Caribbean-style getaways from Long Island for stress-free travel

Dreaming of turquoise water, warm breezes and a midwinter escape? You’re not alone, and for most Long Islanders, Caribbean travel is still very much business as usual. But with travelers paying closer attention to international headlines and looking for flexibility, some are also exploring warm-weather alternatives that deliver the same beachy payoff with easier logistics, shorter travel times or no passport required.

Local travel advisers say there’s no reason to hit pause on Caribbean vacations or cruises and no need for panic. Instead, they’re encouraging travelers to stay informed, book smart and remember that there are plenty of sun-soaked options that feel just as indulgent.

"Disney Cruise Line itineraries are operating as usual, and none of their Caribbean or Bahamas sailings have been officially rerouted or canceled due to the situation involving Venezuela," said Maria Latwaitis, of Holbook-based Think Happy Vacations. "Disney Cruise Line's standard destinations remain focused on the Caribbean, Bahamas, Mexico and other planned regions not near Venezuelan ports."

For travelers who want a backup plan — or simply want to switch things up this season — April Rose D’Andrea, of Massapequa-based Lifted Travel, says several destinations consistently deliver Caribbean-style beaches, luxury resorts and stress-free travel from Long Island.

Florida Keys: Caribbean feel at home

For travelers craving clear water and laid-back luxury, the Florida Keys offer a Caribbean feel with domestic convenience. D’Andrea recommends Islamorada as an easy road-trip destination from Miami, with the option to pair it with a ferry connection from Naples.

"You still have those turquoise waters and it really doesn’t feel like Florida," she said.

Cheeca Lodge & Spa (81801 Overseas Hwy., Islamorada, cheeca.com, 305-664-4651) sits on about 27 acres and rates start around $400 a night, which makes it accessible for many travelers. They also offer a Girls' Island Getaway Package, which includes two 50-minute Swedish massages, one half-day cabana rental and a $200 food and beverage credit for $434 per night.

For a splurge, Little Palm Island (28500 Overseas Hwy., Little Torch Key, 305-684-8341, littlepalmisland.com) delivers an adults-only, five-star escape. The private island resort brands itself as the only American private island resort, with the entire island owned by the property. Springtime rates average about $2,400 per night.

"It’s a true luxury experience — no kids, incredible food and wine, and they host big culinary, music and wellness events," D’Andrea said. "You truly feel like you're on your own private island."

Florida Gulf Coast: Old Florida offers a relaxing escape

Florida’s Gulf Coast continues to draw travelers looking for calm waters, powdery white sand and dramatic sunsets. A major newcomer is the Four Seasons Naples (801 Gulf Shore Blvd., N., fourseasons.com, 239-944-7600) which opened in November, with spring rates averaging about $1,250 per night.

"You’re getting those white sand beaches, warm waters and incredible sunsets," D’Andrea said.

Anna Maria Island also offers a quieter barrier island near Sarasota known for its charming beach cottages, bikeable streets and laid-back, Old Florida atmosphere.

"It’s a great option for travelers who want beautiful beaches without the crowds and a slower pace than South Florida," D’Andrea said, noting it’s especially popular with couples and families who value walkability and relaxed coastal dining.

Long Islanders can find direct flights to Sarasota from MacArthur Airport from carriers Breeze and Southwest, with round-trip fares in March as low as $163. Anna Maria Island is then a 40-minute drive from Sarasota Bradenton International Airport. Stay north of Pine Street on the Gulf side and you’ll be near restaurants and beautiful beaches. Rental agency websites like Seabreeze Vacations, Beach Boutique, Once Upon A Beach, Duncan and Sato offer direct booking for home rentals just a few blocks from the beach.

U.S. Virgin Islands: No passport ease

For travelers who still want true island energy without international travel, the U.S. Virgin Islands remain a strong option. St. Thomas and St. John offer snorkeling, beach coves and luxury resorts with the convenience of domestic flights.

"No passport is required, which makes it especially appealing for families and travelers who want easy logistics," D’Andrea said.

She highlights Lovango Bay (Lovango Cay 1, lovangovi.com, 855-938-5348) a private island accessible by ferry from St. Thomas or St. John, blending upscale dining with a barefoot-luxury vibe.

"It’s very boho. There's high-end food, but you can walk around in a sundress or barefoot," she said.

Guests can stay in tree houses, villas or glamping tents and day visitors can reserve beach access even if they’re not staying overnight.

Miami: New openings for fun and nostalgia

Miami continues to evolve as a resort destination with major hotel transformations.

The Andaz Miami Beach (4041 Collins Ave., hyatt.com, 844-509-0787) reopened in May 2025 following an $80 million interior renovation of its former Confidante property. D’Andrea says it’s ideal for families, girls’ trips and travelers who want nonstop energy.

"It’s vibrant and fun. You can even order chicken tenders with caviar at the pool," she said. "There’s a movable pool floor with live performances, and the culinary program is by José Andrés."

The iconic Delano Miami Beach (1685 Collins Ave., delanohotels.com, 305-359-7409) also reopened after being closed for six years for extensive renovations, bringing back its art deco roots and throwback glamour from the 1980s and ’90s.