For brilliant beaches: Jamaica

Click the picture above to see more of Jamaica’s sights

Jamaica’s coastline is breathtakingly diverse, from postcard-classic Seven Mile Beach in the west at Negril - just down the road from Rick’s Café - to the discreet northeast, where snorkellers splash at Port Antonio’s San San. No visit to the hippie south coast’s golden Treasure Beach is complete without the Pelican Bar - on a sandbar miles from land, sip rum waist-high in the Caribbean.
Island high: Bed down next to a private beach at the Jamaica Inn in Ocho Rios, where Marilyn Monroe and Winston Churchill were guests. 

For the great outdoors: Vancouver Island, Canada

Vancouver Island is an outdoor anorak’s paradise. You can spot humpback whales breaching in the morning and go zip-lining in the afternoon. There’s bird watching and fishing, or, if you don’t mind getting wet, snorkelling with salmon in the Campbell River. Surfers find Canada’s best swells in Tofino on the west coast (everyone else: retire to the plush Wickannish Inn to watch).
Island high: Leaping from North America’s first bungee jump, above the Nanaimo River. Reward yourself with a Nanaimo bar - a local treat with butter icing and chocolate.

For rich history: Malta

Too often Malta is seen as a flop-and-bake sun destination, but there’s more to it than that. You can just as easily wander the Hypogeum, an underground burial site dating to 4000 BC, as sift through burnished Renaissance relics at private-palace-cum-museum Casa Rocca Piccola (pictured above). Don't miss Caravaggio’s masterpiece in the magnificent Valletta cathedral, and definitely don’t miss a seaside lunch of octopus stew or dolphinfish pie.
Island high: Wake up to a view of vineyards at the palatial Xara Palace in Mdina, an atmospheric walled city.

For thirsty travellers: Madeira

Home to the world’s most indestructible wine, Madeira’s hilly landscape is carpeted in mimosa forests and, unsurprisingly, vines. Taste their fruits at Blandy’s Wine Lodge in Funchal, then stock up on rare vintages at cellar shop Pereira D’Oliveira. Follow with dinner at Michelin-starred Il Galo d’Oro, because from seafood to honey-laced desserts, Madeira is for foodies too.
Island high: Continue the boozy theme with a vinotherapy massage at The Vine.

For glam hotels: Maldives

The Maldives caters to the desert-island diva fantasy perfectly, with dozens of world-beating hotels. Set over 15 hectares, at Ayada you can hike before a steam in the Turkish bath; at eco-luxe Six Sense Laamu, you can dip your toes into the blue from your thatched overwater villa; and at Veela Private Island, pretend you’re Robinson Crusoe - except with knock-out wine, private plunge pool and personal butler.
Island high: Still not remote enough? Head for Coco Privé  Kuda Hithi, a castaway-chic island in the North Malé atoll.