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How to island hop in the Caribbean this winter

As flights increase and regional connections improve, multi-island adventures are getting easier to plan

Ferry terminal at Blowing Point in Anguilla.
Ferry terminal at Blowing Point in Anguilla. (Courtesy:

Visiting more than one Caribbean country on a single vacation has typically been a surprisingly complex proposition unless you were sailing or cruising. Attempting it by plane has often entailed paying ultra-costly fares that required travelers to backtrack to a US airport due to a dearth of inter-regional connections, some served by tiny carriers with poor track records for safety and timely performance. 

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Interest in island-hopping is on the rise, says Margie Hand, travel adviser at Andavo Travel, a Virtuoso agency. “Many want to do a longer trip but are afraid they will get bored being in one location, and want to maximize their time and see as many places as possible.” This year, larger airlines are responding to such demand with new inter-island routes that go beyond the well-trodden ferry hops from St. Maarten to Anguilla or from St. Thomas to Tortola. It’s good timing, as consumer demand for tropical getaways continues to soar, and the Caribbean region expects to record a 10% to 15% year-over-year increase in overseas arrivals in 2023. 

Take Cayman Airways’ flight connecting Grand Cayman and Barbados, which debuted this year. You previously had to fly north to Miami, power through a minimum three-hour layover, and head back down to the Caribbean for a late-night arrival in Barbados. Now, the trip takes just three hours and 15 minutes.

That’s one example among many. The year-old Dominican national carrier Arajet has added pan-Caribbean routes to 23 destinations in recent months; new planes and fares include coach bus transfers between Punta Cana and Santo Domingo. Virgin Atlantic began offering inter-island flights connecting Barbados with Grenada and the Grenadines in June. And such smaller regional carriers as Tradewinds are striking code-sharing partnerships with major US airlines to help make connecting flights more seamless.

Getting to your first island is easier, too, with improved international flight access to the Caribbean from hubs such as Miami, New York-JFK,  Boston, Atlanta, Los Angeles, Denver and Seattle. It’s worth noting that ferry service, long seen as a relatively easy way to combine island visits, is also expanding: Major providers Makana Ferry, Val Ferry and L’Express des îles are adding high-speed access to locations where few commercial flights land, such as Eustatius and Saba.

All this is opening up the ease of combining neighbouring or contrasting Caribbean destinations—say, Dutch- and Spanish-speaking places—in a single trip, allowing travelers to appreciate each island’s unique attributes.

Here are six island-hopping adventures that have become possible, along with the logistical details you need to know and a recommended trip length that lets you get the unique flavor of each destination, far beyond the walls of a resort. 

Puerto Rico, US Virgin Islands and British Virgin Islands (7 days)

Getting there: Long-established regional airline Cape Air keeps expanding its inter-island routes between Puerto Rico and the US Virgin Islands.  Starting on Dec. 15, two daily flights will operate between San Juan and St. Croix. Low-cost Frontier Airlines also now flies nonstop from San Juan to St. Thomas, with one-way fares starting at just $19.

The ideal trip: Stay at one of two new luxury resorts at Frenchman’s Reef, which has finally recovered from Hurricane Irma on St. Thomas. Then make a pit stop in Vieques, Puerto Rico, where wild horses roam untouched beaches; the island has bioluminescent bays that you can explore in night-time kayak excursions. From there it’s off to San Juan, where the dining scene is booming. 

Your next flight is on Cape Air or Tradewind Aviation to Tortola, capital of the British Virgin Islands. Use it as a jumping-off point to visit the archipelago’s smaller islets, where you’ll find some of the Caribbean’s most spectacular resorts. The Aerial is a new, 16-room, fitness-minded, all-inclusive resort on Buck Island with an on-site ranch for rescued animals. And at the newly reimagined Bitter End Yacht Club—a BVI icon taken down by a pair of 2017 hurricanes—bragging rights include some of the only overwater bungalows in the broader region. 

The Dominican Republic and Jamaica (8 to 10 days)

Getting there:  Since late 2022, the low-cost carrier Arajet has connected two of the Caribbean’s most visited countries—Jamaica and the Dominican Republic—on a first-ever direct flight between their capital cities. Brand new Boeing 737 MAX  8 jets carry 185 passengers in  comfortable seats, and flights generally depart on time. As a bonus, American Airlines will kick off a twice-weekly direct route from Miami to Ian Fleming International Airport in Jamaica’s Ocho Rios starting in February 2024.

The ideal trip: While many travelers might see Jamaica and the Dominican Republic as interchangeable for visits to all-inclusive mega-resorts, visiting both allows you to contrast their histories, cultures and topographies that go well beyond sand and sea.

Overnight in a former Spanish colonial home that’s been turned into lavish rooms, suites and villas at Casas del XVI in Santo Domingo’s buzzy colonial zone, where cobblestoned streets are lined with museums, sidewalk cafes and local art shops, and weekly merengue concerts take place on Plaza España.

