Caribbean 101

by  ShermansTravel Editorial Staff | Jan 14, 2013
Aruba aerial shot
Aruba aerial shot / stevelink/iStock

When winter gets underway, many of us start dreaming of a Caribbean vacation. The region's appeal is undeniable: Swaying palm trees, swaths of beach, turquoise waters, and great nightlife are just some of the islands' draws. But knowing you want to hit the beach and choosing which island to visit are two different matters. Considering the region is home to hundreds of islands, many with incredibly different personalities and offerings, first-timers are easily confounded by the array of choices, and even return visitors can make mistakes. Our Caribbean 101 Spotlight is meant to help you decide which island suits you best – whether you're heading south for the first time, or the hundredth.

We've reviewed 23 of the most popular islands below, and broken them down into seven categories so you can most easily browse based on your interests. After all, if all you want is a beach vacation, there's no point considering islands that don't have any (indeed, while it may come as a surprise to some, many Caribbean islands lack beaches of note). Some of our top islands fall into several categories (their varied offerings usually make up a large part of their appeal).

Flickr / twicepix

Best on a Budget

Of course, you can still have a magical Caribbean getaway while keeping your savings account nice and full. Many island visitors take advantage of cruise packages, all-inclusive resorts, and budget-conscious activities when making their escape. That being said, these options are fairly popular, so don’t be surprised when crowds of like-minded travelers touchdown the same time you do.

For those looking for the most bang for their buck, Aruba is one of the safest bets. It's become a hugely popular package destination in recent years, in part for its gorgeous resorts and its regular nonstop flights from the U.S. But the island’s biggest selling point is its weather, which remains dry and balmy year-round. Likewise, the Bahamas and the Dominican Republic have accumulated a devoted following among cruise-ship passengers, package-seeking travelers, all-inclusive trippers, families, and singles looking for a good time with an affordable price tag.   

Jamaica and Puerto Rico see their fair share of rowdy college kids once Spring Break season rolls around, but make no mistake, both islands are rich with culture the whole year. Jamaica holds a deep history, vibrant culture, and passionate political past that make it a fascinating place to visit at any time. Nature enthusiasts will enjoy the Green Grotto Caves – limestone caves once used to hide runaway slaves – and the fog-shrouded Blue Mountains covered in coffee fields and laced with rivers and waterfalls that invite rafting and scenic tours. Puerto Rico also offers a myriad of natural and cosmopolitan delights for savvy travelers. While most package trips will get you to San Juan, independent travelers are becoming increasingly fond of Vieques, a small island six miles off the coast that recently opened to tourism after being decommissioned as a U.S. military base. The island caters to sophisticated, eco-minded tourists with small boutique hotels, a huge wildlife refuge, and about 42 miles of pristine beach.

The U.S. Virgin Islands of St. Croix, St. Thomas, and St. John are the only American-owned islands in the Caribbean – all of which have their own distinct personality – and since all three are easy to reach by ferry or seaplane, you can use any one as a base for your holiday. St. Johns, in particular, boasts pristine landscapes, thanks to the National Park Service, which preserves much of the land, and, although there's no nightlife to speak of, St. John's wondrous beauty and appealing resorts and restaurants draw visitors seeking a relaxed Caribbean ambiance.

Both St. Croix and Trinidad provide a wealth of history and culture. Trinidad is home to a melting pot of different cultures from India, Syria, Venezuela, Africa, Europe, and many more, which makes for abundant cultural festivals (in fact, Trinidad's Carnival is revered by many as the best party in the Caribbean). Outside of the congested and commercialized capital of Port-of-Spain, the island's wildlife sanctuaries offer some of the Caribbean's richest ecosystems. St. Croix has a distinctly Danish flair, evident in the architecture of capital Christiansted, ranked as a National Historic Site. The varied landscape here ranges from arid, rocky terrain in the east, to a small jungle enclave in the west, with beautiful beaches lining the coast in between.

