HOW many islands make up the Caribbean, you reckon? Fifty? A hundred? Try thousands — more than the number of stars you can see on a clear night (city folk: ask around what one of those are) — officially divided up into 30 or so nations and territories.
We’ll say it, because nobody else seems to be able to: That’s 20 or so too many. And if you think that’s harsh, just hang around the region for awhile and see for yourself. It all starts to look like variations on a theme, with too many islands offering little you can’t get elsewhere. That’s fine, perhaps, until you start weighing the often prohibitive cost of transportation, or the baffling absence of basic public safeties that we are expected to somehow overlook.
Unfortunately, few of us have little time to seperate the musts from the also-rans, turning the search for the perfect Caribbean destination into a very expensive game of trial and error. Luckily, we’ve been to pretty much all of the major Caribbean destinations, so you don’t have to.
Our idea of perfection? Ease of access, for starters. Many of these islands are basically places to lay on or near a beach for a week. It shouldn’t take all day to get there. Then there’s safety. High rates of robbery or murder, or instances of random targeting of vacationers will bump even the most beautiful island right off of our lists; you should probably follow the same rule. Finally, if we can satisfy questions about convenience and peace of mind, there’s the final, most important question: What’s there? Boring’s fine, but does the island provide experiences truly worth traveling for?
With that in mind, we’ve selected our top Caribbean islands for 2011. Here goes:
1) PUERTO RICO
The easiest, breeziest Caribbean isle is also one of the best. No passports, no roaming fees on your smartphone, no currency exchanges. Add in frequent nonstop flights on a competitive route, and you’ve got the closest thing the region can boast to a no-brainer. Want big city? San Juan’s not bad, not bad at all, with its historic charm and even a modern transit system. Want to really kick back and relax? Head west to surf-y Rincon, a short drive from the airport in Aguadilla, which has its own nonstop flights from New York.
Dream trip Book into a Old San Juan’s classic Hotel El Convento for a couple of days, explore the city’s historic heart, then either drive (four-five hours) or fly (much shorter) over to Rincon for a stay at the legendary Horned Dorset Primavera, an elegant Relais & Chateaux-flagged hideaway.
Hot deal A current, island-wide promotion offers four nights for the price of three at 25 properties, including breakfast. Book the “Puerto Rico Sparkles” package — which also discounts tours and car rentals — at seepuertorico.com before Feb. 15; valid for travel through Apr. 15.
Get there Multiple airlines offer nonstop flights (3-4 hrs).
Sample fare $300 or more in high season.
2) ST. JOHN
There’s a thin line between heaven and hell, particularly in the U.S. Virgin Islands, another no-passport-needin’ Caribbean destination. We’d rather sit in the dentist’s chair for a week than suffer through an hour in surly St. Thomas. Sketchy St. Croix, maybe, if it were one of the only islands around. But it’s not, and as such, it resides far down our list of must-sees. Civilized and sleepy St. John, however, now that’s a keeper. With two-thirds of the land inside National Park Service-controlled territory and tiny Cruz Bay (home to New York chef Zak Pelaccio’s newest outpost of the Fatty Crab empire) being as close as it gets to city life, this is one kickass place to kick back and take it easy.
Dream trip Most people will end up staying at the island’s popular Westin resort, however, for us, there are just two ways to do St. John. One, make like Biff and Miff and book into the WASPy, Rockefeller-founded classic that is Caneel Bay, an expensive but integral part of the St. John experience since, oh, forever. The other, a far more affordable choice, is to go eco —- sample from four different lodging options with Maho Bay Camps, ranging from fancy camping to more sturdy options. Wherever you park, there are plenty of beaches, hiking and snorkeling on tap.
Hot deal Take advantage of the USVI-wide promotion that offers $500 off a stay at participating resorts on St. John when you book a minimum of five nights by Mar. 31. Travel Mar. 3-May 31; use code VIESC11 (visitusvi.com).
Get there Multiple airlines offer nonstop service (3-4 hrs) to St. Thomas. From here, take a $6/RT ferry (15 min.) to Cruz Bay.
Sample fare $450 and up in high season.
3) BARBADOS
Is it possible to out-England England? This former colonial holding does its damnedest. Afternoon tea, Pimm’s on the breath of local barflies, people wearing white chatting about cricket — chalk it up to the whole three and a half centuries this Peeps-shaped isle spent under the thumb of various His and Her Majesties; one of the region’s most hilarious little island nations has only been on its own since 1966. The flashy Platinum Coast, north of bustling Bridgetown, is like flypaper to the sort of dreadful Brit celebs that make reading the likes of Hello! magazine such a joy. But the truth is, that’s just a small part of the Barbados experience. From the quieter south coast to the wilds of the East, there’s plenty of off-the-beaten-path to explore. Did we mention this is one of the warmest islands in the winter? Tomorrow’s weather forecast, by way of example: 83 degrees.
