monteriggioni tuscany hilltown italy hiking tour

Monteriggioni, Tuscany

Built in the 14th and 15th centuries, medieval hilltowns tower above the Tuscan landscape. Our hikes bring us from one hilltown to another as we savor the heritage and cuisine of Tuscany.

Photo by Brian McGilloway

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Medieval Hilltowns and the Isle of Elba

Siena, San Gimignano, and the Isle of Elba

Medieval Hilltowns and the Isle of Elba route-map

Trip Details at-a-Glance

Cost From: $4895  
Length: 9 days
Arrive: Florence, Italy
Depart: Florence, Italy
Lodging: 2 nights restored palazzo, 6 nights fine hotels
Meals: All meals included except 3 dinners
Activity: Hiking / Trekking, Cultural Adventures
Trip Level: A mix of easy to moderate walks and hikes, 2-5 hours a day, van support


  • Siena, with its flamboyant Gothic architecture
  • Hike to jewel-like hilltowns and on the enchanting isle of Elba
  • Meet local winemakers and cheesemakers
  • Charming hotels, from a restored palazzo to a delightful seaside hotel
  • Wine tastings, picnics of southern Tuscan culinary treats

I loved this trip—my 4th with WT. Extremely well planned and wonderfully executed. The Trip Leaders were terrific.Diana E.—Washington, DC

Choosing the Right Trip

We work hard to help you choose the right trip for you, paying attention to your individual interests, abilities, and needs. If you have questions about the level of comfort or any of the activities described in this itinerary, please contact us.


We are proud to have an exceptionally high rate of repeat travelers. For more information, we would be happy to put you in touch with a client who has traveled with us.

Departure Notes

Once you have signed up on the trip, we send a complete packing list, relevant health information, and required travel documents.

Tuscany beckons, with its harmonious landscapes and ancient towns cradled within medieval walls. We’ve crafted a unique journey of off-the-beaten-path hikes to abbeys and castles, to jewel-like walled towns set on promontories, and village to village along the spectacular coast. We set the stage by exploring on foot in Gothic Siena, with its shell-shaped town square, the focus of Sienese life since 1340. Heading into southern Tuscany, we trace a route via the tiny villages of Sovana and Pitigliano, the lush Mediterranean island of Elba, site of Napoleon’s famed exile, and San Gimignano, a vision of medieval Tuscany, whose 14 stone watchtowers make it instantly identifiable from miles away. Gourmet trailside picnics and visits to wineries and cheesemakers add to our Tuscan delights.

Itinerary at a Glance

For a more complete description, Download Full Detailed Itinerary

Days 1-2
Florence / Siena / Montalcino

We walk the medieval lanes of Siena, then set out for country hikes to cinnamon-brick Monte Oliveto Maggiore, Tuscany’s grandest monastery, and to the extraordinary abbey of Sant’Antimo, with its fantastic setting amid olive groves and wild forests. In the wine town of Montalcino, known for ruby-red Brunello di Montalcino, we sample the wares. Overnights are in dazzling San Quirico d’Orcia, a walled town of Etruscan origin.

Days 3-4
Pienza / Pitigliano / Sovana

Roaming Etruscan pathways, we hike from tiny Pienza, a perfect window into 15th century Italy, and from Pitigliano, located in one of Tuscany’s wildest regions. Medieval Pitigliano was known for its flourishing Jewish community, and we roam the narrow alleys of the old Jewish quarter, now restored. Overnights are in the undiscovered hilltown of Sovana.

Days 5-6

Ferrying to Elba, a magical island surrounded by the blue Tyrrhenian Sea, our hikes bring us to headlands overlooking the sea and past small chapels and hermitages.

Days 7-9
Volterra / San Gimignano

Back on the mainland, we explore Volterra and its Etruscan relics, and hike through vineyards to discover the abandoned medieval village of Castelvecchio. Overnights are in charming San Gimignano, and we climb one of its famous stone towers for fantastic views. Depart on Day 9 from Florence.

