The Best of the Caribbean

OK, let’s be honest: As large and grand as the Caribbean is, it’d be damn near impossible to truly say definitively what item in particular tops all others to be considered “the best.” Several members of the C&L staff have traveled extensively in the Caribbean, so we’re combining that knowledge with general research to offer a list of some pretty freakin’ sweet places to visit. Try them out and let us know what you’ve found that was better. (Note: Most of this information was ascertained before last year’s devastating hurricane season, so we can only hope that the fabulous residents of these destinations are safe and have been able to return to normalcy.)

Best Outdoor (Land-Based) Activities

1. Horseback riding in St. Maarten

Pretty much every island offers horseback riding for tourists—certainly some better than others. But you’d be hard pressed to find a better experience than the one offered at Lucky Stables in St. Maarten. A guide leads you through an iguana farm and up a small mountain with picturesque views. You come down in end up thigh-deep in the blue waters of Cole Bay. Perfect for all ages and abilities.

2. Golfing in the Dominican

Golf in the Dominican Republic has exploded recently, with Punta Cana on the east coast as its epicenter. The jagged coastline and pristine beaches make for a phenomenal backdrop for some of the prettiest and most challenging courses you’ll find, and the weather is almost always perfect. Courses such as Casa de Campo, Punta Espada, and Cocotal are just some of the island’s highlights.

3. Meeting Monkeys in Honduras

It’s not everyday you can have a monkey sitting on your head (unless you live in Costa Rica), and there’s no better place to do it than Gumbalimba Park, Isla Roatan, Honduras. The park starts on a sandy beach, then quickly climbs up into the jungle, home to waterfalls, botanical gardens, a picturesque rope bridge, and nature preserve, loaded with native reptiles, colorful birds, and, of course, monkeys that will jump on your head (and steal your sunglasses).

Best Outdoor (Water-Based) Activities

1. Diving in Bonaire

The Caribbean as a whole is home to some of the best scuba diving in the world, and Forbes and Scuba Diving magazine are among the many that say Bonaire is tops in the region. With 100 feet of visibility, 86 marked dives, and nearly 500 species of fish around, it’d be hard to argue otherwise. Surrounded by near-shore reefs, you can almost literally jump in the ocean anywhere and have a great dive.

2. Boating in Antigua

Because of the cragged coastline of Antigua, the many coves are perfect for yachties and rum-swilling sailors who want to enjoy the splendors at sea off the Leeward island. Antigua treasures its heritage—formerly the port to Royal British Naval Commander and rum connoisseur, Lord Admiral Horatio Nelson—on the high-seas and hosts the international regatta, Antigua Sailing Week, every year. The relatively calm waters off the beaches are the perfect place to try out sailing for beginners and the island is host to many sailboat charter companies if you want a longer excursion.

3. Swimming with Stingrays in the Caymans

Many Caribbean destinations offer stingray encounters, some where a guide holds one stingray while 60 people line up to give it a quick “good-luck kiss.” Stingray City, however, is not like that. Located several miles offshore in Grand Cayman’s North Sound, guests can jump out onto a sandbar and be in chest-deep water as dozens, if not hundreds, of the glorious cartilaginous fish swim through the masses looking for food. Numerous tour groups run boats out there at the same time, and for better or worse the rays have associated the engine noise with food and come running. Err, swimming.

Best View

1. Gros Piton, St. Lucia

If you’re up for a little adventure, opt to climb the Pitons in St. Lucia. The taller of the two mountains, Gros Piton, standing 2,530 feet tall and linked to the Petit Piton, is actually the easier to climb, although you still need to be with a tour or have a guide. Gros Piton is the best bet for a sweat-inducing activity that is suitable for many ages and levels of experience, and produces a view that looks out over the crystal Caribbean Sea and the lush eco system on the island below. It is often called “the best view in all of the Caribbean.”

