Best walking holidays in May 2027

Did you grow up with teachers who, when you said “Can I go out to play now?” would respond, “May I go out to play now?” Well, this isn’t school and yes you can go out and play, and in the month of May, you definitely may! There are so many reasons to travel in May, of course, the season of flowers and festivals, and still cooler climes for colossal climbs. On a more serious note, we also like to mark the fact that UNESCO’s Day of Living Together in Peace is on 16 May. Because, at TNA we believe that tourism is a promoter of peace, even in these uncertain times. And we have walking holidays in many post-conflict regions or countries, where trails now bring neighbours together, and sustain future generations to live side by side.

Where is the warmest place in Europe in May?

Our walking holidays in the Balearics, the Canaries, Turkey and Greece all rank very highly for warm temperatures in May, yet not too hot for hiking. We are opting for Crete and Corfu, however, as our May sunny specials. With Crete, this is for two great reasons, the first being that this is when the wildflowers all start to push through. From Cretan orchids to the beautiful bellflowers of campanula, or blankets of yellow poppies and buttercups, it’s a bouquet of natural beauty in May. The second reason is Samaria Gorge, which opens 01 May every year. It’s the hiking highlight on this Walking the Gorges holiday, it’s the jewel in the White Mountains crown, and it’s also protected by national park status.

One of Greece’s finest trekking trails, through Samaria Gorge in Crete, is rightly protected by national park status.

With Corfu, we recommend May because it’s before the crowds hit its superb Corfu Trail. This is one of the best walking holidays in the Ionian Islands, a 200km adventure into the heart of the archipelago’s second largest island. Walk it in segments or do the whole thing in two weeks, reading the work of its most famous resident, Gerald Durrell along the way. Exploring Corfu on foot takes you far away from raucous resorts into small coastal and inland communities. Enjoy milder May temperatures topping at 23C and seawater at 19C, walk through traditional villages, along sand dunes and saltwater lagoons, cool down in coastal forests and warm up as you climb to the highest point on the island, Mount Pantokrator (906m).

“I had a great time walking the Corfu Trail. Everything went well, the trip notes and navigation app were spot on, my luggage was delivered no problem…I experienced amazing views, fabulous beaches and met some wonderful people. As a solo traveller, I never felt alone and would recommend the Natural Adventure Company to anyone looking for a truly amazing hiking experience.” Margo C hiking the Corfu Trail.

Best walking holidays in May in the Balkans

Via Dinarica

The Via Dinarica is unbalkanievable! For hikers who want to explore the Balkan countries it really is a very special journey. It’s also been a special one for the local and regional communities who worked together to create it in 2010. They had a vision not only to put their countries on the map but to do so in a sustainable and adventurous way.

The Via Dinarica takes you on a journey of around 1,200km across the main ridge of the Dinaric Alps, through Croatia, Bosnia-Herzegovina, Montenegro, Albania and North Macedonia. You don’t have to do it all at once of course, but just choose a holiday covering one segment. Each section is a microcosm of the region’s complex history but also of its magnificent natural heritage. Not all sections are open in May, with some of the higher passes opening in June. However, our Via Dinarica in Croatia and Bosnia-Herzegovina tour runs May-June and then August-September. There’s also a long window of wanderlust on our Bosnia small group holiday, which has dates from May to the end of August.

Western Balkan Mountains and Belogradchik Rocks, Bulgaria

Otherwise known as Western Stara Planina, the power of nature really does blow you away from the get go on this walking holiday in the Western Balkans, which opens up in May. Starting off with three days at Belogradchik Rocks, a towering collection of natural sandstone sculptures, carved over centuries into a May maze of adventure trails. This Western Balkans holiday also takes you to Vratsa Karst Nature Reserve, a major karst region with forest and waterfall trails, gorges and traditional villages.

