Key West sailing advise

[tamicatana]

Totally didn’t think about the KL hotel and boat guys, very good suggestion.

https://www.keylimesailingclub.com/amp-home/

Old Keysey, not high end resort. They had a TPI Lagoon cat (Endless Summer) that they took pax out on for sunset cruises. When last I was anchored in the cove, the fella had one of the 1988 America’s Cup catamarans that he planned to fix up and charter. You get a 22’ Catalina with your room. Water toys. Neat bar next door. IMO, good choice.

[Gary5122]

Just the 2 of you for a honeymoon on a catamaran? Sounds like a lot of wasted space and constant work for the two of you.

[JasonS]

Having sailed the Keys on our 40 foot catamaran this entire winter and some time every year for the last 8 years, I would t recommend going on your own for a honeymoon. Safety aside, it’s a lot of planning, work, and potential for stormy weather. It could be a short marriage! Either get a captain/chef (interview them prior to booking) or do a land based honeymoon and rent boats. There are quite a few properties that include day sailboats on their amenities list. And so much to do in the Keys. Enjoy your honeymoon!!

[dksail]

We had to hire a captain in Croatia for a trip because of license requirements that we did not have. I was really bummed but it turned out to be the best thing ever. Our captain knew all of the best spots, got us into restaurants that we didn’t know about, cleaned the boat, caught the fish, and took all the stress away. We had 15 years of sailing experience at the time, and it was worth every penny.

We had lots of privacy when we wanted it, and so did he. It will depend on the captain’s personality.

[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.

[Library70]

It's possible that a captain from the charter company could spend a day or two on the boat with you and then sign you off for the rest of the week. It's worth asking.

[boatman1]

Well, assuming the cat renters that you’ve spoken to change their minds and agree to rent bareboat, or you find another boat, you might have an idyllic time, or it more likely prove to be a chore. It’s hot and frequently flat calm (or blowing a hurricane) in September, so expect beaucoup motoring. Unless you really want to go to Fort Jefferson you’ll probably putz around up towards Content Key and/or Newfound Harbor. Protected anchorages and good cruising, but September? I think that the several previous responders to your original post who’ve suggested staying ashore somewhere on the keys makes sense. If diving is an activity that attracts you, you’ll most likely enjoy a better experience staying at a place that can get you out to the good dive areas (probably in a nasty old powerboat) . The most romantic, memorable, honeymoonish memories that I’ve got were on a hobi cat - you can rent one of those for sure.

[Peeew]

There are companies out there (cruise Abaco comes to mind if you don’t mind the Bahamas) that will put a captain on board for as many days as you need one and will remove him/her daily after you are anchored or docked. It’s a nice way to have privacy while learning.

[capn_billl]

I third the Sailing cottages.

You get a no stress sail. You aren't challenging yourself in what should be a relaxing time.

I'm taking a cat down to Key west AFTER hurricane season which September is peak.

Get a short bareboat on a less challenging itinerary after the honeymoon when you get more sailing hours under your belt.

[Herb Miller]

The Key Lime Sailing Club has already been mentioned, and I heartily endorse it. That is where I learned to sail, and was able to take some ASA classes.

You might check with them to see if they will be offering another ASA course that you would like to take while you spend a week or so with them.

The cottages are quaint and private. There is one that is right near the shore. Good luck!

[mcon12000]

I just spent the last six months down there and you DO NOT want to go to Key West on your first solo sail let alone honeymoon. It’s way too dangerous for many reasons.

1. Anchoring anywhere in the area is sketchy at best and the wind is unforgiving. That’s why they call it the bowling alley.

2. The mooring field is the only somewhat safe place to spend anytime and even that’s not guaranteed. I had $17k worth of damage from a boat that broke off its mooring and crashed into me.

3. Other than snipe point the area isn’t exactly a sailing paradise.

4. All those boats you see in the photos anchored everywhere are not what they appear to be. Most are secured by homemade moorings not typical ground tackle and never move (on purpose).

5. The Gulf side is an unimaginable field of lobster traps truly unlike anything you’ve ever seen. The tethered floats tend to stretch just below the surface in the shallow (12’) water making it very difficult to determine what’s a miss and what will be a wrap.

