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Old 05-12-2016, 18:48   #1
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Help/advice - Lewward / Windward Islands First Timer

I'm recently retired and want to take advantage of a window in time to travel and cruise the Leeward / Windward Islands before grandchildren come along.

Help needed: your thoughts and advice on my high level, rough, plan for buying a boat that is retiring out of the charter fleet, already located in the Eastern Caribbean (probably BVI), sailing the Leeward / Windward Islands for one season (Nov 2017- June 2018) from Saint Martin down to Grenada and back up again, and then selling the boat. My follow on plan is to move on to live/travel in Europe for a spell thus the reason for selling the boat.

While I've been sailing/racing for 35 years, done some chartering in BVI, have USCG 25T Masters, ASA Instructor, etc., I've really haven't done anything of this magnitude.

- The boat.
I'm sure everyone says this, but I'm hoping to take my time, and advantage of a large number of boats for sale, and make a good deal on a boat coming out of a charter fleet that a surveyor would say looks to be in great shape. I really don't want to spend a lot of time, or money, fixing or outfitting the boat for what amounts to an 8-9 month adventure. Ideally the boat will already have most of the right amenities and equipment for the trip. I've just started looking, but so far the Jeanneau 32i or 36i has my eye. My budget for the boat is $55-$65K (USD). Ideally when we are done I hope to sell and not lose more than $5-10K. Doable?

- The route.
I'm trying to get my mind wrapped around places to visit and timing. I'm looking at Chris Doyle's guide (Leeward & Windward Islands) which appears to be a great resource with lots of detail. To start with, however, I'm interested to know any overarching thoughts on gotta see places, hints on routes, events (e.g. I'd love to plan timing to be in Antigua for Classic Yacht Regatta), etc.

Your wisdom and experience would be greatly appreciated!

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Old 06-12-2016, 03:40   #2
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Re: Help/advice - Lewward / Windward Islands First Timer

Greetings and welcome aboard the CF, Mike.
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Old 06-12-2016, 04:42   #3
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pirate Re: Help/advice - Lewward / Windward Islands First Timer

Ditto... Welcome..
Contact Moorings in Tortola if your looking for something being decommissioned.. when I bought my Beneteau 331 that's who I bought from.. a 2001 boat bought in '06 for $60,000.. they were asking $65K.
Looked at what Sunsail had to offer in my price and the selection was crap.. poor overall condition/upkeep.
Get your surveyor from off island..
You'll likely have to buy a dinghy and outboard and a few other bits and bobs but.. St Martins only 80odd miles to the East where you can get most everything you'll need at the best prices in the Islands.. the boats are flogged off pretty basic as for charter one does not fit solar etc.. however you can work a good deal on new sails if you want through Moorings as they bulk buy from Doyles.
At your budget you'll be restricted to under 35ft.
Would not worry to much about your abilities going on your resume as its all really day hopping in the main.. leave mornings and arrive evenings.. the BVI-SXM hop is about the longest.. unless you go right down to the Dutch islands off Venezuela.. where its the coming back up islands back to Trinidad will make the start of the trip seem a stroll in the park..
Better to just beam/close reach back up to St Martin.. a 3-4day run.
Selling is more difficult.. look at 1-2yrs for finding a buyer.
Why not just sail her back to Europe.. jump off from SXM in June for the Azores and you can be in Portugal/Spain by August.. after a couple of weeks doing those islands..

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Old 06-12-2016, 18:40   #4
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Re: Help/advice - Lewward / Windward Islands First Timer

Thanks for the reply boatman61 !

A Beneteau from The Moorings would be great too. I'm definitely not hard over on the Jeanneau, and I'm okay with under 35 feet if I must.

I made an initial contact with a broker on Tortola to help find the boat and facilitate the transaction. My thought was to keep an open mind to either boat in order to have a better chance of finding a boat in decent shape for the best price. Do you think it's better to work directly with the charter company versus working through a broker? Advantages, disadvantages?

When you say use a surveyor from off island, is the concern that someone who works on the island day-in and day-out may have other conflicts of interests? I was thinking that someone familiar with the typical problems found on boats coming out the charter fleet might be more likely to know what issues to look for.

I wasn't thinking of going as far as the Dutch islands off Venezuela, maybe stopping at Grenada, but I really have don't have a basis other than I just don't want to feel rushed to make it back before June.

I like the out-of-the-box thought of sailing across to Europe! My wife, however, is set on being land bound (maybe Croatia) for a year or so and travel about (I.e. Not by boat)....that's the deal

I hope it doesn't take me 1-2 years to sell the boat, but you're right I need to factor that possibility into my plan.

Thanks again!

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Old 06-12-2016, 18:50   #5
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Re: Help/advice - Lewward / Windward Islands First Timer

Boats come out of charter May, June.

Contact Moorings/Sunsail Brokerage, Florida for the full list of boats in the Caribbean.

Dont restrict yourself to BVIs. Each island in the Caribbean has charter boats except St Barts and Anguilla. Ummmm, OK, and Monserat, St Kits etc
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Old 06-12-2016, 19:53   #6
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Re: Help/advice - Lewward / Windward Islands First Timer

Thanks MarkJ!

Good point...I'll definitely give them a call. I supposed it should have been obvious, but it never occurred to me that the list of boats coming out are likely knowable right now.

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Old 06-12-2016, 20:03   #7
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Re: Help/advice - Lewward / Windward Islands First Timer

MarkJ, good post.

Sorry side question, what about keeping two boats? I've started to think about this. Keep one in Europe for the summer and fall. One in the islands to winter on...anyone done this? Thinking the same size mid to upper 30s. Have the one for the islands, just need a euro boat...maybe even canal.
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wind, Windward Islands

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