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Caribbean Routing


This document was initially prepared for our European, Australian and New Zealand friends who were crossing the Atlantic and wondering what to see and do when they arrived in the Caribbean.  I subsequently added an additional section when we met many US cruisers in Georgetown, Exuma who were venturing south for the first time and wondering where to to go next. US cruisers can jump to that section by clicking here.

Suggested itinerary for US and Caribbean Cruising when arriving to the Caribbean from Europe

The Caribbean is usually thought of as just the Lesser Antilles –that is the string of islands from the Virgin Islands down to Trinidad.  But there is much more to see than those islands, and cruisers who are anxious to get to the Pacific usually don’t see the best spots and miss out on lots of fantastic cruising.  The Western Caribbean, Bahamas, the islands off South America and the US east coast are all worth exploring. 

 We spent over a dozen years knocking about the Caribbean before starting our circumnavigation and we know some fantastic spots we would like to tell you about.

 In my opinion by far the best part of a circumnavigation is cruising the Caribbean, the US east coast and the So. Pacific.  The biggest difference between Med cruising and Caribbean cruising for me is that in the Med nearly everything we did was done ashore and in fact we saw and did very little that was not the same as land based tourists saw and did.  In essence our boats provided us few advantages over land based tourists and in many cases lots of disadvantages.

In the Caribbean most of what we do is water based and the fact that we are on a boat gives us experiences that others simply do not get.  Beachcombing on deserted beaches, having entire islands all to yourself,  snorkeling for weeks day after day and finding it different and unique every time and feeding yourself off of what you catch or spear- these are for me the essence of the Caribbean.  Plus lots of cruisers and beach parties and a life that revolves around the cruising community.

 Since our lives are ruled by the weather and seasons and most of you are eventually heading for the Pacific let’s jump ahead to the timing for that.  You will want to transit the canal in February or March so you can leave for the So. Pacific in March or April. 

Since you will be getting to the Caribbean in January it is possible to continue on to the So. Pacific but if you are doing that I think you are really missing the point.  

So the real question is one year or two years (or more) in the Caribbean before you transit the Panama Canal.  I would suggest two years though you can see quite a bit in one year. 

 The other weather pattern that will rule your decisions is getting out of the hurricane zone.  Hurricane season is from June 1through November 30.   In the last dozen years it seems to be shifting later in the year and more and worse storms in the later part of the season.  Hurricanes also come up the East coast of the US but protection options are better than in the islands.  Most insurance companies require you to be south of 12 degrees 40 minutes latitude down near Trinidad or So. America or north up in the US during hurricane season.

 The One Year Plan

If you decide on one year the best option in my opinion for seeing the most and missing the least would be to arrive in Tobago at Charlotteville and then work your way north up the island chain through the Bahamas to the US by summer.  Then spend the entire summer cruising up the US east coast to Maine.  In late August or September turn around and start south so that by early October you are back to Annapolis, MD on the Chesapeake Bay. 

 Attend the Annapolis Boat show which is one of the largest in water boat shows in the world in mid October, then hustle south either on the Intracoastal Waterway or outside in the Atlantic.  In December visit Cuba then spend January – March visiting the western Caribbean and getting to Panama in time for your April crossing of the Pacific. 

The highlights of this route are seeing nearly all the islands of the Antilles, the magnificent gin clear waters of the Bahamas, visiting the US including New York and Washington, DC on your boat. Seeing Maine’s rugged coast and Cuba and the much less traveled areas of the Western Caribbean. 

 The only real disadvantages of this route are you are missing Venezuela’s offshore islands, Bonaire and Cartagena, Columbia, and the fact that you will be moving pretty steadily.  You will touch on lots of places but not do most of them full justice.  But if you only have a year I think this would be the best way to spend it.

The routing would be from Tobago up through the Lesser Antilles island chain to the Virgin Islands, on to Puerto Rico’s south coast, Hispanola’s (island of the Dominican Republic and Haiti)  north coast, Turks and Caicos then off to the Exumas and Abacos in the Bahamas and the US coast.

Southbound the next fall would be Cuba, Isla Mujeres, Mexico then south to Belize, Guatemala, Bay Islands of Honduras, then Panama’s San Blas Islands and the Canal.  This will involve some windward work in the trade winds but is doable.

My real recommendation and a much easier route is a MINIMUM of two years in the Caribbean.

 The Two Year (or more)Plan.

