Exploring beautiful natural surroundings is one of the best things about going on holiday – and while holidays should be relaxing, they’re also great opportunities to get active and enjoy being outside. So, for the perfect balance between relaxation and adventure, why not think about a walking or cycling holiday for your next escape?

If you’ve never gone on a walking or cycling holiday before, you might want to check out Headwater, who have been creating relaxing, tailor-made walking and cycling holidays since 1985. Combining beautiful routes, idyllic destinations, and hand-picked accommodation, Headwater’s tours also offer incredible diversity – and you can choose to visit the UK, Europe, the Mediterranean and even Bermuda.

With that said, here are 12 relaxed walking and cycling holidays to get you inspired.

1. Walking in the Algarve, Portugal

Walking in the Algarve, Portugal

The Algarve might be known as a popular holiday destination, but scratch beneath the surface and you’ll discover a whole other side to this stunning region. Away from all the resorts and hotels is the Sagres Peninsula – the Algarve’s ‘Wild West’ – which is breathtakingly beautiful, wild, and remote.

This is a land of golden beaches, soaring cliffs, secret sea caves, and flower-filled meadows – a place where lush valleys, dense pine forests, and dramatic coastline hide fascinating wildlife. Whitewashed villages and old castle towns perch upon rolling hills, and all around, the Atlantic Ocean crashes.

A walking holiday in the Algarve allows you to make the most of the natural beauty and absorbing culture of this region. You’ll follow the Rota Vicentina and Fishermen’s Trail; hiking over hills dotted with almond trees, through orchid-rich forests, along craggy cliff tops, and over pristine beaches.

You’ll stay in a variety of accommodations, from rustic village houses to chic hotels, all of which have pools. Three dinners are included, so if you’re looking to enjoy delicious Algarvian cuisine, you’re in luck. You can feast upon fresh fish, tangy cheese, local vegetables, and superb Portuguese wines.

2. Walking in the Dolomites, Italy

Walking in the Dolomites, Italy

The jagged peaks of the Italian Dolomites might be best known for their ski resorts, but this gorgeous region also boasts brilliant walking trails – particularly if you’re up for a challenge! A week’s walking tour is the perfect way to discover the stunning natural setting and enjoy jaw-dropping Alpine views.

With over 1,000km of trails, you can choose the route that’s right for you – from soaring ridge paths that offer dazzling vistas over the Austrian Alps to gentler hikes along the mesmerising Alta Pusteria Valley, which turns into a green paradise in the summer.

You can also explore the world-famous Tre Cime (three huge peaks that have become a symbol of this mountainous region) and wander through the pretty villages and hamlets that are scattered over these slopes. If you’re into bird-spotting, keep your eyes peeled for eagles, hawks, and woodpeckers!

During this tour, you’ll stay in the four-star Park Hotel Bellevue, where you’ll enjoy delicious dinners in the elegant dining room (meals include a weekly five-course banquet and themed Tyrolean buffet evening!). Plus, with a spa, pool, sauna, and steam room, you’ll have plenty of chances to relax and indulge, too.

3. Walking in the Loire Valley, France

Walking in the Loire Valley, France

If you’re interested in a more leisurely walking holiday where you can enjoy fine food, style, and lots of history, you might want to head to the Loire Valley. Known for its outstanding wines, sophisticated cities, and magnificent chateaux, this entire part of France is a Unesco World Heritage Site.

Following a linear route from the lively city of Blois, you’ll visit sleepy hamlets and historic villages before passing Montrichard, Chenonceaux, and Montlouis and reaching the River Cher. While the path might be gentle, the views of fertile river valleys and unspoiled landscapes are sensational.

A walking tour here will include visits to some of France’s most opulent chateaux and aristocratic estates, where you can marvel at the lavish banquet halls and imposing crenellated towers. The sprawling vineyards that surround these chateaux are some of France’s best, so wine enthusiasts are in for a real treat.

This holiday is the perfect blend of discovery and luxury. You can spend the morning hiking through river valleys and sunny fields, visit historic towns like Amboise and grand chateaux in the afternoon, and spend your evenings feasting upon delicious local cuisine and wine in fine dining restaurants.

4. Cycling in Veneto, Italy

Cycling in Veneto, Italy

If you’d like to visit Italy but are more of a cyclist than a walker, why not head to Veneto for a cycling holiday?

While most visitors may head to this part of Italy to visit Venice, this relatively undiscovered corner of the country is a chance to experience quiet, rural Italian bliss – with a side of cycling.

Known for its sparkling lakes, charming villages, Roman ruins, and gently-rolling green countryside, Veneto is perfect for lazy, leisurely cycles. The valley is cut through with countless quiet lanes and with a selection of long and short routes to choose from, you can be as active or relaxed as you like.

You’ll spend sunny days cycling past olive groves, vineyards, and cherry orchards while getting a real insight into genuine Italian country living. If you fancy exploring further afield, Venice, Vicenza and Padua, with their stunning Renaissance architecture, are all within easy reach.

