San Juan, Puerto Rico  

Puerto Rico is the easternmost island in the Greater Antilles chain and an unincorporated territory of the United States. It had been inhabited for hundreds of years by the indigenous Taino people before Christopher Columbus claimed the island for Spain in 1493. Spanish conquistadors used enslaved Tainos and Africans to tend their large sugar cane plantations, as well as help build a fortified governor’s palace (La Fortaleza) and two massive forts to protect San Juan Bay from repeated attacks. After the Spanish-American War of 1898, Spain ceded Puerto Rico to the U.S.; in 1917, residents were granted U.S. citizenship. Today, the “Island of Enchantment” dazzles with its vibrant culture, Old San Juan — a colonial charmer with leafy plazas and mix of Gothic, Renaissance and Baroque architecture — and the UNESCO World Heritage-designated La Fortaleza and fortresses of San Felipe del Morro and San Cristobál. Natural wonders include a slew of gorgeous beaches, lush reserves like Caja de Muertos and El Yunque — the only tropical rainforest in the U.S. — surreal bioluminescent bays, and Cueva Ventana, a cliff-side cave with Taino petroglyphs and much-photographed “window” overlooking the Arecibo River Valley.

Carambola Beach, Saint Kitts and Nevis  

Terre-de-Haut, Iles des Saintes, Guadeloupe 

The Iles des Saintes, a tiny cluster of islets off the southern coast of Guadeloupe is what the doctor ordered, if he ordered an unspoiled Caribbean experience. No franchise duty free, no big hotels, no casinos. It is what much of the Caribbean used to be like. Stroll around the little town of Bourg de Saintes. Shop for real French cosmetics from the sidewalk vendors. Grab a seat and a beer and revel in the weather and the pace of the past.

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.