For a more complete description, Download Full Detailed Itinerary

What the Trip is Like

This trip is Level 3, Moderate. The hikes vary from 2 to 6 miles on moderate to steep trails. Although you carry only a daypack on the hikes, there are a few steep ascents and descents, and some of the trails are on rocky, uneven terrain, so we recommend you make a special effort to be in good physical condition. Daily brisk walking and/or regular hiking (or using a stair-climbing machine at your gym) are excellent preparatory exercises. You should wear well-broken-in hiking boots for maximum comfort on the trail. Our van usually meets us at midday, bringing a wonderful picnic lunch of local breads, cheeses, fruits, and wines. On “town” days we will have lunch at local cafes. Our luggage is transported for us by van, so it is always possible to ride in the van if you wish to opt out of a day's hiking.

Please note that in Europe, the dinner hour is considerably later than what it is in the US. We do our best to secure early reservations for our groups, but most often the evening meal will be at 7:30 PM.

We spend most nights in small, picturesque inns, full of Italian charm and ambience. All hotels are chosen for their local history and central location. Since they are often in historic buildings the rooms may not conform to the international standards that you may be accustomed to in more cosmopolitan areas. We hope that you will be able to enjoy them for their charm and local color. Our leaders always try to assign rooms in a fair way so that all participants experience an equal advantage throughout the trip as a whole. Single rooms can be requested, but are not always available, due to the limited space in some of our hotels. If you require a single room, please make the request as early as possible. European single rooms are often smaller than US singles.

Explanation of Trip Levels


Departures & Leaders

Oct 5-13, 2014

Apr 28-May 6, 2015  Lisa Halderman
May 19-27, 2015  Ellen Santucci-Masi
Sep 24-Oct 2, 2015  Lisa Halderman
Oct 9-17, 2015  Lisa Halderman

Trip Cost

Prices are for 2014
$4895 (13-15 members)
$5195 (10-12 members)
$5495 (6-9 members)
Single supplement: $525
Forced single supplement: $325
more on pricing

Trip Cost Includes:

  • Expert leadership of a Wilderness Travel Trip Leader and local guides
  • Accommodations in small comfortable inns
  • All meals included except 3 dinners
  • Land transportation, airport transfers as noted in the Full Trip Brochure

Trip Cost Does Not Include:

International airfare, any meals not specified after each itinerary day in the Full Trip Brochure, wine at dinner (except at welcome and farewell dinners), airport departure taxes, individual arrival or departure transfers, optional tipping or gratuities to leaders or staff, additional hotel nights that may be necessary due to airline schedule changes or other factors; pre-trip expense of medical immunizations (if any), travel insurance or passports; and other expenses of a personal nature (alcoholic beverages, laundry, etc.).

Trip Payment Schedule

At time of reservation: $500
120 days prior to departure: 20%
60 days prior to departure: Balance

Cancellation and Transfer Fee Schedule

More than 90 days prior to departure: No charge!
46-90 days prior to departure: 25% of trip cost
45 days or less: 100% of trip cost

Relais Palazzo del Capitano

Relais Palazzo del Capitano

Days 1 to 2 (2 nights), San Quirico d’Orcia, Italy

This small hotel, a beautifully restored 15th century building with old world charm, is a nice surprise in the heart of the unspoiled village of San ...
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Sovana Hotels

Days 3 to 4 (2 nights), Sovana, Italy

In Sovana we stay at one of the following properties:

Hotel Sant'Andrea

Hotel Sant'Andrea

Days 5 to 6 (2 nights), Sant’Andrea Marciana, Elba, Italy

Some of the best things about this charming family-run hotel are the spectacular views from the garden overlooking the sea (they’ll leave you ...
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San Gimignano Hotels

Days 7 to 8 (2 nights), San Gimignano, Italy

In San Gimignano, we stay at one of the following properties:

Note: Listed above are our signature accommodations for this trip. Although it is highly unlikely, we may make substitutions when necessary.

Our Trip Leaders

Here are the Trip Leaders scheduled for this journey (please note that leader assignments are subject to change).