The two year option would be landfall in Tobago then go to Trinidad for Carnival (mid February) - which is a fantastic lifetime experience.  Then between March and June you visit the western Caribbean with the goal of arriving in Florida by hurricane season (June1).  You will sail through the islands along the So. American coast but not spend much time there as you can do more the following year.  The goal is to maximize your time in Central America.   You then spend your summer cruising the US East coast north to Maine, arriving back south to Annapolis for the boat show in October.  November you come down the ICW down to Florida.  Then you spend the winter visiting Cuba, the Bahamas, and hopping your way down through the Lesser Antilles islands to arrive in Trinidad by June when hurricane season starts.  After doing whatever boat work is necessary in the yards there, you then spend the summer moving on across the top of So. America visiting Venezuela, the ABC islands and Cartagena, Columbia to arrive in Panama near the end of the year.


This itinerary visits 90% of the areas you want to see, plus for those cruisers going slow and desiring a third season, there are numerous options to leave the boat for more inland

travel in either north or South America.  You can drive a campervan across the US to see the Rocky Mountains and Grand Canyon, travel inland in Mexico and Central America to see the Mayan and Aztec pyramids or go down through So. America visiting the Amazon Basin, the magnificent Inca civilization at Machu Pichu and Patagonia.  Boats can easily be left in Trinidad or up the Rio Dulce in Guatamela or in the US itself.

 The routing would likely be Tobago, Trinidad, Venezuela’s offshore islands, Bonaire.  Then you have a decision to make- your next goal either is Providencia or San Andreas Island.  To get there you can continue short hops through Curacao, Aruba and Cartagena or just take off from Bonaire which will give you a more off wind but longer sail. Then enjoy Honduras, Guatemala, Belize and Mexico.  Depending on your timing you can either do Cuba before reaching Florida or visit Cuba the next fall on your way south.  From Florida the route up the east coast of the US is the same as in the year one plan- ie June through November to go up north and back south.

That puts you back in Florida in November, ready to head south as winter arrives.

The traditional route south has been Abacos and Exumas in the Bahamas, then to the north coast of Hispanola (the island of DR and Haiti), however more and more boats now go through the Windward Passage and do the South coast of Hispanola, then the south coast of Puerto Rico to the Virgin Islands.   From the Bahamas to the Virgin Islands will be to windward but the guidebooks will explain good strategies to accomplish this and dozens and dozens of boats take this route every year. Usually the strong easterly winds really won’t kick in until about 22 degrees south.

 Now let’s talk a bit about each area and I will tell you our favorite spots.

 In the Caribbean the wind blows 15-25 knots from the east all year long.  You sail north and south so are always on a close to beam reach in good winds.  Because most of the islands are large (20-25 miles long) and run north south the swell does not wrap around the entire island, so almost all the islands have fantastic secure anchorages on their lee (west sides).  Only a few places have rolly anchorages- (Tobago, Saba, Statia) and in these cases a stern anchor or bridle usually takes care of it.  We find in many anchorages the outer part will be rolly but if you go ALL the way to the head of the bay it will be much calmer and less rolly.  Our recommendation is don’t be shy about motoring up to the head of the anchorage and looking for an open spot.

Generally each island is its own country and each is an easy day sail apart.  Most hops island to island are about 25 miles with half of that being in the lee with no swell and half being in the open gaps between the islands.  Some islands you might stay a few days, others a few months.

 There is a seasonal wind shift from NE to SE from January – June but it is minor.  From the Caribbean all the way to the US should be downwind on either route.

Navigation Notes:

We like the Doyle cruising guides for the Caribbean.

Old guides are usually OK but for the ICW along the US East coast make sure to use a current guide as some dredged spots and markers do change.  Also make sure you understand the ICW’s unique buoy marking system.

In the Caribbean and US we use a different buoyage system- all US sailors learn “Red, Right, Returning”-   that is keep the red buoys on your right side when returning from sea.

 Favorite Spots –
Trinidad and Tobago
Tobago Cays
Iles des Saintes
St. Barts
St. Martin
St. John
Bahamas- Exumas especially
Carolinas- US
Washington, DC and New York- US
Bay Islands-Honduras
Guatemala- land touring
Bonaire- scuba diving
Aves and Roques-Venezuela
Cartagena, Columbia
San Blas- Panama


Tobago. --If possible stop at Charlotteville on the far east end and take a bus in to Scarborough to clear in.  (If customs demands it you will have to go to Scarborogh to clear in but by then you will have enjoyed Charlotteville for a few days – it is the best spot on the island). 

Tobago is one of the least visited islands because it is upwind from the others.  10 years ago there was minimal tourism so it was a pristine place.   It does have a few rolly anchorages unlike most of the islands because it sort of runs E-W rather than N-S.

Go to Sunday school in near the airport- a party with pan music that starts at 5 pm Sunday and goes til dawn Monday.

