Caribbean 101 Guide

• Main
• Getting There

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 25 of the most popular islands below, and included quicklinks to information on how to get there by plane. But, to start, we've also listed some of our top island picks by interest – beach, price, golf, diving, culture, you name it – to help you fine-tune your research. 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 a large part of their appeal); simply click on those that interest you to jump straight to our review, or, pick and choose from the full list that follows.

ShermansTravel Experts' Favorites:
Aruba (affordability), Barbados (a bit of everything), Cayman Islands (diving), Nevis (romance), St. Barths (chic), Turks & Caicos (beach)

Most Affordable
Aruba, Bahamas, Dominican Republic, Jamaica, Puerto Rico, US Virgin Islands

Most Expensive
Anguilla, Antigua, Bermuda, Barbados, Nevis, St. Barths, Turks & Caicos

Best for Being on the Beach by Lunch
Bahamas, Bermuda, Cayman Islands, Dominican Republic, Jamaica, Puerto Rico, St. Martin, Turks & Caicos, US Virgin Islands

Best for All-Inclusive Trips:
Aruba, Bahamas, Barbados, Dominican Republic, Jamaica, Puerto Rico, St. Kitts, St. Martin

Best for Seclusion and Romance
Anguilla, Nevis, Saba, St. Barths, St. Vincent & the Grenadines, Tobago, Turks & Caicos

Best for Families
Bahamas, Turks & Caicos, Dominican Republic, Jamaica, Virgin Islands (US), Virgin Islands (British)

Best for the Chic Set
Anguilla, Antigua, Barbados, Bermuda, Cayman Islands, Curaçao, Nevis, St. Barths, St. Maarten/St. Martin, St. Vincent & the Grenadines

Best for the Beach
Anguilla, Antigua, Dominican Republic, Martinique, St. Barths, Turks & Caicos, Virgin Islands (US), Virgin Islands (British);

Best for Culture/History
Barbados, Curaçao, Dominica, Grenada, Guadeloupe, Jamaica, Martinique, Nevis, Puerto Rico, St. Maarten/St. Martin, St. Croix, Trinidad

Best for Diving/Snorkeling:
Anguilla, Bonaire, Cayman Islands, Dominica, Grenada, Guadeloupe, St. Kitts, St. Lucia, St. Thomas, Tobago

Best for Gambling:
Aruba, Bahamas, Curaçao, Dominican Republic, Jamaica, St. Maarten, St. Kitts

Best for Golf
Barbados, Bermuda, Jamaica, Nevis, St. Kitts

Best for Nightlife
Aruba, Bahamas, Barbados, Dominican Republic, Jamaica, Martinique, Nevis, St. Barths

Best for Shopping
Bahamas, Curaçao, Guadeloupe, Martinique, St. Barths, St. Maarten, St. Kitts, St. Thomas

ANGUILLA
Touted as having some of the Caribbean's best and least-crowded beaches, the tiny, secluded, island of Anguilla, located at the northern fringe of the British Leeward Islands, remains a laid-back Caribbean outpost where fishermen still head out to sea in hand-made boats and developments haven't entirely spoiled the island's natural charms. Because of its many pristine delights, well-heeled jet-setters have staked their claim on Anguilla and posh resorts and villas abound – some even say it rivals St. Barths in the luxury department. Offshore islands, like the Prickly Pear Cays, are excellent for diving, thanks to caverns popular with barracudas, and non-threatening nurse sharks (tour boats will take you there from Sandy Ground). Elegant dining offers delicious local fare and fine cuisine, while a reggae and string-band music scene keeps visitors grooving after sunset. Overall, this serene spot is one of the chicest islands around, with everything you need for a pampering island getaway – for those who can afford the price tag. Find out how to get there.

