Puerto Rico

Aug 16th.

A quick 2 1/2-hour flight from Miami, Puerto Rico is an intoxicating blend of Spanish, Indian, and African influences, all melded into a tropical atmosphere of beaches, rainforest, and a fast-growing element of luxury. Whether you’re exploring the time capsule of Old San Juan, the posh designer boutiques of Condado, the beach towns on the island’s southern and eastern coasts, or the pristine jungle of El Yunque, Puerto Rico’s distinct culture and lively spirit is never far from sight.

Don’t Miss

  • Taking advantage of the city’s free hop-on, hop-off trolley.
  • Catching a salsa performance at Old San Juan’s Nuyorican Café.
  • Perusing the 1,000-piece art collection at the 130,000-square-foot Museo de Arte de Puerto Rico, the most extensive Caribbean art museum.

St. Thomas

Aug 16th.

Home to the biggest cruise port in the Caribbean, St. Thomas seems at first glance a place with little to offer beyond duty-free shopping. In reality, this 32-square-mile island has more texture than meets the eye. Along the narrow streets of capital Charlotte Amalie, you’ll find reminders of the 17th-century Danish settlers, such as the 99 Steps, constructed of old ships’ ballast bricks, and the 1679 Blackbeard’s Castle Tower (named for that legendary pirate). Beyond town, hilly roads with staggering views of untouched coastline lead to little hamlets like Frenchtown, where some of the residents still speak Creole. But the real appeal of this island is found along its perimeter: miles upon miles of white-sand beaches.

Don’t Miss

  • Taking in views of St. Thomas Harbor while sipping rum punch under the palm trees at Hotel 1829’s terrace bar.
  • Checking out the West Indian antiques and paintings by Camille Pissarro on display at Haagensen House, a restored 19th-century Danish banker’s house in Charlotte Amalie.
  • Day-tripping to nearby St. John island, a 6,000-acre national protected park that’s just a short ferry ride away.

Jamaica

Aug 16th.

One of the largest landfalls in the Caribbean, Jamaica is ringed with some of the world’s most spectacular beaches. But there are plenty of other ways to amuse oneself in paradise. Adventure sports from mountain-biking to diving to fishing abound. The tropical vegetation attracts a stunning array of exotic birds (and bird-watchers). A food renaissance has elevated island cooking into a compelling nouvelle cuisine, albeit one that retains a traditional local flavor. And, of course, the inimitable range of musics pioneered here—from ska to reggae to dub to dancehall—endure and echo down every lane and on every fragrant ocean breeze.  

Don’t Miss

  • Cooling off at Treasure Beach, the Blue Lagoon, and other secluded swimming holes around Port Antonio, where the likes of Errol Flynn and other celebrities frolicked in the 1940’s.
  • Tasting Jamaican jerk where it was invented, at Boston Bay. The fiery, tangy meat is best enjoyed on the sand in front of one of the shacks lining the shore with a Red Stripe in hand and reggae beats in the background.
  • A boat ride through the Black Mountain Morass swamps, Jamaica’s answer to the Everglades, where native crocodiles lurk and tangy pepper shrimp is the local delicacy.

Bahamas

Aug 16th.

Like a scattered string of pearls, the islands of the Bahamas stretch from their most northerly point (less than an hour’s flight from Miami) south across 500 miles of the Caribbean Sea. The still-relatively-young commonwealth, which achieved independence in 1973 after 325 years of British rule, encompasses 700 different islands-each with its own character. But whether they’re havens of unspoiled wilderness, decadent celebrity-studded oases, or glitzy gambling and entertainment meccas, all are suffused with the same laid-back, carefree, distinctly Bahamian attitude.

Don’t Miss

  • Getting out on the water—whether by swimming at Harbour Island’s spectacular pink beach, bonefishing off Andros, or whizzing through the massive Atlantis waterpark on Paradise Island.
  • Taking part in (or at least watching) the wild parades of Junkanoo, the islands’ most exuberant local celebration.
  • Sampling fabulous Bahamian dishes like conch fritters, fried grouper burgers, and stone crab claws—along with bottles of the great local beer, Kalik.

