St. Maarten is on sail during famous regatta

St. Maarten is on sail during famous regatta

PHILIPSBURG, ST. MAARTEN - To paraphrase Shakespeare, how many times have I visited St. Maarten? Let me count the days. I began my love affair with this Caribbean island nestled in the heart of the Leeward Islands some 30 years ago, making landfall there during a sailboat charter with The Moorings, a yacht charter company headquartered in Clearwater, Fla. My arrival coincided with the staging of the Heineken Regatta, which was in its infancy then, but what has become one of the premier sailing events in the world, attracting some 300 sailboats from around the globe. While it is a sailing competition, the affair is best described as a gigantic party that brings together locals and tourists in a four-day festival of fun. In fact, the regatta’s motto is “Serious Fun.”

The regatta, held the first weekend in March each year, showcases both sides of the island, which is shared by two nations — the Netherlands and France. It is a small island, but it has a big appetite for pleasure. Sadly, the activities slated for the French side and centred in Marigot, the capital, were suspended in 2015 due to the lack of funding. But the Dutch were not deterred, and in Philipsburg, the capital, the party rages on, featuring local and international bands and top name acts at outdoor venues, as well as varied entertainment at the bars and pubs located in and around the boardwalk meandering along the beach. On Sunday, the last day of the gala, the scene moves to Kim Sha beach for one gigantic, exhausting finale featuring the headliner act and concluding fireworks.

My modus operandi lo these many years has been virtually the same: Check into my hotel on Thursday as early as possible, since the first party is that evening at Port de’ Plaisance Resort and Casino, where live music, food and souvenir vendors, Heineken Regatta memorabilia and much more help kick off the events in grand style. There are excellent hotels on both sides of the island, ranging from all-inclusive resorts like the Sonesta Maho Beach in Maho Bay, the luxurious Sonesta Ocean Point Resort, to small boutique hotels such as L’Esplanade on the French side. In between, there are family-oriented hotels, including Oyster Bay Resort on the border between the Dutch and French side, which was my base in 2016, and Great Bay, a newly remodeled resort near the heart of Philipsburg.

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Left: Sailors charter yachts from the Moorings company. Right: Sailors from around the world come for the regatta.

The Sonesta Maho Beach and Sonesta Ocean Point resorts are two of my favourite hotels because this lively quarter is home to a great casino, disco and specialty shops and restaurants like Bamboo Bernie’s and Cherri’s Cafe adjacent to the hotels. The parking garage also is a plus if you rent a car. The Maho area is so popular with tourists that parking on the street is next to impossible.

After attending festivities at Port de’ Plaisance, well into the early morning hours, Friday is a day to experience one of the many magnificent beaches in order to get some rest and prepare for the celebration on the boardwalk in Philipsburg. Two of the best and most visited strands are Cupecoy and Orient Bay. Orient Bay is a clothing optional beach that is generally clogged with Europeans who are extremely fond of the lax rules regarding nudity. The French portion of the beach is sans clothing while the other half is not. Other options include Baie Rouge (Red Beach), Friars Bay and Mullet Bay, the latter within walking distance of the hotels.

After working on a tan and getting some much-needed rest, I usually head back to the hotel in plenty of time to get ready for the boardwalk bash. Philipsburg will be a challenge when it comes to parking, so arrive early and take in all the sights. The city is noted for its duty-free shopping, local handicrafts and souvenir stands. Stores are situated mostly along Front Street next to the placid waters of Great Bay, and Back Street one block away. Locals also set up booths wherever they can to hawk their wares to passersby. Cruise ships dock in St. Maarten in great numbers, anchoring at one of the most modern piers in the Caribbean, and give their guests an opportunity to soak up some vibrant Caribbean atmosphere … with a little European touch, as the island likes to boast. The problem with cruise ships is they usually don’t stay overnight, depriving their passengers of an opportunity to take part in an exceptional island vacation experience.

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Left: There is lots to celebrate during the regatta. Right: St. Maarten also offers some historic sites.

For many visitors, including myself, it seems more sensible to stay on the Dutch end of the island and sample the French-owned territory on day trips. In Marigot, you’ll find boutiques filled with the latest fashions from Paris, the finest in French perfumes, exquisite jewelry and, of course, many restaurants majoring in delectable French cuisine. Grand Case, just a few kilometres north of Marigot, is famed for its street of restaurants specializing in every kind of fare imaginable and prepared in a variety of ways. Café Calmos is always on my list for lunch or dinner. For a grand adventure, hike Pic du Paradis, the highest peak on the island, and do the zip line, one of the longest in the Caribbean. Views from the mountain include all of St. Maarten/St. Martin, and surrounding islands of Anguilla, Saba and St. Eustatius.

An especially good day to saunter over to Marigot is on Saturdays when the market along the waterfront opens. It is jammed with vendors selling everything from fruit to wooden carvings to island music. Scattered among all the trappings of booths and tables are locals cooking tempting barbecue chicken, fish and beef on outdoor grills the size of small Volkswagens. There also is an air-conditioned upscale mall nearby if you need a break from the sun. Before the race events were cancelled, you could watch the sailboats arrive in the bay at the end of the second day’s races. A brief hike up to Fort St. Louis offered an extraordinary view of the racing and the finish. Later that night, the yachtsmen and other partygoers joined in the intense revelry.



Above: Beautiful beaches abound in St. Maarten.

Even without the Marigot leg and accompanying festivities, the event is still a compelling three-day affair worth planning a vacation around. Visitors who want to get more immersed in the happenings can go out on sightseeing boats for a few dollars to get a close up view of the sailing. But at the end of every day and into the wee hours, there is that commitment to serious fun.

“In the States and elsewhere, a lot of regattas are very serious,” said Robbie Ferron of the St. Maarten Yacht Club. “Here, it is very simple: You get up in the morning and go race. Then you go party. Then you go to sleep. Then you do it all over again.”

And that’s why I keep coming back!


The Heineken Regatta is scheduled for March each year. / Sailings with the Moorings (sail yourself or hire a skipper) start from $3,056 U.S. - 7 nights / 2 passengers. Power Charters start from $9,065 - 7 nights / 2 passengers. Crewed voyages (with captain and chef) start from $11,410 - 7 nights / 2 passengers / How to book a Moorings trip: Typically travellers books 3-4 months out - You can book online at or by calling 888.788.0653 - You need only 30 per cent of your trips cost to reserve your vacation. / Oyster Bay: / Sonesta Ocean Point Resort: / For more events, check out the St. Maarten website




St. Maarten


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