The Caribbean region enjoys a reputation as a tropical paradise, an eco-tourism destination full of beaches, luxury resorts, quaint tourist towns, and cruise ships pulling into port. Its economy, in fact, relies largely on tourism, ranking first in the world in terms of its proportion of total GDP at 14%. With so many different destinations in the area, it can be hard to pick just one (or a few) to visit. Wherever you go, if you’re planning a relaxing vacation to the Caribbean, make sure to purchase Caribbean travel insurance to protect yourself against any unexpected events, illnesses, or injuries that may occur on your trip.
The vast majority of tourists come to the Caribbean on cruise ships, and many cruise lines divide their itineraries into “Western Caribbean Cruises” and “Eastern Caribbean Cruises.” This distinction is largely informal and doesn’t reflect any official political or cultural differences between the two. Generally speaking, the “Eastern Caribbean” usually refers to islands east of Hispaniola like Puerto Rico, the U.S. Virgin Islands, the British Virgin Islands, and Saint Martin / Sint Maarten. The eastern side is largely considered the better option if you’re looking to go beach-hopping. This article will focus on the eastern region. For more information about Western Caribbean travel destinations, please see Western Caribbean travel insurance .
If you’re visiting these destinations as part of a cruise, you should purchase cruise travel insurance. Cruise insurance features coverage options like emergency medical coverage, coverage of pre-existing conditions, the ability to make independent travel arrangements, and trip cancellation.
Puerto Rico is an unincorporated territory of the United States. Its capital is San Juan, and it had a population of about 3.3 million as of July 2018. As a U.S. territory, Puerto Rico is the most Americanized of the Caribbean Islands; its official languages are Spanish and English, and aspects of American culture (like popular chain restaurants) have made their way to San Juan in particular. As a tourism destination, its variety of beaches attract both casual beachgoers and experienced surfers. It’s also home to the only tropical rainforest in the U.S. Forest System as well as the famed Bioluminescent Bay.
Old San Juan is the second-oldest city in the Americas. It’s a UNESCO World Heritage Site featuring hundreds of restored Spanish colonial buildings from the 16th and 17th centuries. El Morro Fort, built in 1539 and located on a peninsula above the ocean, is one of the top cultural attractions in the country. About an hour’s drive outside the city is El Yunque National Forest, a tropical rainforest covering 43 square miles. Sites to see in the forest include La Coca Falls, Baño Grande, Baño de Oro, and La Mina Falls.
Vieques, an island off of Puerto Rico’s eastern coast, is a popular beach resort featuring upper-class hotels, galleries, and dining and shopping opportunities. The island still maintains a small-town feel; you won’t find any large hotels or condominium complexes. One of the most popular attractions on the island is Mosquito Bay, also known as Bioluminescent Bay, where swarms of underwater phosphorescent dinoflagellates emit a beautiful glow that visitors can see from a boat, canoe, or kayak.
Other can’t-miss tourist attractions in Puerto Rico include the Arecibo Radio Telescope, a 20-acre satellite dish set in a sinkhole; the Rio Camuy Caves, the third-largest cave system in the world; and surfing and whale-watching at Rincon, also called “Little Malibu” and home to a large number of American expatriates.
If you’re considering becoming an expat, check out the health insurance requirements for expatriates .
U.S. Virgin Islands
The United States Virgin Islands, another unincorporated U.S. territory, were purchased from Denmark in 1917. They consist of three large islands—St. Croix, St. John, and St. Thomas—and about 50 smaller islands and keys. The capital and largest city, Charlotte Amalie, is located on the island of St. Thomas. Visitors come for the climate, tropical scenery, fishing and diving opportunities, and free-port status. Natural attractions include six national parks and a collection of bio-diverse reefs ideal for underwater wildlife sightings.
