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7 Day Charter Itinerary in St. Maarten / St. Martin – St. Barths – Anguilla

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The two-nation island of St. Maarten/St. Martin is the perfect place to start and finish a charter, plus visit its bays, offshore isles and more while cruising for a week. Located a little over 100 nautical miles southeast of the U.S. and British Virgin Islands, this 34-square-mile island is bordered by the Atlantic Ocean and Caribbean Sea. Getting to nearby islands like Anguilla and St. Barths takes a bit more blue water sailing than island-hopping in the Virgins. Thus, the St. Maarten/St. Martin’s cruising grounds are perfect for those who have chartered the Virgins and ask, ‘what’s next!’.

“This group of islands (St. Maarten/St. Martin-St. Barths-Anguilla) is ideal for yacht charter vacations for many reasons, says Ian Pedersen, senior marketing manager for the Clearwater, FL- based The Moorings, which has a base at Marina Fort Louis in Marigot, French St. Martin, and offers bareboat, skipper only and crewed sailing charters on monohulls and multihulls. “First, it is extremely easy to reach compared to some other popular Caribbean charter destinations, with major airlines providing flights directly from the U.S. Another aspect of these islands that immediately becomes apparent upon arrival is the cultural diversity. Its French and Dutch heritage is on full display, making for a very interesting contrast as you traverse the main island of St. Martin/St. Maarten. Each side boasts its own unique features and culture while remaining very accessible to visitors overall. Beyond the main island, the ease with which sailors can travel to the nearby islands of Anguilla and St. Barths adds another dimension to this region. Anguilla is ideal for more laid-back, quiet escapes, while St. Barth is the playground of the rich and famous – a truly incredible stop while on charter.”

Sampling Anchorages on St Maarten and St Martin

Dream Yacht Charter, headquartered in Annapolis, MD, also operates a base in St. Martin, located at Marina de L’Anse Marcel, about 5.5 miles northeast of Marigot. Here, power and sailing catamarans and sailing monohulls are available for bareboat, skippered, by the cabin and crewed charters.

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Photo: ARohrmann / The Moorings
Photo: ARohrmann / The Moorings

St. Martin is a logical place to start a 7-day charter since both major charter companies have bases here. After that, it’s a personal preference whether to head to Anguilla first, then south to St. Barths or vice versa. Here’s an example of the latter:

Photo: St Martin - Caribbean Travel Organization
Photo: St Martin – Caribbean Travel Organization

Sample Charter Itinerary in St. Maarten / St. Martin plus St. Barths and Anguilla

Day 1: Marigot: The capital of St. Martin is a beautiful stop on any itinerary, according to The Moorings & Sunsail’s Pedersen. “Home to Fort Louis overlooking the harbor, as well as an outdoor marketplace, this a wonderful, quaint spot. For those wishing to set sail right away, Grand Case nearby is famous for its abundance of restaurants, ranging from casual beach bars to true fine-dining French cuisine.”

Day 2: Eastern St. Martin. There are wonderful stops on the eastern side of St. Martin. World-famous Orient Bay is here, as well as Pinel Island just offshore, which is a fantastic, sheltered mooring site. Alternatively, guests can choose to visit Tintamarre, an uninhabited island about two miles offshore featuring spectacular snorkeling.

“Stop at Tintamarre to sunbathe on the beautiful beach at Baie Blanche,” suggests Dan Lockyer, Dream Yacht Charter’s vice president of global tourism. “Then, sail on to Ile de la Fourche for sea turtle spotting and remote hiking trails with an impressive view.”

Photo: St Barths Tourism Board
Photo: St Barths Tourism Board

Day 3: St. Barths. From the eastern side of St. Martin, past Tintamarre and Ile de la Fourche, it’s a straight shot to St. Barths, where visitors arrive in Gustavia Harbor. The entire island is accessible via a short taxi ride once you arrive in Gustavia, with clubs, bars, restaurants, or countless beaches at the ready. 

“Make sure to explore little known Shell Beach and scenic Saline Beach,” says Dream Yacht Charter’s Lockyer. Less than a mile from Gustavia, Shell Beach is famous for living up to its name with thousands of shells on the sand. Saline Beach is a secluded strip of sand bordered by the salty sea with a clothing-optional section. 

Photo: St Barths Tourism Board
Photo: St Barths Tourism Board

Day 4: Anse de Colombier. Travel to the western tip of St. Barth to stay in this quiet bay. A welcome respite from bustling Gustavia, this bay is only accessible by boat and there are no hotels, restaurants or shops here. Anse de Colombier is a super snorkeling spot, known for oftentimes hundreds of large orange starfish.

Day 5: Philipsburg. The capital city of Dutch St. Maarten, Philipsburg is perhaps the most ‘touristy’ part of this itinerary. This is where the cruise ships dock, so there are lots of shops, restaurants and even casinos downtown to choose from. “While there, I highly recommend taking a short taxi ride to Maho Beach, which is world-famous for being just next to the airport and the airplanes approaching their landing just feet overhead. It is quite a unique and exhilarating experience, and makes for quite the photo opportunity,” says The Moorings & Sunsail’s Pedersen. 

Photo: Anguilla Tourist Board
Photo: Anguilla Tourist Board

Day 6: Anguilla. For those who desire a quieter crowd-free charter experience, Anguilla is perfect. It’s easy to spend a couple of days here. If there’s just one day, then sail from Philipsburg to Road Bay, Anguilla to clear customs, then anchor in Crocus Bay to enjoy serenity at the edge of the world. There is something special about being here, on a yacht, facing northeast and knowing that if you just set sail you wouldn’t see anything until you reached Iceland. 

For those who do have an extra day or two, sail northwest a couple of nautical miles to the Prickly Pear Cays. There’s spectacular snorkeling, soft sand beaches, and these uninhabited cays are an important seabird nesting area. An open-air restaurant here serves lobster, burgers and more for lunch.

Charter Itinerary in St. Maarten Photo: ARohrmann / The Moorings
Photo: ARohrmann / The Moorings

Day 7: Return to St. Martin. Clear customs and enjoy your final day on the island before returning to the yacht in the morning.

Photo: ARohrmann / The Moorings
Photo: ARohrmann / The Moorings

Policies regarding the COVID-19 virus are changing constantly globally as well as locally in the Caribbean. However, one fact that remains constant for guests to keep in mind that St. Martin/St. Maarten, Anguilla and St. Barths are different countries. To travel between them requires a passport, customs clearance, and each island will have its own COVID regulations. These regulations are subject to change over time, so be sure to confirm with official government websites what their current protocols and procedures are before you arrive.

Helpful Links to Charter Companies:

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    • Wendy, you’re not wrong, unfortunately. We are all looking forward to the days when everything opens up. Hopefully we can all dare to dream a little bit and it is fun to plan a trip. (Even though we aren’t certain when that trip will actually be allowed to happen).


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Carol M. Bareuther, RD, is a St. Thomas, U.S. Virgin Islands based marine writer and registered dietitian.

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