 From there go to Trinidad- different island same country.  Birthplace of Carnivale-

Carnival is in February and is a week long party of unbelievable proportions.  However, much of the cool stuff is the lead up to it so you need to get there 3 weeks early for many of the events.  There are no spectators for Carnival- just 60,000 participants-including you.  (And 30,000 of them are the MOST BEAUTIFUL WOMEN IN THE WORLD— honest Trini women are the most beautiful we have seen anywhere!!  Trinidad is a unique place in that the cultural talent in art, music and dance are unrivaled for a country this size.  It is also an excellent place for boat work with lots of big yards that can do any repair.

 Near Venezuela buy their Anniversario aged rum for $6 or the nearly as good Cacique for $3.  

 Tobago Cays- atolls like the So. Pacific- nothing between you and Africa but a few feet of coral reef.  Fantastic snorkeling and beach parties.

Bequia- a small traditional island where they still go after whales in the traditional manner they have for centuries -in 18 foot skiffs with hand thrown harpoons. Every 2-3 years they get one and it feeds the entire island.

 The French islands are sophisticated and in places, fancy; the other islands low key.  You can load up on cases of fantastic French wine for under $4 per bottle. 

 Iles de Saintes- small and quaint with French charm and great baguettes.  No air service so it is less crowded and touristy.

 St. Barts- sophisticated but in a good way.  Jimmy Buffett used to live here and it is the real home of “Cheeseburger in Paradise”.

 Antigua- The Classic yacht regatta is a fantastic sight with boats as old as 100 years.  And don’t miss the weekly party and BBQ at Shirley Heights overlooking the bay.

 St. Martin- the French side- awesome restaurants at Grand Casse and the best nude beach in the world at Orient Beach. Plus two giant chandleries.

 BVI- as easy as cruising but lots of charter boats and moorings in all the bays.   However the great scenery and hundreds of comfortable anchorages and pure ease of cruising there explains why it is the world’s most popular cruising grounds. 

 St. John- really pristine.  A US National Park.

 The Bahamas-- totally fantastic- almost as good as the So. Pacific.  Super friendly locals and gin clear water.  Anchor  in 5 meters over blindingly white sand, then swim over to the coral reef nearby and spear a grouper or lobster for dinner- that is in the unlikely event you did not catch a 20 lb  Mahi mahi while trolling earlier in the day.    Have an entire 5 mile long beach to yourself.  The main downside to the Bahamas is you get sick of eating lobster, conch and Mahi mahi as they are all so plentiful.  (And there are even more of them in Cuba).  Mostly shallow waters so superb snorkeling and no need to scuba dive.


Carolinas- buy fresh shrimp for a few dollars from the shrimpers you pass on the ICW.  A unique part of the US.  Visit Ocracoke Island, Charleston, Hilton Head, Savannah and other great cities of the South.

 The entire coast of the US is filled with fascinating anchorages and friendly places and people.  Most of the time you will have a good anchorage just a few miles away. 

 New York is wonderful and not too expensive at the marina in Manhattan or the ones on the New Jersey side.  Take the subways into NYC or use the ferry from NJ to Manhattan.

The trip up the Potomac to Washington DC is very worthwhile.  Instead of a $200/nite hotel you have your boat anchored in the heart of the city off the Washington DC Yacht Club.  The facilities at the DC yacht club are excellent and used to be very cheap. 

Spend a week seeing the Smithsonian Air and Space Museum and all the government stuff.

 I suggest going all the way north to Maine which is fantastic. If you are in Maine in August or early September that is perfect.  Lobster pots everywhere and hardy Maine lobstermen coupled with rugged scenery. 

 Get south as far as Annapolis, MD in the Chesapeake by mid October for the boat show.  The Chesapeake could provide a lifetime of exploring in itself.  After the boat show make tracks south down the Intracoastal Waterway (ICW) or outside as needed to Florida.

 We have not visited Cuba but everyone raves about it.  Unspoiled.

Belize has fantastic reefs – atolls like the south pacific.  Visit Glovers reef.  Scuba dive the blue hole.  Fantastic snorkeling. 

 Bay Islands of Honduras- Snorkel with Whale Sharks off Utila.  Fantastic diving at Roatan and Utilla.  Utilla is the cheapest place on the planet to get certified as a diver if you are not yet one.

 If you get stuck in this area you spend the hurricane season safely up the river in Rio Dulce in Guatemala from where you travel inland.  Really fantastic Mayan Indian descendents throughout the country.  Wonderful markets near Panahachel.  Leave the boat for travel to So America if you want. Do the Amazon and Macchu Piccu and Patagonia and the Chilean channels - via the car ferry from Puerto Mont.

 Bonaire- world class scuba diving.  Easiest place in the world for diving from your dinghy.  Great place to get certified if you aren’t yet a scuba diver. 

