hike past Volterra’s towers and tour an alabaster workshop.

Following breakfast we transfer into the countryside to begin our walk through oak forests and vast wheat fields, surrounded by cypress trees and stone farmhouses. At the hamlet of Ulignano we stop for a picnic lunch at a farmhouse. Continuing our hike, we'll see Volterra's towers and steeples across the valley. After a van shuttle to Volterra, we enjoy a tour of an alabaster workshop. This calcareous substance is mined in this area and has been widely used for centuries since the Etruscan craftsmen carved it originally for urns. The secrets of this handicraft have been handed down for ages and still represent one of the finest peaks of Italian artistic handicraft. Breakfast and dinner included.

Hiking: 7.5 mile; Terrain: Rolling hills; Elevation gain: 800'.

Day 3

Wine tasting at a women-run winery; explore the village of San Gimignano.

We transfer to Certaldo, to hike a route that affords us wonderful views of the "city of the towers," San Gimignano, and the imposing mass of the Villa Monte in the distance. We stop at Cesani, a small women-run winery which produces excellent Chianti and Vernaccia. A short tour is followed by a home-cooked lunch in which each course is paired with one of their wines. From here we transfer to San Gimignano to explore this exquisite medieval village. We finish the day in Colle di Val d'Elsa, an authentic Tuscan hilltown whose historic center still thrums with the rhythms of everyday life and is home to Italy's finest crystal makers. We spend the next two nights in Colle. All meals included.

Hiking: 7.5 miles; Terrain: Rolling hills with dirt and gravel pathways. Driving:1.5 hours.

Day 4

Hike along to Colle di Va D’Elsa and spa visit in the afternoon.

A scenic loop walk from Colle brings us to a country residence set alongside the Via Francigena, which connects San Gimignano to Colle. We enjoy the wonderful views of the Tuscan hills and San Gimignano's distant towers while eating lunch on the terrace. Continuing on our hike we arrive back into Colle, with the afternoon free to peruse the crystal shops or head to the spa to enjoy the sauna and Turkish bath. Dinner is on your own, providing the opportunity to choose from a variety of authentic local trattorias and restaurants. Breakfast and lunch included.

Hiking: 9.5 miles; Terrain: Rolling hills with dirt and paved pathways; Elevation gain: 500'.

Day 5

Embrace Siena with a cooking class and guided visit of its most notable sites.

We transfer to beautiful Siena, one of Italy's most enchanting cities. Our day begins with an authentic Italian cooking class where we’ll share our freshly prepared feast for lunch. After lunch we enjoy a guided tour of Siena. Conquered by the Medicis in 1559, Siena became a backwater, frozen in time, making it one of Europe's finest examples of a preserved Gothic city. The high concentration of buildings from the 12th-14th centuries makes Siena unique, and the main square, "Il Campo," is considered by many to be Italy's most beautiful piazza (the famous bareback "Palio" horse race is held in the square twice each year). Our local guide will explain the mayhem and passion associated with the race and then take us to visit the Duomo and its medieval treasures. Late afternoon we transfer into the Chianti countryside to our Tuscan villa, where we will spend the next two nights. Breakfast and dinner included.

Guided walking tour: 2 hours; Afternoon walk: 2.5 miles.

Day 6

Hike through the Tuscan countryside, passing medieval forts and renaissance villas.

Today's hike begins at the Villa San Donato in Perano, a magnificent 18th century villa that dominates the surrounding countryside. We visit the medieval walled hamlet of Vertine before continuing our hike through vineyards and olive groves and past stone farm houses and the 17th-century Villa Vistarenni. We stop for lunch in the village of Gaiole, enjoying expansive views over the famed Tuscan vineyards. We return to Radda in Chianti, where the remainder of the afternoon is free to swim in the pool, explore the town's medieval center, or rest. We enjoy a final dinner together to celebrate our time in Tuscany. All meals included.

Hiking: 8.4 miles; Terrain: Rolling hills with dirt and grass pathways and some rocky sections; Elevation gain/loss: 1,150'.​

Day 7

Our trip ends and we bid Arrivederci to our traveling companions.

The trip concludes with a group transfer to the Florence airport; we plan to arrive by 10:00 a.m. Depart for home this afternoon or continue your adventure in unforgettable Italy. Breakfast included.

Driving: 1 hour.

Gear List

The key to staying comfortable while on an active trip is layering. To get maximum comfort with minimum weight, you need versatile layers that mix and match to create the right amount of insulation, ventilation and weather protection. Try to bring only what is necessary—this will help you and the field staff.

What to pack

You might also consider

Travel documents

  • Airline Tickets (Confirmation and Itinerary)
  • Final Bulletin (Emailed Prior to Departure Date)
  • Valid Passport

Contact Us

Feel free to give us a call at 800-622-2236 should you have any questions regarding the gear list. The staff at our stores and Direct Sales (800-426-4840) will also be happy to help you with gear questions. Or check out REI Expert Advice , which has great information to help you prepare for your trip.