The Caribbean islands are famous for their sunshine—and rightly so. Is there anything more daydream-worthy, more symbolic of languor and ease, than those ubiquitous images of sugary white beaches, dappled palms, and turquoise lagoons sparkling in the sun?

Sunsets in the Caribbean don’t get nearly as much attention. But they should. Those gorgeous stretches of sand and sea (well, at least the western-facing ones) are every bit as spectacular in the light of the setting sun, with Easter egg–colored clouds floating overhead. Especially when you have someone to share them with.

For centuries, sunsets—particularly sunsets over the sea—have inspired romantic musings. In his epic poem Evangeline (published in 1847) Henry Wadsworth Longfellow put it like this:

Softly the evening came. The sun from the western horizon Like a magician extended his golden want o’er the landscape; Trinkling vapors arose; and sky and water and forest Seemed all on fire at the touch, and melted and mingled together.

With all that melting and mingling and fiery touching, it’s no wonder so many sunset-watching spots seem custom-tailored for couples. Grand Cayman’s Seven Mile Beach, for example—though public, and actually closer to five-and-a-half miles—is long enough that starry-eyed duos find plenty of space for intimate evening strolls or picnics. And at St. Lucia’s Jade Mountain resort, honeymooners (or wannabes) can soak together in private infinity pools—some as large as 900 square feet—while watching the sun go down.

In the Caribbean, though, romance doesn’t always have to mean seclusion. It’s hard not to have an enchanted evening at Jamaica’s famous Rick’s Café, for instance—lingering on the cliffside terrace for grilled seafood and Tropitinis, then dancing to live reggae music as the sun dips low. The same can be said for gathering among island locals on Antigua’s highest hill, Shirley Heights, with its sunset views over sweeping beaches and sailboats bobbing at anchor.

Of course, each one of these spots can be the perfect setting for romance—as long as you bring the right person. But that’s not up to the islands; that’s up to you.

Peter Island Resort, Peter Islandpeter-island

Every evening, this resort runs a “Sunset at the Loop” tour for guests. Participants are taken to an overlook of Deadman’s Bay on the west side of the island and plied with hors d’oeuvres and bubbly while they watch the sun set over neighboring St. John.

Mount Sage National Park, Tortola

Set within a tropical refuge, the Mahogany Trail winds a quick 300 yards up to the summit of Mount Sage. At 1,716 feet, it’s the highest point in the Virgin Islands—and the best place to watch the sun set.

Jade Mountain, St. Lucia

From this resort’s west-facing rooms you’ll see the sky’s red-orange hues reflecting off the Caribbean; upgrade to a suite and you’ll get a panoramic lookout from a private infinity pool.

Boqueron Beach, Puerto Rico

Head to this mile-long stretch of white sand on Puerto Rico’s southwestern coast—and keep your eyes peeled for the famed “green flash,” (caused by refracted light rays) right before the sun disappears below the horizon.

On the Rocks restaurant at Eden Rock Hotel, St. Bart’s

From the open-air deck of this French restaurant overlooking St. John’s Bay, you’ll have a front-row seat for both the sunset and the schools of parrot fish that dart beneath the surface of the sea.

Sunshine’s Grill, Nevis

The outdoor tables at this laid-back spot on Pinney’s Beach are an ideal place for watching the sun drop behind the green hills of St. Kitts (and for sipping some locally famous “Killer Bee” rum punch).

Landfall Park, San Salvador, Bahamas

A simple stone cross at Fernandez Bay, on San Salvador’s west coast, commemorates Christopher Columbus’s first landfall in the New World. Many a visitor has snapped the sun setting into the water with the monument in the foreground.

Seven Mile Beach, Grand Caymangrand-cayman

Though it’s actually a little less than six miles long, this powdery crescent on Grand Cayman’s western coast has plenty of room to spread out a blanket for a sunset picnic.

Rick’s Café, Jamaica

This bar and café perched on Negril’s West End Cliffs is famous for the spectacular sunset-viewing from its expansive terrace—and also for the wild after-dark parties that spill onto the beach below.

Shirley Heights, Antigua

From the highest point in Antigua—where the remains of General Shirley’s 17th-century fort still stand—the sun sets beautifully over English Harbour and Galleon Beach. Go on a Sunday night and you’ll meet locals who gather there for a regular sunset party.