Three Islands, Three Worlds

Chartering in St. Martin, St. Barths and Anguilla


If you’re looking for variety on a tropical bareboat charter, head to St. Martin and its neighbors, St. Barths and Anguilla. Each island is a world of its own, the distances are short, the winds are predictable, and the food is divine.

Cruising here means landing at Princess Juliana Airport on Sint Maarten where the final descent flies over Maho Beach with jumbo jets coming to within feet of the sand just before touching down. People come from all over to watch this spectacle and to get tossed by jet exhaust when the big birds take off again.

St. Martin is also called Sint Maarten because half the island is French and half is Dutch but there’s no official (or even visible) border between the two sides. We landed on the Dutch side and took a taxi to the Dream Yacht Charter (DYC) base in Anse Marcel on the French side.

At the end of May, the season begins to wind down which means fewer crowds and better boat availability so we were upgraded to a 2019 Lagoon 450 S catamaran named Panui. Our itinerary was laid out carefully to maximize time and minimize expense. You see, officially you need to check in and out of each country which is a slow and often expensive process. We decided to take a land tour of the Dutch side because traveling by car lets you skip this bureaucracy and then stick to the French side by boat. Since St. Barths is also French, that leaves only Anguilla to worry about.

Anguilla is north of St. Martin with pristine beaches and a laidback vibe. However, Anguilla is British, so we were facing paperwork, Covid tests and fees. We found cheap Covid tests in Marigot, the capital of French St. Martin, filed our paperwork with the base and then pointed our bows north.

We arrived at Sandy Island first. It’s a spit of sand and coral with one beach bar that’s only open when someone comes over by boat, starts the generator and plugs in the blender. We dinghied to the beach via a narrow channel and landed right when everyone had gone so we had the place to ourselves. The next day, we sailed up to Prickley Pear Cays (also a part of Anguilla). This pair of uninhabited islands has moorings on the south side but then you dinghy around to the sandy beach on the north side with its protective outer reef. Aside from pangas ferrying hotel traffic, we again were alone but this time, there was an open bar, so we idled the afternoon away with cool drinks and sand between our toes.

The next morning, we cut between Anguilla and St. Martin, heading northeast. It was the sole bash to windward of our week but it only lasted two hours and then we turned south toward St. Barths on the horizon, enjoying a brisk beam reach sail all the way down.

Unlike low key Anguilla, St. Barths is the glitzy sister of the trio. The capital of Gustavia is like Rodeo Drive with high fashion boutiques, fine dining and a superyacht clientele that frequents the island’s exclusive racing season including the St. Barths Bucket and Heineken regattas. It may not make sense to sail to the Caribbean to shop for a Dolce & Gabbana bag, but if you want one, you’ll find it here.

We anchored by Les Gros Islets and dinghied to the city dock to check in. The process here is very dialed-in due to the volume of upscale visitors and we were out looking for lunch in no time. We found a gourmet French meal at Le Repaire and then, to burn off some of those calories, we walked up to the lighthouse. The views of Gustavia Harbor and our anchored boat in the distance were worth the sweaty stroll. St. Barths has its own crazy airport where small prop planes drop vertically from the sky and then level out on the short runway on the windward side. They come in so dramatically, you think they’ll knock you on the head with their landing gear.

We stocked up on some provisions and spent a quiet night just outside of town. The next morning, we headed to nearby Ile Fourchue, a high-sided island with a deep harbor. It’s a quiet place with great hiking and it’s making a comeback after it was nearly denuded by goats. In early days, it was the hideaway of Balthazar Biguard, a Frenchman fleeing the French Revolution. He lived his hermit lifestyle here for many years and is buried on the island.

It was nearing the time to start heading back north so we set sail for Tintamarre Island National Park where we caught a mooring and reset ourselves back to broad beaches and leisurely swims after the glamour of St. Barths. Because Tintamarre is a park, we couldn’t stay the night on our mooring, so we headed west two miles and anchored off Ile Pinel and its two bars, both of which were blissfully closed so we enjoyed a quiet night.

For our last evening, we returned to the northwestern corner of St. Martin to Grande Anse, a colorful tiny town with one main street chock full of galleries and eateries serving up giant lobsters and local beer. The DYC marina in Anse Marcel is just around the corner so we didn’t have far to go to return our boat. However, the marina entrance is narrow and tricky which is why the base insists on driving guests out and also back in. Since they had my VISA card on file for damages, I didn’t put up a fuss and when I saw that it took three guys and a dinghy to get the boat back into the slip, I didn’t feel a bit bad about relinquishing the helm

These islands are a sailor’s paradise, but DYC also charters powercats so powertboaters can cruise as well. The next time you want to go to only one place but want to experience multiple worlds, start on St. Martin. You won’t be disappointed.


  • Stay out of Simpson Bay and Phillipsburg on Sint. Maarten for check-ins. Fast, cheap and easy check-ins can be done in Margiot at Ile Marine fuel dock or in Anse Marcel at the marina.
  • See at least one jet land at Maho but stay out of the path of those taking off unless you’re looking for a heavy exfoliation by way of flying sand.
  • Provision lightly because you won’t want to miss the many bakeries, pastry shops and restaurants serving up the best island-influenced French fare.