Time your adventure perfectly with 420 tours departing in January 2026 in Europe. Seasonal highlights and optimal conditions await, backed by 340 verified experiences.
Imagine wandering through Cyprus’s Akamas Peninsula in winter, when mild temperatures and a riot of wildflowers transform the landscape into a natural wonderland. The Cyprus Winter Walking tour is an 8-day, self-guided hiking holiday designed for experienced and senior travelers who cherish both nature and tranquility.
Set between Drouseia and Agios Georgios Tis Pegeias, this moderate-activity trip meanders through the Akamas National Park and the Laona plateau, weaving past traditional villages, lush orange groves, and sun-drenched vineyards. Some trails end at the inviting Mediterranean coast, where rare tulips and orchids bloom and migrating birds begin their return to Europe.
The journey is enriched by the warmth and hospitality of the Cypriot people, whose friendly welcome adds a memorable touch to your adventure. Unlike crowded resorts, this tour emphasizes authentic local experiences and unspoiled scenery. With accommodation, transport, and meals included, you’ll enjoy the freedom to explore at your own pace—making it an ideal getaway for those who value natural beauty and genuine cultural connections in a serene, off-season setting.
We visited Western Cyprus in early November and found it hotter than we expected, which made the walking a little more arduous. The scenery on the Northern side of the Akamas Peninsula was beautiful with aromatic pine forests and lovely views. The accommodation was excellent and the transfers were perfectly organised. Overall a lovely early winter break.
Discover the Tuscan countryside and culture on this 8-day self-guided walking tour. Through the extensive footpath network of the area, roughly following the traces of the Via Francigena, one of Europe’s most important ‘highways’ in medieval times, you walk from village to village and experience a full immersion in the world-famous Tuscan landscape. The tour is perfect as an introduction to the region and a great choice for people who love museums, galleries and Gothic and Romanesque architecture. You have plenty of time to visit attractions on most of the days.
You will also have time to visit all the beautiful medieval villages and historic towns along the Via Francigena: starting from beautiful Lucca, you’ll pass through Fucecchio, San Miniato, Gambassi Terme, the stunning San Gimignano with its medieval skyscrapers and Monteriggioni, admired by Dante in his Divine Comedy. An optional detour can bring you to beautiful Colle Val d’Elsa and the tour ends in Siena, arguably the most perfectly preserved medieval town in Tuscany. This tour threads together some of the most attractive towns and villages in Tuscany in an eloquent procession.
However, the emphasis of the tour is to enjoy the countryside, the rolling vineyards, the poppies in spring and the wild cyclamen in autumn. The area north of Siena is an amazing landscape of rolling hills, alternating vineyards and forests, while cypresses line the way leading to the distant farmhouses. Walking here is an unforgettable experience and many of the views have barely changed for hundreds of years.
Accommodation and some meals are included. You spend a night in one of the best agriturismos in Tuscany, and the final night in the heart of Siena, in one of the most characteristic little hotels.
This is a moderately easy tour which is suitable for those who have some experience of walking and a good general physical condition.
Trekking and Hiking
Tour Type
Private Tour
Accommodation
Hotel, Hostel
Age Range
18-99 yrs
Operated in
English
Destinations
Siena, Tuscany, Lucca, Altopasci
Siena, Tuscany, Lucca, Altopascio, San Miniato Alto, Gambassi Terme, San Gimignano, Monteriggioni
A winning combination of walks in stunning scenery and top quality hotels in which to relax at the end of the day. Being self guided was a great experience, walking notes very clear, and you can go at your own choice of pace and stop whenever you want. Highly recommended.
Trekking and HikingAdventure
Tour Type
Private Tour
Accommodation
Hotel, Resort
Age Range
12-99 yrs
Operated in
english
Destinations
Funchal, Madeira, Santo Da Serra
Funchal, Madeira, Santo Da Serra, Ponta De Sao Lourenco
This holiday was made extra special for us by the professionalism and kindness of the Headwater reps - Tony & Ludmilla. The one day when we got soaked, they came to our rescue and collected us early with no no fuss whatsoever. Apart from that one day the weather was kind and the walks spectacular
La Gomera is a stunning island with an amazing variety of landscapes and stunning views. Our experience felt very authentic and we enjoyed the local hospitality. The hiking was enjoyable but tough. I would certainly rate some of the ascents and descents as challenging rather than moderate. The terrain is often rocky but it is the areas with small stones, particularly on the downhill that can lead one to be on their feet one minute and on the ground the next! It can be very slippery with all the loose gravel and stones and needs solid concentration! In spite of this we enjoyed the trip very much and would heartily recommend visiting La Gomera.
Walking tours
Tour Type
Private Tour
Accommodation
Hotel, Guest House, Villa
Age Range
18-99 yrs
Operated in
english
Destinations
San Sebastian, Santiago De Compo
San Sebastian, Santiago De Compostela, Tenerife, San Sebastián de La Gomera, Hermigua, Vallehermoso, Chipude, Laguna De Santiago