Anguilla Tourist Board

Best Smart Splurges

We understand, you don't want to break the bank to fund a dream vacation. Sure, it’s nice to get away for a while, but no one wants to return home to a pile of bills. However, sometimes spending a little extra cash can be a worthwhile investment if it leads to a more memorable travel experience while also helping you get more for your money. Some of our choices were selected because of their elegant features, while others were picked for boasting some of the best deals in the seas.

Anguilla, located at the northern fringe of the British Leeward Islands, is home to lavish resorts and villas, fine dining, and some of the Caribbean’s best and least-crowded beaches – perfect if your idea of luxury requires solitude. Foodies will delight in Anguilla’s culinary offerings, which often put a twist on local fare. The island also hosts two of the region’s largest wine cellars, at Malliouhana Restaurant and Koal Keel Restaurant.

Antigua boasts a beach for each day of the year – that’s 365, for those keeping score – and is a big draw for those who crave the finer things. Explore the historic harbor that once served as Britain’s main naval base during the Napoleonic wars, or climb to Shirley Heights to enjoy reggae music, barbeque, juicy libations, and Technicolor sunsets. Antigua is also a popular spot for weddings, with many resorts offering honeymoon packages for couples wanting to start their union off on a fancy foot.

Since Bermuda is often thought of as a Caribbean island, even though it's nowhere near the region, we've included it here to give it due coverage – and make the argument that this is one island not to visit in winter. Bermuda sees a swell of tourists in the late spring because of its close proximity to the U.S; the isle is a mere two-plus hours from the East Coast, perfect for a quick getaway. Enjoy a round of golf at Riddel’s Bay Golf and Country Club, the oldest course in Bermuda, or merely spend your time sunning yourself on the island’s famous pink-sanded beaches.

One of the richest islands in the British crown, Barbados has a compelling West Indian culture that's part upper crust – cricket games, tea-time, and starched shirts still prevail here – and part Creole, with steel-drum music and fish fries on offer. The island remains a cut above many in the region, with fine beaches, superlative service, great dining, and numerous spas to choose from when you feel the need to unwind.

The two islands that form the federated nation of St. Kitts and Nevis couldn't be more different. The larger St. Kitts has morphed into one of the Caribbean's leading package and cruise-ship destinations, complete with casino-resorts and all-inclusive plans. Darling Nevis, however, lures visitors with plantation-style inns and intimate restaurants. Since the two islands are connected by a short ferry ride, you can easily enjoy the best of both on one trip, but choose your preferred home base based on whether you want Caribbean fun in the sun (St. Kitts) or a secluded, high-end getaway with a loved one (Nevis).

The French-owned St. Barths has earned its reputation as the bi-continental set's playground, but remains a surprisingly laid-back place where one enjoys the simple pleasures, be it lingering in cafés, with the inimitable scent of galettes, Gauloises and hibiscus hanging in the air; basking on the beautiful beaches, of which there are more than a dozen picture-perfect settings to choose from; or enjoying a sunset cocktail overlooking the azure Caribbean.

Revered as one of the last frontiers of the Caribbean, the Turks and Caicos islands are tailor-made for a long-weekend beach vacation. The islands of Parrot Cay and Grand Turk offer even more exclusive retreats; the former is a private 1000-acre island home to a single super-posh resort, the Parrot Cay Resort, while Grand Turk, the chain's capital island, has more history than main island Providenciales, better diving, and quaint inns, but is less developed for tourism.

The Bahamas is a great spot for the shopaholic, with plenty of upscale and bargain stores to choose from. Glamorous megaresorts, glitzy casinos, fine restaurants, historic sights, and spirited nightlife are all guaranteed in the chain's most popular destinations, Paradise Island/Nassau (New Providence Island) and Freeport/Lucaya (Grand Bahama Island).

Though the Dutch-owned half of St. Maarten is often awash with tourists, the French-owned half of St. Martin  boasts luxury resorts, gourmet cuisine, and a distinctly more sophisticated and prosperous ambiance. No matter which side you choose, you'll be treated to beautiful beaches, some of the Caribbean's best duty-free shopping, superb restaurants (mainly in the island's French capital of Marigot and nearby Grand Case), and low-key casinos and ample nightlife (in the Dutch capital of Philipsburg). However, if you’re looking for an intimate getaway, this is not the place for you.

