5 Best Sailing Ports in the Caribbean

Best sailing ports of the Caribbean run like a coconut drift. First of all, on my list, I always name the same five every time. The memories collected in these ports are fond ones.

Secondly, my list of Best Sailing Ports of Call in the Caribbean list isn’t about the Caribbean you know.  It’s about the Caribbean you have yet to discover.  All the places you may have never thought about and destinations that will fascinate and move you.  It’s about finding your new Caribbean. Sailing in these best sailing ports of the Caribbean has given me life lessons.

  • Best Sailing Ports – Exuma Cays, Bahamas

First and foremost, the Exuma Cays are my home base for Yacht Freebird.  Therefore, the Cays offer the most beautiful canvas in the world to enjoy a tropical lifestyle aboard a boat or from shore.

What is there to do? Consider fishing, sailing to remote anchorages and uninhabited islands, kayaking in protected waters, scuba diving the blue holes, beach combing, and exploring. How does that grab you?

Also, the Exuma Cays offer 300 plus islands and cays, each with a world of experiences to explore. An island chain of such size and beauty is unique in the Bahamas.  No one believes the description of the waters. Photos do not do justice to the clarity and turquoise hues of the water.  The expanse of untouched beaches and land is astounding. Celebrities like Johnny Depp, David Copperfield, and Faith Hill reside here.

Consequently, my favorite adventures of the best sailing ports in the Caribbean are available in an anthology: Bluewater Walkabout: Into the Caribbean. You can get it as a free download here.  I hope it will inspire you to sail these magical waters.

  • Best Sailing Ports–Trois Ilets, Martinique

Best Sailing Ports

Next on my list is Martinique. We burst into view through the sea haze on our approach in an earlier boat, dubbed Scud. After anchoring off St Anne in the afternoon, we clambered ashore to explore the small village, located just outside the entrance to Cul de Sac Marin.  The forest of masts marked the hotspot of the sailing scene in the French West Indies back then.

First and foremost, Martinique isn’t the Caribbean you know.  It’s a fascinating, intoxicating place that rewards sailors who journey outside their comfort zone.  A fascinating French culture, delectable food, and endless discovery await you.  Nearby are the sugary beaches of Les Anses d’Arlet, the capital, and Fort de France.  

Best Sailing Ports

Be sure to drop in on any of the 11 rum distilleries. 

So, what makes this rum so unique?  It is the rhum agricole production technique. Whereas rums produced elsewhere consist of molasses, a by-product of sugar production, the rhum agricole method used in Martinique begins with freshly squeezed sugar cane juice.  It is taken directly from cane stalks. The unique process yields rums that are more comparable with fine cognacs.  These offer greater complexity and a more varied array of natural flavors.

As a result of my travels, my favorite adventures of the best sailing ports in the Caribbean are available in an anthology: Bluewater Walkabout: Into the Caribbean. You can get it as a free download here.  I hope it will inspire you to sail these waters into the unknown.  Discover. Sail. Cruise.

  • Best Sailing Ports–Bay, Barbados

Best Sailing Ports

Next on my list is Barbados. First and foremost, it’s best to set Barbados as a landfall after an Atlantic crossing, but we beat against headwinds to reach the protected anchorage in Carlisle Bay.

Additionally, the only cruising area is along the sheltered west coast.  The east coast is rocky and exposed to the Atlantic breakers.  Breakers bring surf, so of course, Bathsheba was hot on the list to visit too.  Our sons wanted big waves to surf!

Ask locals in Barbados where they go on vacation, and they’ll likely answer Bathsheba. The rocky, raw town is rightly famous for its surfing.  Even so, it’s also a charming, utterly laid-back place with great little beach restaurants and jaw-dropping scenery.

Barbados boasts one of the lowest crime rates in the world due to their free schooling.  A jitney driver said, “The first thing our government did after independence in 1966 was to introduce free education. Anyone who gets straight As at A-level can go to university anywhere in the world and have the government pay for everything.”