ANTIGUA & BARBUDA
Boasting 365 beaches (or, “one for each day of the year”), Antigua (pronounced an-tee-gah), the larger of the two islands, has made a name for itself among the rich and the famous for its coral reefs, miles of sugar-white sand, calm waters, and remote, high-end beach resorts. Though no longer British in governance, cricket is still played here and a historic harbor that served as Britain's main naval base during the Napoleonic wars is a popular tourist draw, with Shirley Heights (the historic fort atop the harbor), attracting locals and tourists alike to toast the sunset with live reggae music, BBQs and juicy libations. Antiguans claim the two best beaches 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. Tiny Barbuda, 27 miles away, remains largely undeveloped, but does boast pink-and-white sand beaches, barrier-reef-protected waters, and a couple of super-deluxe resorts; it's the perfect spot to fully escape day-to-day life, if you can afford such luxury. Find out how to get there.

ARUBA
While much of the Caribbean can become unbearably hot after April, the remarkable Dutch-owned ABC islands – Aruba, Bonaire, and Curaçao – are located on the fringes of the hurricane belt and thus blessed with dry, balmy weather all year long. Of the three, Aruba is the most developed for beach tourism; it's become a hugely popular package destination in recent years, complete with multiple casinos – which accept US dollars – glittery, high-rise beach resorts, and regular nonstop flights from the US. In the process, it's also generated the highest repeat-visitor rate in the Caribbean. Why? While it's definitely got the white-sand beaches and quality diving, food, and nightlife, its best selling point is that it's guaranteed to have good weather – no matter when you go. Only Bonaire and Curaçao can match that, but you don't go to those islands for the beach: Bonaire is a diver's haven, while Curaçao appeals to history and culture buffs who may never actually set foot on the sand. Find out how to get there.

BAHAMAS
More than 700 islands and thousands of cays make up the Bahamian archipelago, which, at just 55 miles east of Miami, boasts some of the easiest beaches to reach from the US. Granted, they're not technically part of the Caribbean (they're actually Atlantic islands), but their beautiful sands, crystalline waters rimmed with great barrier reefs, and sun that shines practically year round are certainly Caribbean worthy. The chain has created a devoted following among cruise-ship passengers, all-inclusive trippers, families, and singles looking for a good beach time with an affordable price tag. Glamorous megaresorts (think Paradise Island's Atlantis Resort), glitzy casinos, fine restaurants, bargain and upscale shopping choices, 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). That said, it doesn't have to be all party-time in the Bahamas; the rustic and more remote Out Islands, easily reached by ferries or charter flights from the main islands, still seem a world away. Ecotourists in search of raw natural panoramas and unspoiled beaches head to spots like Eleuthera, where amazing beaches, excellent diving, charming fishing villages, and few crowds await. Find out how to get there.

BARBADOS
The easternmost Caribbean island, Barbados has long been popular with British expats, who've flocked to its upscale resorts and golden-sand beaches for over a century. 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. While it has suffered somewhat in the posh department with the advent of package trips, the island remains a cut above many in the region, with fine beaches, superlative service, great dining, excellent golfing, and bona fide culture; when you're not on the beach, you can explore plantation houses and Anglican churches by day, and attend nightly calypso parties and barbecues by night. St. Lawrence Gap has the greatest concentration of bars and restaurants, but the quieter, Atlantic-facing side boasts a good number of attractions, including the Andromeda Botanical Garden. While prices here reflect the island's stately ambiance, it's still cheaper to visit than St. Barths and boasts a similar level of service. The island is also renowned for its annual Jazzfest each January; book early to assure your attendance. Find out how to get there.

BERMUDA
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. Indeed, Bermuda's Atlantic location makes it closer to Washington, DC, than it is to points south; as a result, like much of the northern United States, this balmy British isle only kicks into high-season in late spring and summer – while other islands of its ilk are becoming too hot to bear. With its fantastic golf, gorgeous bougainvillea, splendid pink-sand beaches, and endearing pastel-colored houses, Bermuda is a great place to kick back for a weekend. Indeed, its proximity to the United States makes it ideally suited for a quick getaway – at around two+ hours from the East Coast, you can be there by lunch. That said, a weekend is all you may be able to afford – this dose of British culture can cost a pretty penny. Find out how to get there.