Flickr /

Best for Families

Planning an expert family vacation can be tricky. You want to pick a spot that keeps the attention of the rugrats, but don’t want the entertainment to be limited for mom and dad. With islands hosting anything from scuba diving to salsa dancing, you’re guaranteed to keep the kids happy, while getting in some rest for yourself.

The Bahamas draw a ton of families, due to their glamorous megaresorts (Paradise Island's Atlantis Resort, home of the famous waterslide that bisects a shark tank, is always a hit) and casinos and nightlife. Kids can also delight in nature tours, kayaking adventures, and get up close and personal with some of the island’s native species, including dolphins and iguanas.

Puerto Rico is another prime spot for the whole family, for its Old World charm, dense thickets of nature trails, zip lining, and more. Best of all, because it’s a U.S. territory, it doesn’t require a passport for U.S. citizens.

For families who would rather spend their vacation traipsing through nature instead of lounging on the beach, many islands offer a bevy of tours to educate and excite people of all ages. Turks and Caicos are protected by a natural 499-mile-long barrier reef, creating superb turquoise waters for miles and perfect for diving and snorkeling. The U.S. Virgin Island of St. Thomas was rated by National Geographic as one of the top spots in the world for sailing, scuba diving, and fishing. The British Virgin Islands, though more difficult to reach by plane, are ideal for families who love to explore beautiful bays and hidden coves.

Flickr / Boss Tweed

Best for Romance and Seclusion

There’s a reason the stereotypical romantic getaway is on a private island, cut off from the world, with nothing to keep you company but your beloved and an impeccable sunset. The Caribbean is a fashionable spot for newlyweds, honeymooners, and long-time married folks hoping to forget their troubles.  

For couples longing to spend their time gazing lovingly into one another’s eyes, there’s no better plan than to stake out a spot on one of the Caribbean’s less-traveled islands. Chic, but often pricey, destinations such as Anguilla, Nevis, and Turks and Caicos bring luxury resorts, vibrant nightlife, and lavish scenery (whose beauty is incomparable to that of your loved one, of course).

The British islands of St. Vincent and the Grenadines are sleepy and romantic outposts whose surrounding waters are renowned for providing the Caribbean's best sailing conditions. St. Vincent is blessed with some superb beaches (most of which are actually black) and a tropical tranquility unspoiled by mass tourism. The Grenadines, a small chain of 32 islets due south of St. Vincent, are mostly uninhabited and only visited by beachcombers and sailors; three exceptions are Bequia, offering postcard-perfect sands and charming Creole houses; Mustique, where villas and extravagant homes accommodate the rich and famous, from the late Princess Margaret to music-icon David Bowie; and Petit St. Vincent, home to the secluded, high-end Petit St. Vincent Resort.

Laid back Tobago’s beachy atmosphere attracts vacationers who want to scuba dive along the offshore reefs, explore lush rainforests, and bask on powdery sands. The island also offers a number of wedding packages, ranging from the traditional “I do’s” to underwater nuptials.

Cayman Islands Department of Tourism

Best for Active Travelers

While many like to get away to slow down the pace of life, plenty of others prefer a vacation full of energy. Scuba diving, snorkeling, diving, and golfing are all prevalent activities throughout the Caribbean, whose clear waters and abundant landscapes can be enjoyed from behind a camera lens or up close. For adventure lovers and adrenaline junkies, the islands bring their A-game.

The best places to start on an outdoor-focused trip in the Caribbean are on some of the regions most pristine shorelines. Antigua locals claim the two best beaches of its 365 are Dickinson Bay and Half Moon Bay, but, if you're looking for a more private reprieve, deserted Green Island, off the island's east coast, may be your best bet. Martinique, most popular among French visitors in the winter, likewise has plenty of beaches to choose from. Of the island's many beaches, head south to spectacular Les Salines, an unspoiled strip of white-sanded shoreline that hugs an azure bay trimmed with palm trees. Crystal waters and well-groomed sand may also be found in St. Barths, Turks and Caicos, the U.S. Virgin Islands, British Virgin Islands, Jamaica, and the Dominican Republic.

