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Top places to visit in Italy when on a walking holiday

Tue 05 Mar 2024

Tuscany in Italy

Italy is home to ancient cities, stunning landscapes, amazing cuisine, and gorgeous weather. It is also one of the best destinations in the world to visit on a walking holiday. With everything from mountains to coastal paths, Italy has all that you need for a walking trip to remember. There are enough must-visit locations for a hundred tours, but this guide highlights some of the best places to visit for your next walking holiday in Italy.


Renowned for its rolling hills, vineyards, and historical towns, the beautiful region of Tuscany is a walker’s paradise. Tuscany is also home to treasured Italian cities like Florence, bringing a perfect mixture of urban exploration and rural rambling.

This region of central Italy is of the most picturesque variety, with walking tours in the Tuscan countryside, including visits to medieval towns like Siena, Florence, and Pisa, with their rich history and art. Scenic landscapes and vineyard tours are also joined by historical gems like the Leaning Tower of Pisa.

A walking holiday in Tuscany also provides the opportunity to trek along part of an ancient pilgrim route known as Via Francigena. Including Lucca and Siena, the route pierces the Tuscan countryside, showcasing vineyards, hilltop towns, and medieval architecture.


The Colosseum in Rome

Home to ancient ruins and historic pathways, Rome is the perfect place to visit during a walking holiday. The eternal city has a little something for everyone, including world-famous attractions.

Your on-foot exploration can include visiting the Colosseum and Roman Forum, as well as treading in the footsteps of gladiators and emperors. You can also wander over to Vatican City, exploring the stunning Sistine Chapel, St Peter’s Cathedral, and Vatican Museums.

Or how about the legendary Appian Way? One of the oldest and most important roads of the Roman Empire. When you throw in beautiful villas, world-class restaurants, and refreshing Italian gelato, Rome is a highlight to truly savour. 

Apennine Hills

The Apennine Hills stretch across the Italian peninsula, with the area near Bologna offering lush landscapes, wooded hills, and quaint medieval villages. With lovely walking trails amid diverse scenery, you shouldn’t miss it when visiting Bologna.

This region is perfect for those looking to discover Italy's hidden gems, and the trails here cater to all levels of hikers, from gentle walks through the countryside to more challenging hikes up the hills.

Highlights include panoramic views, historical sites, and the opportunity to explore the traditional life of the Italian countryside. The area is dotted with WWII ruins, castles, old monasteries, and churches that hark back to a bygone era.


The Dolomites in Italy

Nestled in the northern Italian Alps, a Dolomites walking holiday offers dramatic peaks, lush valleys, and epic trails. Part of the beautiful province of Trentino, the famous Dolomites offers a staggering backdrop that any hike would be proud of.

With an extensive network of well-marked paths, ranging from leisurely strolls to challenging hikes, the Dolomites cater to all levels of walkers, promising breathtaking vistas at every turn.

Exploring the wider province of Trentino is also recommended, thanks to its charming alpine villages, rich cultural heritage, and picturesque castles. Walkers can look forward to lakes, meadows, and forests to juxtapose with epic mountain scenery.


Nestled in the heart of Italy, Umbria boasts a timeless beauty, rich history, and artistic treasures, making it an idyllic destination for a walking holiday. The region's diverse landscapes, from rolling hills to picturesque countryside, provide a perfect backdrop for leisurely strolls or challenging hikes.

Medieval marvels like Città di Castello and the enchanting town of Gubbio offer glimpses into Umbria's past, while cities like Perugia and Arezzo showcase its powerful artistic legacy. The picturesque churches of San Bernardino and San Francesco are must-visits, and the spiritual St. Francis Way pilgrimage route winds through the region's stunning landscapes.

You can also look forward to enjoying Urbino, a UNESCO World Heritage site, across the border in Marche, with its grand Renaissance architecture. So, whether you’re exploring medieval towns, traversing serene countryside, or embracing Umbria's artistic legacy, Umbria promises an unforgettable experience.

Lori, from the travel blog Travlinmad, loved her visit to Umbria and spoke to us about why people should be excited about exploring the area: “Umbria is most often acquainted with the number of charming small towns that one could ramble around for days visiting attractions, churches, and basking in the history of the setting.

“The town of Assisi is one such town and is a must-visit for learning about its significant religious history as the home of St. Francis of Assisi. But Umbria also has some of Italy’s most diverse landscapes from fertile plains containing Roman ruins and structures to towering mountain ranges waiting to be soared above or explored from below.”

Lake Como & Lombardy

Group hiking near Lake Como

Lombardy is one of Italy’s most sought-after destinations, thanks in part to its glamorous lake district. Lake Como (Lago de Como) is an essential stop during a walking holiday in the area, offering crystal-clear waters framed by majestic mountains, lush forests, and charming lakeside villages.

Menaggio, one of the picturesque towns dotting the lake's shoreline, serves as a perfect starting point for exploring the region's natural treasures. Walking along Lake Como offers panoramic views of Lombardy’s shimmering waters, along with the area’s majestic mountains.

The views from the surrounding hillsides are enough to take your breath away, with the slopes themselves dotted with villages, castles, ancient ruins, and vineyards, making it easy for you to become immersed in Lombardy’s rich history and stunning scenery.

Although the most well-known lake is Lago de Como and the stunning resort of Bellagio, the Lombardy region actually has six lakes to visit. When travel blogger Piccavey travelled to the region, her favourite was Lake Iseo. “Especially taking a boat ride past the three islands on the lago,” she told us. “Visiting the charming fishing village of Peschiera Maraglio seems like time travel. There are no cars on the islands, so it makes it an ideal place to get away from it all.” 

The best walking holidays in Italy

  • Tuscany
  • Rome
  • Apennine Hills
  • Dolomites
  • Umbria
  • Lake Como & Lombardy

As you can see, Italy has an abundance of treasures to discover on a walking holiday. From ancient ruins and medieval towns to rolling hills and towering mountains, it’s all here and waiting to be enjoyed.

These are just some locations you can experience in Italy, but we hope this has whetted your appetite to explore for yourself.

From a leisurely walk to a challenging hike, if you would like to make Italy your next adventure, book a walking holiday with Ramble Worldwide. 

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