St. Croix is the largest of the U.S. Virgin Islands at 22.7 miles long and 8 miles at its widest point. It’s best known as a destination for honeymooners, cultural tourism, and scuba divers. The town of Christiansted, the former capital under Danish rule, offers the ideal glimpse into the islands’ past through attractions like the Christiansted National Historic Site and Salt River Bay National Historic Park. There’s also the St. Croix Heritage Trail, a 72-mile driving tour that passes through many of the island’s historical and natural attractions. Buck Island’s main draw is the Buck Island Reef, a scuba destination featuring coral grottoes, shipwrecks, and a variety of marine life—President John F. Kennedy even named the reef an underwater national monument in 1961.
St. John, the smallest of the major islands, is known for its largely untouched natural beauty. Virgin Islands National Park, established in 1956, covers about two-thirds of the island and features hiking trails, protected bays, beaches, underwater gardens, and petroglyphs (rock carvings) from the islands’ oldest inhabitants. Popular beaches in the park include Trunk Bay Beach, Cinnamon Bay, Hawksnest Bay, Honeymoon Beach, and Maho Bay.
St. Thomas is a volcanic island about 40 miles east of Puerto Rico. It’s branded as the most cosmopolitan of the U.S. Virgin Islands, especially as the location of their capital, Charlotte Amalie. One of the most popular cruise ports in the Caribbean, Charlotte Amalie offers restaurants, entertainment, boutiques, jewelry stores, and other shopping opportunities. Make sure to check out tourist attractions like Coral World Ocean Park, an interactive marine exhibit, as well as the 99 Steps leading to the top of Blackbeard’s Castle, built in 1679. There’s also Magens Bay, named one of the most beautiful beaches in the world and the perfect spot for water sports like snorkeling, swimming, kayaking, and more.
British Virgin Islands
The British Virgin Islands (BVI) are a British Overseas Territory making up the eastern portion of the Virgin Islands archipelago. They consist of four major islands—Tortola, Virgin Gorda, Anegada, and Jost Van Dyke—and about 50 smaller islands and keys. The capital, Road Town, lies on the island of Tortola. The BVI’s population as of July 2018 was about 35,800. As tourist destinations, all four major islands are perfect for diving, snorkeling, and sunbathing. Anegada is a fisherman’s paradise, while Virgin Gorda and Jost Van Dyke gear toward nature lovers and boaters.
Tortola is the largest and most urban of the British Virgin Islands. Road Town is the country’s commercial center and sees lots of traffic from charter yachts, ferries, and cruise ships. In town, Waterfront Drive and Main Street feature shops, restaurants, and historic forts and sugar mills. The crescent-shaped Cane Garden Bay is the most popular beach on the island, a gathering place for locals, visitors, and passing sailors alike. Conversely, Smuggler’s Cove, located on the west end of the island, is a sheltered, secluded beach for people looking for a quiet, serene beach experience. It’s also a good spot for snorkeling.
Virgin Gorda houses one of the BVI’s most famous landmarks, The Baths. The bay is scattered with granite boulders forming small pools and grottoes that practically beg snorkelers to come explore, as well as a sand-bottomed, underwater cave popular with photographers. Gorda Peak National Park offers a break from the traditional tropical atmosphere with its 107 hectares of semi-rainforest and dry forests. The park’s observation tower provides breathtaking views of a seascape dotted with smaller islands and keys. The North Sound is a major water sports hub with protected waters set aside for activities like diving, sailing, jet-skiing, water-skiing, parasailing, and more.
The island of Anegada is a well-known diving and fishing site. It’s surrounded by a maze of coral reefs that have sunk more than 300 ships perfect for scuba exploration. Loblolly Bay and Cow Wreck Bay Beach feature white-sand beaches and calm shores. Horseshoe Reef is one of the largest reef systems in the world and provides more than ample reef and bonefishing opportunities. The island’s interior is home to wildlife like flamingos and rock iguanas. The whole island is protected against development by the BVI National Parks Trust, so Anegada tends to attract more adventure travelers than luxury vacationers.