Albanian Coast and Llogara National Park

With sea temperatures at a nurturing 19C in Albania’s Adriatic and Ionian Seas during May, it’s a soothing time to saunter and swim on our Coastal Albania walking holiday in Llogara National Park. Spend a week in the shadow of the Ceuranian Mountains, clinging to the coast and strolling through traditional villages along ancient shepherds’ trails. In May the aroma of wild mountain herbs and citrus groves is perfectly piquant, and temperatures of around 23C are divine for taking on hikes to Llogara Pass (1,043m) or Dhjopuri Saddle (1,600m) just beneath Mount Qorre (2,018m). This is a Balkan beauty if you want to combine the coast with local communities, in landscapes where Ceuranian Mountains feel like an early summer cure-all.

You won’t feel blue in Albania’s Llogara National Park, you will be surrounded by it.

Where to hike during the long weekends in May

If you’re based in the UK, you are lucky enough to have two public holidays in May, one at the beginning and one at the end. This is the perfect time to choose a long weekend of hiking and, doing a quick search using our Duration Filter, you can see that we have a good collection of four day walking holidays, but even more five day ones. Imagine spending May day trekking up Mount Toubkal in Morocco, or Montserrat in Catalonia? Those are spring breaks with bells on. Or how about a longer May weekend getting into Garda or Gorges du Verdon before the crowds descend in summer? These are bank holiday weekends that won’t break the bank.

Find flower power in Madeira in May

Throughout the year, Madeira is a culture fest, driven by a tight-knit community passionate about sharing its unique traditions, gastronomy and heritage. The island’s standout celebration, however, is the famous Festa da Flor (Flower Festival) in Funchal, spanning several weeks in May. Featuring intricate floral carpets along the streets and a symbolic Wall of Hope, it’s the icing on the Madeira cake if you visit during this time. Make May all about Madeira, by combining forays into their wildflower trails with the flora festivities going on everywhere else.

If you go walking in Madeira in May, be prepared to go with the floral theme. It’s Flower Festival time.

Walking holidays in May in Sweden

The West is best in Sweden at this time of year, because temperatures are higher here than in the east, and so walking holidays open a little earlier. On our Bohuslän Archipelago walking holiday in West Sweden, the season runs from late April through early October. May brings pleasant conditions with temperatures reaching up to 20°C. While it might still be a bit cool for a swim, you’ll find plenty of saunas along the route as you traverse this captivating archipelago of smooth granite rocks and tranquil islets. Board ferries to visit Marstrand and Koön Islands, which host around a thousand residents and remain blissfully quiet in May before the summer yachting crowd arrives. Heading further north, discover the car-free haven of Dyrön Island, offering serene trails through coastal woods and along rocky shores. And don’t miss the chance to visit its spectacular sauna.

The island of Smögen is a smörgåsbord of prettiness, just one of many in the Bohuslän Archipelago.

Challenging hiking trips in May in the UK

May is an ideal month to head high on the Isle of Skye for a late spring adventure. During this time, the munros and meadows across the largest island in the Inner Hebrides are blanketed in vibrant yellow gorse, cowslips and lesser celandine, all peppered with pink wild orchids. It provides a scenic backdrop for embarking on Skye’s Coast to Coast walking holiday. Accommodated in two traditional B&Bs, you’ll have distinct routes right at your doorstep. Highlights include the signature coast-to-coast path from Loch Scavaig to Sligachan through the dramatic Cuillin Mountains, alongside excursions to the legendary Fairy Pools and the Old Man of Storr pinnacle. Additionally, the island comes alive with music during May thanks to the Skye Live Festival.

The Old Man of Storr on the Isle of Skye. If it’s wilderness you’re after, the Skye’s the limit.

We hope this has given you a few ideas for walking holidays in May with a can-do attitude. You can see all our walking holidays in May here, from Mallorca to Corsica, the Cyclades to the Carpathians, and do not hesitate to contact us for more information. You may also enjoy reading our blogs, How to prepare for a hiking trip, Our guide to the Isle of Skye, What to do in Corfu on a natural adventure and Levadas in Madeira are a gift to hikers.