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Old 31-05-2024, 21:08   #16
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Re: 1 season in the Caribbean, what would you do?

Buy in the Chesapeake and head south for the Bahamas is a great plan. BUT going around Cape Hatteras is not something you should try on your first cruise. Get a boat that can go down the ICW (mast 63' or less not counting the vhf antenna that bends under bridges). For the Bahamas get a boat with draft less than 6ft

The ICW is a very pleasant trip in the fall and a great way to get used to cruising and a new boat. First time cruising wives enjoy it too. After you do it 3 or 4 times it gets boring but the first time is a lot of fun and a great way to ease into the lifestyle.

Leave around October 1. Look for an insurance policy that lets you go as far south as Georgia during hurricane season. Waiting for November means you are fighting the crowd and the weather in November is just not very nice until Charleston.

Head to Bahamas in December before the worst of the norhterly cold fronts begin. You can't cross the Gulf Stream if there's a north wind blowing against the current as the waves become vicious. You just have to wait in Florida. In Jan/Feb the wait can be 10 days.

In January and February the nothern Bahamas (Abacos) are pretty cool. Save them for the trip home in the spring. April is the best cruising weather month in The Bahamas.
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Old 01-06-2024, 08:26   #17
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Re: 1 season in the Caribbean, what would you do?

All that is very true. But we are trying to reply to the OP’s desire. Answers fall in 2 categories
1: buy in Florida and limit cruise to Bahamas (NOT Caribbean)
2: buy in Caribbean and sail in Caribbean

Sailing from the Bahamas is either take a couple of months to hash windward and have a very short trip in Caribbean, and a beat up boat OR sail a bit North and EAST so you can make the Virgins or St Martin or (better) Antigua. But then you end up selling in Caribbean.

That is why some of us suggested buying in Grenada or Trinidad (or thereabouts) and sailing NORTH. You do not waste time bashing to the East against the trade winds. Sure, you will spend time in Grenada, but yiu get it back at the end.

Either way this is a tight trip with a risk of failure. I just feel it is better to take the hard part early and then enjoy your visit. Sailing back is easy.
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Old 01-06-2024, 08:34   #18
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Re: 1 season in the Caribbean, what would you do?

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Originally Posted by blackc2004 View Post
I am going to take a sabbatical for one season at work. November - May and buy boat and spend the time in the Caribbean (yes, I have sailing experience). So far of the people I've spoken to there have been two suggestions

1) Spend the whole season in the Bahamas.
2) Join the Salty Dawg rally down to Antigua and then spend those 6 months traveling back north.

If you were doing this and starting to plan it, what would your route/itinerary be or what other suggestions would you have?
Well, you COULD spend the whole time in the Bahamas and relax. Get a shallow draft boat you can poke into the places not commonly visited as well as the normal places. The Bahamas are my favorite part of the Caribe from FL to Trinidad. It's more of a Nature trip. Superb snorkeling.

But of course you can also go pretty far down if you wish. But I wouldn't probably try to go too far. It'll be higher stress.
Once you get past the DR, you can amble and turn around when the time says you should. VI's, St Martin etc are fun. The Bahamas are more fun from a nature side. Further down is more fun for dining and etc.
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Old 03-06-2024, 14:18   #19
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Re: 1 season in the Caribbean, what would you do?

For a 6 months, I'd explore the southern Bahamas then cruise north as the weather warms. The northern Bahamas get pretty chilly during the dead of winter.
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Old 03-06-2024, 14:31   #20
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Re: 1 season in the Caribbean, what would you do?

Consider buying in Grenada - there are generally a reasonable number of good boats for sale and competent marine yards to help with any maintenance. Then sail Grenada and the Grenadines and head up the chain to Martinique or Guadaloupe. Great sailing, great scenery and great people. We had two wonderful seasons and then sold our boat with no problem in Grenada.
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Old 03-06-2024, 14:36   #21
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Re: 1 season in the Caribbean, what would you do?

You said you have sailing experience, but do you have cruising experience (beyond a bareboat charter) and do you have offshore sailing experience? If either of those is a no then definitely go for the Bahamas. Even if they are both yes the Bahamas is still a great choice.

