Each week our holiday hero, Neil Simpson, digs into a great holiday theme and does all the legwork so you don’t have to. This week: hiking holiday for beginners.
Walking holidays promise fresh air, fantastic views and the opportunity to escape from the hustle and bustle.
“Our customers come from all walks of life, from busy professionals to retirees, and we also have a lot of solo walkers,” says Neil Lapping of tour operator Macs Adventure. “Many new customers are looking for a new challenge on a walking holiday. Our job is to help them find the route that suits them and is often not too strenuous, so they can enjoy the journey alone from home.
Holiday hero Neil Simpson shares his guide to the best walking holidays for beginners. These include Explore’s Taste Of Italy – Walking In Puglia Holiday, which takes walkers to the ancient city of Matera (pictured in the background).
“Walkers can immerse themselves in the landscape and culture along the way. Our self-guided holidays offer the freedom to explore at your own pace and experience so much more on foot.’
Walking holidays are easier than many beginners expect. Hotels are booked along the route and luggage is transported between them.
Finding your way is just as easy. You will receive a welcome pack with easy to follow daily instructions. Many tour companies also allow you to follow the route via a phone app.
Daily distances on beginner holidays are modest, with plenty of time for lunch and sightseeing.
A six-day walking holiday from Sintra to Cascais, Portugal with Macs Adventure is a classic first option. It starts in the fairytale town of Sintra with time to explore the castles, palaces, monasteries and tropical gardens. The route is mostly flat, with daily walks of six to ten miles following inland forest paths and coastal paths along cliffs to the coastal town of Cascais. It costs from £710 per person, excluding flights.
Other hikes aimed at beginners take place in Mallorca, Scotland, the Azores and Italy’s Chianti region (macsadventure.com).

Macs Adventure’s six-day walking holiday from Sintra to Cascais in Portugal starts in the fairytale town of Sintra. Pictured is the city’s Pena Palace
Wine tasting stops are a highlight of a seven-day Chateaux & Vineyards vacation through France’s Loire Valley. It’s one of Inn Travel’s easy breaks, with days off to kick off your walking boots and enjoy the well-chosen hotels along the way, including a converted 18th-century school and an old coaching inn.
Distances on walking days vary from nine to eleven miles. From £1,080 per person excluding flights (inntravel.co.uk).
If you prefer to walk in a small group, the Taste Of Italy – Walking In Puglia holiday in Southern Italy with Explore is worth considering. A tour guide accompanies between ten and sixteen walkers on visits to the bakery and cheese dairy, pasta courses and wine tastings. You will also travel back in time among the ancient rock churches and cave dwellings of Matera. Daily hikes range from just two to five miles, and since you’re traveling in a group, there’s no map reading to do. From £1,400 per person plus flights (explore.co.uk).
If you don’t fancy changing hotels every night, or you’re worried about keeping up with other walkers, Flexi Walking is a smart category offered by Ramblers Holidays. Each day has shortcuts and check-off points where you can take a break and rejoin the other walkers later.
The seven-day stay in Tavira, the pearl of the Algarve, also includes a boat trip to the island of Tavira for walks on one of the most beautiful beaches in Europe.
Walking is between six and ten miles a day, through orange groves, pine forests and along the sea. From £1,290 per person, including flights to Faro (ramblersholidays.co.uk).

Take a stroll along the beautiful beach of Tavira Island (above) during Ramblers Holidays’ 7-night break in Tavira, the Pearl of the Algarve
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James is an author and travel journalist who writes for The Fashion Vibes. With a love for exploring new cultures and discovering unique destinations, James brings his readers on a journey with him through his articles.