Walking Holidays for Beginners

Walking holidays are becoming more and more popular, and we couldn’t be happier about it! Even people who’d never considered an active vacation are starting to embrace the idea, drawn by the chance to spend days surrounded by nature, enjoy the physical and mental health benefits, and explore areas in a way that’s far deeper and more meaningful than a traditional, fast-paced trip. The world of hiking trails offers so much to discover!

This means that even those of you without much experience or fitness—or who are used to shorter trips—might feel ready to take on a walking holiday.

In this blog, we’ll share some suggestions for easy hiking trails and routes included in our catalog, perfect if you’re just starting out.

Consider your level of training! 

The first thing to do is to be honest with yourself about your fitness level. We all have different levels of endurance, and the difficulty of a hike depends on so many factors—it’s not the same for everyone.

The key is to not get discouraged, but also not to overestimate your abilities. For example, if you’re used to hiking for a few hours in the mountains on weekends, that doesn’t automatically mean you’re ready for a multi-day trek covering several kilometers a day!

For more tips on why the idea of a “difficult trip” is so relative and the factors that can make it easier or harder, check out this article.

Once you’ve got a good sense of where you’re at, let’s dive into some of the best trips for beginners in our collection.

The Cammino di Oropa

The Cammino di Oropa is one of the best trails we recommend for beginners. It’s a stunning route through the nature of the Biellese region, just an hour from Milan. Starting in Santhià, you’ll hike to the Marian Sanctuary of Oropa, one of the largest in the world, over four days of walking through incredibly diverse landscapes: magical forests of the Biellese Alps, the morainic amphitheater of the Serra di Ivrea, ancient sanctuaries, breathtaking lakes, castles, and fortified villages.

We offer a traditional version and an easier one, making it even more accessible for first-time hikers.

Why choose this trail?

• The beauty and variety of the landscapes make it a short but rewarding journey.
• Reaching the stunning Marian Sanctuary of Oropa is a memorable achievement for a first trail.
• Unique accommodations in small hotels and sanctuaries.
• The chance to extend your trip and explore the enchanting Biellese region, including the Oasi Zegna.

The Heart of the Via Francigena

This route takes you through one of the most scenic and breathtaking sections of the Via Francigena in Tuscany. While the entire trail is beautiful, the Tuscan stretch is particularly iconic, with its rolling hills dotted with cypress trees and farmhouses, charming villages, and historic towns.

The simplified version of the Heart of the Via Francigena is perfect for beginners. It includes private transfers and sections you can cover with frequent and reliable public transport, allowing you to walk fewer kilometers each day while still enjoying the best parts of the trail. Another option is a long weekend from San Miniato to San Gimignano, ideal for testing your endurance, even though the first day is a bit longer.

Why choose this trail?

• The thrill of walking the most famous trail in Italy.
• Iconic Tuscan landscapes, historic towns, and charming villages you’ll never forget.
• The opportunity to add extra days to your trip for further exploration.

Lake Como

This itinerary lets you soak in the beauty of Lake Como, a global symbol of elegance and charm. Designed for first-time hikers, this route showcases different aspects of the lake and its surrounding areas.

You’ll start in the lovely town of Lecco, following the Sentiero del Viandante along the eastern shore to romantic Varenna. After a day exploring Bellagio, accessible by ferry for stunning lake views, you’ll continue to the picturesque Orrido di Bellano and Colico. The trip concludes in Chiavenna, where you’ll admire waterfalls and enjoy traditional mountain flavors in a local Crotto.

Why choose this trail?

• A variety of experiences, from lakeside walks to mountain vistas.
• Frequent and convenient train and ferry connections.
• Short, flexible days that let you adjust the pace to your energy levels.

The Chestnut Route

This trail is ideal if you’re drawn to the mountains but not quite ready for the Dolomites. The Chestnut Route offers a “softer” introduction to mountain hiking in the heart of South Tyrol. You’ll explore the lively town of Bolzano, charming villages like Chiusa—beloved by poets and artists—and breathtaking landscapes.

The route includes private transfers and public buses to reduce daily distances, leaving you to enjoy the most scenic parts of the trail.

Why choose this trail?

• A chance to experience the magic of the Dolomites in a less demanding setting.
• Perfect for mountain lovers who want a manageable, beginner-friendly adventure.
• Two route options to suit your fitness level: easy or more challenging.

Exploring the Arezzo Area

This trip takes you through a surprising region that inspired great artists like Michelangelo, Dante, and Leonardo da Vinci. You’ll walk through landscapes immortalized in the Mona Lisa and mentioned in the Divine Comedy.

Along the way, you’ll visit gems like Arezzo, Anghiari, and Sansepolcro, medieval treasures that transport you to another time. The walks are easy and scenic, perfect for a first hiking trip combining history, beauty, and culture.

Why choose this trail?

• Discover the lesser-known Arezzo area for a sustainable and unique travel experience.
• Walk through landscapes that inspired some of the greatest works of art in history.
• Flexible daily walks with options for loop routes or rest days.

Conclusions

Being a beginner or lacking experience doesn’t have to hold you back. These trails offer some of Italy’s most beautiful landscapes while keeping daily distances manageable and providing options for rest days or transfers. Just let us know your situation, and we’ll help you find the perfect trip!