From Medieval Hill Towns to Seaside Villages
Hiking Tuscany and the Cinque Terre
Overview
We explore two irresistible Italian realms in full WT style, with stunning hikes each day and expert Trip Leaders who bring this celebrated Italian region to life. Our hikes cross Tuscany’s harmonious landscape, discovering terraced vineyards, tiny hamlets, and classic hill towns on our way from San Quirico d’Orcia, once a stop on the Via Francigena pilgrim trail, to unforgettable San Gimignano. After a walk on Lucca’s historic walls, we head to Cinque Terre, where five ancient villages nestle on cliffs and along deep coves on the Ligurian Coast. We connect these seaside villages with breathtaking hikes, sample Liguria’s fresh-caught seafood, and ferry to Palmaria Island for a final hike with spectacular Cinque Terre panoramas.
Arrive: Florence, Italy
Depart: Pisa, Italy
Highlights
- Visit the vineyards of Chianti, with a picnic at a family-run winery
- Experience the beauty of the Tuscan towns of San Quirico d'Orcia, Pienza, Siena, and San Gimignano
- Walk the famed coastal trails that connect the five Cinque Terre villages
- Ferry to Palmaria Island for a spectacular hike and coastal views
- Enjoy Trip Leaders who know all the best trails, trattorias, and local delicacies!
Itinerary
Heading into celebrated Chianti wine country, we’ll stretch our legs on a hike in world-class vineyards that have been lovingly tended since the 1700s, followed by a picnic at a family-run winery. The next day, we hike through woodlands to the grand Romanesque Abbey of St. Antimo, then enjoy some free time in the wine town of Montalcino, with overnights in the small medieval town of San Quirico d’Orcia.
We walk right from our hotel into the iconic Val d’Orcia, with its wheat fields and cypress-lined roads, following a trail that brings us to tiny hilltop Pienza, a prime exemplar of 15th century Italy. We’ll also visit medieval Siena, where we’re joined by a local specialist guide for a walking tour of this glorious city, one of the most flamboyant examples of medieval architecture in existence. In the quintessential walled Tuscan town of San Gimignano, whose 14 stone watchtowers make it instantly identifiable from miles away, we hike down through olive groves to the village of San Donato for a picnic lunch. San Gimignano’s medieval core was recognized as a UNESCO World Heritage Site in 1990.
Lucca, birthplace of Puccini, is one of the most graceful of Tuscany’s provincial capitals, encircled by an imposing ring of Renaissance walls. We walk the remarkable city walls, attend an evening concert in a historic church, and hike on an ancient aqueduct that crosses the serene Vorno Valley.
The five Cinque Terre villages are centuries-old towns on the cliffs of the Ligurian coast. Our hikes connect these impossibly picturesque villages, and we ferry out to Palmaria Island, part of the Cinque Terre World Heritage area, for our final hike. Depart on Day 10 via Pisa.
Accommodations
Scroll through our signature accommodations for this trip below. Although it is highly unlikely, we may make substitutions when necessary.
What the Trip is Like
This trip is rated Level 3, Moderate, according to our trip grading system. While we do not see major elevation gain or loss, you will need to be comfortable hiking up to 6 miles a day and being on your feet for 4-5 hours a day. Trail conditions, weather, and the group's level of fitness can affect hiking times and pacing.
Average Hiking Day
Review Trip Level Details
- 2.5 hours
- 4 miles
- 500-600 feet gain/loss
- Day 2: 6 miles, 3 hours, 900 feet gain, and 700 feet loss
We traverse a variety of terrains, from dirt roads through rolling hills in the southern part of Tuscany to steep, rocky sections on the coastal paths of Liguria where you will need to be able to hike on uneven surfaces and occasionally downhill over loose rocks. Some parts of the trails are ancient stone staircases which can be quite steep and hard on the knees. The coastal trails are narrow, have drop offs of varying heights, and often have passing hikers, so you will need good balance. On most days, we hike in the morning and visit a town or historical site in the afternoon.
The weather in Tuscany and Cinque Terre in late spring and early fall is usually very pleasant, with temperatures in the 70s°F (80s°F in Tuscany) during the day, and in the 50s°F and 60s°F at night. There can be cool breezes and occasional showers at any time during these seasons.
