Discover Italy’s Beauty Your Way 

Welcome to the ultimate walking experience in Italy—where history, beauty, and adventure meet. At Macs Adventure, we've crafted the perfect self-guided walking holidays to immerse you in Italy's rich culture, dynamic landscapes, and culinary delights. 

Whether you're a seasoned walker or a casual explorer, our expertly curated self-guided trips offer something for everyone. From the rugged cliffs of the Amalfi Coast to the serene vineyards of Tuscany, we invite you to step out of your comfort zone and create unforgettable memories. 

Get started today and discover the true essence of Italy!

Browse our Italy Walking Trips.

Why Choose a Macs Italian Walking Holiday? 

Variety of Destinations 

From the coastal charm of Cinque Terre to the majestic Dolomites, explore Italy's diverse regions with our hand-picked routes. 

Expert Curation 

Our travel experts meticulously plan each trip to ensure you experience the best Italy has to offer, including those must-see places as well as local secrets. Our self-guided trips immerse you into the heart of a region where authentic experiences are abundant, and you can explore at your own pace. 

Sense of Community 

Join our Macs Adventure Facebook Community, with over 15,000 members of passionate adventurers who share tips, exchange stories and support each other. Be part of a community that loves exploring just as much as you do.

Best Places to Walk in Italy

Pearls of the Riviera - Cinque Terre

Cinque Terre, located in Italy's Liguria region, is a string of centuries-old seaside villages that cling to the rugged Italian Riviera coastline. Linked by a series of footpaths, walking is one of the best ways to visit each of the five towns and enjoy the spectacular scenery. If your idea of la dolce vita is walking by day and dining on seafood specialities by night, the Cinque Terre will exceed your expectations. 

When to Walk Cinque Terre

Late spring (March-May) and autumn (September-October) are the best times for walking holidays in Cinque Terre. Spring brings clear blue skies and warm weather, while autumn is full of rich reds and fiery ambers from the terrain’s fauna and flora. April welcomes the Sciacchetrail - the hiking race of the year! Starting and ending in Monterosso, hikers join in every year to race across Cinque Terre - be sure to cheer them on! Monterosso also hosts May’s Lemon Festival, where locals compete for the biggest lemon grown, as well as offering lots of lemon-flavoured treats. 

Browse our Cinque Terre Walking Trips.

The Dolomites and the Alta Via 

Experience the exquisitely magnificent peaks, fantastic network of high trails, and wide-sweeping views of the Dolomites. Our hikes allow you to witness the majestic scenery and mountain culture of the Dolomites while immersing you in Italian mountain life. Known in the Dolomites as enrosadira, the alpenglow seen from your mountain rifugio is a sight you’ll never forget. These Dolomites hikes aren’t for the fainthearted. They’re a big challenge, but the enormous sense of accomplishment that comes with conquering the trails is the best feeling.

When to Walk the Dolomites and the Alta Via

July to September is the best time to take on this trail. Not only is the weather delightfully bright, but the mountains have fully awoken with undisturbed nature. Look out for alpine flora such as bell flowers, rhododendrons and gentians popping up between rocks or grassy meadows. You might even spot native animals on your route, including marmots, roe deer, and foxes. Don’t forget to look to the skies and spy the majestic golden eagle!

Browse our Dolomites Walking Trips.

Tuscany - Where Time is on Your Side 

Fabulous Tuscany should be savoured rather than rushed. Our Hill Towns of Tuscany walking trip lets you step back in time and stroll picturesque hills between historic and architecturally renowned towns. Discover the sweet life among aromatic vineyards and bountiful olive groves filling the landscape in every direction.

When to Walk in Tuscany

If you can handle the heat, Tuscan summers deliver cloudless skies, minimal rain and trails blooming with sunflowers and poppies. But, it can be quite stifling for walking. Spring offers cooler weather and emptier walking paths as the spring flowers begin to wake. For travellers looking to see the spectacular vineyards that Tuscany is famous for, autumn may be the season for you. The temperature is still toasty warm, perfect for walking through full and colourful vineyards - ready for harvesting in late autumn, which is a must-see extravaganza to experience.

Browse our Tuscany Walking Trips.