BONAIRE
Consistently ranked the Caribbean's top dive spot, undeveloped Bonaire, which, along with Aruba and Curaçao, is part of the Dutch-owned ABC island chain off the coast of Venezuela, easily deserves the title. With over 80 surrounding dive sites, the island is a true divers' paradise and this, more than its beaches (of which there are none to mention) or nightlife (of which there is equally none), is why people come here. Indeed, the landscape is scruffy and arid, and there are few attractions – save a few slave huts from the island's days as a salt quarry – above ground. Expect to stay in practical, diver-oriented hotels. For posher digs and cosmopolitan flair, head to Curacao; for casinos and beaches, visit Aruba. Find out how to get there.

CAYMAN ISLANDS
The three British islands that form the Caymans – namely, Grand Cayman, Cayman Brac, and Little Cayman – have long been popular with divers and celebrities, but each has its own appeal. Lying between Cuba and Jamaica, the chain is among the closest isles to the United States, and, at under two hours by plane from Miami, hosts some of the easiest beaches to reach. As its name suggests, Grand Cayman is the largest and most developed of the three, with deluxe condos and luxurious resorts lining Seven Mile Beach (which is actually only 5.5-miles long), one of the Caribbean's finest swaths of sand, and some 100+ offshore dive sites. Those seeking a more private experience head to the secluded beach at Rum Point (in the north), near the island's hugely popular Stingray City, where families delight in swimming with, and feeding, some very social (and safe) stingrays. The other two islands, Brac and Little Cayman, some 89 miles away, are separated by a seven-mile channel and offer the utmost in Caribbean splendor; Brac also boasts great wreck diving around a 330-foot Russian frigate, the MV Captain Keith Tibbetts, while Little Cayman's impressive Bloody Bay Marine Park is itself a big draw. You can puddle-jump between the three on Cayman Airways to experience each of the island's delights in one fell vacation shot. While you're there, don't forget to try the Caymanian drink of choice, the Mudslide, with vodka, Kahlua, and Irish cream. Find out how to get there.

CURAÇAO
The most industrialized of the Dutch-owned ABC Islands (Aruba and Bonaire are the A and B), Curaçao (pronounced coo-ra-sow) is also the trio's most sophisticated, offering visitors a unique taste of cosmopolitan Dutch living in a Caribbean setting. The stunning capital, Willemstad, evokes 17th-century Amsterdam, but adds brilliant colors to its gingerbread roofs and wedding-cake trims; the lot is so remarkable that it's earned a UNESCO World Heritage Site designation – exceedingly rare for a Caribbean city. With some 55 different cultures living here, you're more likely to find international cuisine of the sort you'd expect of New York, although restaurants in under-developed parts of the island do serve local dishes like iguana. While there are beaches here, they're pebbly and scruffy, with more cacti than palm trees; the deep-blue waters are more spectacular than the island scenery, and harbor snorkeler- and diver-friendly shipwrecks, fish, and rock formations. That said, if you want a typical beach vacation, visit Aruba; if you want first-class diving, go to Bonaire. You visit Curaçao if you're looking for a culture-rich holiday in a tropical setting – this is one island that actually makes it possible. Find out how to get there.

