Top 10 Caribbean Charter Destinations: A Charter Captain’s Picks Beyond the BVI
“If I could take a group anywhere, where would I take them?” Fifteen years of charters, one ranked answer.
ALL AT SEA’s focus this month is chartering, so I thought I’d rank my top 10 charter destinations around the Caribbean. Seven of them already have a week-long plan in ALL AT SEA’s 7-Day Charter Itineraries, linked under each pick, for sailors ready to discover the many great charter destinations beyond the BVI.
Plenty of worthy places didn’t make this list. The Florida Keys, Mexico, Grenada, and St. Kitts & Nevis strike me as better cruising destinations than charter destinations, although I’ve run charters in most of them. Guadeloupe, Martinique, and Bocas del Toro are amazing, but I haven’t spent enough time in each to rank them fairly. Then there’s the Dominican Republic, with three different possible charter areas, which would have been my No. 11.
So how did I choose?
I thought back over 15 years as a charter captain sailing throughout the Caribbean basin and asked myself one question:
If I could take a group anywhere, where would I take them?
Here’s my answer.
10. U.S. Virgin Islands: Nature Just Beyond the BVI.
Everyone wants to go to the British Virgin Islands and I get it. The protected waters, line of sight navigation, and ample bars make it a must see. What they forget about is the sheer number of other charter boats. The answer is as little as one mile away in the USVI. I loved when guests wanted me to take them around St John, which is 2/3 national park and there are a few anchorages where we would be the only boat. On top of this people love the floating pizza and taco boats, the best burger ever, bays where swimming with turtles is almost a given—including one aptly named Turtle Bay, amazing hiking, great historical sites, better snorkeling, and an all-around more relaxed vacation. I tell people if you want the floating pub crawl then the BVI, but if you want a more chilled and nature-oriented week then the USVI.
7-day itinerary: U.S. Virgin Islands →
9. St. Martin, St. Barts & Anguilla: Three Islands, Different Worlds.
The bad news is you have to deal with exiting and entering three different government bureaucracies. The good news is you will find three islands with four totally different vibes. Most charters will start in Saint Martin/Sint Maarten, which has been split between the Dutch and French peacefully for almost 400 years. Each side has its own flair and charm from the casino and cruise ship chaos of the Dutch side and the wine and cheese of the French. The large lagoon is fantastic and watching ships pass the lift bridge is entertaining as is Maho Bay next to the airport where you swear the planes are so low you can touch it. The island is dotted with bays providing safe harbor. 15 miles south is St Barts and even though it is also French it provides a totally different vibe and is one of the cutest and well laid out islands in the Caribbean. Five miles north of St Martin is Anguilla and its 33 different beaches. This British island is the definition of relaxed.
7-day itinerary: St. Martin, St. Barts & Anguilla →
8. St. Lucia: Pitons, Waterfalls & Plenty to Explore.
You would think sailing on only one side of this small island would limit the things to do and see, but you would be wrong. I have taken several charter groups here (one was for a full two weeks and included 3 days on the southern end of Martinique just 20 miles away) and they never had a boring day. The highlights are the Pitons, two peaks that rise right out of the water, and Sulphur Springs, often promoted as the Caribbean’s only drive-in volcano. Both are part of one of the few World Heritage sites in the Lesser Antilles. Add to that the many waterfalls within hiking distance of various bays, the large beach of Rodney Bay, the British fort on Pigeon Island, good snorkeling on reefs and wrecks, and Marigot Bay that is split in two by a sand bar and you have an amazing week. The cherry on top will be if you are visited by Gregory, The Fruit Guy, while in Rodney Bay. If you have met him, you know what I mean.
7. Abacos: Easy Island-Hopping in The Bahamas.
The Bahamas are absolutely amazing and The Exumas gets most of the attention, but I feel it is much better as a cruising location while the Abacos is the better chartering location. Part of my reasoning for this is how most destinations are within 15 miles of the centrally located Marsh Harbour. If you want sophisticated Caribbean living, check out the Marsh Harbour–Hope Town–Man-O-War Cay triangle, but what amazes me is how you can be by yourself outside of this small area. To the south you will find the Pelican Cays Land & Sea Park and Little Harbour and to the north you can find the amazing little town on Green Turtle Cay and an unbelievable amount of small island paradises. One thing I would recommend is not coming in January and February due to it being a bit chilly.
6. Puerto Rico: Culebra, Vieques & Underrated Cruising.
While I took charterers along the southern coast and found what I think is the best bioluminescent Bay (this will be part of an upcoming top ten list), I am talking about the east coast and offshore islands of Culebra and Vieques. Almost every anchorage I take people to is secluded and I tell people this is what the Lesser Antilles were like 40 years ago with a Spanish flair. Flamenco Beach on Culebra has two WW2 tanks on it from the time it was used as target practice for the US Navy. The tiny island of Culebrita is one of the best day trips you will have and Vieques has the last Spanish built fort in the New World along with the famous Bio Bay. Plus, there are dozens of smaller islands between them and Puerto Rico. I am amazed how all of this is undiscovered by most charterers and sits only 20 miles from St Thomas.