2. Fryes Bay, Antigua

If you want to chill out and experience one of the best sunsets in the world, head to Sheer Rocks, the restaurant and lounge perched high above Fryes Bay in Antigua. The dramatic westward-facing cliffside setting makes for the ideal dinner location, particularly during sundown. With an emphasis on local ingredients, the inventive cuisine at Sheer Rocks will keep you there long after dark.

3. Porte d’Enfer, Guadeloupe

In the ultimate anthesis, Porte D’Enfer translates to “hell gate,” whereas one look leads you to believe you are in the exact opposite place. Located on the east coast of Grande Terre Island in Guadeloupe, this elongated lagoon winds its way into the land, beginning with cliffs and crashing waves, before surrendering to a beach that features warm, calm, turquoise waters.

Best Places to Party

1. Trinidad Carnival

Carnivals are wonderfully common in the Caribbean, and no one does it better than Trinidad and Tobago. The island features numerous carnivals throughout the year, but the zenith takes place in the streets of Port of Spain for two straight days leading into Ash Wednesday with Trinidad Carnival. Music, dancing, colorful costumes, and tasty beverages make it the place to be.

2. Rick’s Café, Jamaica

If you said Rick’s Café was the most fun place, on the most fun island, in the most fun region of the world, it’d be hard to argue otherwise. Located in Negril, Rick’s is a restaurant and bar that sits atop a 35-foot cliff—that people jump from. Said to be home to the best place in the Caribbean to enjoy a sunset, no trip to Rick’s would be complete without a taste of its “World Famous Rum Punch.”

3. Le Ti, St. Barth’s

St. Barth’s is known for its extravagance—and maybe decadence—and no place personifies both like Le Ti. If you’re looking for an after-hours experience to end your night, and don’t mind being surrounded by beautiful women wrapped in feather boas with lots of tabletop dancing going on, then this may be the place for you.

Best Places to Eat

1. Anguilla

No island in the Caribbean appears to have embraced gastronomic tourism the way Anguilla has. From gourmet restaurants to beach shacks, this British Territory truly has something for everyone. Influenced by Caribbean, African, Spanish, French, and English cooking, seafood is obviously a staple of the repertoire, but its collective take on barbecue is what has foodies from around the globe taking notice.

2. Nevis

Nevis joins with nearby island St. Kitts for form one country, with Nevis being one of the more secluded and harder reach Caribbean destinations. As such it caters to a more affluent, upscale crowd, and as one would imagine that means great food. With rich soil, Nevis produces fantastic produce. Traditional foods on the island have a West Indian influence, with goat being one of the more popular dishes. With no chain restaurants to be found, local eateries take advantage of the natural geography and dramatic backdrops to create magnificent dining experiences.

3. Cayman Islands

Regardless of which island you are visiting—Grand Cayman, Cayman Brac, or Little Cayman—you will not find a shortage of local restaurants with the potential to delight. Because of its banking industry, the Caymans have traditionally been one of the wealthier nations in the Caribbean, and as such, some of the best chefs in the world call it home. With that international influence, you can literally have a gastronomic tour of the world without leaving the paradise that are these islands.

Best Place to Drink Rum

1. Papa Zouk, Antigua

No rum lover, beach bum, or sailor can make the trip to Antigua without stopping at Papa Zouk, the legendary rum bar that carries more than 200 varieties of the local spirit. Just outside of the town of St. John’s, it has been dubbed the best rum bar in the Caribbean many times over and is worth a trip for the atmosphere alone. The spirit of local and artisan rum at Papa Zouk is a nod to the heritage of the island as a British naval stronghold, sailing destination, and sugar producer.

2. Soggy Dollar Bar, British Virgin Islands

Located right where the blinding-white sand meets the most stunning turquoise water you’ll see is the Soggy Dollar Bar, where boats anchor just feet away so patrons can wade in. This is where the Painkiller was created, a perfect concoction of dark rum, cream of coconut, and pineapple and orange juices, with fresh-ground nutmeg on top. (We know this amazing place was devastated by Hurricane Irma, and we wish them well in hopes they can rebuild.)