The Amalfi Coast - An Italian Favourite 

A walking holiday on Italy’s southern Amalfi coastline takes you on mountain paths high above the deep-blue Mediterranean Sea and between idyllic Italian villages. Amalfi is chaotic yet peaceful, brimming with life yet offering serene moments with a cold glass of wine on a terrace.

When to Walk the Amalfi Coast

If you’re heading to the Amalfi Coast for its striking fauna and flora, spring is the perfect time. Its unique terrain creates valleys and meadows of pretty wildflowers, framing your view as you stroll along. As you move closer to local towns, you’ll spot bold wisteria climbing white-stoned buildings, as well as ruby red and bright pink oleander flowers that smell just like honey! If you’re looking to embrace the arts and culture of Amalfi, head to Ravello between July and September for the Ravello Festival. During this time, the town hosts exhibitions, ballet performances and classical music in churches and piazzas for you to enjoy.

Browse our Amalfi Coast Walking Trips.

Piedmont – For World-Class Cuisine and Wine 

Perhaps a region that flies beneath the radar, the Piedmont Walking & Wine trail winds through Piedmont, Italy’s paradise region for wine connoisseurs and gourmets. Our walking holiday explores the Langhe region, blessed with fertile lands that produce prized white truffles and prestigious red wines like Barolo. Immerse yourself in the joy of every glass and every bite as you explore this culinary haven.

When to Walk in Piedmont

Spring naturally brings the best conditions for walking, with slowly rising temperatures and beautiful scenery beginning to bloom. But Piedmont is known worldwide for its many food festivals. In spring, there’s the annual Asparagus Festival. May hosts their wine festival, Vinum - where you can taste Piedmont’s delicious full-bodied red, Dolcetto - and autumn brings the biggest crowds with the White Truffle Harvest. For music fans, enjoy the rhythmic tones of July’s Monforte Jazz Festival, and if you want to experience it all, head to the Douje D’or Festival during the first two weeks of September. 

Check out our Piedmont Walking Trip.

Puglia – An Overlooked Gem 

Imagine walking along cliffs that scan turquoise waters. The coastal trails here provide unmatched views and a sense of tranquillity that's hard to find elsewhere. The region’s historic routes and ancient paths lead you through olive groves and past unique landmarks like the Trulli houses in Alberobello. And after a day of walking, reward yourself with Puglia's culinary delights, including orecchiette pasta and fresh seafood. 

When to Walk in Puglia

May, June, and September offer pleasant walking temperatures with minimal rain and days averaging 20℃ (70℉). This makes for comfortable walks through Pulgia’s ancient olive groves and trailing vineyards. Puglia is known for its many Saint celebrations. March to May, in particular, is a busier period with pilgrims arriving to celebrate the La Festa di San Nicola - a festival worth experiencing as the streets are filled with colourful lights, parades and fireworks painting the sky. June also hosts many magical musical evenings.

Browse our Puglia Walking Trips to find the right Italian walking holiday for you.

Umbria – The Green Heart of Italy 

A region rich in natural beauty and historical significance, the gentle rolling hills and verdant landscapes make it perfect for both novice and experienced walkers. Trails often lead to charming medieval towns like Assisi and Spoleto, where you can immerse yourself in local culture and history. Enjoy farm-to-table meals featuring truffles, olive oil, and regional wines that make Umbria a food lover's paradise. 

When to Walk in Umbria

We offer trips to Umbria from April to October, with late autumn offering warm, drier conditions for walking. For more secluded and peaceful walks, early spring provides fewer crowds. The temperature is mild with rainy periods, but this combination provides lush green fields and beautiful wildflower meadows to come to life. April is a great time to celebrate Easter in Umbria, with the chance to taste their traditional sweet bread, Colomba di Pasqua. Those seeking a cultural experience, head to Umbria in June for the Festival dei Due Monti (Festival of the Two Worlds) - the most famous festival in Italy, where the town celebrates opera, ballet, drama and music.

Browse our Umbria Walking Trips and pick from our Slower Adventures to the Full Italian Via Francigena pilgrimage.

