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.
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…
Destinations Unlocked:Let our travel expert Stefano help you find your perfect Culture trip
Looking for an expert's perspective?Uncover my top 3 recommended places from each continent on the map.
1. GuatemalaAn express adventure for those with limited time off. Prepare yourself incredible experiences. You will hike a volcano, visit mayan temples and witness a ceremony and take in beautiful colonial Antigua.
2. BelizeA quick trip not too far away for those seeking a relaxing mini break. You will have plenty of free time to relax but also some awesome activities to experience the rainforest and the caribbean sea.
3. MexicoAn exciting mini trip exploring the lesser known colonial towns of central Mexico. This is hte perfect trip for someone with limited time off and still wants to turn on explorer mode and do something different.
1. EcuadorA remarkable 8 days adventure through the Andes and the Amazon rainforest. The best choice for adventure seekers wishing to visit the 2 most iconic areas of South America, in only 1 week and no flights.
2. PeruAn alternative itinerary to classic Peru, from Cusco to Arequipa. This itinerary is great combination of highlights Cusco and Machu Picchu with the lesser known Arequipa and Colca Canyon.
1. ItalyThe ultimate Italian experience from the vibrant streets of Naples to the breathtaking sceneries of the Amalfi Coast followed by Matera and down to Puglia with its golden beaches, intense flavours and fascinating destinations.
2. ScotlandEmbark on this great adventure starting from London all the way to Scotland with a true Scottish experience made of breathtaking sceneries, whisky tasting and ..lots of fun! Ideal for train lovers and explorers.
3. PortugalA wonderful train journey around Portugal, from the romantic city of Porto to the Douro Valley, to the beautiful Aveiro all the way to Lisbon and Sintra. The perfect trip to train, culinary and culture lovers.
1. South KoreaDiscover incredible temples, mountains and modern cities on this 10 day adventure. This trip is perfect for those seeking immersion in the cuisine, culture and natural wonders of South Korea.
2. ThailandFrom Bankgok to Angkor Wat to Ho Chi Minh City and everything in between - adventure through the heart of South-East Asia. Taste the delights, see history brought to life and unwind on a Mekong River cruise.
3. Sri LankaA fantastic adventure that showcases Sri Lanka's fantastic landscapes, wildlife and flavours. With 3 epic rail journeys, 3 UNESCO heritage sites and time to relax, this trip has loads to offer at a great price
1. MoroccoAn epic journey across Morocco: from Casablanca to Marrakech, through the blue city of Chefchaouen to the wonders of the desert and deep to the High Atlas Mountains - this trip has it all! Ideal for true explorers!
2. EgyptFrom Cairo to Aswan, this trip brings the land of the pharaohs to life. You'll visit the Pyramids, Valley of the Kings and Luxor Temple and cruise down the Nile in style. This is the perfect way to explore Egypt.
Explore some of the best islands and coastlines in the world with our hand-picked Sailing Trips. Take to the seas and then enjoy our selection of fabulous land activities too.
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, especially if you opt for a day rental through SamBoat. You don’t even need to know how to sail as many come with skippers included in the price. Dream Yacht Charter also offer an excellent range of vessels to rent for a week or longer across the Caribbean.
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.
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.
Meanwhile, 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 too always be in your luggage.
Amy Blyth contributed additional reporting to this article.
Volcanic Iceland Epic Trip
meet our Local Insider
HOW LONG HAVE YOU BEEN A GUIDE?
WHAT DO YOU LOVE ABOUT YOUR JOB?
It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.
WHAT DESTINATION IS ON YOUR TRAVEL BUCKET-LIST?
I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!
Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.
KEEN TO EXPLORE THE WORLD?
Connect with like-minded people on our premium trips curated by local insiders and with care for the world
Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.
Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.
Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.
Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.
We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.