3. Reggae Beach Bar & Grill, St. Kitts

It’s hard not to like a place where you can sit on chairs partially submerged in the ocean, order a snorkel or kayak at the bar, or walk around and pet a goat, pig, or monkey. The restaurant specializes in seafood and barbecue, and for the rum drinker, there’s nothing like their Reggae Colada.

Best Beaches (Collectively)

1. Antigua

If it’s beaches, water sports and laid-back, beachfront leisure you want, the island nation of Antigua and Barbuda is the quintessential Caribbean destination for you. The island and its inhabitants boast “365 beaches” (one for every day of the year, as they say) and there are endless sandy coves to discover on the idyllic island.

2. Anguilla

Anguilla has every type of beach you could ask for—easy access, secluded, scenic views, and waves for surfers. Little Bay, Sandy Island, and Shoal Bay East are just some of the can’t-go-wrong choices, and The Reef resort at Merrywing Bay is so perfect Sports Illustrated shot its swimsuit issue there in 2017.

3. Turks and Caicos

Turks and Caicos may not be the richest island in the Caribbean, but it may be one of the most beautiful. Pristine white sands gently give way to stunning, crystal clear waters. As such, many resorts have jumped in to take advantage, and offer “all-inclusive” accommodations around the island, creating one of the more heavenly settings one can hope to find on the planet.

Best Shopping

1. St. Thomas 

One of the most famous and popular shopping destinations in the world, St. Thomas offers a little bit of everything, from local merchants and trinkets, to a portside mall, to luxury shopping on the boutique-lined main street of Dronningens Gade.

2. Saint Barthélemy

St. Barth’s is all about style and is one of the top vacation destinations for pleasure and leisure seekers from around the world. It has long been recognized as one of the most fashionable resort islands in the world. Whether you’re strolling through the designer boutique-lined, cobble stone streets, sipping a cocktail on the white sand beaches or anchoring in the harbor on one of the many glamorous yachts, St. Barth’s delights the senses of anyone who relishes in luxury. The French flavor, glamorous clientele and quaint infrastructure of this island is one of the many reasons people consider it the chicest of all of the Caribbean destinations.

3. Curaçao

Willemstad, Curacao’s colorful capital, is loaded with shopping options, including a beautiful stone fort on the water that has been transformed into shopper’s haven. Add in small boutique shops, a floating market, and several duty-free zones, and you have a serious chance to damage your bank account.

Best Places to Walk

1. St. Lucia Waterfalls

Diamond Falls are the most famous waterfalls in St. Lucia and are easily accessible. Saltibus Falls, which is two cascading falls, however, requires visitors make about a 90-minute walk along a rainforest trail to reach them. Even more secluded is the dramatic Sault Falls, which cascades more than 50 feet on the less crowded, Eastern side of the island. The mostly downhill hike required to reach the falls is well worth the seclusion you’ll find when you get there.

2. San Juan, Puerto Rico

Few places can match the history, culture, charm, and overall beauty of San Juan. There is certainly plenty to do if you so choose, but there are also plenty of other serine and beautiful paths to take. Walking along the ocean up to the San Felipe del Morro Fortress, surrounded by cliffs, with crashing waves and a cool breeze is about as good as it gets.

3. Eagle Beach, Aruba

OK, so you can make a case to put just about any Caribbean beach on this list, but there’s just something about Eagle Beach in Oranjestad, Aruba. Famous for its “low-rise” resorts across the street, beach itself features a wide swath of white sand and truly not a whole lot else. Because it doesn’t need to. Be careful where you walk, however, as newly hatched turtles can be found making their way down to the ocean during certain parts of the year. Often recognized as one of the best beaches in the world by travel magazines, a stroll by the water near sunset will leave you with no doubt as to why.

Check out Costa Rica and 10 of our favorite destinations here in the US. 

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