Visit our Popular Forums

bw1960 · 05-02-2021, 07:54

Hello,

My wife and I have never sailed before. We are looking to spend a week on a sail boat off the southern tip of Florida and sail around the Caribbean area.

My plan is to start with a day 1/2 day trip up in Lake Michigan and see how that goes then take a 2-3 day trip in Florida before testing something longer.

I'm looking for a couple that would like to charter their boat. I did find a website that had sail boat owners who would do such charters but have been unable to find that website again. Any ideas?

Thank you,
Bruce

BCCLover · 05-02-2021, 08:22

You may want to dial back your expectations a bit, both from the POV of trying to find someone (either an individual or a company) willing to charter a boat to an inexperienced sailor to attempt a pretty ambitious journey (Florida to the Caribbean is not a cake walk) and also for the scope of your wishes. It might be that your nomenclature is not clear and you really are talking about chartering for a week in the Florida Keys, which is far more doable given your time frame and sailing expertise.

There are charter companies, I believe, in the Keys, though they might have requirements on either experience or in hiring a captain to accompany you.

Good luck!

**GordMay** · 06-02-2021, 02:00

Greetings and welcome aboard the CF, Bruce.

LittleWing77 · 06-02-2021, 05:14

Welcome, BW & Spouse,

Try the Moorings or SunSail or a Florida Keys Charter company and tell them you have no sailing experience. These are called "skippered charters" (captain alone). I used to be a captain out of the British Virgin Islands (Tortola) and do week-long charters just as you describe where the captain runs the boat for you and you both would help sail it.

The most likely places you will find these charter bases are warm places.

Good luck,
LittleWing77

carlosproa · 06-02-2021, 09:55

How much money are you looking to spend? There are too many outfits catering from the luxury to the penny pinchers:

Boat bookings.com is one of the outfits
VRBO has a section for boats
Clickanboat.com is more affordable
Sailonline.com has a good tutorial for you.

With COVID, things are a bit dicey outside the USA. The FL keys will entertain you for a week, but if you want to fall in love with cruising and relative close to the USA then you cannot beat chartering in Bahamas.
If you are still want to touch US territory then Puerto Rico is not a bad choice. I have no experience in St Thomas or St. Croix but prices are probably double.

DMF Sailing · 06-02-2021, 10:24

Quote:

Originally Posted by LittleWing77

Welcome, BW & Spouse,

Try the Moorings or SunSail or a Florida Keys Charter company and tell them you have no sailing experience. These are called "skippered charters" (captain alone). I used to be a captain out of the British Virgin Islands (Tortola) and do week-long charters just as you describe where the captain runs the boat for you and you both would help sail it.

The most likely places you will find these charter bases are warm places.

Good luck,
LittleWing77

Seconding LittleWing here. There is no better way to learn if you will actually like ocean sailing and/or live-aboard cruising than taking a skippered charter for a week. There is also no safer way.

You don't want your Caribbean adventure to end up the way it did for these guys.