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HeadwaterTravel is one of life’s greatest adventures, though travelling in the summer months can make it more challenging than enjoyable. Costs of everything soar – from flights to hotels to car hire – and you can also expect longer airport queues and an increased chance of delays and cancellations.

But, the good news is that travelling in shoulder season is an easy way to avoid these issues.

Shoulder season refers to the period of time between peak season and off-season – a time when the weather is still fine, but you won’t have to deal with throngs of tourists and heavily inflated prices.

For countries in the northern hemisphere, the peak season is summer and the off-season is winter, which means the shoulder seasons are spring and autumn.

Travelling during shoulder season won’t only mean you save money and avoid stress, it also means you get to explore destinations when they’re at their loveliest – so you can enjoy warm, pleasant weather rather than the scorching heat of the summer sun.

To give you some shoulder season inspiration for your next break, we’ve partnered up with Headwater, who are leading specialists in self-guided walking and cycling holidays.

Some of Headwater’s most popular destinations come into their own during the spring and autumn months. So why not consider booking a shoulder season holiday at one of the following destinations?

1. Cyprus

Known as the crossroads of three continents – Europe, Asia, and Africa – Cyprus is an island that’s like no other place in the world. It’s a true jewel of the Mediterranean; a place where Greek culture and history collide with Middle Eastern influences.

The island boasts endless white sand beaches on its exterior, and dramatic gorges, mountains, forests, and waterfalls in the interior.

While Cyprus is a popular holiday destination, its summers are extremely hot, with temperatures regularly approaching 40°C. But, visiting in shoulder season is a far more pleasant experience, as temperatures still hover around the mid-20s °C – plus, you’ll avoid the crowds.

During Headwater’s seven-night holiday, you’ll get to discover the true beauty and diversity of this island.

History buffs can visit UNESCO churches, abandoned villages, and the Baths of Aphrodite (the cave where the ancient Greek goddess was said to bathe), while nature enthusiasts can hike along the dramatic Avakas Gorge and through the forested foothills of the Troodos Mountains.

The perfect mix of history, culture, nature, and beaches, this tour will make you fall head over heels for Cyprus.

Soak up the splendour of Cyprus

2. Salzburg, Austria

Salzburg, Austria

Salzburg may be one of Austria’s smallest provinces, but it’s a top contender for the most scenic.

This is a region that brings to mind the Alpine meadows and dramatic peaks of The Sound of Music, the Austria of fanciful childhood dreams – a place where you can visit hilltop castles and Baroque palaces before trekking along snow-capped mountains and relaxing on pristine lakeside beaches.

Due to its popularity, Salzburg can be expensive, particularly during high season, so if you want to explore this spectacular region without breaking the bank, you might want to think about visiting during shoulder season.

During Headwater’s seven-day tour of Salzburg, you’ll stay in the village of Strobl, which is located on the shores of Lake Wolfgang, one of the region’s most picturesque spots.

This is a holiday that’s all about appreciating the Great Outdoors; you’ll be walking and cycling through picture-perfect villages, past gleaming Alpine lakes, and along serene wooded valleys. You can also explore ice caves, go on boat trips, and try your hand at watersports. And if you’re into culture and history, the fairytale city of Salzburg will have you thinking you’ve fallen straight into a dream.

Explore the Alpine beauty of Salzburg

3. Devon, England

Devon, England

Devon is one of the most popular holiday destinations in the UK – and for good reason. With its wild, mysterious moors, winding country lanes, green river valleys, charming towns, and blissful beaches, it offers something for everyone.

During the summer months, however, when the kids are off school, it can become unpleasantly busy – which is why visiting during shoulder season makes sense.

One of the best ways to explore this gorgeous county is by foot, hiking along Dartmoor’s famous moorland tracks and the picturesque paths that stretch along the south coast.

Headwater’s seven-night walking tour allows you to see the best of South Devon and Dartmoor, from the spectacular scenery of Erme Valley to Plymouth’s magnificent and historic waterfront.

You’ll stay in hand-picked guesthouses, small hotels, or pubs that are close to the Coast Path. You’ll start in Plymouth, where you can learn all about its maritime history, and end in the pretty market town of Buckfastleigh.

Along the way, you’ll trek along wooded cliffs and golden beaches, and past rugged coastlines and winding rivers, admiring the epic views as you go.