DOMINICA
Scuba divers already know this remote Caribbean island thanks to its brilliant coral reefs, magnificent sea life, and bubbling underwater hot springs. But Dominica (pronounced domin-ee-ca and not at all related to the Dominican Republic) recently earned a new title, of “Whale Watching Capital of the Caribbean,” which confirmed this island's eco-friendly status. Set between Martinique and Guadeloupe, and often visited by 40-ton whales, who like to socialize, mate, and play off its shores, a boat excursion from Dominica promises a 90% chance of spotting one up close. Visitors come to Dominica for sights like this – not for its beaches, of which there are none worth mentioning. Instead, this eco-tourist haven boasts some of the Caribbean's best diving and one of its most pristine rainforests, where hiking trails lead to a boiling lake, waterfalls, and natural hot springs. For the former, you'll find accommodation in serviceable dive hotels; for the latter, expect atmospheric rainforest lodges of the sort you'd associate with Costa Rica. This is as close as you can get to sampling the Caribbean as it would have been when Christopher Columbus discovered it; to wit, what few Carib Indians remain in the region reside here, on a reserve along the Atlantic coast. Find out how to get there.

DOMINICAN REPUBLIC
The Dominican or DR (as it's known in shorthand) has recently become a hugely popular package destination that vies with Cancun in affordability and atmosphere. The second-largest country in the Caribbean (after Cuba), as well as one of the most affordable, the Dominican has something for everyone, from Vegas-style casinos, nightclubs, and all-inclusive resorts, to horseback riding, golf, surfing, diving, and some 1000 miles of white-sand beaches. Punta Cana, on the island's eastern coast, is the island's top draw, with the Caribbean's longest stretch of sand, while Puerto Plata, in the northwest, is a solid secondary consideration. If you want to go in the off-season, consider visiting in October, when Puerto Plata, Santiago, and a few other towns host a Latin Jazz Fest attracting legendary acts like Sade, Carlos Santana, and Chuck Mangione. Find out how to get there.

GRENADA
Striking, unspoiled beauty is the essence of Grenada (pronounced gre-nay-dah), where sheltered white-sand beaches, cascading waterfalls, dense rainforests, and crystal-clear waters abound. Part of an independent, three-island nation (with Carriacou, the largest of the Grenadines, and Petit Martinique), Grenada's secluded and seemingly undiscovered aura is its greatest appeal. Home to an underwater volcano and the largest shipwreck of the Caribbean, scuba diving is prime here, with most diving facilities located just 15 minutes from the popular white sands of Grand Anse Beach. It's not all about sand and scuba here, though, as Grenada is also known as the “Spice Island” for the abundance of mace, cloves, cinnamon, vanilla, cocoa, and nutmeg produced here. You can sample its history in old plantations, like the River Antoine Estate, the Caribbean's oldest waterwheel-powered distillery; in Market Square (in the capital city of St. George), where spices are sold in colorful handcrafted bags; or in the island's signature Nutmeg Colada, a coconut cream, grated nutmeg, and rum libation usually made with the island's own fragrant River Antoine rum. Though nightlife is fairly quiet here, you'll still be able to experience the swaying sounds of calypso, reggae, folk, and even jazz under the stars. Find out how to get there.

GUADELOUPE
This is the Caribbean à la française; a butterfly-shaped island (separated down the middle by a narrow saltwater channel) that is sure to have you fluttering about to sample its fine beaches, exquisite Creole cuisine (some of the best in the Caribbean), and encounters with its French-speaking, laid-back locals. One of the region's most varied destinations, Guadeloupe offers package resorts on Grande Terre – the ones near white-sand Plage Caravelle and the town of Ste-Anne have the best sands, but Gosier, near the capital of Point-a-Pitre is popular for its proximity to the bustling city, where great markets and shopping are found. Basse-Terre, in contrast, has quieter resort offerings near the black-sand beach of Plage Malendure, a glittering sandy cove that's a primary point of access to the large Pigeon Island Underwater Park, one of the Caribbean's best dive sites. It's also close to the Parc National Guadeloupe, a UNESCO Biosphere Reserve encircling the rumbling La Soufriére, where an array of natural splendors, from lush rainforest and tall ferns, to orchids and pineapples, is found. In addition to these “mainland” choices, three offshore islands – Marie-Galante, La Désirade, and Les Saintes – also invite visitors, either for day-trips or overnights; of the trio, Terre-de-Haut (part of Les Saintes) is particularly appealing to beach lovers seeking an intimate getaway in secluded resorts with fine service. No matter where you choose to spend your holiday, you're likely to hear more French spoken than English; Guadeloupe is, after all, a French island, which also means Euros are the main currency here. Find out how to get there.