We spend most nights in small, picturesque inns, full of Italian charm and ambiance. Since they are often in historic buildings, the rooms are not always of uniform or international size. Our leaders do their best 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 the hotels. If you prefer a single room, please make your request as early as possible.
Our lunches will vary from picnics in a scenic spot to small trattorias known for their excellent local cuisine. Picnic lunches will include local breads, cheeses, fruits, and wines. On some days, we will have lunch at a local farm or in a home (agriturismo) where regional specialties are prepared. Dinners will be at our hotel or a restaurant in town. 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.
Our van will transport the group's luggage, so you only need to carry a daypack for items you need during the day (rain gear, sweater, camera, water bottle, etc.). Trip members are always free to skip a day's hike and travel to the next destination in the support vehicle (or remain at the hotel if we are not transferring that day).
Client Testimonials
"I was a tour guide myself in my younger years; thus, I feel qualified to address all the fine qualities of this experience. Wonderful human touches brought so much life to this trip: the cozy restaurants, charming hotels, the farms and vineyards, and above all, our three guides—lovely human beings, and so professional. Superb!"
Al D.
Twin Lakes, CO
"This was a great itinerary that was well organized and well executed. We had great food and wine at every destination and very well-informed trip leaders."
Bill B.
Highland Park, IL
"I LOVED THIS TRIP. As I look back, I have nothing but happy memories of each and every day. Our group was amazing as far as getting along and making new friendships. I have a new love for Italy and the countryside, as well as the traditions and language, all because of this trip and these guides and all the careful prep put into the whole thing. Cannot thank you enough."
Carolyn H.
Jupiter, FL
"Outstanding trip, thank you! I absolutely loved the hiking and felt like we were seeing off-the-beaten-tourist-track places. Great guides, really good food, and the Italian Riviera was spectacular—especially the last day hiking out of Portofino to the cove with the big seafood lunch on the beach. What a way to end the trip! It was fabulous in every way. This was one of my favorite trips ever, and I've traveled extensively throughout the world. I can't wait to do another one with you."
Cybele L.
Sharon, CT
"I was very impressed with this trip. Our guides were wonderful, and I loved seeing some of the out-of-the-way villages we hiked through. It was great to be off the beaten path."
Judy E.
Methuen, MA
"Our trip was fabulous on every front—we felt very well taken care of."
Laila D.
Twin Lakes, CO
"This was a well-designed trip which we very much enjoyed. Our Trip Leader JoAnn was well informed, organized and very engaging throughout our trip. We learned a great deal on our hikes and so enjoyed the museum tours and the guides she chose to lead them. We have always spoken highly of WT to our friends and family."
Lynne H.
Weems, VA
"Excellent lodging at hotels that we would return on our own. Can't say enough about the talents of our leaders in putting together the picnic lunches. This was our first trip of this kind, and I expect we'll be back. Sicily? Dolomites? All in all, it was a great value for the money, and I so appreciated the mix of hiking and in-town visits. "
Mary L.
Jamaica Plain, MA
"I enjoy reliving the beauty of the countryside, the plethora of information received, the charm of the medieval cities, the delicious picnics, and the company of interesting, intelligent, cheerful people—both fellow tour members and the wonderful trip leaders."
Susan M.
Burlingame, CA
"It was an overall wonderful experience—we didn’t have to think about anything (other than what to order for dinner)."
Tom K.
Sudbury, MA
Other Trips You Might Like
Browse All Trips
Small Group Adventure
Hiking Amalfi and Capri
Italy
Level 3+
9 Days
From $7,195
Small Group Adventure
Hiking Corsica and Sardinia
France, Italy
Level 3+
11 Days
From $6,995
Small Group Adventure
Hiking Puglia and Matera
Italy
Level 3
10 Days
From $6,695
Private Journey
Rome and Tuscany Private Journey
Italy
Level 2/3
7 Days
From $5,995
Book your trip today
Our Area Specialists know every detail about our tours. They will be happy to answer any questions and help you choose the journey that’s right for you. Contact us to learn more or book your trip today!
Itinerary
Submit the form below to download itinerary
Trip Levels
With more than 200 different adventures to choose from, we want to help you find the trip that’s right for you. Our Trip Level system ranks each trip in two ways: a number rating from 1 to 6 according to the activity, and general travel rigors. 1 is the easiest and 6+ the most difficult.