Hike Devon’s famous South West Coast Path

4. Lanzarote, Canary Islands

Lanzarote, Canary Islands

One of the best destinations to visit during shoulder season is Spain’s Canary Islands, because their location, off the coast of northwest Africa, means they enjoy a pleasant climate all year round.

There are seven main islands, each with its own appeal. But if you’re interested in hiking, spotting rare birds, admiring other-worldly landscapes, and enjoying delicious food, head to Lanzarote.

Headwater’s seven-night walking tour of Lanzarote allows you to see the very best this stunning island has to offer.

Lanzarote’s terrain is so unique that it’s often compared to Mars and has been certified as a Biosphere Reserve. You’ll have plenty of chances to explore rugged volcanic craters, barren lava fields, and dramatic white and black sand beaches.

Birdwatchers can spot rare species at Chinijo National Park, while foodies can feast on some of the best food and wine in the Canaries. You’ll also visit the unspoilt island of La Graciosa, stroll through renowned artist Cesar Manrique’s famous Cactus Garden, and when you just want to relax and do nothing, your hotel’s swimming pool, sun terrace, and hot tub is the perfect place to unwind.

Experience the magic of Lanzarote

5. The Loire Valley, France

The Loire Valley, France

France has long been one of the most popular holiday destinations for Brits – and it’s no less popular with the rest of the world! That’s why, if you want to avoid overcrowded towns and hiked prices, it’s best to avoid visiting in summer.

Shoulder season is actually the perfect time to visit much of France, and in particular, the famous Loire Valley region.

Located in Central France, the Loire Valley is known for its dense forests, meandering rivers, sleepy wine villages, sprawling vineyards, vast sunflower fields, and grand aristocratic estates. Interspersed with winding traffic-free lanes, it’s the perfect destination to explore by bike, and on Headwater’s seven-day cycling tour, you’ll be doing just that.

This is a laidback holiday where the focus is on history, food, and culture. You can enjoy lazy cycles to the region’s most opulent chateaux, from Amboise and Chambord to the renaissance splendour of Chenonceau.

Along the way, you’ll visit historic towns like Blois, pedal along shady riversides, stroll through tranquil gardens, and sample the exceptional food and wine this region is known for.

Cycle through the splendid Loire Valley

6. Andalucia, Spain

Andalucia, Spain

Andalucia is one of Spain’s most diverse regions, and while most travellers head here for summer, it’s best explored in spring and early autumn – particularly if you’re into hiking.

The Picos de Europa is Spain’s third-highest mountain range and arguably the most beautiful, with scenery that includes jagged limestone peaks, wildflower meadows, steep river gorges, and lush, forested valleys.

During Headwater’s seven-night walking holiday, you’ll be based in a characterful family-run hotel in the picturesque mountain village of Arenas De Cabrales, the gateway to the Picos de Europa. From here, you’re perfectly situated to enjoy a week of hiking through this stunning landscape – and can choose challenging treks up steep Roman paths, or more leisurely walks through rugged gorges.

If you’re interested in wildlife, keep an eye out for wild boars, wolves, and even bears, and in the sky, golden eagles, griffon vultures, and many other birds.

When you’re not hiking, you’ll also have plenty of time to sample the delicious local cuisine in Arenas De Cabrales and soak up the absorbing culture. In the evenings, you can enjoy relaxing meals at your hotel, and drinks on the gorgeous garden terrace.

Discover the rugged beauty of the Picos de Europa

7. Madeira, Portugal

Madeira, Portugal

It might be a Portuguese island, but Madeira is nothing like the mainland. Just like the Canary Islands, it’s Madeira’s location that makes it such a good choice for a shoulder season break.

Located off the northwest coast of Africa, nearly 500 km north of the Canaries, Madeira’s sub-tropical climate has given it the nickname, ‘The Island of Eternal Spring’. But Madeira is so special it has another nickname; ‘The Pearl of the Atlantic.’ Though, this isn’t hyperbole – as this island is genuinely breathtaking.

Madeira is dazzling in its diversity; boasting magnificent mountains, cultivated vine terraces, jaw-dropping coastal trails, and flower-strewn levadas (which are the island’s unique waterways and perfect for walking along).

Headwater’s seven-night tour of Madeira will take you from quiet wine villages in the north to the buzzing capital of Funchal in the south. And on the way, you’ll enjoy plenty of hikes – along the coast, over mountains, and across clifftops.

