Sailing the Caribbean - not as out of reach as you might think

Why should a Caribbean sailing holiday be out of reach? Short answer is, it probably isn’t.
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Is sailing on the Caribbean just for a lucky few? Renting a private vessel and cruising through a warm, salty-breezed heaven - does it sound out of reach? Not so, say the yacht charterers of the Caribbean

And it's not just for yachties and experienced sailors, but even if you are a landlubber eager to chalk up an unforgettable, fully crewed, tropical vacation on the open water it simply just not so hard to do - or expensive, if you do it the right way.


As Dennis Dori of Charter Sailing Unlimited, a U.S.-based charter yacht brokerage company with ties to hundreds of vessels for hire all over the Antilles, described it recently, 'A lot of first-timers are pleasantly surprised by how doable it is -- chartering a yacht and making their dream sailing trip a reality, and there’s truly no better or easier place in the world to do it than in the Caribbean.'

So, there are obvious questions that you need to know the answer to:

Must I know how to sail?

Yes, if you’re chartering a 'bareboat,' meaning a fully equipped sailing yacht without a captain or crew.

No, if you opt for an all-inclusive crewed yacht charter package that comes with a skipper, crew and chef.

Both options are readily available throughout the Caribbean and you probably already know which one is for you.

While bareboat charters are more common (and cheaper), the crewed option is a great way to gain some guided sailing experience or just kick back on a private yacht and enjoy a worry-free vacation. A 'skippered bareboat' is an alternative for non-sailors who need a captain but don’t want to spring for a whole crew.

You said it didn't have to be expensive. How much will it really cost?

Prices range widely, depending on the vessel, passenger and crew size, and which month you travel in. High season in the Caribbean runs from mid-December through late April.

Typical all-inclusive rates for a week on a fully crewed sailing yacht run from US$1,800-2,500 per person (for a standard-sized group of four to six people), plus incidentals and 10-15 percent gratuity. Couples can lower their costs by opting for a 'cabin cruise' -- chartering a single berth on a boat shared with other guests.

How do I find the right boat for me/us?

An experienced broker accredited with a recognized chartering organization such as the Charter Yacht Brokers Association or American Yacht Charter Association can tailor a charter sailing vacation to your needs without adding to the cost.

The Moorings and Sunsail (and they are jointly owned by the one company) operate the two largest charter yacht fleets, with several bases spread across the Caribbean, so this is a good place to start, but there are some very good local charter operators which come up easily in Google when you have done enough research to decide a destination.

Where?

The Grenadines - The Windward Islands

This must be one of the sweetest and most unspoilt chains of islands in the Caribbean. Stretching from St. Vincent to Grenada they have always been a natural draw in boating circles.

Pristine, sandy coves. Storybook harbours. Isolated coral reefs. Traffic-free cays hanging off the Atlantic-battered rim of the Caribbean Sea.

Tobago Cays - my best pick in the Caribbean
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The wonderful thing about the Windwards is that you can sail in the lee of the islands - flat seas and good winds - merely feeling the full strength of the Atlantic swells as you cross the straits between the islands.

Still you can expect gustier, choppier, more exposed sailing conditions compared with the calmer Leeward waters of the British Virgin Islands -- a good place to practice before coming here if you are a little uncertain.

Here you'll experience some of the best hideaways in the Caribbean -- Canouan, Bequia, the Grenadian island of Carriacou, and topping them off - the Tobago Cays, a group of five mirage-like isles shielded from the Atlantic Ocean by a horseshoe barrier reef where the diving is superb.

As well as Sunsail and The Moorings (headquartered on Canouan in the Grenadines) there are several local outfits and entrepreneurs offering competitive deals on virtually everything else that floats.

Spanish Virgin Islands

Rated highty recently by CNN as a cruising destination, the Spanish Virgin Islands, a mini-archipelago wedged between Puerto Rico and the U.S. and British Virgin Islands, is the closest thing to experiencing the Caribbean 40 years ago.

Spanish Virgins - this could be you
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A world apart from the USVIs and BVIs (the Caribbean’s yachting and boat chartering capital) the quieter 'Spanish' chain -- ceded to the United States along with Puerto Rico in 1898 -- was until recently best known as a restricted U.S. Navy weapons testing ground.

Today, this untrammeled archipelago is a haven for weekend warriors from Puerto Rico (less than 10 miles away) and savvy charter vacationers who know a well-kept Caribbean secret when they sail one.

Fajardo, a bustling port on the eastern tip of Puerto Rico, is a natural point of departure for crewed or bareboat sailing charters to the Spanish Virgin Islands.

Trips are as flexible as your budget and time restrictions and best discussed with a reliable charter broker or company specializing in the area -- including Florida-based Virgin Island Sailing and Puerto Rico’s Sail Caribe among several others.

A short, breezy cruise from Fajardo puts you at anchor in the pristine bays and protected reefs of the area’s two principal isles, Vieques and Culebra, along with several picturesque cays that haven’t seen much of a crowd since the Spanish galleon days.

Culebra, the more secluded of the two islands, is home to a host of sandy bays, remote anchorages, enticing dive sites and a wildlife refuge occupied by sea turtles and thousands of seabirds.

Vieques has stunning beaches, a pair of friendly island communities and the area’s hallmark nighttime stop at Puerto Mosquito -- a surreal bay illuminated by millions of light-producing micro-organisms -- one of the last glowing 'biobays' on earth.

San Blas:

If you are looking for something really unspoiled, then the San Blas Islands of Panama, an archipelago comprising approximately 378 islands and cays, must be my all time pick. Only 49 of the islands are inhabited. They lie off the north coast of the Panama, east of the great canal.

San Blas - over 300 islands just like this to explore
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The 49 inhabited islands are home to the Kuna Indians, who have largely rejected interference with their unique life style.

As long as you respect the islands, the Kuna Indians are very welcoming, and it is possible to visit the islands where they live by arrangement.

For the rest, there are just 329 islands (some of which disappear each year, sadly) to explore at your leisure, and hundreds of unspoilt anchorages.

Some long-range cruisers have sailed there and found heaven, so leave only when they need to have their visa renewed.

While Sunsail and The Moorings are absent, there are several reliable yacht charter companies, and the situation every year improves as to the quality and variety of choice.