Getting to the eastern Caribbean from the the US east coast mean either sailing from Virginia (or north) to the Virgin Islands (or south/east), or taking the Thorny Path. Taking the thorny path with only six months sounds very unappealing - you will be too focused on making progress when you can rather than enjoying where you are. Sailing from Virginia down is a 1500 mile offshore passage - not something to be taken lightly. A passage of that length puts you in weather that will not be well forecast at the outset.
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Old 03-06-2024, 15:16   #22
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Re: 1 season in the Caribbean, what would you do?

Having done exactly what you’re proposing to do, I would urge you to consider a more focused program of chartering at your preferred destinations. It just takes too much time, money, and sweat (labor) to find, survey, buy, fix up, repair, equip, learn, and sell a boat for this to work in your limited time frame. You’ll come back exhausted not refreshed. Also consider the time you’ll spend sailing to, between and from your destinations rather than actually being there. You could blow weeks someplace waiting for a weather window, or waiting for parts for a critical repair. No Boat is 100% ready to go, most are not even close. Not even a new boat. A truly near ready to go Boat would be top dollar. And it’s fantasy to think you’ll be able to buy a boat, spend money on it, and sell it at a price will cover your costs. I know on the front end it seems like a bunch of charters would be a lot more expensive. But at best you’re going to have only a few weeks of pure enjoyment. I suggest just pay for those and skip the rest.
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Old 03-06-2024, 15:24   #23
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Re: 1 season in the Caribbean, what would you do?

The hard part is getting down to the Caribbean, so considering the boats that are there for sale. Most of them will be well equipped for crusing.
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Old 03-06-2024, 17:37   #24
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Re: 1 season in the Caribbean, what would you do?

There is a Kirie Feeling 446 in Rodney Bay St Lucia that belongs to a friend of mine. He's been sailing it every year from January to May, but he's not getting any younger. He just sold his plane and may be interested in selling the boat. It would be pretty much turnkey.
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Old 03-06-2024, 18:27   #25
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Re: 1 season in the Caribbean, what would you do?

I bought a boat in the Chesapeake and sailed it a few months to discover any bugs and addons I wanted. Then I sailed offshore in early November to the Abacos and had a great winter. It took me 5 days so I brought two friends. ( I don’t singlehand overnights). I did make my way slowly south to Georgetown ( way too busy for my taste ) and then slowly back up North to The Abaco’s and back home. An easy six month trip. I have done this a few more times and I still find new places to anchor. 6 ft draft works well for the places I want to go. The busiest harbors seem to be the ones with the shallow entrances and are not to my taste. Bring a decent dinghy with a good motor. You will sometimes need to cover some distance for food shopping and various fun things like snorkeling etc.
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Old 04-06-2024, 03:18   #26
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Re: 1 season in the Caribbean, what would you do?

It's hard to argue with a full season in the Bahamas. Lots of other cruisers, places to visit, provisions, etc. Also it's close enough to the US that it's a shorter distance back if you need to return early for any unscheduled reasons.
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Old 04-06-2024, 05:18   #27
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Re: 1 season in the Caribbean, what would you do?

Another consideration is the crime situation in your options. Outside of Nassau and grand Bahama islands crime seems to be non existent in the Bahamas. There is a reason that you almost never see dinghies etc locked up in the Bahamas.
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Old 04-06-2024, 05:31   #28
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Re: 1 season in the Caribbean, what would you do?

We are selling our Beneteau 411 located at Nanny Cay Marina, BVI. If you want a turn key boat for sailing next season, you should check it out. We just put her in storage for the summer and if she doesn't sell, will be returning to spend a few months on her next winter.

I get all the comments about any boat you buy needing work after purchase because it's mostly true, but you can't get more turn key than this. You can pretty much hop on Teelin and cruise around the Caribbean then bring her back to the States to sell.
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Old 04-06-2024, 06:44   #29
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Re: 1 season in the Caribbean, what would you do?

I would buy a boat in the BVI coming out of charter this summer, then island hop down to Grenada or Trinidad. At the end of your sabbatical, list the boat with a broker and fly home. No more worries.
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