A Beginner's Guide to Island Hopping in the Caribbean
You can easily take in a string of delicious Caribbean destinations on a single trip by mastering the art of island-hopping. Our guide to small island-hopping shows you how with must-visits and travel tips and learning more about the Caribbean culture.
The close proximity of the Caribbean’s small islands makes them ideal for a hop, skip and a jump from one to the other in a daisy chain of island explorations. Fancy diving down to a shipwreck in Aruba one day and getting up close with flamingos on Guadeloupe the next? Then read on…
Where to visit in the Caribbean
The island of St Martin (or St Maarten) is a great destination to start exploring the eastern side of the Caribbean. It’s divided roughly down the middle between the French Republic and the Kingdom of the Netherlands, and so it offers visitors a two-nation vacation. The Dutch side of the island is known as the party side for hosting the Heineken Regatta, a four-day sailing race with concerts and other festivities. Meanwhile, in true French fashion, the other side of the island features quaint, romantic restaurants, designer boutiques and nude beaches.
From St Martin, journey to the islands of Anguilla and enjoy its secluded coves, before heading to St Barts to do some celebrity spotting and Saba, which is known for its diving site at Saba Marine Park. Puerto Rico, the jewel of the Caribbean, is also a popular choice. The island is known for its cuisine – a mixture of Spanish, African, and Taino – plus its strong rum.
Elsewhere, you can get pretty much anywhere in the Caribbean from San Juan (thanks to regional carriers such as Cape Air and Seaborne), and a number of islands are even closer by ferry and plane, such as Culebra, Vieques, British Virgin Islands and the US Virgin Islands. The Dominican Republic is also only a very short flight away.
You can do all the island-hopping you want in the Guadeloupe Islands and stay within the same territory. This beautiful archipelago has five islands within easy reach by ferry and air from the main island of Grande Terre/Basseterre, each with its own character and flavor, from tiny Terre-de-Haut to beach paradise Marie Galante. From Guadeloupe, you can easily access the islands Dominica, Martinique and St Lucia below and Montserrat, St Kitts and Nevis, and Antigua and Barbuda.
The so-called ‘ABC’ islands of Aruba, Bonaire and Curacao, at the western edge of the Leeward Antilles chain, are also a popular island-hopping loop. Aruba is a popular tourist destination with several big-name beach resorts; Bonaire is best known in scuba-diving circles for its spectacular undersea life; Curacao charms with its Dutch-influenced architecture.
Must-visits on your multi-island trip
St Martin is famed for its white-sand beaches but there’s one that stands out from the rest. Maho Beach, which lies near the airport, is where tourists come to photograph planes passing just feet above their heads as they swoop in to land. If you prefer natural wonders, catch the ferry to Pinel Island in St Martin’s Nature Reserve, where you’ll find palm-fringed sands and shallow waters ideal for snorkeling. To learn about the island’s Dutch heritage, take a trip to Fort Amsterdam near Philipsburg. Here, you can explore the ruins of this former military base and take in sweeping hilltop views.
There’s no shortage of historic sites in Puerto Rico. Start by touring grand La Fortaleza, the governor’s official residence, which was built between 1533 and 1540 to defend the harbor. Continue to the island’s longest-serving settlement, Old San Juan, a National Historic Site filled with 16th-century fortresses, cathedrals and cobbled streets. For a change of pace, you can hike rainforest trails to crashing waterfalls in El Yunque National Forest or relax in hillside thermal hot springs in Coamo. When the sun goes down, marvel at Puerto Rico’s bioluminescent waters in Mosquito Bay, which light up when touched.
If you’re visiting Guadeloupe, don’t miss Jardin Botanique. This seven-acre haven, in the heart of the islands, showcases exotic Caribbean flora and birdlife. Think bamboo forests and pink bougainvillea, flamingos and arboretums. If you can drag yourself away from Guadeloupe’s pristine beaches, spend a day at Carbet Falls in the National Park. These three waterfalls cascade down a mountain surrounded by tropical rainforests and hiking trails. Looking for the perfect sunset? Then head to Pointe des Châteaux, a clifftop peninsula on the eastern end of Grande-Terre where you can watch waves crash onto the rocks.
