Bridgetown, Barbados 

Bridgetown, a UNESCO World Heritage Site, is a refined capital city that elegantly showcases its four centuries of British lineage. This charming island was initially inhabited by Amerindian communities 1,500 years ago, but in the 17th century, Barbados emerged as one of the most prolific sugarcane producers worldwide. At its zenith, the revenue from this sweet crop surpassed the combined income of all other British colonies.

At Sea

St. Johns, Antigua and Barbuda

Antigua is blessed with an abundance of shining white beaches, and many of these have sprouted top-end resort hotels that engender golf courses and other amenities counted among the best in the Caribbean. A pleasant drive up through farms and tiny villages leads to the commanding fortress on Shirley Heights, from which you can survey the town and the harbor of Nelson’s Dockyard across the island. Once a carenage for British frigates, today it is an enclave of shops and restaurants.

Spanish Town, Virgin Gorda, British Virgin Islands

The emerald island of Virgin Gorda invites visitors to slow down and smell the frangipani. Third largest of the British Virgin Islands, this lush and lovely gem is ringed by champagne beaches and famous for its unique coastal pheonomonon known as The Baths, where massive granite boulders and the white sand form a series deep tide pools, secret grottoes, and rock arches. Gorda Peak marks the highest point on the island at 1,370 feet, while the surrounding parkland comprises some of the Caribbean’s last remaining dry forest. 

Sopers Hole (Frenchmans Cay), BVI

This snug harbor at the West End of Tortola is the classic Caribbean yacht haven, tucked between the high ground of West End on one side and Frenchman’s Cay on the other. It was a notorious den for pirates in the past, who used the high ground to watch for naval ships or potential victims. The marinas and resorts were hard hit by hurricanes Irma and Maria in August and September 2017. But most services have been restored and the community is eager to welcome visitors again. 

At Sea

Port Elizabeth, Bequia, St. Vincent and the Grenadines

Bequia’s Admiralty Bay is a favorite yachtsman’s anchorage. They ferry ashore to join the friendly, low-key locals “under the almond tree,” the chosen meeting place. Stroll along the Belmont Walkway to the Gingerbread for homemade nutmeg ice cream, or Frangipani, run by the daughter of a former prime minister. Continue to lovely, golden Princess Margaret Beach, or round the bend to Lower Bay. Don’t miss the excellent craftsmanship at the Sargeant Brothers Model Boat Shop, it’s a Bequia specialty.

Bridgetown, Barbados

Bridgetown, a UNESCO World Heritage Site, is a refined capital city that elegantly showcases its four centuries of British lineage. This charming island was initially inhabited by Amerindian communities 1,500 years ago, but in the 17th century, Barbados emerged as one of the most prolific sugarcane producers worldwide. At its zenith, the revenue from this sweet crop surpassed the combined income of all other British colonies.