Cruising
America's Great Loop
© 1993 - 2017 CaptainJohn.org

The very first thing you should know, is that the Caribbean (including all that territory commonly referred to as the
Bahamas) consists of more then 7,000 Islands and Cays that stretch from Florida south to Venezuela. For long distance
voyagers the wonderful thing about the Caribbean is you can cruise the entire north & south of it while having only two sections
(or two nights) where you must cruise through the night.  Planned correctly, the rest of the voyage can be cruised in daylight,
spending  your evenings watching the sun set while anchored in a peaceful, protected Island cove. The Caribbean sea is in fact,
the most popular cruising and sailing area in the world.  The island chain is 2,500 miles long  and no more then 160 miiles wide.
Next to America's Great Loop, it offers the safest, most scenic and friendly voyaging in the world.

From Marsh Harbour on Great Abaco (a quick puddle jump from Nassau) the Spanish Virgin Islands (aka, the Passage
Islands), are wedged between Puerto Rico and the U.S. and British Virgin Islands, and are the closest thing to experiencing the
Caribbean 400 years ago.
A world apart from the USVIs and BVIs the quieter “Spanish” chain -- 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 boaters from Puerto Rico (less than 10 miles away) and Fajardo, a bustling port on the eastern tip of Puerto
Rico, is a natural point of departure for sailing to the Spanish Virgin Islands.
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.
As the saying goes: "Money can't buy you happiness" but it sure  can buy you a
boat seaworthy enough, to cruise right into the middle of it.  
-  Capt
John
Yes, sailing the Caribbean is the type of
bucket-list activity most of us dream about.
If you are visiting this site after cruising through
our "America's Great Loop website" you already
know my philosophy on living a-board and
cruising is "going small, going now, and staying
out longer".
As a result, our purpose is to encourage and
inform
you that voyaging off into the beautiful
turquoise waters, among the pristine sandy
beaches of the Caribbean is a lot easier, safer
and much more affordable than you probably
assume.  That of course, is provided you
prepare yourself in advance, so you know what
to expect.
Sailing the Caribbean
The Caribbean is high quality shockingly
beautiful cruising. It offers a boat load of
awesome destinations.

Cruising it is mostly about persistence. It is
as easy as pointing your boat in the right
direction, not hitting anything, and you’re good
to go.

Safe cruisers who make smart decisions and
have a positive attitude find all the good stuff
the Caribbean has to offer.

We've never seen Pirates in the Caribbean.
We've never felt threatened in any way. We've
never had anything stolen. Everyone we've
ever met in the Caribbean have been the
friendliest of friendlies.
For more on sailing the
Caribbean, click next.
between the islands are predictable, with steady Trade Winds and consistent seas.
The Leeward Islands involve a series of short island-hops among some strikingly different islands, including the British and U.S.
Virgin Islands, British Anguilla, Dutch St. Marten, Saba Island, St. Baths, St. Kitts and Nevis down to Antigua.  With almost
constant northwesterly winds, cruising in this area follows a simple path up and down the island chain.
It is much gentler on the Caribbean side than the Atlantic Ocean side. For the most relaxing conditions with a following St.
Marten with a stop at Saba Island, St. Kitts and Nevis.  From St. Marten it is possible to visit both Anguilla and St. Baths in St.
Marten with a stop at Saba Island, St. Kitts and Nevis.  From St. Marten it is possible to visit both Anguilla and St. Baths in two
easy day sails. Few areas in the Caribbean offer a better contrast in tempo, culture and activities then this. The Virgin Islands
are scattered over a short distance and include some magical smaller islands, that are only accessible by boat.
The Windward Islands in the southern Caribbean part of the chain start in Martinique and end in Trinidad off the coast
of Venezuela, and includes the popular cruising grounds of the Grenadines and the Tobago Cays.
The prevailing winds are east or southeasterly in summer, northeasterly in winter, so the easiest route is to head south,
keeping the wind off the beam. Passages between the larger island of St. Lucia and Martinique can be completed in a day, but
the big difference between sailing here compared with the Leewards is the greater shift in wind conditions in the passages
between islands. The relatively flat Leewards do not interfere as much with wind direction and speed as the steeper ridge
islands of St. Lucia, Martinique and Grenada. The safest tactic is to remain within the lee of each island. The majority of
cruisers head straight to the Grenadines, where there is a lively cruising community and endless opportunity to explore the 30
smaller islands in this area.
The main sailing season in the Caribbean runs from November to July. By the end of July, most Caribbean cruisers are
either back in the states, or waiting out the entire hurricane season in Trinidad or Tobago, or in the "ABC islands": Aruba,
Bonaire, Curacao.
I especially enjoy being anchored off a resort. Knowing that my boat is part of the reason their guests pay so much for a
same Tiki Bars at night, wander the same grounds during the day, and enjoy the same amenities the island has to offer.
The bad news is that there are fewer then 75 Marinas.  Most of which are bunched
knots on this knots on this route the voyage would take 10 days - if you voyage through
the night.   route the voyage would take 10 days - if you voyage through the night.   
Island hopping anchored in a paradise island cove. This is why most sailors take at least
a month  (if not two or three) to cruise the distance.  Some of these places are almost
impossible to leave after you get there, simply because they are so beautiful.   

The islands stretch in an arc from off the tip of Florida to off the coast of
Venezuela, the sailing areas fall into three main categories: the Leewards or Caribbean
side, the Windwards or Atlantic side, and the offshore U.S. Islands. Combined, these
sails between anchorages. The main sailing considerations to consider before shoving
off :
    1. Hurricane season, which runs from June to November.
    2. Fuel range and places to provision.
    3. Fresh potable drinking water.

What may surprise you,
is the lack of fresh water turns back as many sailors, as
lack of fuel turns back power boaters.  The very beauty of the uninhibited islands and
Cays remain uninhibited for the very reason
they do not have (or do not sell) fuel or
fresh water
. So for those vessels that burn fuel, the venture is very limited. For those
that sail, the adventure can be limitless - if they are capable of carrying enough fresh
water, or best of all, have an onboard water-maker.  
Anchored - on the set of
Pirates of the Caribean.
My oldest son John Jr., is a very
accomplished sailor. Here is pictured at
the "End of The World Saloon" on our last
voyage to Bimini Island.
Capt. John - The Frugal Voyager - Capt. John - The Frugal Voyager - Capt. John - The Frugal Voyager - Capt. John - The Frugal Voyager - Capt. John - The Frugal Voyager - Capt. John - The Frugal Voyager - Capt. John - The Frugal Voyager