If diving or any other adventurous sports are on your travel itinerary, we’d recommend purchasing hazardous sports travel insurance. Most base insurance plans aren’t able to cover higher-risk activities like ziplining, cliff jumping, and scuba diving, but by purchasing this add-on plan, you’ll be able to protect yourself against any incidents.
Finally, Jost Van Dyke houses one of the most beautiful beaches in the British Virgin Islands, White Bay. The bay is protected by a barrier reef that keeps waters calm and ideal for swimming and snorkeling. Beachside restaurants are happy to offer snacks and refreshments after a few hours out in the sun. Another common destination on the island is Great Harbour, featuring a beach strip lined with bars and restaurants; it’s become a popular destination on New Year’s Eve in particular.
Saint Martin / Sint Maarten
The island of Saint Martin, about 200 miles east of Puerto Rico, is divided into two territories owned by the French (Saint Martin, to the north) and the Dutch (Sint Maarten, to the south). As of July 2018, the French side had a population of about 32,000 and the Dutch side of about 42,000. The French side’s capital is Marigot; the Dutch side’s, Philipsburg. The entire island is only about 12 miles long and 12 miles wide, so you’ll have plenty of time to experience both cultures even if you’re only there for a day.
The French half of the island, with its restaurants, fashion boutiques, and street vendors selling croissants and pastries, feels lifted straight out of Paris. Its capital, Marigot, features an open-air market and duty-free shops, as well as the historical Rue de la Republique. Grand Case has been called the “culinary capital” of the island and is a must-visit for food-lovers. Freshly-caught fish go straight from the boat to the kitchen. Orient Bay Beach is the most popular nude beach in the Caribbean. Children or general animal-lovers will enjoy the Butterfly Farm (Le Ferme des Papillons).
The Dutch side features brightly colored buildings, colonial-style streets, and a more Caribbean atmosphere. The capital, Philipsburg, features a waterfront boardwalk and the parallel Front Street, with bars, restaurants, bustling streets, and Segway tours. The Guavaberry Emporium boasts a variety of products from liquor to hot sauce made with the island’s native guavaberry. The St. Maarten Museum presents exhibits about the history of the island from pre-Columbian times to the modern day. Maho Beach lies at the end of St. Maarten’s Princess Juliana International Airport, and beachgoers can watch (and hear) passenger jets take off and land only a few hundred feet above. The island’s shallow waters also lend themselves to beginning scuba divers.
Caribbean cuisine’s influence comes from a variety of cultures. Highlights from Puerto Rico include mofongo (mashed plantains mixed with seasoning, vegetables, and meat of your choice; lechon asado (spit-roasted suckling pig); and arroz con gandules (Puerto Rican rice with pigeon peas). In the U.S. and British Virgin Islands both, try fungi—not the mushroom, but dumplings made from salted cornmeal and okra, usually served with boiled fish or saltfish. Callaloo is a soup or stew made with meat, okra, and leaves from the callaloo bush. And in Saint Martin / Sint Maarten, you can again try callaloo soup—the national dish—or the French-Caribbean fusion meal of your choice.
Caribbean Hurricane Season
Be careful to plan your vacation around hurricane season, if at all possible. Hurricane season officially runs from June 1 to Nov. 30 of each year, although peak season for the Western Caribbean in particular lasts from mid-August to early November. We also recommend that you research your travel insurance policy’s coverage for hurricanes to stay informed about what scenarios are (and aren’t) covered, as well as which plan best fits your needs.
Eastern Caribbean Travel Insurance
We highly suggest that part of your travel preparation include purchasing travel health insurance and travel insurance. Travel health insurance provides medical coverage while you’re abroad. Standard benefits include coverage of trip interruption, emergency medical evacuation / repatriation, return of mortal remains, and accidental death & dismemberment (AD&D). Travel insurance primarily provides coverage for prepaid, non-refundable expenses like emergency medical care, trip interruption, lost luggage, emergency cash transfers, rental car coverage, and flight accidents. Our licensed, experienced representatives will be happy to help you select the plan that best fits your needs.