As the number of flights increases and regional connections improve, multi-island adventures become easier to plan
Visiting more than one Caribbean country on a single vacation is usually a surprisingly complex proposition, unless you were sailing or cruising. Attempting to do so by air often involved paying ultra-expensive fares, forcing travelers to return to a US airport due to a lack of inter-regional connections, some of which were served by small airlines with poor safety and on-time performance.
Interest in island hopping is increasing, says Margie Hand, travel advisor at Andavo Travel, a Virtuoso agency. “Many want to take a longer trip, but are afraid they will be bored if they are in one location, and want to maximize their time and see as many places as possible.” This year, larger airlines are responding to this demand with new inter-island routes that go beyond the well-trod ferry connections from St. Maarten to Anguilla or St. Thomas to Tortola. It's good timing as consumer demand for tropical vacations continues to rise and the Caribbean expects to see a 10% to 15% year-on-year increase in overseas arrivals by 2023.
Take the Cayman Airways flight connecting Grand Cayman and Barbados, which debuted this year. Previously, you had to fly north to Miami, have a minimum three-hour layover, and return to the Caribbean for a late arrival in Barbados. Now the journey takes just three hours and fifteen minutes.
That is one of many examples. Year-old Dominican national carrier Arajet has added pan-Caribbean routes to 23 destinations in recent months; new aircraft and fares include coach bus transfers between Punta Cana and Santo Domingo. Virgin Atlantic began offering inter-island flights connecting Barbados to Grenada and the Grenadines in June. And smaller regional airlines like Tradewinds are forming codeshare partnerships with major U.S. airlines to make connecting flights more seamless.
It's also easier to reach your first island, 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 the ferry service, long seen as a relatively easy way to combine island visits, is also expanding, with major providers Makana Ferry, Val Ferry and L'Express des îles adding high-speed access to locations where few commercial flights land. such as Eustatius and Saba.
All this makes it easier to combine adjacent or contrasting Caribbean destinations – for example, Dutch- and Spanish-speaking places – into a single trip, allowing travelers to appreciate the unique qualities of each island.
Here are six island-hopping adventures made possible, along with the logistical details you need to know and a recommended trip length that will let you experience 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-standing regional airline Cape Air continues to expand its inter-island routes between Puerto Rico and the U.S. Virgin Islands. Beginning December 15, there will be two daily flights between San Juan and St. Croix. Low-cost Frontier Airlines now also flies nonstop from San Juan to St. Thomas, with one-way fares starting from just $19.
The ideal trip: Stay at one of two new luxury resorts on 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 pristine beaches; the island has luminous bays that you can explore during night kayaking trips. From there it goes to San Juan, where the food culture flourishes.
Your next flight is with Cape Air or Tradewind Aviation to Tortola, the capital of the British Virgin Islands. Use it as a starting point to visit the archipelago's smaller islands, where you'll find some of the Caribbean's most spectacular resorts. The Aerial is a new fitness-oriented, 16-room all-inclusive resort on Buck Island with its own ranch for rescued animals. And the newly redesigned Bitter End Yacht Club – a BVI icon brought down by a pair of 2017 hurricanes – boasts some of the only overwater bungalows in the wider region.
The Dominican Republic and Jamaica (8 to 10 days)
Getting there: Since late 2022, low-cost airline Arajet has been connecting two of the Caribbean's most visited countries – Jamaica and the Dominican Republic – on a first-ever direct flight between their capitals. 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 launch a twice-weekly direct route from Miami to Ian Fleming International Airport in Ocho Rios, Jamaica, starting in February 2024.
The Ideal Trip: While many travelers may consider Jamaica and the Dominican Republic interchangeable for visiting all-inclusive mega-resorts, visiting both allows you to contrast their histories, cultures, and topographies that go far beyond sand and sea.
Overnight stay in a former Spanish colonial house transformed into opulent rooms, suites and villas at Casas del concerts take place. Plaza España.