Sicily – Step Back into Italian History

The island of Sicily offers a unique blend of natural beauty, cultural richness, and remnants of ancient tales. Trails often pass ancient Greek and Roman ruins, adding a historical dimension to your walk. From coastal paths to mountainous trails, Sicily offers a variety of landscapes that cater to all levels of walkers. Embrace la dolce vita on our Slower Adventure in Sicily. The island’s renowned culinary delights of fresh seafood and traditional pastries call for longer lunches where there’s always room for dessert.  

When to Walk in Sicily

For the most picturesque scenery in Sicily, early spring and late autumn are the best seasons to book your walking holiday. Spring welcomes a rainbow of wildflowers, while autumn displays warm ambers as the leaves begin to change. For a true floral fiesta, visit Sicily in May and embrace the Infiorata Flower Festival. Honouring the beauty of spring, the town of Noto is blanketed with flowers and petals as parades, live music, and food stalls take over the streets.

Check out our Sicily Walking Trip.

Italian Lakes – Elegance and Charm 

The Italian Lakes region is a dream come true for anyone who loves scenic beauty and serene environments. Trails around Lake Como and Lake Garda offer panoramic views that are nothing short of spectacular. From easy lakeside walks to challenging mountain hikes, there's something for everyone. Discover picturesque villages where you can relax by the water, enjoy local cuisine, and soak in the Italian lifestyle. 

When to Walk Around the Italian Lakes

We offer walking holidays through Lake Como between April and October. While early spring displays the lake’s flora at its best, June to September hosts Lake Como’s annual festival with lots of live music and fireworks. Our Dolomites to Lake Garda walking trip is available between June and September when the mountain wildflowers are at their brightest, and the lakefront is alight with summer excitement. 

Browse our Italian Lakes Walking Trips and the different routes to match your preferred type of trip.

How Self-Guided Travel Works 

We Plan Your Routes 

Our adventure specialists have developed hundreds of hand-crafted, tried and tested adventures in over 30 countries. Our extensive route-mapping process makes your self-guided adventure seamless and easy to navigate. 

You Choose Your Itinerary 

Select your destination, start dates, travel companions, trip type, activity (walking or cycling), and level of challenge, and set off at your own pace. There’s truly something for everyone. 

We Handle the Logistics 

We take care of booking your accommodations and luggage transfers, leaving you free to focus on enjoying your adventure. All you need is your backpack with essentials for the day. Our local providers are vetted for your comfort, convenience, and safety. So, you know you’ll be coming back to a nice, warm bed after a long day of walking.

You Lead the Way 

Our Macs Adventure app details your entire itinerary with GPS tracking, ensuring you never miss a landmark and you never get lost! All your info and documents are stored there, too, so there’s no paperwork to carry.

Why Choose Self-Guided Travel?

Freedom and Flexibility

Travel at your own pace and make your experiences uniquely yours. Self-guided travel offers the freedom to linger where you love and move on when you’re ready. 

Authentic Experiences

Immerse yourself in local culture and cuisine with our hand-picked, locally-owned accommodations, dining options and sightseeing suggestions. 

Environmental and Social Impact

Travel more sustainably and interact with locals outside of large groups. Your experiences become more personal and enriching. And by offering walking and cycling holidays, we’re keeping it low-impact on our routes with as little of a footprint on the environment as possible.

Support When You Need It

Enjoy the best of both worlds—independent travel with professional support. Our team is available 24/7 to assist you during your adventure, when you need us.

Traveller Testimonials 

"Macs did a great job of organising this trip, and the accommodations were first-rate! The route descriptions were also excellent. The Amalfi coast is spectacular." – Taylor 

"We really enjoyed this trip. Everything was well organised, and it all went together very well. The walks were great but quite hard work. Hotels were excellent. Lovely part of the world." – Alex 

"What a fabulous time seeing the amazing countryside and lovely people of Tuscany. We experienced far more of the country by travelling with Macs with no worries about the accommodation, which was amazing." – Jamie

Experience Italy Like Never Before 

Ready to begin Your Italian Adventure? Explore the best walking holidays in Italy with Macs Adventure and create memories that will last a lifetime. Our Italy specialists are here to help connect you with your perfect adventure. 

Get Started Now

Join the Macs Community 

Connect with fellow walking enthusiasts in the Macs Adventure Facebook Community, share your stories, and stay updated with the latest news and exclusive offers from Macs Adventure. 

Join Now