Divers flock to Aruba to explore its famous Antilla Shipwreck, a German war ship blanketed in coral and tube sponges. Aruba’s other key attraction is swanky Renaissance Island where pink flamingos tip-toe through the shallows. Hop over to Bonaire for more unspoilt Caribbean sands, including 1,000 Steps Beach and Klein Bonaire, a tiny uninhabited islet set in a marine park where turtles nest. Nearby Curacao is the perfect place to get a glimpse into the Caribbean’s Dutch past in its capital Willemstad, Unesco-listed for its colorful colonial architecture. Don’t miss Curacao’s Hato Caves either, which were formed over 300,000 years ago from marine coral limestone and contain Amerindian Arawak cave drawings.
How to travel
There are a few options for island-hopping in the Caribbean. The most popular is booking a cruise, but you can easily go it alone and create your own island-hopping loop by taking advantage of the numerous ferries that go back and forth between all of the islands.
Alternatively, charter a boat – it’s not as expensive as you might think. You don’t even need to know how to sail as many come with skippers included in the price.
Catching a flight should be your last resort. Though traveling by air to the smaller islands in the Caribbean is relatively inexpensive, it’s not environmentally friendly. This option makes sense only in cases where the islands have a significance distance between them.
When is the best time to visit the Caribbean?
If you are wondering when is the best time to go island-hopping in the Caribbean, this is what we recommend – it’s best to plan your island-hopping loop in either spring or at the beginning of summer, when the weather is calm. The Atlantic hurricane season starts in early June and runs until the end of November, while most of the storms hit during peak hurricane season between August and October.
General safety and travel tips
All major Caribbean islands have excellent mobile coverage. But for those islands with a very small population, such as Culebra and Vieques near Puerto Rico, a portable radio might come in handy. Sunscreen, mosquito repellant and bottled water should also always be in your luggage.
8 must-visit islands, according to our writer Alex Picerne
Grand Cayman
Natural Feature
December-April
What to do:
Dive at Eden Rock and Devil’s Grotto
Queen Elizabeth II Botanic Park
Walk around Camana Bay
Best beaches:
Seven Mile Beach (West Bay Beach)
Rum Point
Smith Cove Public Beach
Saint Barthélemy
Natural Feature
November-June
What to do:
Snorkel at L’Orient Beach
Surf at Toiny
Windsurf at Grand Cul de Sac Beach
Best beaches:
St Jean Beach
Shell Beach
Grand Cul de Sac Beach
Jamaica
Natural Feature
What to do:
Dive in Frenchman’s Cove
Snorkel along the Rockhouse
Blue Mountains National Park
Best beaches:
Winnifred Beach
Seven Mile Beach
Boston Beach
Barbados
Natural Feature, Swimming Pool
January-April
What to do:
Surf at Bathsheba Bay
Sail at the Barbados Yacht Club
Harrison’s Caves
Best beaches:
Mullins Beach
Crane Beach
Paynes Bay Beach
British Virgin Islands
Natural Feature
Mid December-April
What to do:
Dive at Rhone National Marine Park
Hike at Sage Mountain National Park
Smuggler’s Cove
Best beaches:
Elizabeth Beach
White Bay Beach
The Baths
The Bahamas
Natural Feature
December-April or June-September
What to do:
Check out the Thunderball Grotto
Beachcombing in Lucayan National Park
Dive around Andros
Best beaches:
Pink Sands Beach
Cabbage Beach
Gold Rock Beach
Puerto Rico
Natural Feature
December-April
What to do:
Grab a drink at El San Juan
Explore La Fortaleza in Old San Juan
El Yunque Rainforest
Best beaches:
Flamenco Beach
Luquillo Beach
Bahia Beach
Dominican Republic
Natural Feature
December-February
What to do:
Windsurf at Cabarete
Santiago and Jarabacoa Waterfalls
Diving in Punta Cana
Best beaches:
Playa Boca Chica
Playa Rincon
Sosua Beach
Amy Blyth contributed additional reporting to this article.