This is also a chance to stay in a wonderful agriturismo on the edge of the village of Villaganzerla. Family-run, friendly, and with a pristine pool, you won’t only be able to enjoy traditional Italian cooking here, but you’ll also get the opportunity to try fruit picking or to tour the local grappa distillery!

5. Walking Puglia and Matera, Italy

Walking Puglia and Matera, Italy

Another excellent destination for an Italian walking holiday, particularly if you’re fascinated by ancient civilisations and cultures, is Puglia. Located in the heel of Italy’s boot, Puglia is defined by its miles of dramatic coastline, compelling history, and warm and passionate people.

If you’re looking for glimpses of ‘traditional Italy’, you’ll find that here. This is a place where Vespas speed down narrow and historic alleys, ancient towns bake beneath the scorching sun, and locals tuck into bowls of pasta and sip wine in local trattorias (restaurants).

Puglia is also home to two fascinating UNESCO sites. These are the spectacular cave-houses of Matera, which are believed to be one of the world’s longest continuously inhabited human settlements; and unique Alberobello, with its hobbit-like, conical stone trulli huts. The white city of Ostuni is also unmissable.

A walking holiday here allows you to discover the beauty and history of this spectacular region at your own pace. You’ll stay in lovely local hotels, tuck into mouth-watering food and wine, and have plenty of time to learn about the incredible culture and history of this special part of Italy.

6. Walking in Madeira, Portugal

Walking in Madeira, Portugal

The island of Madeira is like nowhere else in the world. Though it belongs to Portugal, Madeira is a subtropical paradise that’s bursting with exotic colours, dramatic landscapes, and wonderful wildlife. Known as the Island of Eternal Spring and Pearl of the Atlantic, Madeira deserves all the superlatives.

This enchanting island seems tailor-made for a walking holiday. Though it’s small, Madeira enjoys incredible diversity, and each day is different. One day you’ll be trekking over a lunar-like volcanic landscape and the next you’ll be strolling along Madeira’s unique network of Levada water channels.

If you’re interested in flora and fauna, you’re in the right place. You can hike along coastal trails dotted with frangipani, camellia, bird-of-paradise, dragon trees, and lilac jacaranda; watch whales, dolphins, and sea lions swimming in the azure sea; and spot more than 40 species of bird in the sky.

After long days of exploring, you can enjoy unrivalled comfort. In Santana, your hotel boasts sunny vineyards and sea views; in Santo da Serra, you’ll stay in a charming 1920s hotel; and in Funchal, your five-star hotel is set within gorgeous botanic gardens. The fine Madeira wine is just another bonus!

7. Cycling from the Julian Alps to the Adriatic

Cycling from the Julian Alps to the Adriatic

If you’re hoping to explore several countries on a cycling holiday but want to have time to soak up your surroundings, then why not visit Slovenia, Austria, and Italy? It might sound intense, but the Julian Alps to the Adriatic cycling holiday allows you to make the most of these beautiful countries.

Beginning on the shores of Slovenia’s magical Lake Bled, you’ll cycle at your own pace through the scenic countryside – admiring breathtaking views of the Julian Alps and glistening mountain streams. On your way into Austria, you’ll pass lush forests, sun-drenched hamlets, and rolling river valleys.

For pretty much the entire route, you’ll get to enjoy picture-perfect rural views and when you reach the final leg of the journey, you’ll be rewarded by glistening vistas of the cobalt blue Adriatic. In Italy, you’ll also have plenty of time to explore medieval villages, renaissance towns, and historic hilltop castles.

If you’re into history, you can also visit the UNESCO-listed ancient city of Aquileia, where you can admire Roman ruins and early Christian cathedrals. You’ll stay in varied accommodations; a luxury hotel in Slovenia’s Bled, an Italian alpine lodge in Tarvisio, and a grand hotel on sun-kissed Grado.

8. Cycling in Lake Constance, Switzerland

Cycling in Lake Constance, Switzerland

Another holiday that gives you the chance to explore three countries is the Lake Constance cycling holiday. Bordering Germany, Switzerland, and Austria, and surrounded by towering Alpine peaks, this peaceful part of the world provides you with beautiful cycling routes that are enjoyably flat.

You’ll cycle alongside lakeside paths beside the turquoise lake and its pristine pebbly beaches, past fields packed with bobbing wildflowers, and through vineyards and cherry orchards. If you fancy a dip, the crystal-clear waters of Lake Constance are perfect for swimming.

If you’d like to explore the surrounding towns and villages, you’ll have plenty of time for that too, and there’s lots to see and do in the local area; from visiting baroque churches and fairytale castles to strolling down the pretty, cafe-lined waterfronts of historic and characterful towns.

You’ll be staying in a varied range of accommodation, including an old coaching inn and a stylish riverside hotel and a luxurious lakeside mansion. Plus, you’ll never be far from the water and can enjoy sunny evenings dining alfresco – perhaps trying local specialities like kretzer (perch) and zander (pike-perch).

9. Cycling in the Cotswolds, England

Cycling in the Cotswolds, England

For something a little closer to home, you might want to head to the Cotswolds for a cycling holiday. As England’s largest Area of Outstanding Natural Beauty, the rolling hills, pretty meadows, and quiet country lanes of the Cotswolds make it ideal for cycling, particularly if you want to take it easy.