In Kingston, you can take a Blue Mountain coffee tour by bicycle at Craighton Estate and catch Jamaica’s best roots, rock, reggae talents live at Kingston Dub Club while spending nights in a white, wood-framed cottage with veranda at Strawberry Hills. Once you’ve gotten a taste for each country’s cultural calling cards, venture to their coveted coastlines: Punta Cana lies two hours east of Santo Domingo, and Ocho Rios is just an hour north of Kingston. 

Antigua, Anguilla and St. Barts (8 days)

Getting there:  Despite their proximity, this trio of islands—all known for attracting barefoot luxury travelers and fewer crowds—are rarely combined. That’s a shame, given their diverse cultural tapestries. In French-speaking St. Barts, you can have Paris-worthy pain au chocolat by the sea for breakfast; Antigua has spectacular steel pan bands, and the beaches in Anguilla’s Shoal Bay are second to very few. It’s now possible to fit this all into a single itinerary using new flights from Anguilla Air Services (thrice-weekly between Antigua and Anguilla) and Tradewind (Antigua to St. Barts). 

The ideal trip:  Antigua’s Curtain Bluff, a dreamy, all-inclusive resort perched atop a peninsula, is debuting a multimillion-dollar renovation this season, including an expanded fitness facility and a new infinity oceanfront pool—reason enough to consider a trip. In Anguilla, the exquisite Cap Juluca, which sits on one of the island’s most tranquil coasts, will debut a highly anticipated Spa by Guerlain in spring 2024; until then, you might opt to stay at the 63-room, ultra-colorful Malliouhana, where a rebranding has yielded such delightful new amenities as Anguillan guava cheese pastries at turndown. Want something more active? Aurora Anguilla has been busy expanding; by the end of 2023 it’s expected to open up a huge entertainment and water park, along with a sports center that’ll include pickleball, basketball and wall climbing. 

If you’re adding a stop in St. Barts, consider the five-star Hôtel Barrière Le Carl Gustaf, whose 21 terrace suites have the rare advantage of being located within walking distance of some of the island’s most popular restaurants, such as Shellona on Shell Beach.

Barbados, Grenada and St. Vincent and the Grenadines (8 to 10 days)

Getting there:  This combination is easiest if you’re staying at the palm-lined, oceanfront Bequia Beach Hotel in St. Vincent and the Grenadines, whose VIP transfer has long offered its own flights back to either Barbados or St. Lucia on its nine-seater aircraft, in partnership with Bequia Air. (These islands are 30 minutes and 15 minutes distant, respectively.) You can combine that with Bequia Air flights that also complete the circuit with Barbados and St. Lucia. For other options, try the aforementioned routes on Virgin Atlantic or Caribbean Airlines, which connect many of the same points.

The ideal trip:  Heading this far south in the Caribbean affords exploration of the crowd-free Windward Islands, where African, European and Asian cultures fuse in small spaces. Mix beach time with Bajan food in Barbados, hike a volcano in St. Vincent and learn all about chocolate production in cocoa-rich Grenada. If you add Barbados, consider a stay at the island’s first new hotel in years, the all-inclusive, 422-room Wyndham Grand, whose two-balcony suites offer expansive views of the island’s south coast.

Cayman Islands and Barbados (6 days)

Getting there:  Cayman Airways has just kicked off twice-weekly direct service between Grand Cayman island and Barbados, a connection that Caribbean officials described as a milestone in boosting connectivity between the eastern and western Caribbean regions. The schedule is timed to allow seamless connection with Cayman Airways' new direct flight from Los Angeles; the first-ever direct route from LAX to the Caribbean takes just six hours.

The ideal trip:  While most might think the Cayman Islands and Barbados offer similar experiences due to their shared ties to the British Empire, they are distinct in many ways, from governance to size and cultural vibe. The Cayman Islands is a British overseas territory famed for coral reefs while Barbados is a former colony whose white sand beaches, caves and rugged cliff sides are complemented by an Afro-Caribbean flair. It’s a foolproof combination made better by the 2021 reopening of the iconic  Ritz-Carlton Grand Cayman on Seven Mile Beach; a multiyear redesign of interior spaces has resulted in a brighter, much more locally inspired aesthetic. (Heads up: The renowned annual Cayman Cookout festival will celebrate its 15th anniversary Jan. 10-15.)

St. Kitts and St. Maarten/St. Martin (7 days)

Getting there:  A new route between St. Kitts and St. Maarten on Makana Ferry shuttles travelers between the two islands in 90 minutes. From Dutch St. Maarten, you can easily make your way to French St. Martin, or take additional Makana Ferry routes to the less-visited islands of Saba and St. Eustatius or to St. Kitts, depending on how much time you have.

The ideal trip:  Stay at the jet-setter favorite La Samanna facing Baie Longue beach on St. Martin. Match that with a few nights at the clifftop Sunset Reef on St. Kitts or the Four Seasons Nevis, known for exceptionally attentive service and a breezy aesthetic. If you’re looking to plan a trip to coincide with major culture events, the Saint Kitts and Nevis National Carnival, “Sugar Mas,” kicks off in mid-December and lasts through Jan. 2. It makes an especially colorful start to the year.  

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