For those who want to see what lurks beneath those glittering waves, be sure to check out the Cayman Islands. The three British islands – Grand Cayman, Cayman Brac, and Little Cayman – have long been popular with divers and celebrities, but each has its own appeal. The largest, Grand Cayman, hosts over 100 dive sites. Those seeking a more private experience can head to the secluded beach at Rum Point (in the north), near Stingray City, where families delight in swimming with, and feeding, some very social (and safe) stingrays.

The remote Dominica is well known among scuba divers because of its brilliant coral reefs, magnificent sea life, and bubbling underwater hot springs. However, the spot recently earned the title of “Whale Watching Capital of the World,” and is home to gorgeous rainforests, where hiking trails lead to a boiling lake, waterfalls, and natural hot springs. Grenada is another hot spot for nature lovers; it features an underwater volcano and the largest shipwreck in the Caribbean, so scuba diving is prime, with most diving facilities located just 15 minutes from the popular white sands of Grand Anse Beach. Guadeloupe is an ideal dive site, as well as a perfect spot for exploring natural terrain. Parc National Guadeloupe, a UNESCO Biosphere Reserve encircling the rumbling La Soufriére, holds an array of natural splendors, from lush rainforest and tall ferns, to orchids and pineapples.

The British-owned island of St. Lucia remains mostly untouched, with velvety green mountains, a simmering volcano, banana plantations, and miles of white- and black-sand beaches. A string of package-catering resorts concentrated around Rodney Bay overflow with British tourists and not much else, but a few special hideaways, like the intimate Anse Chastanet, are found on the southwestern shoreline, overlooked by jungle-cloaked mountains. This too is where you'll find the island's renowned Soufrière Marine Management Area, one of the world's top diving destinations.

If the only green you’re concerned with are of the putting variety, look no further than Bermuda, who plays host to the PGA Grand Slam of Golf each year. (The season-ending showcase will take place at the Port Royal Golf Course this October.) Barbados, St. Kitts, and Nevis are also well known for their exceptional courses.

Dominican Republic Ministry of Tourism

Best After Dark

A tropical island is all well and good during the day, but what happens once the sun goes down? For many, that’s when the fun really starts. The Caribbean nightlife scene is a bumping playground for night owls and party animals alike. Pick your poison: dancing, drinking, fine dining, gambling, and the islands are sure to please. The Caribbean is so packed with liveliness, you may need an extra day sprawled on the beach to recover.

Of the three Dutch-owned ABC islands (Aruba, Bonaire, and Curacao), Aruba is the most developed for beach tourism. In recent years, it's become a hugely popular package destination for its multiple casinos – which accept US dollars – and glittery, high-rise beach resorts. It’s also generated the highest repeat-visitor rate in the Caribbean, in large part due to its nightlife. The Bahamas main island megaresorts hold plenty of casinos, as well as travelers willing to push their luck. St. Lawrence Gap in Barbados has the greatest concentration of bars and restaurants, but the quieter, Atlantic-facing side of the island boasts a good number of attractions, including the Andromeda Botanical Garden. For a night you’ll never forget, check out the Dominican Republic, with its Vegas-style casinos and rollicking nightclubs. The Jamaican clubs are heavily influenced by the island’s signature sound, reggae, while the Martinique scene pumps zouk – the island’s dance music - and West African-influenced indigenous drum beats blended with modern synthesizers.

Low-key casinos can be found in St. Martin and Curacao, while Nevis and St. Kitts are home to casino-resorts and Calypso music.

Up next...

Four Travel Adventurers to Follow on Twitter Now

Find The Best Cruises
Find a cruise

Find the best deals!

Click on multiple sites to get the lowest prices

Click on multiple sites to get the lowest prices