7 Day Charter Itinerary in St. Maarten / St. Martin – St. Barths – Anguilla
A 7-day St. Martin sailing itinerary — St. Maarten, St. Barths and Anguilla — day by day, with anchorages, distances and where to clear customs.
A St. Martin, St. Barths, and Anguilla charter itinerary offers a perfect blend of sailing, culture, cuisine, and island-hopping adventure. With French, Dutch, and British influences spread across three distinct destinations, this cruising ground is a natural next step for sailors looking beyond the Virgin Islands.
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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.”
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.
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:
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.”
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.
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.
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.
Day 7: Return to St. Martin.
Clear customs and enjoy your final day on the island before returning to the yacht in the morning.
Helpful Links to Charter Companies:
- Dream Yacht Charter: https://www.dreamyachtcharter.com/destination/st-martin/
- The Moorings: https://www.moorings.com/destinations/caribbean/st-martin-yacht-charters
- Sunsail: https://www.sunsail.com/yacht-charter/caribbean/st-martin
Frequently Asked Questions About Chartering St. Martin, St. Barths, and Anguilla
Is St. Martin a good charter destination?
Yes. St. Martin offers excellent air access, modern marinas, diverse anchorages, outstanding dining, and easy access to nearby islands such as St. Barths and Anguilla.
How many days do you need to charter St. Martin, St. Barths, and Anguilla?
A seven-day charter allows enough time to visit all three destinations. However, many sailors prefer 10 to 14 days to fully explore the anchorages, beaches, and attractions.
What makes this cruising area different from the Virgin Islands?
The sailing involves longer open-water passages and more exposure to offshore conditions. In return, sailors enjoy a blend of French, Dutch, and British cultures, world-class dining, and a greater sense of adventure.
Is St. Barths worth visiting by yacht?
Absolutely. Saint Barthélemy is famous for luxury yachts, upscale restaurants, designer boutiques, beautiful beaches, and a sophisticated atmosphere unlike anywhere else in the Caribbean.
What is the best anchorage in St. Barths?
Anse de Colombier is one of the most popular anchorages. Accessible primarily by boat, it offers calm waters, excellent snorkeling, and a peaceful setting away from Gustavia.
What is special about Anguilla?
Anguilla is known for uncrowded beaches, relaxed anchorages, excellent restaurants, and a quieter atmosphere than many neighboring islands.
What is Tintamarre known for?
Tintamarre is an uninhabited island popular for snorkeling, swimming, and wildlife viewing. Its remote setting makes it a favorite stop for charter yachts.
Why do people visit Maho Beach?
Maho Beach is world-famous because arriving aircraft pass directly overhead on final approach to the nearby airport, creating one of the Caribbean’s most photographed experiences.
Do you need to clear customs when visiting Anguilla?
Yes. Visiting yachts must complete customs and immigration formalities when entering Anguilla from St. Martin or other neighboring islands.
What is the best time of year to charter this region?
The peak charter season runs from December through April, when trade winds are consistent and weather conditions are generally ideal for sailing.
What This Means
This cruising ground offers a completely different experience from the Virgin Islands.
- French, Dutch, and British cultures blend together
- Open-water sailing adds a sense of adventure
- The dining and nightlife are among the Caribbean’s best
- Each island delivers a distinct personality
For sailors wondering “what’s next?” after the Virgin Islands, St. Martin, St. Barths, and Anguilla provide an ideal answer.
Carol Bareuther has written for ALL AT SEA since 2004.
Worth your time?
Thanks — noted.
Information is so out of date it’s not worth reading. Today this itinerary is impossible.
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).