Venezuela-  The Aves are like a Pacific atoll- uninhabited and you can stay for weeks feeding yourself on the fish you catch.  The Roques are small isolated islands that do not see many visitors.  Both are awesome diving and snorkeling with plenty of fish and lobster to eat.

 Cartagena, Columbia- classically beautiful Spanish city.

 San Blas- home to the Kuna Indians – a matriarchal society where the women control the wealth and run the family.  Friendly and very photogenic.  And you will buy lots of Molas-  fabric art pieces.

 Because the wind in the Caribbean is nearly always easterly when you do encounter one of the few rolly anchorages you can usually rig a bridle to keep you into the swell.  This can be done with just your one primary anchor.  If you are not sure how to do that you can read about it on my website at www.ventanasvoyage.com  then go to the seamanship page.

 At some point read the articles on my website about So Pacific routing and my secret of how to spend 6 months in French Polynesia instead of the 3 they normally allow. Click here to go there now.

Suggestions for US boats heading south from Georgetown, Exuma.

Every year a large number of boats jump off from Chicken Harbor and make the passage south to Puerto Rico and the Virgin Islands.  The suggestions that follow present a possible multi-year cruising scenario for those boats.  Leaving GT you can visit Long, Rum, Conception as time allows, and then follow either the suggestions in Gentleman's Guide to Passages South by Van Sant, or the newer suggestion in the free Cruising Guide available online which advises going to the South coast of Hispanola rather than the north.  We have gone direct GT to Puerto Rico once,GT to Luperon on the north coast of DR once,  once via Turks and Caicos for fuel, and once direct from Norfolk, VA.  We have not tried the windward passage route south of Hispanola so we cannot comment on that.  The other routes all involve windward motorsailing work but pretty much follow the Van Sant descriptions.

Regardless of when you arrive in Puerto Rico enjoy its south coast and the Spanish Virgin Islands, then St. Thomas and St. John in the USVI and then the BVI.  If it is still early in the season you can start southwards via the island chain, and if in a hurry continue on towards Central America during the hurricane season; but for most boats who are on open ended cruises, you will have enjoyed slow travel through the Bahamas and it is now approaching hurricane season so you will need to get south.  

My suggestion would be to go to St. Croix then depart from there.  Depending on what course you can lay you could head for St. Lucia, St Vincent and the Grenadines, Grenada or Trinidad.  It will be a 3-4 day passage.  If you can lay St. Vincent you can enjoy that area then from there do an overnighter to Tobago (not the Tobago Cays).  If you arrive in Tobago by July 1 you should be OK with your insurance policy.  Enjoy Tobago for a few months then move on to Trinidad to spend the rest of the summer, or alternatively if your insurance policy allows you can also spend time in Grenada.  If you were unable to lay the St. Vincent area you will likely just end up in Trinidad missing Tobago which would be a shame.

Enjoy the myriad of activities Trinidad has to offer, do your boat work, fly home or fly off to South America to explore inland.

In November or December when the hurricane season is over make a 4 day passage north to the VI.  Then as you slowly head south through the islands, the combination of the curving island chain and seasonal winds moving from NE early in the year to SE by April gives you predominantly reaching conditions.  (If you island hop north you will be hard on the wind all the way to Antigua).

If you don't leave Trinidad in December and want to join the biggest party you can imagine you stay in Trinidad until carnival at the end of February then follow the same route.

Year two then finds you back in Trinidad in June.  Do your boat work, travel home if you need then proceed through Venezuela's offshore islands to the Roques, and Aves.  Next is Bonaire for diving and snorkeling, Curacao and then westwards.  Aruba does not offer much for sailors but does have casinos and cruise ships. Continuing on your circuit you now approach the Western Caribbean which is markedly different from the Eastern Caribbean Islands and has far fewer boats. 

From Curacao either coast hop or make the 4 day jump to Cartagena, Columbia.  Another short overnighter will bring you to the San Blas, Islands of Panama. If Panama grabs you head to Bocas del Toro.  You can spend hurricane season in this area or farther north in the Rio Dulce of Guatemala.  Your trip north will be much easier if you wait for a calm period and retrace your route to get at least as far east as the San Blas or even Cartagena before making the jump to Providencia Island, the Vivorillos Cays and on to the Bay Islands of Honduras.  From there you go up the Rio Dulce in Guatemala to be safe for hurricane season.  If you are a very deep draft boat check out the clearance on the bar before counting on this option.  After the Rio experience you enjoy Belize, Mexico, Cuba and are then back to the US.

Then you can start over and do it all again.

If you only read the US cruisers section I suggest you also read the  previous section as there are more details contained in those descriptions.



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