Brimstone Hill, St Kitts
A UNESCO World Heritage Site which dates back to the 1690s. A fortified citadel that marks St Kitts’ importance as a strategic island during the naval wars between the French and the British. Beautifully preserved with majestic views over the neighboring islands.

Castillo San Felipe del Morro, San Juan, Puerto Rico
Another World Heritage Site, this time dating back to 1539. Designed to protect Old San Juan during the time of Spanish conquest, the six-meter-thick walls alone are impressive, but it is the garitas, or sentry posts looking out over the ocean that demand photos. One of the most striking symbols of Puerto Rico and the New World.

Pitons, St Lucia
The original twin peaks, perhaps – Gros and Petit Piton are two mountains that tower some 3,000 ft above St Lucia’s southwest coast. Covered in lush vegetation, Gros Piton is accessible by hiking trail, with guided tours taking roughly two hours to reach the summit, with its understandably spectacular views.

Shoal Bay Beach, Anguilla
This two-mile stretch of talcum powder sand and turquoise water on the quiet island of Anguilla is regularly voted one of the top beaches in the world. The attraction here is to be somewhere utterly beautiful without ever having to share it with hordes of sun seekers. Nevertheless, this being Anguilla, there’s a good chance that the person taking a seat next to you at one of the unassuming beach bars is a Hollywood celeb looking for a bit of down time.

The Baths, Virgin Gorda, British Virgin Islands
The island of Virgin Gorda is part of the British Virgin Islands, but is reached only by a ferry from Tortola. Its main attraction is the area called ‘The Baths’, a cluster of giant granite boulders interspersed with translucent pools. A word of warning: while Virgin Gorda is remote, The Baths can get crowded when the cruise ships are in. Come late in the afternoon to have them to yourself.

Punda, Willemstad, Curacao
Dating back to the 17th century, Punda is a tightly packed but colorful district on Sint Anna Bay in Willemstad, capital of Curacao. The buildings are all painted in quaint pastel shades, and the narrow streets bustle with shoppers, while boats from nearby Venezuela putter into the dockside to offload fresh produce. A perfect place to grab a Dutch coffee, watch the world go by, and appreciate the floating Queen Emma pontoon bridge to Otrabanda or watch the tankers and cruise ships slip beneath the giant Queen Juliana arch, 185 feet above sea level.

English Harbour, Antigua
A historic district that was the base of the British Navy fleet in the Leeward islands during the time of Lord Nelson (who ironically loathed the island). Nowadays, it is home in the season to sleek classic yachts and impressive megayachts, but all the old buildings, sail lofts and store buildings are still in place. For the best view, hike up to Shirley Heights, scene of a wild jump up on Sunday nights.

Maho Beach, St Maarten
Not the best beach in the Caribbean by any standards, but the perfect place to watch jet planes come in to land and take off just meters above your sunglasses. The airport runway starts just the other side of a narrow road next to the beach, with only a chain link fence thereafter. The nearby Sunset Beach Bar is reputedly the closest bar to an international airport runway in the world. Every day, throngs of diehard plane spotters and adrenaline seekers congregate near the fence to ride out the hot, sandy jet blast from departing planes, many sent spinning backwards into the water!

Malecon in Havana, Cuba
Choosing a single place in historic Cuba is a challenge, but no single location possibly provides access to the spirit of the place as the Malecon, the sea wall promenade that runs along Havana Bay from Old Havana to Vedado. All day, but especially in the evening, ‘Habaneros’ congregate along the Malecon, watching the waves roll in, chatting and enjoying yet another sunset and some spontaneous entertainment. Sadly, many of the seafront architecture is in a shocking state, but the spirit remains.

El Faro a Colon, Santo Domingo, Dominican Republic
How this majestic location is not better known worldwide is a mystery. The 676 foot tall monument on the exit to the capital is a cathedral, cultural center, and not least the resting place of Christopher Columbus’s remains. Inaugurated by the Pope to wild scenes, El Faro a Colon is also a lighthouse with powerful beams capable of projecting a cross into the sky visible from neighboring Puerto Rico.