Dream trip The island has successfully cast itself as a very upmarket destination, and while it is certainly true that this is the land of $700/night (or worse) hotel rooms, this is also a great place for less demanding types just looking to get a little winter sunshine on the cheap. If you can get a room, the Peach & Quiet guesthouse, on a privileged oceanfront spot near the airport on the South Coast, is one of the island’s best values, with rooms around $100 throughout the season. Our recommendation, however, is to rent an apartment and settle in — this is an easy island to navigate on your own, and you ought to take advantage of that. Look for local listings on the trustworthy Flipkey.com.
Hot deal It’s super last minute — book by Thursday — but for $639pp, you get RT air from New York and 5 nights at the Allamanda Beach Resort, good for stays Mar. 1-Apr. 24 (cheapcaribbean.com).
Get there Multiple airlines — including JetBlue — offer nonstop service (4-5 hrs).
Sample fare Approximately $400 and up in high season
4) ST. BARTS
What can be said, except this: Some places are popular for a reason. Rich people go to Aspen because it is gorgeous. We all brave Hamptons traffic because the beaches on the East End of Long Island are pretty much the best you can find anywhere near New York City. St. Barts became an A-list playground because it is awesome. It’s funny, though — for most of its modern life, this French holding was a worthless pile of rocks, valuable only as a shipping center, rarely useful for things like agriculture. But in the last couple decades, that’s all changed — everyone from Diddy to Jeter can be seen living it up here in the high season. There’s another side to the island though, perfectly suited to those whose names have never appeared in Page Six — good, cheap-enough French restaurants, topless beaches, getting caught in scooter traffic jams, and other bits of awesomeness from la patrie.
Dream trip On the map, the capital city of Gustavia looks really tiny. But you’d be amazed how much is packed into its tiny, harborfront footprint. Base yourself here for a few fun days of spying on celebs — they’re everywhere. Hang on the town-adjacent Shell Beach, indulge in a little window shopping at the likes of Louis Vuitton, dress the part and try to blag your way into Le Yacht Club. You’ll feel like the help staying at the no-frills, harborfront Sunset Hotel, but the cost — around $150 in high season — makes it all better. When Gustavia starts to feel confining, rent a scooter and explore the island — just mind the completely inappropriate Hummers some opt to get themselves around in.
Hot deal The modest Hotel Les Mouettes in L’Orient features seven beach-adjacent cottages, with rates of $190 and up through Apr. 14 (st-barths.com).
Get there Multiple airlines serve nearby St. Maarten with daily nonstop flights (3-4 hours). Catch the $117/RT ferry over to Gustavia (greatbayferry.com).
Sample fare Around $600 in high season.
5) NEVIS
Celebrity moms like Debra Messing and Kelly Ripa were left reeling in 2008 when Hurricane Omar blew ashore here, putting the hurt on their favorite family vacation spot, the island’s legendary Four Seasons Resort, which remained closed until late last year. A lush little gem topped by a dormant volcano, Nevis has a wonderfully exotic, Hawaiian look and feel. Its diminutive size and safe atmosphere lend a certain small-town charm; the only settlement of any real size here, Charlestown, has a unique historic flair. Overall, though, it’s safe to say that Nevis is one of the most worry-free beach destinations at an East Coaster’s disposal.
Dream trip There are more lodging options at various price ranges than you might expect on such a small island, but you just can’t top the Four Seasons for sexy. Book in here (they’re currently offering a four nights for the cost of three deal), ditch the wife and kids by the beach-facing pools and nab a couple of tee times on the incredibly scenic golf course, with views of Nevis Peak. When you’re feeling relaxed, you might actually want to go climb that peak, come to think of it, being that it’s the crown around which the rest of the sombrero-shaped island’s brim can’t avoid looking upon. The best man to guide you is Lynnell E. Liburd — he’s been sherpaing tour groups up the mountain for the last 20 years (nevisnaturetours.com).
Hot deal The “Exciting Adventure” package at the Oualie Beach Resort is a steal at $154/night – 62 percent off rack. It includes a $75 breakfast credit; stay a minimum of four nights, through Apr. 13 (dealbase.com).
How to go American Eagle flies from San Juan 3x weekly (1 hour).
Sample fare All in from New York, the fare can be close to $700 during high season.