Bareboat Charter: St. Martin Itinerary Tips

St. Martin, Anguilla and St. Barth

Sailors have long been known to frequent St. Martin for the endless beaches and combination of French and Dutch culture. Charter boat clients love the options for anchorages around the island. It’s proximity to St. Barth and Anguilla make St. Martin the perfect starting and stopping point for charter boat captains who want a different experience than what can be found in the British Virgin Islands. The Caribbean culture is more subdued and the French influence plays a role in your provisioning.

If you find yourself considering a charter to St. Martin, these are a few of the sights that you should consider while on your sailing vacation.

TIP: When traveling in St. Martin you will be moving from a Dutch territory to a French territory. This will require you to check-in and out of each country. The same is true for Anguilla and St. Bart. In Anguilla, you will head to Road Bay where you can check in daily and obtain a cruising permit to visit the outlying islands and anchorages outside of Road Bay. In St. Barth, you check-in at Gustavia Harbor. 

• Saint Maarten (clearance info)
• St. Martin (clearance info)
• Anguilla (clearance info)
• St. Barth (clearance info)

Things to See While Sailing From St. Martin

Grand Case – St. Martin

Before hurricane Irma, this spot on the French side of St. Martin was ground Zero for the culinary explorers of this island to find the best restaurants. While some locations have rebuilt, there is still much work to be done. However, the lolos are still in full operation. A lolo is a roadside restaurant with open-air seating and cuisine that ranges from ribs and chicken to sauteed local fish. The prices are affordable and the local culture makes Grand Case a must-do on a bareboat charter vacation. Grand Case is an expansive anchorage with protection from the wind and a sandy bottom for good holding.  There are a few small beach bars for the sailors who want to come ashore for refreshments. The dinghy dock has been rebuilt and is convenient to the food and shopping options.

Pinel Island – St. Martin

While the anchorage is quite shallow, the search for a spot and the narrow entrance is worth the great food found on Ilet de Pinel. Whether you head to Yellow Beach or Karibuni you are in for a tropical island experience complete with wide palm trees and drinks with umbrellas in them. The views from the restaurants are framed by flowing palms and crystal clear water in the bay. Lobsters come fresh from the ocean and the Caribbean drinks are fruity and tropical. The island is home to two restaurants that are only open for lunch and afternoon drinks. Find one of the trails that leads from behind the main building and discover the desolate beaches only minutes from your anchorage. 

Simpson Bay St. Martin

You’ll drop the hook at Simpson Bay so that you have access to what St. Martin has to offer. While the water is clear and warm here the beach at Simpson Bay is not the attraction. Local food in the form of roadside food shacks ( lolos) are not only affordable but a good way to get a feel for the local culture. Have a conversation about places to see and you’ll get so many variations on your answers. Try Maho Beach and watch the airplanes land from a nearby beach bar or drive to Orient Bay for some sunbathing in nothing but your birthday suit.  

Tintemarre – Off St. Martin

This small uninhabited island off the coast of St. Martin is home to two exceptional SCUBA diving sites as well as a few secluded beaches. A quick walk from the powdery sand along a dirt trail will lead you to an abandoned airstrip and remnants of an airplane that may have crashed on the island.  The stories are varied on whether the plane was abandoned or it is the result of a crash. Nonetheless, an afternoon to explore this island is well spent.

Anse de Colombier – St. Barth

You’ll see so many sea turtles that you’ll begin to ignore them. The water is so clear the sandy bottom seems to be within arm’s length. The hikes onshore lead you to the beaches where celebrities frolic in the surf. The beach is uncrowded and picturesque. When the sun goes down the stars in the sky dominate your view.   This anchorage is the pinnacle of bareboat chartering if your goal is to get out on your own and experience life on a sailboat. There are no services on land readily available and the only sights and sounds you will experience are from your fellow boaters and the occasional fish that is lurking beneath the boat. 

Anse de Saline – St. Barth

When you drop anchor in this pristine bay you’ll notice that the beach is desolate. You’ll earn your slice of paradise if the anchorage is rolling and you are forced to maneuver your dinghy to shore. This is only a day use anchorage but if there ever was a beach that you would make a special trip for this is it. The sand is thick with a texture of cornmeal and the bay has some nice protected areas for snorkeling. If you see a person or two tucked away at the ends it may be that they are working on their full-body tan. Yes, some nudists have adopted this beach as their own. Feel free, go ahead and use sunscreen on all of your body.

Bay of St Jean – St. Barth

This bay that is not accessible via a direct anchorage is sitting in the lap of luxury. High-end resorts and expensive restaurants are the norm and the crystal clear water beckons you to sip your cocktail with your toes in the sand while working on your tan. Grab a mooring in Gustavia and take a taxi to this picturesque beach just 10 minutes from town.

Prickly Pear, Anguilla

A day sail from Road Bay in Anguilla is as pristine a location as you can find anywhere in the Caribbean. Prickly Pear is a tiny speck of sand that greets you with shallow warm water that is populated with colorful fish that dart beneath your feet. There is a tiny beach bar that sets up daily as well as an occasional restaurant that may or may not be there when you visit. This location is a snapshot of what the Caribbean must have looked like before developers showed up to snatch up all the great beachfront properties. The anchorage is a 5-minute dinghy ride away from the beach. The trail system allows you to explore this low lying island while directing you to empty beaches with postcard-like qualities.