island-hopping holidays

Our island-hopping holidays are packed with all the things that top holiday wish-lists right now: private ways to travel, secluded spots, new views and enriching experiences. Next year, round up your closest friends and family, or join a small group of like-minded travellers, and head off the tourist trail on our favourite island-hopping sailings and self-drives.

Greece sailing holidays

Best for: Exclusive and authentic adventures by private yacht

Greece is one of our favourite countries to explore from the water. Scattered across the Aegean and Ionian seas, its idyllic islands and secluded bays make island-hopping holidays a breeze – and some places can only be reached by boat, so you can really get off the beaten track. With our partner, Plain Sailing, you can charter a private yacht or catamaran (with your own skipper and host) and choose between two laid-back island-hopping holidays: Sailing Corfu and The Ionian Coast and Sailing the Greek Islands. Yachts and catamarans can sleep between two and 12 people, so this is an incredibly private and exclusive experience for families or groups of friends of all ages.

Scotland self-drive

Best for: Beautifully wild and remote beaches closer to home

This flight-free Scotland self-drive proves that you can find pockets of paradise and empty stretches of sand on home turf. Earlier this year, we teamed up with award-winning tour operator, McKinlay Kidd, to offer tailor-made holidays around the UK and Ireland. The Outer Hebrides Hopscotch self-drive showcases this wild and remote region at the edge of the Atlantic Ocean in all its glory: discover castles and shipwrecks on the Isle of Barra then drive on to the Isle of Harris with its best-in-the-world beaches.

Sri Lanka sailing holiday 

Best for: A new way to explore an Indian Ocean favourite

Hop along the south coast of the Indian Ocean island of Sri Lanka on an intimate voyage, taking in cultural sites, local villages and underwater adventures. Sailing Sri Lanka is a six-night itinerary that showcases the south of the island from a different perspective. With just 10 en-suite cabins, Ocean Diamond 27 is a luxury modern catamaran that was launched in early 2020. It’s an environmentally conscious and socially responsible way to travel, too – the catamaran uses solar power, the boat was built in Sri Lanka by Sri Lankans using locally-sourced materials, and all 10 crew members are hired from island communities.

Croatia sailing holidays

Best for: A private yacht holiday to reach hidden gems

Croatia is perfect for a private yacht adventure. Travel from island to island with up to 12 of your closest family and friends on an exclusive Plain Sailing yacht charter, where you’ll have your own skipper to make sure everything runs smoothly and a host to whip up breakfasts and lunches. There’s a laid-back approach to time and route, so it’s a totally relaxed experience. Our featured sailings in Croatia are Sailing Croatia's Islands from Dubrovnik – which takes in the walled medieval village of Korčula and Trstenik in the heart of Croatian wine country – and Sailing Croatia's Islands from Split, where highlights include the hidden gem of Paklinski Otoci and the luminescent neon blue waters inside Bisevo Cave.

Maldives luxury live-aboard

Best for: Diving adventures and spa treatments at sea

The Floating Resort by Scubaspa is an extra special way to see the Maldives. This 50-metre luxury ‘safari yacht’ hops from one picture-perfect island to another, combining top spa treatments and exceptional diving (the yacht has PADI 5 Star Dive Resort status) as it sails around this beautiful archipelago. If you’re not a diver, that’s not a problem. Guests can choose an inclusive package of dives, spa treatments or a mix of both. There are 19 cabins which you can take over with your friends and family, or you can join a small group of like-minded guests, and itineraries include beach barbecues and trips to tiny desert islands.