JAMAICA
While this Rastafarian island may do duty as a spring-break central every March, the reggae-centric spot has a deep history, vibrant culture, and passionate political past that make it a fascinating place to visit at any time. Despite a turbulent history, prudent travelers can enjoy everything from picture-perfect white-sand beaches, great diving, and river rafting, to spicy food, some of the best golf courses in the West Indies, and a happening reggae-heavy nightlife. Catering to everyone – honeymooners, buffalo soldiers, dread-lock Rastas, and the lot – the island offers an array of accommodations, ranging from luxurious villas to all-inclusive resorts, and even out-of-the-way enclaves. Nature enthusiasts, meanwhile, 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. Negril and Montego Bay are the two most popular vacation zones, with many all-inclusive resorts that make heading to Jamaica for a little rest, relaxation, reggae, and rum-infused libations an affordable proposition. Find out how to get there.

MARTINIQUE
This little piece of France in the tropics features a colorful capital city, Fort-de-France; botanical gardens that spill over with indigenous flowers; charming fishing villages; and, oh yes, absolutely splendid beaches that are very popular with the French in winter, but little discovered by Americans. What truly sets it apart from other isles, though, is the incredibly interesting, albeit tragic, history surrounding its original capital, St-Pierre: Once known as the “Paris of the West Indies”, it was destroyed in 1902 by a volcanic eruption of the island's impressive Mont Pelée (now dormant); exploring its charred remains adds depth to a Caribbean vacation here. Another bit of history that also entices visitors is Martinique's claim as the birthplace of Napoleons's wife, Empress Josephine, whose childhood house is also open for viewing. Of the island's many beaches, head south to spectacular Les Salines, a pristine strip of white-sanded shoreline that hugs an azure bay trimmed with palm trees. Come nighttime, be sure to sample a petit punch (a rum, sugar syrup, and lime juice combo that really does pack a punch) and get down to zouk – the island's local dance music – at one of the island's many night clubs; the West African-influenced indigenous drum beats blended with modern synthesizers is a style unique to Martinique. Since Martinique is a French island, you will be paying Euros here – which can be a pricey proposition. Find out how to get there.

PUERTO RICO
Urbane, infused with Spanish Caribbean culture, but full of beautiful natural beauty, Puerto Rico, the US-affiliated and smallest of the Greater Antilles islands, offers a myriad of natural and cosmopolitan delights for savvy travelers. Besides lounging on the sand, there's plenty to do and see outside of hitting the beach; San Juan's Old World culture can be quite captivating, ditto its restaurants (especially in the cutting-edge dining district of SoFo), sexy salsa clubs, glittering casinos, and happening discos. 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 US military base. Known for its virtually unspoiled sands, this 21-mile-long isle offers quite a different experience than the mainland – indeed, don't come expecting high-rise hotels, luxury complexes, or shopping centers – instead, the island caters to sophisticated, eco-minded tourists with small boutique hotels, a huge wildlife refuge, and about 42 miles of pristine beach. Find out how to get there.

SABA
The sleepy island of Saba (pronounced say-bah), just south of St. Martin, proves that good things do come in small packages. One of the smallest islands of the Netherland Antilles, its hilly landscape is reminiscent of San Francisco's – except that its cliffs plunge into a deep sea, creating a paradise of underwater adventure and exploration. While it has no beaches or historical sites to mention (truth is, it has only one true reef and its sand is mostly grey), the island's unspoiled and undeveloped nature allows adventure-seekers the opportunity to discover a remote tropical beauty, minus the hubbub of major tourism. While the tourism industry is on the rise here (thanks to regular 12-minute flights from St. Martin and the opening of a day spa and new restaurants), many locals still make a living from traditional occupations such as fishing, trade, and needlework. If you are looking for a remote island escape with little to distract you, this “Unspoiled Queen” (as local Sabans call home) is the perfect spot. Find out how to get there.