You can admire the island’s colourful flora and fauna, sample delicious local food and wine, sunbathe by the pool, and relax in stylish five-star hotels.

Discover the magnetism of Madeira

8. Bermuda


Beautiful Bermuda is also an excellent choice for a shoulder season holiday.

Its remote location in the North Atlantic Ocean, 650 miles from the US coast, means that it enjoys a wonderful year-round climate. Plus, thanks to the fact that its waters are warmed by the Gulf Stream, swimming here is a blissful experience. If you’re looking for sun, sea, and sand, it’s an ideal choice.

Because Bermuda is small, a week is long enough to see its most spectacular sights, and on Headwater’s walking tour, you’ll check them all off your list.

As Britain’s oldest overseas territory, Bermuda is a fascinating mix of British and American cultures – although its famous pink sand beaches, secluded turquoise bays, and glittering sea grottoes are worlds apart from either country.

During this tour, you can enjoy gentle hikes through lush woodlands and flower-adorned fields, and learn all about Bermuda’s history in colonial St George, where you can stroll along its pretty harbour, lose yourself in the colourful streets, and visit the 17th-century fort.

You’ll have plenty of time to swim and sunbathe too – and remember to keep an eye out for sea turtles and humpback whales!

Bliss out in Bermuda

9. Malta


Malta is another island that’s a crossroads of cultures, and the influence of European, African, and Middle Eastern cultures means that Malta feels truly unique.

Its glorious landscapes, breathtaking beaches, and captivating culture mean that it can become uncomfortably busy during summer, so visiting in the shoulder season, when the weather is still lovely, is ideal.

If you’re interested in history, you’ll be spoilt for choice. The island has been home to the Romans, Phoenicians, Knights of St John – and both the Napoleonic and British Empires, and their influence can be seen in the island’s architecture and historical sites and ruins. The capital Valletta is a UNESCO world heritage site that’s packed with Baroque buildings and its bustling waterfront is a joy to explore.

On Headwater’s four-night holiday, you’ll not only visit Valletta, but the ancient settlement of Rabat and the walled city of Mdina, where you can feast upon traditional Maltese food.

You can trek along the sensational coastline, admiring views of hidden coves, limestone cliffs, and sparkling azure waters. Jump in for a swim if you get hot – or take a dip in your stylish hotel’s infinity pool instead!

Uncover the remarkable history of Malta

10. The Algarve, Portugal

The Algarve, Portugal

Portugal’s Algarve is one of the most popular holiday destinations for British tourists, so if you want to avoid crowds and hiked prices, it’s best to avoid visiting in peak season.

But there’s another reason why visiting the Algarve during shoulder season is a good idea – and that’s because you get to see a whole other side to this rugged-yet-tranquil region.

On Headwater’s six-night tour, you’ll be exploring the Sagres Peninsula – a place that couldn’t be more different from the overdeveloped resort towns and busy beaches of other parts of the Algarve.

This region is home to sleepy fishermen’s villages, vast golden beaches, dense pine forests, colourful flower meadows, soaring cliffs and lush valleys – and you’ll get to explore them all.

You can enjoy hiking through these stunning natural surroundings and will trek along the Rota Vicentina and Fishermen’s Trail. As you walk through orchid-rich forests and along craggy cliffs, keep an eye on the skies, as this region is home to more than 190 species of birds!

All your hotels have pools so there’s plenty of time to relax – and trying the fabulous local cuisine is just another bonus!

Discover the wild beauty of the Algarve

Final thoughts…

Whether you’re dreaming of a Mediterranean escape or visiting somewhere further afield, travelling in shoulder season is always a smart idea. Not only will you save money and avoid crowds, but the chances are you’ll have a far better travel experience too, free from queues, delays, or cancellations.

All the destinations featured in this article are ideal for a shoulder season break. From the island of Bermuda, adrift in the North Atlantic Ocean, to Cyprus, ideally situated between Europe, Africa, and the Middle East, these destinations come into their own during the spring and autumn months.

The weather is warm without being unpleasantly hot, which means you can spend long days exploring, whether that’s by bicycle or on foot. Plus, booking a Headwater holiday means everything is planned for you, so you can relax, unwind, and focus on soaking in your surroundings.

To find out more about Headwater, head over to their website.