Luxury Family Vacations in May 2025/2026

Where to go on vacation with the family in May

Just before the summer crowds pour in and the beaches become littered with people, A May vacation is the perfect time to get away as a family. Make the most of early school break-ups and Memorial Day weekend and jet off on a vacation filled with warm weather, blue sea and luxurious hotels.

Scroll down for our top places for family vacations in May. Alternatively, browse all of our luxury family vacations.

Top Destinations for Family Vacations in May

Norway

Protruding into the Norwegian Sea, just north of the Arctic Circle, lies the remote Lofoten Islands – or Norway’s best-kept secret. Older children can take a break from revising to exercise their wild side this May with hikes up Reinebringen Mountain and kayak tours through the pristine fjords. But there’s also plenty of activities for younger kids to get involved with. Head out to Borg and live like a Viking for the day, rowing a 78-foot longboat, learning to throw an axe, and indulging in an authentic Viking feast.

Take us there

Peru

You’ll never forget your first step at the archaeological site of Machu Picchu, one of the New Seven Wonders of the World. Before this, however, you’ll head deep into the beautiful Colca Canyon to horse-ride along the highland plateau, spot the mighty Andean Condor in flight and take a dip in the hot springs at Colca Lodge’s eco-spa. But it’s not all rural adventures. This May break also boasts a huge heap of culture in the cities of Cusco, Aequipa and Lima. Whilst the older kids may appreciate the ancient ruins of Huchuy Qosqo and hidden trails of the Sacred Valley more than the young, in Cusco the little ones can revel in the Choco Museum where they’ll make chocolate directly from the cocoa bean in an exclusive masterclass. So what are you waiting for? Follow in Paddington Bear’s footsteps and discover the wildest depths of Peru with your loved ones.

Take us there

Canada

On this curious Canadian adventure, you’ll discover the best of both worlds; gastronomic excellence and culture in Calgary and Vancouver, and rural bliss in UNESCO-acclaimed Banff National Park. The outdoor activities on this trip are great for all ages, with each place offering something new and exciting, making it the ultimate destination for a multi-generational vacation. Discover Canada’s rugged mountain range and scenic valleys via helicopter, horseback and aboard the iconic Rocky Mountaineer train – the best way to travel from Banff to Vancouver with inquisitive kids. Stay at one of our favorite lodges in the whole of Canada to go out in search of black bears and wild whales in the day and cozy up around the wood stove in the evenings for some family time. A perfect end to a perfect trip.

Take us there

Luxury Holiday to Greece with WSJ+ & Black Tomato

Greece

This cultural journey through the heart of Greece combines Athens, Spetses and Peloponnese to give families a good mix of land and sea, history and cuisine and action and relaxation over the May break. On the carefree and car-free island of Spetses, saddle up on your way to the Old Harbor, take a boat out on the glistening Mediterranean water and dine out on the fresh, local cuisine. Upon arrival on the east coast of Peloponnese Peninsula, we’re checking you into your very own Pavillion at a Black Tomato favorite, Amanzoe. This is the perfect place for your family to reside after all the Greek adventures.

Take us there

Croatia

May in Croatia reveals a Mediterranean rhythm perfectly suited to family exploration. Local marine biologists introduce children to the Adriatic's resident dolphins from traditional wooden boats, while archaeologists unlock the secrets of Split's Roman heritage through interactive excavation workshops. In Istria's hilltop villages, families join multigenerational olive farmers to learn time-honored pressing techniques, tasting oils from trees that have produced for centuries. Between cycling through lavender fields and learning traditional stone masonry from local artisans, children discover a Croatia that exists beyond its famous coastline.

Take us there

Morocco

May's mild temperatures create ideal conditions for families to explore Morocco's diverse landscapes. Children join Berber astronomers in the Sahara to learn traditional celestial navigation, while master artisans reveal the mathematical patterns behind intricate zellij tilework in Fez's workshops. Local guides lead families through ancient food souks, teaching children to identify exotic spices before joining a family-run riad for hands-on cooking lessons. Between Atlas Mountain village visits and learning traditional bread-baking techniques in earthen ovens, young adventurers discover how Morocco's heritage lives vibrantly in its present.

Take us there