Sailing: The Leeward Islands

My husband and I love to sail.  Despite living minutes from the Chesapeake Bay, with two young children we don’t get on the water much these days.  Fortunately, we have seafaring friends who invite us to be on their charters when we are able to get away and hoist the sails.  Those of us living in the Northeastern United States know, the Caribbean offers warm tropical island getaways that won’t give you jet lag or ask you to endure hellacious layovers.  Twice we have had enjoyed sailing in the Caribbean with dear friends.

We especially loved the leeward islands St. Martin and St. Barths.  They don’t call these islands the gastronomic capital of the Caribbean for nothing (thank you France).  The food really is better here than many other islands I’ve visited.  I was shocked to find Simpson Bay’s Le Grande Marche a sailor’s provisioning paradise, catering to shoppers who come from both sides of the Atlantic.  We were able to load up on everything from Champaign to Oreos to Brie to beef to beer.  We would eat off the boat most night for dinner, but every good sailor knows to stock up when you aren’t entirely sure where you’ll be eating your next meal.

I remember the first time I helped to anchor a sailboat.  “How do we get on shore?” I wondered to myself, not wanting to say it out loud.  It was then I became acquainted with a sailboat’s personal water taxi – the dinghy.  Dinghy rides are now a favorite part of any sailing adventure.  Getting to know a country from its shorelines gives you an entirely different perspective on a place.  Whether by land or by sea, if you are in the area I highly recommend the following.

Sint Maarten (as the Dutch call it)

  • If you are in Oyster Pond the Dinghy Dock Bar & Restaurant has a fun happy hour and the best fish and chips you or I have ever eaten!
  • Grand Case has a great vibe, artsy, and it’s fun to walk the main drag.  Skip the fancy restaurants and have dinner at Talk of the Town and drinks at Calmos Cafe (as seen on The Travel Channel’s Three Sheets) in Grand Case.  Serendipity had it that a local fashion show was on that night, complete with runway built right on the street. 
  • Dinner at the Claude Mini-Club is a must.  Great views of the Marigot Harbor and legendary buffet.  Learn the history too!
  • La Sarafina and Sucriére for French pastries in Marigot.  Nothing like an early morning dinghy ride to pickup pain au chocolat to enjoy with your coffee on the catamaran!
  • Don’t miss the Sunset Beach Bar to watch planes landing overhead while you drink and eat ’til your heart’s content.
  • Take advantage of the duty-free shopping.  You can find especially good buys on electronics in Philipsburg and jewelry in Maho Beach.  I love JN Jewelers, 3 Maho Plaza.

Saint Barthélemy (as the French call it)

  • Wandering around (more specifically shopping around) the streets of Gustavia.  Evidence of the island’s wealthy residents and vacationers is ubiquitous.  Just in case you need to trade in your Sperry Top Siders for Stewart Weitzman, or your Merona panties for La Perla, this ‘Caribbean East Hampton’ has you covered.
  • Eating almost anywhere is guaranteed to be good.  Talk to the locals and ask for recommendations.  One popular spot worth the price tag is the Wall House.
  • Anse de Columbier for swimming, snorkeling and hiking on shore.


  • Dives, snorkeling or swimming off Sandy Island and the Prickly Pear Cays are popular.
  • The anchorage off Crocus Bay, on the north shore of Anguilla, is quiet and makes for good swimming and a fun evening cooking and playing cards on the deck of the boat.

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