Key West sailing advise

[BoomerTC]

We did something similar (sailed BVI after our 104). Try Dream yacht, it seems they'll rent to anyone. Literally, when I told them we had never chartered before they said "well, just don't hit anything".

BTW, we had a great time. As long as you know your own limitations you'll be fine.

[QuincyScuba]

Ashtray,
My wife and I lived in Key West for a few years on a boat. We had a friend who ran a small charter service. I haven’t talked with him since we left in 2019, so not sure if he is still there however I feel he would be a good person for you to reach out to for local information. I have sent you a pm with his contact information. Good luck and hope you have a wonderful honeymoon.

[upstateny]

Originally Posted by BoomerTC

We did something similar (sailed BVI after our 104). Try Dream yacht, it seems they'll rent to anyone. Literally, when I told them we had never chartered before they said "well, just don't hit anything".

BTW, we had a great time. As long as you know your own limitations you'll be fine.

We also highly recommend dream yacht charters. The worst case is they put a captain on your boat for a day or two. Thinking about it you could bareboat in BVIs and eat on land most of the time reducing all the work. I believe BVIs has minimal quarantine time now and may require your provisions delivered to the boat, which is not a bad thing. BVI sailing is more difficult Dec to Feb.

[Nicholson58]

Originally Posted by tamicatana

The Keys can be difficult. Shallows, thousands of lobster traps, anchoring is EFFIN’ dicey, thunderstorms pop up…

It’s easier to go to the BVI as far as chartering is concerned. Contact TMM or Conch Charters.

I’d suggest Antigua over BVI

Does it matter to the charter people you talked to how big a boat you take out? Maybe they would let you check out a smaller coat.

Chartering also in the Canadian North Channel out of Spanish or a couple other places. One of the top ten cruising grounds according to some polls. We’ve been there. It’s great but late season can get dicey.

Having a pro captain would make likelihood of a successful cruise very high.

[BoomerTC]

Also want to say that my wife and I just chartered with Navigare in the USVI in May for our honeymoon. First time on a Cat (it was a 42') and just the two of us. CYOA handles their operations in the BVI and they were pretty lax (at least for the Navigare yachts) as well. Just two of us on a 42' Cat was great! A lot of empty space but we didn't mind...

With the twin screws, is was super easy to handle, and we picked up the mooring balls first time every time. The north shore of St John is paradise, and Cruz Bay is a funky town with everything you need.

[Nicholson58]

Originally Posted by BoomerTC

Also want to say that my wife and I just chartered with Navigare in the USVI in May for our honeymoon. First time on a Cat (it was a 42') and just the two of us. CYOA handles their operations in the BVI and they were pretty lax (at least for the Navigare yachts) as well. Just two of us on a 42' Cat was great! A lot of empty space but we didn't mind...

With the twin screws, is was super easy to handle, and we picked up the mooring balls first time every time. The north shore of St John is paradise, and Cruz Bay is a funky town with everything you need.

How did you manage to check in to the BVI and then cruise the USVI? Wasn’t allowed when we were there a few years ago. Something new?

[BoomerTC]

Originally Posted by Nicholson58

How did you manage to check in to the BVI and then cruise the USVI? Wasn’t allowed when we were there a few years ago. Something new?

Sorry - Noticed I said "BVI" and not USVI. Navigare has opened a base in St Thomas that is staffed by CYOA. So on that trip we just sailed the USVI.

[VeinDocFL]

If you are determined to do KW then you might consider doing your 114 course at the sailing school there, with the stipulation that they will rent you a cat for your honeymoon. They get a twofer and get to train you and see you in action before turning over someone else’s boat to you. Try Kimber Tracey with Florida Yacht and see if they can work you in.

[RTChafey]

Have sailed there many times. Weather can be dicey or force to cancel a trip. We just sailed this week between Fred and Grace and got very lucky. But as others have said, not a place to take your first bareboat. Very shallow, Tons of pots/traps to avoid, can be lots of wind.

Just a thought. Book a room @ Oceans Edge Resort and day charter a 40' cat with a skipper, there are plenty of short hops you can make from there or the same can be done from Key West Bight Marina (although Oceans Edge is right on the water with 3-4 pools and you can walk to your boat) longer to get to Duval street is the trade off. Will allow you to be involved as much or as little. On the honeymoon evening, you can drink and enjoy and a captain can bring you in after sunset, you won't be allowed to do on your own.

You could do an overnight if you wanted but as you said, would be stuck with skipper.

[merrydolphin]

As a US Sailing instruction that has certified hundreds of sailors to and through “bareboat” level, I can tell you that NOTHING compares to experience “on your own” with no instructor, just other crew. That is why we required multiple trips out on 30 footers on your own with you in charge, BEFORE you can even take the Bareboat course, a 4 day course including overnight anchoring and night navigation, systems, cooking, close quarter maneuvering in 38-42 foot boats. Its sort of like having to log an allotted time as “solo” pilot before you can carry passengers in a plane when learning to fly.
And as others have said, the Keys are a bit tricky. And weather can be not nice in S Florida. Yes the Virgin Islands are much kinder to the new sailor.
And, if a well recognized charter outfit has hesitation to charter to you, there is good reason as beleive me, they WANT to charter to you any way that they can!
Perhaps a Captain would be a good solution AND give you more learning experience without the pressure and responsibility on you. Remember you are complete responsible for the lives and well being of your crew/guests. The boat can be replaced, you can’t!

[smj]

We’ve been cruising the Keys since before GPS and chartplotters became popular and I don’t understand the negative/dangerous comments. A good chart, basic navigational skills and of course a shallow draft catamaran is all you need!
I do however understand the charter company insisting on a captain for this cruise.

[contrail]

Originally Posted by S/V Illusion

No idea what 104 or 114 signifies but it sounds like you bought the sailing school advertising about what that earns you. No reputable charter business would allow anyone with no experience to bareboat. There are already too many incompetent folks sailing around the Caribbean in charter boats who have no clue how to dock, anchor safely or sail through any shallows.

Making due allowance for the fact that you state you have no idea what 104 (bareboat cruising) or 114 (catamaran cruising) signify, I can tell you that almost all of my past students, over many years, have been allowed to charter, on their own, after the courses. In fact, I strongly suggest they do it as soon as possible, whilst their training is fresh in their minds. I do realize that there are schools that may not have that type of record, but your blanket statement is flat out misinformed.

[BBill]

If you are open to the Bahamas...Cruise Abaco charters cats and has "captain by day and alone at night". Basically the capt sails you to an anchorage and leaves you alone for the night. Then returns the next morning to sail to another location. They are also an ASA school. Capt Mark Gonsalves is the owner and instructor with several boats. Best people you will ever deal with. Mark lives on Lubbers Quarters which is a couple miles from Hope Town.

[PaintedKite]

In many instances you can have the captain aboard for just the first day or two. The, if he gives you the thumbs up, you can put him ashore and complete the carter on your own. Definitely ask them about that.