Thoughts on a Caribbean Itinerary

[sollasollew]

Consider picking up a boat coming off charter in one of the islands. You might even be able to approach a charter firm with your idea in mind and inquire about their willingness to help you outfit. I recently chartered in Belize and was not happy with the condition of the boat provided by Moorings. I chartered some years back in BVI from Horizon and would most certainly consider purchasing a boat from them. One benefit of this strategy is that you can get to know the boat (at least the brand and model) before committing.

Eric

[dmgjgmd]

I second the suggestion made by Eric. The biggies (Moorings, Sunsail, etc) will not have the time to mess with you. However others such as TMM may be willing to help you out. I would suggest talking directly with a company owner, and explaining your situation. Typically they will know a year in advance which boats are going to leave their charter fleet. I would then visit their base, and charter the boat you are considering. If it fits your needs, you could then negotiate a purchase price with the owner, which might save brokers fees. If you did not enjoy being on that particular boat, then no deal. The charter company could do any repair work you need, and at reasonable rates. I would insist on talking with both the charter company owner and the boat owner. Most of the charter companies have several bases in the caribbean. Negotiate use of their facilities at other bases as part of the deal. The problem will be selling the boat when you are finished with your sabbatical.

[robbie_d]

Ditto on a couple things..
Osiris Plan is a good one but you can do it on your own boat if you can't get a long term charter.


The Islands are changing FAST... the only thing for sure is they are no longer remote destinations but mainstream tourist traps.. charter bases, resorts and a LOT of cruisers means you will be pinched for anchorages if not forced onto moorings and services will be expensive..Trinidad this year is more expensive to store my boat for hurricane season than sailing it back to the states. So don't expect to be able to live cheap..on a cruise from Trini to FL checkin/customs/cruising permit fees alone now will set you back over $1000 dollars the Bahamas and DR alone are around $500..

Again...don't spend your winter bashing to weather..yes you will spend weeks waiting for weather windows if you come from FL but going South from St Marteen and then back west afterwards is easy all the way..
Get a boat anywhere from the Virgin Islands eastward...You have to do the anegada passage to get to STM but that will be your only test by fire and it's doable most of the time.. 90 miles..do it Overnight..don't give up!!

The big guys do have lots of boats that they hand off to the soon to be glutted with boats guys..moorings boats after 5 years go to Barefoot..you may be able to cut a deal to charter an older boat long term and then deliver it to FL where they sell faster..also don't worry about a BIG or Blue water boat..don't bother "outfitting" the boat....you can buy anything you need down here. In 6 months you will not use enough water to justify a water maker you will never be out of VHF range except for twice maybe so a SSB is not required and you can check weaher on the internet at every island which it only ever takes a day to go from one to the next. Other than a couple passages you can go between islands in a dingy if you watch the weather and smaller shallow draft boats have more anchoring options and are all around less expensive..see number one..

Itineraray depends on where you get the boat but head south first..then head for the Bahamas in mid april-may and do them May -June..you miss the cold fronts that way...
Sell the boat somewhere on the east coast..way easier than in the islands and cheaper now too...

[stationr]

I know this much: Chartering is NOT cruising. First, a disclaimer about my own ignorance: I have never been south of Luperon. But I'm not sure I missed much. Beach bars, jammed mooring fields, music blasting over anchorages, sunbathing, water toys, expensive restaurants and shopping...much of what I have heard about chartering in most Caribbean islands is more of a tourist nightmare than a cruising dream. Great for the sunbathing, rum punch, dancing on the deck crowd, but not for me. Sure, I'd like to see it all some day (even Disneyworld is fun for a day or two) but in some ways the "chartering grounds" are more of an obstacle than a destination in my mind.

I suggest that it makes perfect sense to buy a boat in Florida, peferably one that is already outfitted properly, and sail it south. But don't plan on going past the Bahamas or at most the Dominican Republic. The Exumas are at least as beautiful as the Virgins (some say more beautiful) without all the tourist traps. Even at the height of the season, when there are 500 cruising boats in George Town, you can have a tropical island anchorage all to yourself if you get off the beaten path just a mile or two. You couldn't do it justice in a month or even two, but six months is more than enough time to take a relaxed tour of the Bahamas.

You'll need all three Explorer Chartbooks (you must have the books but even better if you can also have the electronic versions available for Garmin and some other chartplotters), a good VHS, and yes, you will need at least an SSB receiver to get weather or you will have to contact other cruisers who do have one to find out what's coming on a daily basis, because you need to be in the right places for those cold fronts. A watermaker is only needed if you plan to spend weeks anchored at Samana or some other non-inhabited island. Read the Pavlidis guides and Bruce Van Sant's book, find a buddy boat to cross the Gulf Stream, and wait for a good window, and you're set.

When we headed south I was looking forward to getting down to the Virgins and "paradise." We got to the Exumas and I realized we were already there.

[Osiris]

Well, I have been south of Luperon for the last 4 years or more. And what you will find is some real fine and quiet "paradise" islands and anchorages. Puerto Rico has some excessively loud places - it's the Latin thing to blast out music on weekends are 80 billion decibels in the cities and large marinas that the local frequent to party. But there are plenty of small coves that are quiet enough to hear a fish fart.
It is all about what you are looking for . . . you can find loud, fast and hip-hop fun places and you can find laid back family type places and you can find very quiet and peaceful solitude places for lovers and naturists. So each place offers whatever you are looking for and you have the option of going from one style to another as the mood fits.
The more "hopping" places are in the Leewards and northern Windwards while the more family and quiet places are in the lower windwards. Trinidad is not a "Caribbean Island" - it is an industrial gas / oil "big city" kind of place. You go there to get out of the "hurricane box" or to safely store your boat while you fly back home. Otherwise you cruise the Caribbean Islands from Grenada north and west to Puerto Rico. The guide books for cruising - IMHO - Chris Doyle's series are the best and most useful will give you the flavor and information about each place.