6. Back to “The wind!” It’s either blowing 25knts or it calm and I would say it’s calm 15% of the time. Plan on not getting to shore dry at times and some people (not me) won’t even leave their boats when it starts blowing.

Stay north of Key West or consider another destination entirely it’s too dangerous and difficult for anyone just getting started. It’s your honeymoon and I know from personal experience that Key West is not a great way to start the marriage or the sailing experience.

[Sailing Ohm]

The keys can be a relatively difficult place to sail. There is a lot of local knowledge that comes into play.
The thunderstorms can pop up very quickly and will be very unforgiving. They will create very steep waves with short periods in hawk channel of the gulf and can easily damage gear. In winter, the north winds can be strong and will be opposite the current so they’ll create monster waves.
There are relatively few places to safely anchor and there are also many potential dangers due to reefs that an inappropriately anchored boat could damage and be damaged by. As far as money goes it’s likely more costly to damage the reef than to be damaged by it...
You are also in a place where you will assuredly be beating into the winds most of the time (dominate from E-SE) unless you run down to the Tortugas (which are very far away and incredibly remote and likely off limits).
You are also doing this in a relatively narrow area because if you venture outside of hawks channel you are competing against the Gulf Stream.
The gulf side has many many shoals that are constantly changing and can be difficult to navigate.
This also doesn’t take into account the lobster pots which can be horrendous. Literally tens of thousands of them sometimes every 30-50 feet.
I can totally understand a company mandating a captain especially if you have little practical experience.
There aren’t thousands of shipwrecks there because it’s easy.
I also don’t think the northern keys are any easier contrary to what some have said. In fact I think they are a more difficult sail, especially around key largo, as the reefs tend to be shallower and more numerous.

The Keys can be an amazing place to sail when things are ideal but it can also be very unforgiving and can change from perfect to difficult quickly.

[mountaindweller]

I would really look at reconsidering Key West and head for the BVI's. It's really the best place to "dip your toe in the water" after getting your ASA certs. Smaller charter companies, like Conch Charter, have older boats, but would likely turn you loose after a day or two with a captain. Worth checking into. I would wait until after the end of hurricane season. Best of luck!

[nolakennedys]

Originally Posted by tamicatana

Totally didn’t think about the KL hotel and boat guys, very good suggestion.

https://www.keylimesailingclub.com/amp-home/

Old Keysey, not high end resort. They had a TPI Lagoon cat (Endless Summer) that they took pax out on for sunset cruises. When last I was anchored in the cove, the fella had one of the 1988 America’s Cup catamarans that he planned to fix up and charter. You get a 22’ Catalina with your room. Water toys. Neat bar next door. IMO, good choice.

Thank you for that link! Thats very cool, my family and I may take advantage of that prior to sailing down to the keys.

[upstateny]

My wife and I have bareboated with two other couples in BVIs and st Martin for total of 7 weeks over 4 different years never with captain. One of our friends owned a 36’ Pearson. We took 101 and 103. Our 1st charter was with the Moorings in Tortola on a 44’ mono. A captain went out for a sail to check us out. We raised the sails, tacked a few times, and he said ok you guys know what your doing. We took him back and we were on our own. After that we had rented up to 50’ mono.

Few comments:

1) I do not recommend key Lime place in Key West for your honeymoon. We went there 2 years ago before COVID. I would give it maybe 2 stars out of 5 for honeymoon. It’s okay but not fancy. Note Keys don’t have white sandy beaches. Nearest white sandy beech is Miami. If you really have your heart set on sailing on a 22’ day sailor with just you and your new spouse with pail for a toilet then Key Lime is a good place.

2) Bareboat sailing is a lot of work. For six of us sharing the load it worked for us. First time bareboating is just a lot of work. You always have to be thinking ahead. Personally I would never recommend doing your first bareboat sailing on your honeymoon. It’s a lot of work without captain/chef.

3) Think about staying on land in US Virgin Islands or if possible BVIs. Easy sailing after February. Stay on land and maybe look into sailing a few days with Captain. That way you can relax and enjoy your honeymoon. To get to BVIs we always flew into St Thomas and took a Ferry over to Tortolla. The JVD island is a must visit.

Enjoy and relax on your honeymoon.