Why visit just one tropical island when you can visit three in one trip? Whether you’re chartering a boat and living out your best Below Deck fantasies, or taking your time on a slow ferry, there are several ways of getting the most out of your trip to the Caribbean.
Disclaimer: I’ve never been to the Bahamas so for the sake of this blog, pretend like it doesn’t exist as part of the Caribbean.
Charter a Boat
The next time I head to the Caribbean, this is how I’m going to do it. A website called Skippair lets you search by boat type, destination and date to either charter an entire boat yourself or join as a single or couple on a shared charter. Take this 8-day catamaran trip as an example: a little over $1,000/person to visit Martinique, Saint Lucia, and Saint Vincent and the Grenadines. Skippair also covers charters in the Mediterranean, Arctic and Indian Ocean.
Fly from Island to Island
Getting creative with your schedule is key when it comes to relying on flights to get you around the Caribbean. Not all of the smaller airlines show up on Google Flights and you’ll be bummed to find out just how many flights have a connection in Miami, taking you hundreds of miles north before flying south again. We found that Barbados is a hub for getting around the most southern part of the Caribbean (and conveniently, JetBlue flies non-stop to Barbados, Saint Lucia, Grenada, St. Thomas and San Juan during the winter), and San Juan is a reliable hub as well. If you’re relying on flights, consider these handy pairings for the best non-stop combinations:
- Barbados, Grenada, Saint Lucia
- Trinidad & Tobago, Barbados, Grenada
- Antigua, Saint Kitts and Nevis, Sint Maarten
Take the (Slow) Boat
If you’ve got all the time in the world and/or you’re looking to do this on the cheap, there are some ferry routes that make island-hopping possible in parts of the Caribbean. Express des Iles is a ferry company that operates between Guadeloupe, Dominica, Martinique and Saint Lucia. The route between Saint Lucia and Dominica is a little over four hours and costs around $100 per person. We were going to try this route this year, but the ferry wasn’t running on the day we needed to travel (Christmas Day) so we opted to fly. This blog is very thorough in describing the experience on Express des Iles. The ferries in Saint Vincent and the Grenadines are pretty robust, with daily routes taking you to Bequia and Tobago Cays, as well as Grenada. This blog gives a great overview of Saint Vincent ferries. Ferries are also fairly easy to catch between the US Virgin Islands and the British Virgin Islands, with St. Thomas – St. John – Jost Van Dyke – Virgin Gorda a daily route via Inter Island Boat Services.