· · · · ·

The 5 most amazing town-to-town hikes in Italy

Hiking trails of every length and difficulty crisscross Italy, but we didn’t pick the walks below with backpackers in mind. We’re recommending these town-to- town hikes for active travelers who enjoy slow travel. Walk through medieval towns and fields of sunflowers, and enjoy countryside vistas, then arrive at a fantastic hotel and sleep on crisp sheets. Soak in a hot tub or get a massage at the spa. Sit on your hotel terrace with a glass of wine and then enjoy a wonderful evening meal that nourishes body and soul. Luggage can be sent ahead in a taxi. San Gimignano to Monteriggioni, Tuscany Walk from San Gimignano to Monteriggioni along the Via Francigena, the medieval pilgrimage route that connected Canterbury and Rome. The entire trail is almost 1,300 miles long and runs through England, France, Switzerland and Italy, but the San Gimignano to Monteriggioni section is one of the most beautiful of the Italian route. Marked as “difficult”, this path is 30 km long through the Tuscan countryside. Both San Gimignano and Monteriggioni are wonderful quintessentially Tuscan towns. San Gimignano, famous for its many towers, is a medieval hill town encircled by 13th century walls. Visitors can climb a tower for countryside views, walk its iconic streets, or visit the 12th century cathedral, which has frescoes by Italian Renaissance painter Domenico Ghirlandaio. Monteriggioni is much smaller, an almost perfectly circular medieval walled hill town just a few miles outside of Siena. It’s a wonderful place to end a long day of hiking with a glass of local wine while enjoying the views over the Tuscan hills. Monteriggioni Assisi to Spoleto, Umbria Walk along the Via di Francesco, from the iconic city of Assisi to the beautiful town of Spoleto. This can be done over 4 or 5 days: Assisi to Foligno is 20 km; Foligno to Trevi is 13 km; Trevi to Poreta is 12 km; Poreta to Spoleto is 15 km. The Via di Francesco is much less trafficked compared to the Via Francigena, and hikers should have good maps and lots of water and snacks while on the path. The towns have not only excellent hotels and fantastic restaurants, but a lot of history and culture, so allow a few hours each day to explore before heading out on the path. Assisi Amalfi to Sorrento, The Amalfi Coast Spend four days walking along Italy’s Amalfi Coast, from the town of Amalfi all the way up to Sorrento. From Amalfi, walk to under-the- radar Praiano, a gorgeous little town that is somehow mostly skipped by tourists heading from Positano to Amalfi. The second leg of the walk goes along the famous Path of the Gods, which is the highlight of the trail for most hikers. Stop for a long lunch in the town of Montepertuso, at Il Ritrovo or La Tagliata – both offer spectacular food and even better views. Continue to the iconic town of Positano, reached by walking down (literally) a couple of thousand steps. Go meet your luggage at one of the city’s amazing luxury hotels such as the Il San Pietro di Positano. The next day, continue to the town of Sant’Agata dei due Golfi on the Sorrentine Peninsula, enjoying the views of the nearby island of Capri. From there, the final leg to Sorrento is just 10 km. Path of the Gods The Dolomites The Dolomites mountains in northeastern Italy are littered with mountain huts, which are not rustic lean-tos but have actual beds, hot showers, and serve excellent food. Many of these mountain huts, such as the RIfugio Lagazuoi, with an outdoor sauna and renowned chef, are not far off a luxury hotel experience. However, we love the luxury hotels in the valley towns even more, and we recommend walking between valley towns – but not along the valley floor. Reach the next town by choosing one of many gorgeous trails that go up and over the mountain, and then down again. Our favorite two valleys for town-to- town walking in the Dolomites are the Val Gardena valley and the Val Badia valley. In the Val Gardena, walk from Ortisei to Santa Cristina, to Selva. In the Val Badia, walk from San Cassiano to La Villa to Corvara. Enjoy the fabulous hotels and the local culture, which is quite different from the rest of Italy. Val Badia The Cinque Terre This is without a doubt the most famous of these 5 recommendations. The five (cinque) towns (terre) are connected by a mule path that runs along Italy’s northern Mediterranean coast. The towns – Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore – can be hiked in one day, and it’s not even a long day. But spend more time to stop and savor each town. Take a dip in the sea and taste the local wine. Sit with a book and a piece of local focaccia and enjoy the sea breezes. It’s worth mentioning that these towns have become so well-known in recent years that the infrastructure is suffering the effects of too many visitors. For this reason, also consider other nearby hikes in the same area that are just as beautiful, yet still somewhat undiscovered. For example, hike from the south end of the Cinque Terre to Portovenere, or from Camogli to Portofino. Vernazza Madeline Jhawar is Owner of Italy Beyond the Obvious. If you would like to be a guest blogger on A Luxury Travel Blog in order to raise your profile, please contact us.

Did you enjoy this article?

Receive similar content direct to your inbox.


  1. My favorite by far is the 5 towns of Cinque Terre as some of them you can walk along the coast. Some of the towns have beaches but much of the area there is cliff lined so not much in the way of a beach but many breath taking views.

  2. Hi Mark s,

    We have visited the Amalfi Coast once before and love the sound of the Amalfi to Sorrento walk. Can you advise me re the best time of year to make our visit? We love wildflowers.

Comments are closed.