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Home CRUISING

THE BEST OF CARIBBEAN CRUISING: Part One

Caribbean Compass by Caribbean Compass
April 6, 2023
in CRUISING, DESTINATIONS
Reading Time: 6 mins read
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The Timeless Destinations of Puerto Rico and the Virgins

Story by Todd Duff, Photos by Gayle Suhich

My partner, Gayle, and I first arrived in the Caribbean in the early 1990s and what had started, for me at least, as a sabbatical cruise before returning to Annapolis and a life I’d created there turned into what has become a lifelong obsession with these beautiful islands, picturesque far-flung harbors, and warm, friendly people. 

Comprising an area within the tropics of over one million square miles, the Caribbean basin encompasses 28 countries and many different cultural heritages. From the cosmopolitan French of Martinique and Guadeloupe and bustling San Juan to the indigenous people of Panama and the laidback islands of the Grenadines, and with historical sites in the multitudes from pre-Colombian times up through the colonial period, there is a lot to discover in the Caribbean — and there is no better way to see it all than from the deck of your own cruising yacht.

Having spent the better part of the last thirty years living aboard and sailing the Caribbean, east to west and north to south, I’ve found a few special destinations that, to me, epitomize some of the best aspects of this culturally diverse and geographically awe-inspiring region. Allow me to share a few of my favorite places that I’ve visited or lived in, and hopefully this may provide some inspiration to see all of these and more as you make your own voyages of discovery.

The main pier at Boquerón, Puerto Rico

Most sailors arrive in this region from either Europe with initial landfalls in the Eastern Caribbean islands, or from North America making landfall in the Virgins or the Greater Antilles. I’ll start in the latter since this is where I have spent the greatest amount of time over the years.

Puerto Rico is an often-overlooked cruising destination, and this is a shame as it has so much to offer. An east to west cruise along the south coast could start from one of its better-known outlying islands, Culebra, which harbors one of the best anchorages in the whole of the Caribbean, but my favorite spot there is the tiny offshore island of Culebrita, home to a fantastic shallow reef along its southern point full of lobster and fish. Atop the highest point, with a commanding view to the south and east, you’ll find the ruins of the last Spanish lighthouse built in the Americas. Anchor in the lee of the island and there are a couple of trails which lead up to its crumbling yet architecturally impressive remains. The bravest sailors might try to climb the decaying ladder to the top of the lighthouse where the view to the east is quite spectacular.

Along the south coast of Puerto Rico, you’ll find well-known hurricane holes and quaint villages tucked into pocket bays; my favorite is the little town of Salinas. When we first arrived there during the Christmas holidays in 1992 and anchored in the middle of the bay on one starry Saturday night, vibrant Latin music blared out from several surrounding bars packed with holiday revelers creating a chaotic cacophony of popular themes. Farther to the west, Isla Caja de Muertos offers a glimpse of the ultra-clear waters usually only found farther to the west in the Caymans or Belize while nearby Ponce provides great walking tours of the old historic district and ample shopping opportunities.

Lighthouse at Cabo Rojo, Puerto Rico

All the way on the western coast, the excellent harbor at Boquerón can be a fun stop with great dinghy exploration in the mangrove canals and is a popular weekend party place for locals while a few miles to the north, Puerto Real is a small yet popular yachting center with good facilities and is a great place from which to rent a car to explore the western interior and nearby Cabo Rojo, Puerto Rico’s rugged southwestern cape.

The Virgins

While the BVI is world renowned for the Baths on Virgin Gorda, there are many other natural wonders throughout the Virgin Islands. This similar but smaller jumble of rocks on the western side of Beef Island has come to be known to some as the “Mini Baths.”

Back in the Virgins, most cruisers tend to avoid St. Thomas with its often-crowded harbor full of cruise ships and thousands of tourists, but the nearby islands off the southern and eastern coast offer a great escape and after midday are usually devoid of tourist boats. Just to the east, St. John has dozens of great anchorages, most of which are within the Virgin Islands National Park that covers approximately 60% of the island. While one must take a mooring ball when within the park, the price is reasonable, and the fees certainly help offset the costs of maintaining and preserving the natural beauty and historic sites within its borders. If you’re into hiking and snorkeling, St. John is a place you’ll want to visit for sure.

At anchor in Leinster Bay, St. John

The BVI is of course perhaps best known for its popularity with the bareboat charter companies. The world’s largest fleets are based there, and the most populated island of Tortola was my home for quite a while. Unfortunately, the islands get a bad rap from reports of unfriendly officials and rigid, overbearing rule enforcements, but don’t let this put you off! As a whole, BVI islanders are among the friendliest of all the peoples I’ve met in my travels. The natural wonders, idyllic harbors, sun speckled beaches and vibrant party hotspots are something to experience at least once, if not again and again. And if you’re on a private vessel and the charter crowds are getting to be too much for you, there are several great anchorages within the archipelago where you will never see a bareboat charterer. My favorite is South Sound on Virgin Gorda. The entrance is slightly daunting, with a large rock in the middle of the channel, but most cruisers who have sailed as far as the Caribbean will have no trouble entering this excellent harbor. Protected by a nearly continuous barrier reef and with six to eight-foot depths throughout, the swimming and snorkeling here are great, and it’s a nature preserve too, so you’ll see lots of sea life. 

Goats on the beach, Tortola, British Virgin Islands

With dozens of protected harbors, the islands of the BVI and USVI offer amazing natural beauty and with great snorkeling, diving and lots of scenic hikes and scrambles, active sailors can stay busy. And because of the impressively long barrier reef extending south and east from the northernmost island of Anegada, along with a perfectly placed group of smaller islands to the south and east of the main islands of Tortola and Virgin Gorda, the waters from Virgin Gorda in the east all the way to St. Thomas in the west offer sheltered conditions from the Atlantic swells and the consistent, warm tradewinds provide some of the best sailing conditions to be found anywhere.

In part two of this series, we’ll sail east and south to visit the geographically striking and culturally diverse Leeward and Windward islands.

A rainbow at Jost Van Dyke, British Virgin Islands

Todd Duff is the author of Bargain Boats and Budget Cruising and the action adventure Kidnapped from the Caribbean, available from www.seaworthy.com or anywhere books are sold.

Tags: BVIPuero RicoUSVI
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