7-day itinerary: Puerto Rico →
5. Antigua & Barbuda: History, Reefs & Open-Water Sailing.
Earlier I mentioned there are few World Heritage sites in the Lesser Antilles, well another one of the six is Nelson’s Dockyard on the south coast of Antigua. Besides this amazing historical site Antigua has reefs around three-quarters of the island that offer great snorkeling and protected bays to explore. Ashore are many cool things to do and if the weather allows a 30-mile open water sail to the sister island of Barbuda where you will find miles and miles of empty beaches along with the largest frigate bird colony and the optimistically named Highlands that is a plateau about 130 feet tall.
7-day itinerary: Antigua & Barbuda →
4. Belize: Barrier Reefs & Protected Sailing.
For the next three destinations we are moving to Central America and Belize is first up. Sitting on the second longest barrier reefs in the world and the only place outside the Pacific to see atolls (not including Hogsty Reef) Belize has a lot to offer. There are two different 7-day itineraries you could follow for the north part of the country and for the south and both are inside the barrier reef giving you protected sailing like the BVI. Besides the many opportunities to snorkel the barrier reef you can visit interior reefs, mangrove islands, sandy islands, and swim with sharks and rays. Ashore you can tube down rivers, visit waterfalls, and see the Mayan sites of Tikal, Xunantunich and the ATM Caves. I even took one charter to the beautiful Sapodilla Cays at the southern end of the country and then we sailed a few hours to the mouth of the Rio Dulce in Guatemala. We then spent three days exploring 20 miles up the fresh water river with the jungle right at the edge of the water. Magical!
3. Bay Islands: Honduras Off the Beaten Track.
My wife and I were amazed at how much we loved the islands off the north coast of Honduras and could not wait for our different charter guests to arrive. The Bay Islands offer several distinct cruising areas. The main island is Roatan with the party atmosphere of the West End, numerous long bays, and a mangrove channel that helps small boats travel most of the southern coast in protected waters. The next island is Utila, which has a wonderful backpacker feel to it, offers some of the cheapest scuba diving in the world, has a chocolate factory, and is a blast to explore by scooter. The Hog Islands are a group of small islands offering a chance to visit native villages. The final island is the rarely visited Guanaja where most of the population lives on a small island in the bay leaving the main island natural. All of the Bay Islands sit on the same Mesoamerican Reef as Belize, so the snorkeling is amazing. An added bonus is going to the mainland to see the Mayan ruins of Copan, which are as good as any Mayan ruins can be. The one caveat of the Bay Islands is that there will be days of 30+ knots of wind, but that is when you enjoy the long, protected bays and interior snorkeling.
2. San Blas Islands: Isolation Is the Attraction
The bad news about the San Blas Islands is their isolation. The good news about the San Blas Islands is… their isolation. How can the same thing be both? Getting there takes a little effort—about a three-hour drive from Panama City or a full day’s sail—and once you arrive, you leave behind many of the conveniences we take for granted. Provisioning is limited, laundry services are scarce, and modern amenities can suddenly seem very far away. But that isolation is also part of the magic.
Because the San Blas Islands have remained relatively removed from the outside world, the indigenous Guna people have been able to preserve much of their traditional way of life. And while the islands themselves are breathtaking, getting to know the Guna people is one of the true joys of spending time there. And make no mistake—the scenery alone is worth the journey. These islands are sandy little paradises resting atop coral mounds just miles from the lush jungles of the mainland. You can stretch out on beautiful beaches, explore deserted islands, snorkel among spectacular reefs, or travel by river deep into the jungle. But the San Blas experience is about more than beautiful scenery. It is also the opportunity to glimpse a way of life very different from our own. You can visit Guna villages, welcome the “veggie boats” that stop by to supplement your provisions, and—perhaps best of all—watch as local artisans paddle up in traditional dugout canoes to offer their handmade molas for sale. These remarkable works of art are created by layering and hand-stitching brightly colored fabrics into intricate patterns, pictures, and designs. In many destinations, isolation is something to overcome. In the San Blas Islands, it is something to treasure. It is precisely because they are a little harder to reach—and a little farther removed from the modern world—that the islands and the Guna culture remain so wonderfully distinctive. Sometimes the inconvenience of getting somewhere is exactly what keeps it worth going to.
1. The Grenadines: Shane’s Ultimate Caribbean Charter.
If you take the BVI, throw in a little Bahamas, and add authenticity you will get The Grenadines! This chain of islands sits between St Vincent and Grenada and each island offers something different. Bequia has their whaling history, Mustique is for the uber rich, Mayreau’s village is so inviting, the Tobago Cays have you anchor behind a barrier reef knowing the next land in front of you is Africa, Union Island has a reef shallow enough a local built Happy Island on it out of conch shells, Carriacou is one of the few islands that is part of Grenada instead of St Vincent, and there are several other islands in between to explore. The Grenadines offer great sailing, great locations, great restaurants and bars, great shore-side activities, and great snorkeling, but to me it is the locals that take the cake. Of course they are trying to make money also, but rarely in the Caribbean will you find people so excited to show off their islands to foreigners.
7-day itinerary: The Grenadines →
Mouth Off! What are your favorites? Comment below… Now Go!
Shane McClellan has written for ALL AT SEA since 2016.
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