Consequently, my favorite adventures of the best sailing ports in the Caribbean are available in an anthology: Bluewater Walkabout: Into the Caribbean. You can get it as a free download here.  I hope it will inspire you to sail these magical waters. Break out of your comfort zone.  Explore.

  • Best Sailing Ports–Samana, Dominican Republic

Best Sailing Ports

Next on my list of best sailing ports–the DR. Maybe you’ve been to Punta Cana or La Romana. But this is a different kind of Dominican Republic, filled with still-undiscovered places and laid-back fishing villages. The Samana peninsula is one of the most beautiful stops in a vast Caribbean country.

So of course, on our approach into Samana Bay, a humpback whale graced us with her presence. The bay provides a nursery for the whales until their young can fatten up.  They need to grow in preparation for their voyage back north. Coastal areas around Samana are the hub for humpback whale-watching.  The whaling season in the Dominican Republic is during January – April. The region is considered the D.R.’s best-kept secret.  It is due to its incredible diversity and beautiful uncrowded beaches.

Best Sailing Ports

Most noteworthy, each year 3 to 5 thousand humpback whales return to Bahia de Samana.  Due to the adjacent waters, the female bear their young and mate for the following year. From January until March, frolicsome males vie for the attentions of females. Sky-rocketing, lob tailing, and flippering were the typical antics.

Of course, if you’re into beach walking, you’ll find them on the north coast.  Next, just jump onto any one of a litany of buses that pull into town every morning.

Therefore, my favorite adventures of the best sailing ports in the Caribbean are available in an anthology: Bluewater Walkabout: Into the Caribbean. You can get it as a free download here.  I hope it will inspire you to explore these fascinating ports. Get free. Get going.

  • Best Sailing Ports–de Sac, St Martin

Best Sailing Ports

Next on my list–St Martin. The French side of St. Martin remains an in-the-know destination for discerning yachtsmen. Because of the world-class food of Grand Case and the pretty amazing beaches, the island beckons to sailors. And the neighborhood of Cul de Sac is a fabulous place from which to see it all.  Because of the quick access to the beach oasis of Pinel Island, it is just a short drive to Grand Case Boulevard. Make sure you visit Ma Doudou for homemade local punch!

Winding through the streets of central Marigot, visitors will love discovering old Creole houses.  The homes boast the traditional Saint Martinoise style.

Additionally, my favorite adventures of the best sailing ports are available in an anthology: Bluewater Walkabout: Into the Caribbean. You can get it as a free download here.  I hope it will inspire you to sail these incredible islands.

  • Best Sailing Ports–Soufriere, St. Lucia

Best Sailing Ports

Next on my list–St Lucia. Soufrière is a quarter on the Southwest coast of Saint Lucia in the West Indies. Soufrière was the former capital of Saint Lucia during French rule. And now, it is a small sleepy fishing port with an emerging tourism industry.

For this reason, with active teenagers on board, we hit the road to take in all the sites.

No doubt the Pitons or volcanic peaks offer fantastic hiking.  First and foremost, there are two pitons.  For example, there is Gros Piton.  It reaches 771 meters high, and the Petit Piton reaches 743 meters.  So, we took a jitney to the trailhead of Gros Piton to begin our hike. Additionally, the trail offered us a cultural and botanical experience.  It is not just a stroll to a pretty view. In time, we made our way on back roads through sparkling, unspoiled Caribbean countryside.

Best Sailing Ports

Interestingly enough, the view appeared more typical of half a century ago. Then we reached the historic village of Fond Gens Libre. There, we headed up a beautifully laid out trail onto the rugged seaward flank of the peak, engulfed in cold mist by this time.

In the end, we were forced back from the summit. Sulfurous fumes raided our lungs. Today, a guide is required to reach the summit. Sadly, a couple of hikers died while trying to explore the top.

Get Bluewater Walkabout: Into the Caribbean as a free download here.  I hope it will inspire you to sail these mystical islands.

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