Island hopping – exploring multiple destinations in one vacation – is the pinnacle of travel experiences, particularly in the Caribbean. Nonstop aquatic activities, seafood delicacies, and a wealth of cultural traditions typically characterize these adventure-filled itineraries.
While many travelers choose their favorite cruise line to visit several destinations in one trip, others prefer to go at their own pace. With the countless memories that await on each shore, there are also a few unavoidable considerations, such as travel expenses and transportation. The cost of island hopping in the Caribbean may seem steep initially, but it doesn’t always have to be. If you’re finally ready to fulfill your island-hopping dreams, consider these strategies and tips from trusted travel veterans.
Island Hopping Strategies, According To Caribbean Travel Experts
One of the first important decisions you’ll make during planning is which islands will make the cut. While opting for your bucket list of islands feels like the natural right choice, connectivity by land and sea ultimately dictates the journey. Limited availability on regional airlines can drive flight prices over $500, making island hopping feel exclusive to the elite. Instead, taking advantage of alternative public transportation modes, finding flight deals, and planning your route geographically can help make the trip more affordable.
Many Islands, One Nation
Caribbean destination expert Steve Bennett says one of the easiest ways to build a multi-island itinerary is to choose places that offer several island experiences without hopping borders. Bennett, co-founder and editorial director of Uncommon Caribbean, has been a go-to resource for Caribbean culture and travel for over twenty years.
For this island-hopping strategy, Bennett recommends destinations such as St. Kitts and Nevis, Trinidad and Tobago, Antigua and Barbuda, the U.S. Virgin Islands, or the British Virgin Islands. He also suggests looking at more spacious nations like The Bahamas, which has more than 700 islands on its own.
“If there are three main islands in USVI — St. Croix, St. Thomas, and St. John — you can look at a week of doing a couple of days here, a couple of days there,” Bennett shares of a USVI island-hopping plan. “In the case of St. Kitts and Nevis, Antigua and Barbuda, or Trinidad and Tobago, those island pairs are so different from each other [and] make it pretty easy.”
The biggest benefit of staying within one nation’s borders is only going through customs once, in addition to language and currency staying the same. Multi-island nations typically offer vastly different experiences from one island to the next, and exploring the many sides of one country could prove easier than hopping between countries.
Pick An Island Group
Veteran travel journalist Sarah Greaves-Gabbadon offers another method for destination selection. The self-described “Carivangelist,” also known as JetSetSarah, is an avid champion of the Caribbean’s marvels for travelers of any taste.
“The most inexpensive and convenient way would be to choose an island group and hop within that group,” Greaves-Gabbadon shares. “One of the reasons why I love the Turks and Caicos Islands is because you can have a vacation from your vacation when you’re there. You can easily hop on the ferry from Provo, the main tourism hub. In half an hour, you can get over to North Caicos.”
Greaves-Gabbadon says prepared travelers typically book packages that include the ferry fee and a rental car awaiting your arrival at the terminal.
“They give you a map [and] you can explore all the beaches of North Caicos, then drive across a narrow causeway to Middle Caicos,” she says of island-hopping in Turks and Caicos. “You have another set of restaurants, guesthouses, and beautiful, deserted beaches to explore. You can do it for a day or stay overnight at small hotels and return in a few days. It’s a great way to see beyond Provo because there’s so much more to the Turks and Caicos.”
She suggests several other island groups, including multi-island stops in the British Virgin Islands via yacht charter, starting in Tortola. Or, from St. Vincent, travelers can explore the Grenadine islands of Canouan and Bequia, one of JetSetSarah’s four favorite islands.
“Those archipelagos are made for line-of-sight sailing and island hopping,” she says. “Same with The Bahamas, but not Nassau (New Providence). If you’re in the Out Islands of The Bahamas, for example, in the Exumas or the Abacos. When you’re island hopping, it’s probably more convenient and easier to hop by boat than by plane.”
Things To Consider When Planning Your Island Hopping Itinerary
Beyond locations, several other aspects of the trip require planning ahead. According to the experts, here are a few things to remember when planning your trip.
The Caribbean Is Much Larger And More Diverse Than You Think
Some travelers assume the islands are closer than they actually are; however, the Caribbean spans over a million square miles. Hopping between islands is a game of logistics, but it’s also an opportunity to explore the region’s diversity. From the Papiamento language of the ABC Islands (Aruba, Bonaire, Curaçao) to French in Martinique and Spanish in Puerto Rico, the range of a Caribbean island-hopping trip can be vast — and potentially costly, depending on your interests.
Pack And Prepare For Multi-Island Needs
One trip can take you to several nations, depending on which islands you visit, so plan accordingly. Packing a universal outlet adapter is always a good idea, and U.S. travelers need a passport for every island except Puerto Rico and the Virgin Islands.
Currency can also change from one stop to the next, though most destinations accept USD. Other currencies you may need include euros in places like Guadeloupe, Martinique, St. Barts, and Saint Martin, or the Eastern Caribbean dollar, the official currency of eight Caribbean nations, including Grenada, Saint Lucia, and Montserrat.
Consider Air vs. Ferry Travel For Inter-Island Transit
The beauty of many Caribbean islands lies in the variety of transportation options available. Some islands are accessible only by ferry or boat, and many routes are often more cost-effective by sea.
While regular ferry options are limited to certain destinations, they provide a scenic addition to the trip, typically costing between $20 and $100. Alternatively, several regional airlines serve inter-island flight needs across the Caribbean. Top airlines to consider include InterCaribbean Airways, Caribbean Airlines, Bahamasair, Winair, Sunrise Airways, LIAT20, and Cayman Airways.
Manage Your Expectations And Stay Flexible
A reality of island life is the unanticipated change in plans that may result from several factors. Weather conditions impact flight and ferry schedules. Local holidays are another time when public transit is limited or not operating.
To minimize last-minute mishaps, reserve transportation between islands ahead of time and coordinate on-island travel if you must. Getting around an island is much easier than getting between them, so having your connecting plans secured is highly recommended.
While seeing multiple Caribbean islands in one vacation is possible, it will require some preparation, patience, and financial planning. The diversity in people, flavors, and cultural energy across the Caribbean makes it one of the most visited regions in the world for good reason.
Though there may be changes in customs, currency, and language from one island to the next, the imprint of the Caribbean’s colorful spectrum is well worth the travel challenge.