ST. BARTHS
Ironic that a tiny, rocky Caribbean island ill-suited to agriculture and populated only by poor Norman and Breton fishermen should wind up luring Rockefellers and rock stars, real and reel royalty. But even as the French-owned St. Barthélemy, affectionately known as St. Barths (or Barts – both are correct) has earned its reputation as the bi-continental set's playground, it 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. The delightful capital, Gustavia, exhibits a decidedly French flair, and offers ample opportunities for window shopping and people watching at its bountiful boutiques and haute-cuisine eateries, but most people in search of “beach resort” atmosphere head to St. Jean, where posh resorts, shops, and bars line the beach. Sightseeing attractions (old forts, museums, aquariums, distilleries) are few compared to other Caribbean islands; this is an island to savor the good life, albeit at a luxurious Euro-centric price tag. Find out how to get there.

ST. KITTS & NEVIS
The two islands that form the federated nation of St. Kitts and Nevis couldn't be more different – bustling St. Kitts, the larger of the two, has morphed into one of the Caribbean's leading package and cruise-ship destinations, complete with casino-resorts and all-inclusive plans, while darling Nevis (pronounced nee-vis), lures visitors with plantation-style inns and intimate restaurants. While Nevis has more history and romance (it's not only the birthplace of Alexander Hamilton, one of the founding fathers of the United States, but also boasts lovely scenery of ivy-covered stone sugarmills, lush hiking and horseback-riding paths, and overgrown sugarcane fields), St. Kitts has more action: You'll find a busy capital city, a thriving nightlife scene, and great wreck diving off its shores. Both, however, have great golf courses. 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). Find out how to get there.

ST. LUCIA
Outside of the tourist-developed section between the capital, Castries, and the white-sand lined northern part of the island, the British-owned island of St. Lucia remains mostly untouched, with lush rainforests, velvety green mountains, a simmering volcano, banana plantations, and miles of white- and black-sand beaches. With a South Pacific feel, St. Lucia offers posh spa resorts in an exotic, tropical setting that manages to be popular with honeymooners, couples, and families alike. A string of package-catering resorts condensed 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 you choose to come in off-season, a superb jazz festival, usually held the first weekend in May, showcases tons of acts from the US, Latin America, Africa, and Europe. Find out how to get there.

ST. MARTIN/ST. MAARTEN
One island with two very different halves, St. Maarten, owned by the Dutch, and St. Martin, owned by the French, is a booming Caribbean hot spot with a cosmopolitan flair that attracts a mix of package tourists and European travelers. While there's something to attract visitors to both sides, the Dutch side has more resorts, shops, and activities than the French – and hosts the island's only major airport – granting it more of the island's share of tourists; it's also where most package trips arrive. That said, the French half boasts luxury resorts, gourmet cuisine, and a distinctly more sophisticated and prosperous ambiance. No matter which side you choose, you'll still 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). So long as you can handle huge crowds of visitors, especially on cruise-ship days in Philipsburg, the island is a great choice if you're looking to hit the beach fast – it's among the few to boast regular nonstop flights from the US and offers a wide-range of choice. If you're looking for an intimate getaway, this is not the place. Find out how to get there.

ST. VINCENT & THE GRENADINES
A well-kept Caribbean secret until recently, when it figured as the setting for Pirates of the Caribbean, 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. Unsurprisingly, they've become popular with the yachting and boating crew. Lush St. Vincent is often used as a launch pad for exploring the other atolls and 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 sleepy Bequia, offering postcard-perfect sands and charming Creole houses; glamorous Mustique, where luxurious 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. Find out how to get there.