This part of the UK is famous for its picture-perfect villages and distinctive honey-coloured houses, which are made from Jurassic limestone. And a cycling break is a great chance to explore some of the most scenic, characterful villages like Chipping Campden, Bourton-on-the-Water, and Winchcombe.

There’s plenty of history to be found in this bucolic region, too. You can visit Sudeley Castle, which is the last resting place of Katherine Parr (the sixth wife of Henry VIII); stroll through the ancient Saxon city of Winchcombe; and visit Snowshill Manor, a National Trust property full of historic treasures.

You’ll be staying in charming bed and breakfasts in some of the loveliest towns, where you’ll enjoy a warm welcome and cosy accommodation. Plus, thanks to the wealth of pubs, cafes, and restaurants in this region (including some Michelin-starred restaurants), you won’t be short of excellent places to eat.

10. Cycling in Piedmont, Italy

Cycling in Piedmont, Italy

If you’re passionate about food and history and you love Italian culture, Piedmont may be your perfect holiday destination. Located in northwestern Italy, the pretty pastoral scenery here is perfect for cycling around leisurely, while stopping off regularly to sample the region’s famous cuisine.

Boasting UNESCO vineyards nestled between softly-rolling hills; dense pine forests by sparkling rivers; and sun-drenched hilltop hamlets beside ancient castles, the scenery here is absolutely idyllic and the quiet, traffic-free country roads provide a wonderful vantage point.

This part of Italy is known for its gastronomy, and you’ll have plenty of time to discover just how delicious the food and wine here are! You can feast upon local delicacies like white truffles, filled pasta, porcini risotto, and panna cotta, and wash it down with world-class wine like Barbaresco and Barolo.

Piedmont’s beautiful towns are also a joy to explore. From the peach and ochre houses of Barolo to the geranium-decked houses of Monforte d’Alba, it’s a treat for your eyes as well as your taste buds.

Lodgings on this holiday are also luxurious and include stunning villas, grand country houses, and four-star hotels.

11. Walking in Istria, Croatia

Walking in Istria, Croatia

Croatia’s Istrian peninsula is dazzlingly beautiful, with an interior of rolling hills, fertile plains, lush orchards, hilltop towns, and a coastline that’s studded with bays and inlets. It’s the perfect place to explore on foot, stopping at your leisure to visit scenic villages and try the diverse regional cuisine.

Beginning in the medieval hilltop village of Motovun, you’ll stroll along high ridges above the truffle-rich valleys and fruit orchards. You’ll then reach the fortified hill town of Buzet before having the chance to climb Mount Vojak, where you can enjoy 360° views of the Dolomites and Switzerland.

The Adriatic Riviera is next and you’ll stay in the coastal town of Opatija, where elegant villas line the shore, unique shops sit beside historic churches, and restaurants back onto lively marinas. There’ll be plenty of time to try local cuisine like fresh fish, homemade pasta, truffles, and sample regional wine.

You’ll also have the chance to swim every day and visit Venetian castles and Renaissance palaces – and you’ll even get to stay in a stunning converted 17th-century palace in Motovun.

In Buzet, you’ll stay in a grand converted townhouse with a pool, and in Opatija, you’ll be in a sleek waterfront property.

12. Cycling in Puglia, Italy

Cycling in Puglia, Italy

Puglia is one of the most beautiful and intoxicating parts of Europe – so much so that it gets two mentions in this article! While a walking holiday in Puglia makes a wonderful escape, cycling the heel of Italy is also a fantastic experience, and allows you to discover more of this captivating region.

Sandwiched between the Adriatic and Ionian seas, you’ll have plenty of opportunities to explore the gorgeous coastline, and admire spectacular views of olive trees and azure seas. You can cycle through ancient forests and historic towns, and because the region is mainly flat, it won’t be too much effort.

When you need a break from cycling, you can visit fascinating and unique UNESCO world heritage sites, explore lovely towns with extravagant architecture, and savour the mouth-watering cuisine Puglia is so famous for. You’ll be staying in three and four-star hotels, so there’ll be plenty of comfort too!

Final thoughts…

Whether you’re tempted by Italian hilltop towns, Slovenian lakes, the Croatian countryside, Portugal’s Algarve or our very own Cotswolds, we hope this article has provided some travel inspiration.

The brilliant thing about a self-guided walking or cycling holiday is that it gives you the chance to explore on your own terms. You can stroll or pedal at your own pace, stopping off whenever you want, and taking time to soak up your surroundings and find the perfect balance between relaxation and discovery.

Headwater are the ultimate self-guided specialist and their tailor-made tours combine gorgeous routes, intriguing destinations, and hand-selected accommodation for walkers or cyclists of all abilities. With Headwater’s expertise behind you, you’ll know you’re going in the right direction and visiting all the best destinations.

So why not change the way you think about travel and holidays and treat yourself to a walking or cycling holiday you won’t forget? 

Or, for even more ideas and inspiration for your next trip, you might want to visit the travel section of our website.