Lisa Halderman

Departure Dates: October 5-13, 2014, April 28-May 6, 2015, September 24-October 2, 2015, October 9-17, 2015

Lisa Halderman experienced Italy in 1973 as a high school exchange student. She earned her degree in Italian Literature, completing her final year at the University of Padua. Her studies have immersed her in the world of Italian art, architecture, politics, and history. An avid gardener, Lisa also ...
Click here for a full bio and list of all upcoming trips

Ellen Santucci-Masi

Departure Dates: October 5-13, 2014, May 19-27, 2015

Ellen Santucci-Masi was born and raised in New Jersey, but always knew she would travel someday, and she did. She studied French, Spanish, German, Italian, and Latin, knowing that languages would allow her gather insights into different cultures. She eventually settled in Florence, Italy, where ...
Click here for a full bio and list of all upcoming trips

Client Comments

I loved this trip—my 4th with WT. Extremely well planned and wonderfully executed. The Trip Leaders were terrific. Diana E., Washington, DC Each day was a new and wonderful surprise. I can’t say what was my favorite because it was all so great. Sally W., Atlanta, GA I just loved it. Every day we said “can it get any better than this?” and every day it did. Alice S., Shaker Heights, OH This was our third WT trip and we really had a great time. The Trip Leaders made the trip. Kathleen H., Boxford, MA Loved the variety—art, history, food, wine, and walking. The cooking “class” was great fun. Carol I., Medford, OR A great balanced trip with lots of variety—hiking, town tours, wine tasting, history, and architecture, all in the wonderful scenic beauty of Tuscany. Diane V., Washington, DC The secret to this trip is not only a great itinerary but also two Trip Leaders who work well with each other. Their combined personalities and vast knowledge were outstanding. Karen M., Gainesville, GA My friends are really getting tired of hearing about how wonderful it was! Carol D., Portland, OR The trip was absolutely great and we had a wonderful time—I enjoyed every day. Between the two Trip Leaders, we were spoiled rotten. The two of them made the trip informative, fun, and every day was a treat. Peter V., Sandy MABX, Bermuda The trip ran incredibly smoothly. Accommodations were fantastic, picnic lunches, dinners, and itinerary were all excellent. First time I’ve used Wilderness Travel, and I had a first-class experience! Michael F., Westlake Village, CA I couldn't wait to write to tell you what a wonderful trip I've just had. The trip was memory-making in so many ways and much of that was due to the excellence of the three trip leaders. Ruth F., Washington, DC A fabulous trip with a fabulous Trip Leader. Frank C., Ontario, Canada This was the most amazing trip I have ever been on. I look forward to vacationing with WT again. Carrie O., Alexandria, VA I liked it so much I’m going on another WT trip as soon as I can! Leila H., Eastford, CT
My sister and I had the time of our lives. We ate like queens, enjoyed the company of our guides and fellow travelers, and really relaxed for the whole trip. Patty B., Freeport, ME Outstanding cuisine adventures...picnics and most dinners. Hikes were varied and most interesting, and we enjoyed being 4 different locations, away from the touristed, overpopulated spots. Linda R., Darnestown, MD The itinerary was superb, the guides the best, the hikes varied and interesting, the fellow travelers fully compatible, the picnics wonderful, and the local guides terrific. The combination of these features and the wine tastings, cooking lesson, and interesting conversations made for an excellent trip. Michael R., Darnestown, MD I was so impressed with this trip. It was really top quality in all ways: the itinerary, the hotels, the food, the size of the group, and especially the guides. And the picnics on the trip were outstanding! Jean G., Redondo Beach, CA Our expectations were high going into the trip, but were nonetheless exceeded. We have been looking for an active and intelligent tour company for areas in which we don't wish to travel independently, and believe we have found it! David M., Friendswood, TX I really enjoyed this trip, my first to Europe. Italy was my dream come true, thanks to WT! Christy O., Aromas, CA This was a great trip. The rhythm of the days was so pleasing, and having all of the logistics handled by Wilderness leaves you open to truly experience the people and places you visit. It is a guilty pleasure that we hope to repeat. Jack M., Santa Fe, NM A great mixture of hiking, art, history, local culture, food, wine and laughter, shared with ten other wonderful new friends. All this in exquisite surroundings. Toby K., Grantham, NH A magical Italian adventure: great hiking trails, beautiful venues for overnight stays, and many amazing cultural/historical sites. John M., Woodbridge, VA I loved the trip. It was a perfect combination of cultural knowledge, hiking, and unbelievable food—the cooking class was great! Charlotte F., Redwood City, CA We loved our trip—everything from the food to the hikes to the fellow travelers was fantastic. We loved getting to visit so many non-touristy towns, and we especially loved the cooking class on the last day! Sharon C., Philadelphia, PA