In Kingston, take a Blue Mountain coffee tour by bike at Craighton Estate and see Jamaica's best roots, rock and reggae talent live at the Kingston Dub Club, while spending nights in a white wooden cottage with veranda in Strawberry Hills. Once you've gotten a taste of each country's cultural calling cards, head to the coveted coastlines: Punta Cana is 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 close proximity, this trio of islands – all known for attracting barefoot luxury travelers and fewer crowds – is rarely combined. That's a shame, given their diverse cultural tapestry. In French-speaking St. Barts you can eat Parisian pain au chocolat for breakfast by the sea; Antigua has spectacular steel pan tires and the beaches in Anguilla's Shoal Bay are second to none. It's now possible to fit it all into a single itinerary with the help of new flights from Anguilla Air Services (three times a week between Antigua and Anguilla) and Tradewind (Antigua to St. Barts).
The Ideal Trip: Antigua's Curtain Bluff, a dreamy, all-inclusive resort atop a peninsula, is undergoing a multimillion-dollar renovation this season, including an expanded gym and a new oceanfront infinity pool—reason enough to consider a trip. In Anguilla, the exquisite Cap Juluca, located on one of the island's quietest coasts, will debut a highly anticipated Spa from Guerlain in spring 2024; until then, you can choose to stay at the ultra-colorful, 63-room Malliouhana, where a rebranding has brought such delicious new amenities as Anguillan guava cheese pastries at the turndown. Do you want something more active? Aurora Anguilla has been busy expanding; A huge entertainment and water park is expected to open by the end of 2023, along with a sports center including pickleball, basketball and wall climbing.
If you're adding a stopover in St. Barts, consider the five-star Hôtel Barrière Le Carl Gustaf, whose 21 terrace suites have the rare advantage of being within walking distance of some of the island's most popular restaurants, like Shellona at the Shell- beach.
Barbados, Grenada and St. Vincent and the Grenadines (8 to 10 days)
Getting there: This combination is easiest if you stay at the palm-tree-lined oceanfront Bequia Beach Hotel in St. Vincent and the Grenadines, whose VIP transfer has long offered its own flights back to Barbados or St. Lucia on its nine-seat aircraft, in partnership with Bequia Air. (These islands are 30 minutes and 15 minutes away respectively.) You can combine this with Bequia Air flights that also complete the circuit with Barbados and St. Lucia. For other options, try the aforementioned Virgin Atlantic or Caribbean Airlines routes, which connect many of the same points.
The ideal trip: If you travel this far south in the Caribbean, you can explore the crowd-free Windward Islands, where African, European and Asian cultures merge in small spaces. Combine 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 staying at the island's first new hotel in years, the all-inclusive, 422-room Wyndham Grand, whose dual-balcony suites offer sweeping views of the island's south coast.
Cayman Islands and Barbados (6 days)
How to get there: Cayman Airways just started biweekly direct service between the island of Grand Cayman and Barbados, a connection that Caribbean officials are describing as a milestone in boosting connectivity between the eastern and western Caribbean regions. The schedule is timed to allow for seamless connection to 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 with the British Empire, they are distinct in many ways, from governance to size and cultural atmosphere. The Cayman Islands is a British Overseas Territory famous for its coral reefs, while Barbados is a former colony whose white-sand beaches, caves and rugged cliffs are complemented by an Afro-Caribbean flair. It's a foolproof combination made even better by the 2021 reopening of the iconic Ritz-Carlton Grand Cayman on Seven Mile Beach; a multi-year redesign of interior spaces has resulted in a brighter, much more locally inspired aesthetic. (Note: The famous annual Cayman Cookout festival celebrates its 15th anniversary from January 10 to 15.)
St. Kitts and St. Maarten/St. Maarten (7 days)
Getting there: A new route between St. Kitts and St. Maarten on Makana Ferry will take travelers between the two islands in 90 minutes. From Dutch Sint Maarten you can easily travel to French Sint Maarten, or take additional Makana Ferry routes to the less visited islands of Saba and Sint Eustatius or to Sint Kitts, depending on how much time you have.
The ideal trip: stay at the jetsetter's favorite La Samanna, opposite the beach of Baie Longue on St. Martin. Combine that with a few nights at the clifftop Sunset Reef on St. Kitts or the Four Seasons Nevis, known for exceptionally attentive service and an airy aesthetic. If you want to plan a trip to coincide with major cultural events, the Saint Kitts and Nevis National Carnival, “Sugar Mas,” starts in mid-December and lasts until January 2. It is a particularly colorful start to the year.