TRINIDAD & TOBAGO
This two-island nation, located closer to Venezuela than most of the Caribbean (save the ABC islands), offers a very different Caribbean experience. Trinidad, the larger of the two islands, 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 as the best party in the Caribbean). Inexpensive inns and guesthouses cater to visitors here, while a delectable mix of culinary specialties of international influence offer some of the Caribbean's most unique, and affordable, dining. Outside of the congested and commercialized capital of Port-of-Spain, the island's wildlife sanctuaries offer the Caribbean's richest ecosystems, but its beaches are removed and hard to reach. If sand is what you're after, head to sister island Tobago; here, a more laid-back and beachy atmosphere pervades, attracting vacationers who want to scuba dive along the offshore reefs, explore lush rainforests, and bask on powdery sands, all of which are still relatively free of tourists and overdeveloped resorts. Find out how to get there.

TURKS & CAICOS
Revered as one of the last frontiers of the Caribbean, the Turks and Caicos islands are tailor-made for a long-weekend beach vacation. At just three hours from the East Coast, the chain is one of the closest Caribbean destinations to the United States, with nonstop flights on several airlines. What's more, the main island, Providenciales (known as Provo), is home to one of the best beaches in the entire Caribbean – Grace Bay. As if that weren't enough incentive, the islands here are also protected by a natural 499-mile-long barrier reef, creating superb turquoise waters for miles. While diving and snorkeling are popular here, there's not a whole lot else to do but hit the beach with a good book, replenish your sunscreen, and, perhaps, keep an eye out for JoJo, the islands' resident – and friendly – dolphin. The chain's other islands, 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, while Grand Turk, the chain's capital island, has more history than Provo, better diving, and quaint inns, but is less developed for tourism. Find out how to get there.

VIRGIN ISLANDS (US)
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. Thomas, rated as one of the top spots in the world for sailing, scuba diving, and fishing by National Geographic, has plenty to offer and is easy to get to from the US. Its picturesque capital of Charlotte Amalie, filled with red-roofed white houses, is a duty-free shopping haven and the busiest harbor in the Caribbean; the island's prized beach, Magens Bay, finds high-end resorts and restaurants. A former holding of Denmark, St. Croix is, in contrast, the largest of the three, with a distinctly Danish flair evident in the historic architecture of Christiansted, the island's National Historic Site–ranked capital. 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; the condos and newly added casinos here attract beach goers with a taste for culture. The tiniest, and arguably prettiest, of the three islands is St. John, home to Trunk Bay, an extraordinary beach that's sure to leave the biggest impression of any Virgin Island beach. Scenic sands aside, the waters here are also popular with beginning snorkelers, who delight in following the fun, self-guided underwater trail complete with signage identifying native aquatic life and corals. The isle remains pristine, 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. Find out how to get there.

VIRGIN ISLANDS (BRITISH)
Some 40 hilly, forested isles, islets, and cays compose the lush chain that is the British Virgin Islands, with most of the tourist activity unfolding on three of the isles: the largest and main island of Tortola, with its restaurants, bars, and fantastic Sage Mountain National Park; the posh resort isle of Virgin Gorda, where stellar photo ops await at its mysterious Baths; and the coral atoll of Anegada. Preferred over the more vivacious US Virgin Islands by those in search of a more pristine setting and slower pace of life, the British Virgin Islands are a true escapists paradise. There are no direct flights from the United States (transfers must be made in San Juan, St. Croix, or St. Thomas), warding off less ambitious travelers and promising more seclusion and serenity to beach goers who make the journey to these lovely palm-fringed shores. The plethora of hidden coves and beautiful bays make the islands a haven for beachcombers, and particularly for sailors, who flock here with yachts in tow – in fact, while it's hard to imagine now, these seemingly blissful islands once provided harbor to swashbuckling pirates! As their name implies, the British Virgin Islands are indeed still politically tied to Britain but, English language and political governance aside, a true Caribbean culture is dominant here. Find out how to get there.

See Caribbean Travel Guide