How to Plan a DIY Caribbean Island-Hopping Trip
Island-hopping in the Caribbean is not just for the ultra-rich or yacht-owning elite. You can plan it yourself and have way more fun than being stuck on a floating buffet.
From hopping between St. Lucia and Martinique to catching short ferry rides in the north, this is your guide to DIY island-hopping that beats any cruise.
Why Choose DIY Island-Hopping Over Cruises?
Cruises cram your schedule. You get a few rushed hours ashore, then it is back to the ship. When you go DIY, you move at your own pace. Want to stay longer in Dominica’s rainforests or swim twice in Anguilla’s turquoise bays? You can.
DIY island-hopping also lets you hit the underrated spots. Skip the touristy haunts and head to places like Saba or Marie-Galante. These islands feel untouched, which is rare in the Caribbean these days. Cruises don’t go there, but you can!
Freepik / With DIY travel, you control every cent. Rent a car in Barbados for about $50 a day and find your own adventures.
Ferries between islands cost $20 to $90, depending on the route. Add up the savings and spend it on better food, longer stays, or just more rum.
You also get real food, not cruise food. Stop at roadside BBQs in Trinidad, taste French pastries in Martinique, or try spicy jerk chicken on a beach in Grenada. You will experience each island properly, not through a tour guide’s script.
How to Plan Your Island-Hopping Route
Island-hopping works best when you pair ferries with short regional flights. The southern Lesser Antilles are perfect for ferry travel. Start in St. Lucia, hop to Martinique in 90 minutes, then continue north to Dominica or Guadeloupe. L’Express des Îles ferries are reliable and scenic. Prices range from $75 to $90 per leg.
In the northern Caribbean, the hops are quicker. Anguilla to St. Maarten takes just 20 minutes and costs around $20. Voyager Ferry and AquaMania Adventures run smooth rides between key islands. These aren’t big cruise ports either, so the experience feels local.
Flights help you cover more ground. Airlines like LIAT and Caribbean Airlines connect you to harder-to-reach islands. From Trinidad, you can fly to Tobago, Dominica, or even Grenada. From St. Maarten, you can catch short flights to places like Saba or St. Barth, which are tough to reach any other way.
Karl / Unsplash / When you land on an island, don’t rely on buses. Public transport is patchy at best. Rent a car instead.
Best Hubs for DIY Island-Hopping
Start with the right base. Barbados is a solid option. Grantley Adams International has good transatlantic flights and ferry links to St. Vincent or Grenada. It is well-connected and laid-back, a good combo to start your trip.
St. Maarten is the launchpad for northern hops. You can take a catamaran to Anguilla or a fast ferry to St. Barth. Simpson Bay Resort & Marina is a great place to stay if you want to be close to the action. Plus, the airport is nearby and has connections across the region.
It gives you the freedom to chase waterfalls, find empty beaches, or stop for that roadside mango stand.
Trinidad is more industrial, but it has its perks. It is a central flight hub, and from here, you can reach the smaller islands easily. Spend a day or two in Port of Spain, then head to Tobago or catch a flight to Dominica.
Also, don’t skip travel insurance. SafetyWing offers flexible plans that cover multi-country trips. Worth it if you are ferrying and flying all over the map.