Choose another country or region to see content specific to your location.

Request your free brochure for adventure inspiration. Order Now

Contact
Self-Guided Holidays in Italy

Self-Guided Tours in Italy

Italy Self-Guided Tours

Hidden Umbria Walk

spoleto-fortress
8 Days from USD 1,849

Self-Guided Holidays (Excl. Flights)

Discover Umbria's panoramic scenery and historic hilltop villages

Walking & Trekking

Volterra to San Gimignano Walk

Self-Guided Holidays in Italy
9 Days from USD 2,279

Self-Guided Holidays (Excl. Flights)

Combine fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena

Walking & Trekking

A Taste of Tuscany Cycling

Self-Guided Holidays in Italy
8 Days from USD 2,149

Self-Guided Holidays (Excl. Flights)

Quintessential Tuscany – the landscapes, the food and the people

Cycling

Undiscovered Sardinia Cycling

sardinia
8 Days from USD 2,379

Self-Guided Holidays (Excl. Flights)

Discover the fascinating archaeological sites of Nora and St Antioco

Cycling

Walks in the Italian Dolomites

Self-Guided Holidays in Italy
8 Days from USD 2,479

Self-Guided Holidays (Excl. Flights)

Centre-based walking from the beautiful Tyrolean village of Dobbiaco

Walking & Trekking
New

Cycling the Heel of Italy – Matera to Lecce

Self-Guided Holidays in Italy
12 Days from USD 3,179

Self-Guided Holidays (Excl. Flights)

Starting in Matera, the city of 'Sassi' and a UNESCO world heritage site, and through the local canyons, the 'gravine', you will enter Puglia, a unique landscape sandwiched between the Adriatic and Ionian seas.

Cycling

E-Bike Cycling on the Costa Smeralda

liscia-di-vacca-beach
8 Days from USD 2,549

Self-Guided Holidays (Excl. Flights)

Explore Sardinia's North Western Coast by bike

Cycling

Contrasts of Puglia Cycling

Self-Guided Holidays in Italy
8 Days from USD 2,379

Self-Guided Holidays (Excl. Flights)

Explore Puglia's unspoilt villages, gently rolling hills with a backdrop of the clear, emerald Adriatic

Cycling

Barolo Gastronomic Cycling

Self-Guided Holidays in Italy
9 Days from USD 3,199

Self-Guided Holidays (Excl. Flights)

Scenic self-guided cycling in the UNESCO vineyards of Piedmont

Cycling

This is a beautiful area for hiking, and the variety of self-guided hikes we were given was great. There was everything from short easy rambles to long challenging climbs. The Bellevue Hotel was wonderful, with awesome service and delicious food. Definitely an experience I would be happy to repeat. The only negative factor was that, although we never got lost, some of the route notes could do with updating. It seemed that total hike distances were often understated. Also, we did the last tour of the season, and found that some of the refugios mentioned as lunch stops were closed. I would recommend that anyone going late in the season check before setting out, or be sure to carry your own food.

Rosemary Finch Walks in the Italian Dolomites

This tour was a welcome change from the fast paced touring of the big cities. We became familiar with the topography and vegetation as we hiked daily, also visiting towns known for wines and cheeses. The town of Chianciano provided a magnificent backdrop to our accomodation of Agriturismo La Pietriccia. We were awakened every morning to the rooster crowing. Stefano was an attentive and knowledgeable host. Plenty of food was served at the 4 course suppers. I feel this tour was necessary to complete my knowledge of the culture of Italy!

Susan Hoogenboom A Taste of Tuscany Self-Guided Walking

Loved this trip – it was my first self-guided trip and my first trip with Headwater. They have a great selection of hikes to choose from, right from easy rambles to tough hikes. I did pretty much all moderate and more difficult hikes and the directions and provided maps are excellent.
I stayed at Park Hotel Bellevue in Toblach (Dobbiaco) which is one of the best hotels I have ever stayed at.
Included transportation passes and time tables easily let you get around to all the trail heads and even to other towns in South Tyrol if you do not feel like hiking or if the weather is inclement.

Adventure Coordinators Walks in the Italian Dolomites