Desert Island Fantasy

Illustrations by James Taylor.


Danielle, 28, and
Jamil, 28, business school students, Hamilton Heights

Date: January or March 2008
Budget: He Said: $4,000;
She Said: $4,500
Duration: One week

Jamil Said: “We’re planning the wedding ourselves, so relaxing on the honeymoon is important. I’d be happy to be away from a city, reading on the beach, with good food and good booze at my fingertips. I don’t want to think about or deal with anything. I want clear blue water, white sand, secluded natural lagoons—privacy is huge. All of that said, Danielle’s pretty adventurous. We were in Hawaii last year, I threw out the idea of skydiving, and we did it. We’re always up for trying anything.”

Danielle Said: “Theoretically, I’d love to do Thailand or Australia, but I don’t want to spend half the week traveling. So I’d rather go to the Caribbean or Europe. I love art and history—I used to work at P.S. 1—but I don’t need to go to Florence and see every piece of Renaissance art; I’ve done that. I want to go somewhere peaceful. I want relaxation. I would be open to all-inclusives. That route might be easier—less to worry about.”

Runner-Up Destinations: Puerto Plata, Dominican Republic, and Vieques, Puerto Rico


An aerial view of La Sirena hotel. Photo: Courtesy of La Sirena

Getting There: Take off from JFK or Newark, and arrive at Wallblake Airport seven hours later, following a layover in San Juan, Puerto Rico.

Where to Stay : While each of La Sirena’s airy, all-white rooms is built to please, book room 303 to enjoy an expansive terrace and unparalleled views of Meads Bay and neighboring St. Martin. Or take advantage of the hotel’s honeymoon packages, which include a candlelit dinner, three-day car rental, and free airport transportation (from $2,020;

Relax at the Beach : Anguilla is known for its 33 beautiful beaches, most of which are located on the west coast. Swim and snorkel in the calm waters at Maundy’s Bay. Sip a cocktail at Uncle Ernie’s Bar on Shoal’s Bay; here, the sand turns pink at sunrise and sunset, and people-watching is at its best. Party on Rendezvous Bay’s two-mile white-sand strip, where the Dune Preserve Bar features live music and serves cocktails, chicken, and ribs on the beach.

Visit the Cays : Rent a glass-bottom boat or paddleboat from Anguillian Divers to seek out the small cays and islands, like uninhabited Prickly Pear or Little Bay, both of which are serene spots for a day-trip picnic ( To explore the ocean floor, enlist the assistance of La Sirena’s own certified scuba-dive shop.

Shop in St. Martin : If Anguilla starts to feel too much like a deserted island, go to bustling St. Martin, a mere 30-minute ferry ride away. Stock up on luxury European goods on Rue de la République and Rue de la Liberté—they’re 50 percent cheaper here than in the U.S. because the island is a duty-free port. Eat lunch at Le Pressoir, a charming Creole house turned upscale French bistro.Where to eat: Anguilla is a mere 23 square miles, but there’s an amazing abundance of dining options available, from beachside fish shacks to haute cuisine. Reserve a table at Blanchard’s, a waterfront restaurant with a renowned 3,000-bottle wine cellar and a creative approach to Caribbean cuisine (think jerk shrimp with cinnamon-rum bananas and sesame-crusted mahimahi). Another evening, venture over to cozy Hibernia, where French-Indochinese cuisine is the specialty.

To Do, by Night : Although there is no thumping-bass nightlife in Anguilla, many beachfront bars host live calypso and reggae bands. Relax with a Carib beer or Pyrat Rum, one of 30 different rums available, while listening to steel guitar and drums at the laid-back Pumphouse. For something ritzier, nowhere beats the bar at the Cap Juluca hotel, where you may just bump into a famous American actor or model basking in the serene, paparazzo-free harbor.

Itineraries by Gabe Struck.

Desert Island Fantasy