If you consider New Year’s a momentous event, you could hardly do better than to spend it in the Caribbean, dressed in your summer clothes, wandering the beaches and vibrant village streets while experiencing the island atmosphere — at once laidback and high-energy — building to a crescendo come December 31.

As you get busy planning your trip there, take note of some alternate phrasing: Caribbean locals refer to the occasion as “Old Year’s Night.” It's a twist on what Dick Clark and the throng of frigid folk in Times Square would say.

Suggesting a Caribbean getaway for New Year’s would be incomplete advice if it failed to include special guidance as to getting there. Certainly, you can rely on commercial airlines for transport into the general region of places like St. Barth, Anguilla, Nevis, and Antigua — all luxury landmarks within the Leeward Islands chain — but in this part of the world the last travel legs are the trickiest. Thus, the indispensable value of private air service via Tradewind Aviation, with its scheduled flights to the most desirable destinations within the storied archipelago.


From a trio of hubs in Puerto Rico, Antigua, and the US Virgin Island of St. Thomas, Tradewind whisks its passengers on Swiss-built Pilatus PC-12 jet-prop aircraft, crewed by two pilots each and ultra-comfortable. The cabins are pressurized and air-conditioned, there’s plenty of luggage space, and the in-flight refreshments are complimentary, including wine and beer. If you’ve got a US passport and your itinerary pivots on San Juan, you’ll breeze through the customs and immigration process. Tradewind has a private airport lounge in San Juan, plus a VIP meet-greet option that ensures smooth transfers between flights. Luggage is also complimentary, and likewise your beloved pets are welcome at no charge.

The damage caused in 2017 by Hurricanes Irma and Maria has mostly been repaired, meanwhile this past storm season came and went without incident. Interestingly, the island of Nevis wasn’t affected at all by the twin tempests, nonetheless it’s the site of a major rebuilding and renovation project. Guests at the famed Four Seasons Resort Nevis, which always pulls out the stops to celebrate New Year’s, will arrive to find completely redesigned guestrooms, an updated Great House lobby, and two brand new restaurants.

Mixologists at the Four Seasons are known for selecting a special rum cocktail from their immense menu of them, as an official toast to the sun’s dip below the horizon on the big night. Caribbean vacationers have always been fixated on sunsets, no matter the season, but the last one of the year inspires particular devotion. Once that ceremony concludes, a Grand Tasting buffet rolls out, featuring every variety of gourmet fare, including caviar, king crab legs, lobster, and fine cuts of meat.

Photo: Christian Horan, courtesy Four Seasons

Photo: Christian Horan, courtesy Four Seasons

On the famed French isle of St. Barth, New Year’s is synonymous with film stars, rock stars, and billionaire yachtsmen. Accommodations on a charter yacht are highly favored here, as well as rooms in the island’s many fine hotels — including Le Toiny, Le SerenoCheval Blanc, Hotel Christopher, and Le Barthélemy — all recently reopened or opening in December. Two of the newer luxury resorts, Villa Marie and Hotel Manapany, barely missed a beat after the hurricanes (having reopened in early 2018) and are all the more in demand.

One snug harbor on St. Barth, Port de Plaisance, becomes a New Year’s epicenter. The entire basin — dockside berths and anchor moorings alike — sparkles with seafaring works of art. Coming ashore, yacht guests prowl the nearby promenade with its designer boutiques and jewelry shops. When the night of champagne toasts and fireworks finally arrives, they parade along in a New Year’s Eve Regatta that your cellphone photos won’t do justice to.

While fireworks on New Year’s Eve may seem the sole reason to look upward, another Caribbean pleasure shouldn’t be forgotten — island stargazing, either on beachfronts or the open water. Short charter excursions on boats that make a specialty of leaving the ambient light behind and acting as docents for the starry dome are common in these islands. You should consider getting aboard one of them, binoculars in hand. For most US residents, the arrangement of stars and constellations across the winter sky may prove disorienting at first, with Polaris appearing much lower than one is used to and the three points of Orion’s belt poised considerably higher.

Photo: Curtain Bluff

Photo: Curtain Bluff

Along with St. Barth and Nevis, the Tradewind route map also includes Anguilla, a British territory 16 miles long, and further down the chain to the southeast, Antigua with its rainforests, reef-lined beaches, and posh resorts.

One holiday enclave on Antigua that’s worth booking is Curtain Bluff, which drew raves for its $13-million renovation in 2017 and has continued making guest-pleasing improvements since. These include beautification of its one-bedroom Bluff Suites and redesign of its beachfront Seagrape restaurant. Service on the sand is available from an expanded Beach Concierge service. You’re stretched out on lounge chair, surrounded by turquoise waters, and staff members are bringing you a light lunch… yes, all that.

Of course, world-class relaxation can prompt an urge to get up and get moving. If you’re visiting Anguilla and you brought sturdy footwear, the famed hiking trails offer rugged beauty and fascinating bird life, including the magnificent frigatebird, with its sculpted wing profile against blue skies over famed Windward Point. New lodging options on Anguilla include the 65-room boutique hotel Zemi Beach House and the nine-room Quintessence Hotel, ultra-luxurious and exclusive.

A full-scale travel guide to New Year’s in the Caribbean would surely be book-length — these quick highlights are simply meant to inspire. No matter where your journey takes you, the islands present an unforgettable way to ring in 2019.

Featured Photo: Curtain Bluff