Striking, atmospheric and delightfully unspoilt, the streets of the Azorean capital are lined with historic mansions and houses, blazing white against the cobalt sky, edged and decorated with traditional black basalt stone. A fantastic destination for wildlife lovers, in spring and summer boats head out of here each morning to spot the dolphins, whales, and sea turtles making their way through the Atlantic waters. But the city's three lush botanic gardens, beautiful Azulejo tiling in the ornate churches, and shorefront boardwalk lined with boutiques and restaurants, makes it ideal to visit at any time of year.

Don't be fooled by Horta's isolated location in the Atlantic on the Azorean island of Faial – for centuries, this fascinating city has seen many come and go, playing host to sailors of every stripe, from intrepid explorers to pleasure seekers and naval seamen. The historic tangle of streets, which winds around former merchants' houses and statuesque churches, bookended in time by the 16th-century defensive walls and the gleaming contemporary marina, is perfect for exploring on foot. Horta's rich, seafaring heritage is best experienced with a sunset GT at the world-famous Peter Café Sport – a bar that has been welcoming sailors to the island since 1918.

Island of celebrity hideaways and posh bungalows, considered by many to be the most elite and glamorous of all the Caribbean isles, St. Barts is home to 22 incredible beaches. Anse de Flamanes presents camera-ready scenery, Baie de St-Jean serves up beachside bistros, and Anse de Grand Cul-de-Sac offers an array of watersports.

Puerto Rico's capital makes a strong impression – even before you arrive on shore. Sailing into the harbor, keep an eye out for El Morro, a 16th-century citadel and UNESCO World Heritage Site, Castillo San Cristobal, a fearsome fortress built to scare away invaders, and La Fortaleza, the impressive official residence of the Governor of Puerto Rico. Once ashore, step back in time along cobbled streets and through squares flanked by pastel-colored Spanish colonial buildings. Or take your pick of beaches – will it be the golden-sanded Isla Verde, the snorkeler-approved El Escambrón, or the laid-back Ocean Park? Just don't leave San Juan without sampling a piña colada (or two) – the tropical cocktail was invented here in the 1950s.

Candy-colored houses and sugar-sand beaches give this sweet port town a fairytale appeal. One of the quieter spots on this island, the Samana Peninsula allows easy access to coves and bays straight out of a picture book. Playa Payita, known to the locals as The Little Lagoon, offers aquamarine water to dip into and the shade of bamboo and banana leaf umbrellas to retreat beneath. Playa Fronton, with its coconut palms and backdrop of black rock, is the perfect place to snorkel amid schools of parrotfish, nemos, and sunfish. But the big draw is the humpback whales that visit in winter – there's even a museum dedicated to the awesome creatures. Back on dry land, Los Haitises National Park, home to enchanting caves and ndangered birds, is a pretty place to hike, bike or kayak.Indulging in Samana's coconut-infused and zesty fresh seafood delicacies, taking a boat to the secluded beach at Playa Madama, spotting manatees amongst the mangroves in Los Haitises.

Dive into the waters with one of the largest networks of coral reef in the world. Turks & Caicos has plenty of on-shore activities and places to relax, but the water is where you want to be to get enjoy some of the best diving and snorkeling around.