Book Your Dream Destination & Win a Free Bottle of Wine

Win a bottle of wine!

There’s nothing quite like raising a glass at the end of a long day on the trail, and this month we’re giving you the chance to bring a little of that magic home. We’ve teamed up with The Wine Shed, our local independent wine specialists, to give away six bottles of wine, each handpicked to match one of our walking holiday destinations.

Book a qualifying holiday between 25th May and 1st June 2026 and you’ll be entered into the prize draw for your destination’s bottle, whether that’s a sun-drenched Sicilian white, a robust Tuscan red, or something perfect for toasting the trails of Catalonia, Provence, Crete, or Porto. Six destinations. Six bottles. One winner per draw.

See below the destinations and the bottle of wine that you could win a taste of your destination before arriving.

Sicily’s walking holiday with Involved Holidays is based at the four-star Hotel Baia Taormina, offering seven nights of half-board accommodation as the perfect base for exploring the island. Guests trek across Mount Etna’s volcanic terrain, wander the basalt walls of Alcantara Gorge, and discover the medieval countryside of Forza d’Agrò. Between guided walks and free days, Sicily’s landscapes, history, and warm hospitality have a way of getting under your skin. A glass of local wine on the terrace is the perfect end to a day well walked.

Involved Holidays’ Catalonia Trails and Rails holiday combines coastal scenery, Roman heritage, and rewarding wine country into one beautifully balanced week. Guided walks take in the Torres family’s Castle of Milmanda, the modernist Wine Cathedral in Espluga de Francolí, and the scenic Montsant wine region, finishing in the vine-surrounded village of Marça. A full day in UNESCO-listed Tarragona adds further history to an already rich itinerary. With vineyards at every turn and bold local wines to match, Catalonia is a destination that satisfies walkers and wine lovers alike. 

The Porto Trails and Rails holiday with Involved Holidays takes walkers through the vibrant Ribeira district and beyond, with train day trips to Guimarães, Braga, Aveiro, and the breathtaking Douro Valley, where terraced vineyards line the riverbanks. A walk along the Quinta das Carvalhas trail is followed by a cruise aboard a traditional rabelo boat, once used to carry barrels of wine along the Douro. With an optional visit to historic wine cellars available, this holiday wears its winemaking heritage proudly at every turn. 

Crete is the largest island in Greece, with 4,000 years of Minoan history, dramatic mountain landscapes, and a coastline stretching over 650 miles. Involved Holidays’ Crete walking holiday follows ancient paths to Byzantine monasteries, climbs Mount Juchtas to visit the replica of the world’s oldest wine press at Vathypetro, and crosses by boat to the island of Spinalonga, immortalised in Victoria Hislop’s The Island. With a winemaking tradition as old as civilisation itself, raising a glass of local wine here feels like a genuinely historic act. 

Involved Holidays’ Tuscany and Liguria walking holiday is based in peaceful Marina di Pietrasanta, combining gentle guided walks with some of Europe’s most culturally rich excursions. Walkers explore the walled city of Lucca, the Certosa Monastery above Calci, and the beautiful village of Tellaro on the Gulf of Poets, with an included full-day trip to Florence completing an exceptional week. Tuscany produces some of the world’s most celebrated wines, and after a day walking through this magnificent countryside, a glass poured at dinner feels very well earned indeed. 

Involved Holidays’ Provence walking holiday is based in the ancient city of Arles, a former Roman capital and the place that inspired Van Gogh’s most celebrated paintings. Walks explore the Camargue wetlands, the Alpilles mountains, and the medieval citadel of Les-Baux-de-Provence, with the charming streets of Saint-Rémy adding yet more colour to an already beautiful week. With world-renowned wines produced across the surrounding region, a chilled glass on a sunlit terrace at the end of each day feels like the most natural thing in the world.