Good luck with that one.... Key West is the most sailing unfriendly place I know of. Yea there is a sailing club in one of the north harbors, but it's so far from anything fun. The problem there is it's too shallow everywhere around the northwest side of the Island except in the very narrow channels, and the currents are fierce over there (5-6mph) most of the time. Be very careful if you launch at Simonton st boat ramp, it looks inviting but the north to south 6mph current in front of Mallory square makes it impossible to get back to the launch on a stock TI without motors unless you round out way north around Wisteria and come in from the north (about 3-4 miles out of your way, and too shallow anywhere close to shore (I've lost a lot of rudder pins in that area), you have to follow the very narrow channels up there.
We prefer to sail mostly south of the Island and there is an ok concrete ramp just east of Higgs beach right next to the first building near the Vietnam memorial. Free parking in the parking lot across the street. What we do is launch from the ramp, then go park in the Vietnam memorial parking lot, we disconnect the trailer and pull it along side the car, or in front of the car in the grass (you will figure it out).
There used to be a ramp near the airport near Smathers beach that still shows on some old maps, the ramp was removed a few years ago, the opening in the road is still there but it's posted no parking, and we were told we couldn't launch there. We tried anyway when nobody was looking and got our car stuck in the soft sand (embarrassing). You might be able to park across the road and roll the trailer across to launch (just don't get caught lol), I suspect a lot of the older Hobie cat guys that used to go there years ago are still trying to launch there, not worth the hassle especially since there is a decent concrete ramp a quarter mile to the east with free parking ( BTW it's $2.25 per hour to park at Smathers (thats $4.50/hr with the trailer)), same price to park as Simonton st launch... like I said KW is not a sailing friendly place.
We have a house there and those are the only two launches on the Island that I know of.
If your a car topper or you want to unload the boat in the parking lot, then walk it across the soft sand at Higgs beach and launch there, we do that a lot as well (just disconnect the trailer and leave it across the road next to your car), free parking....
Overnight parking can be a problem, if you stay at the resorts on the south side with big parking lots you can probably park there, but they will want you to disconnect the trailer. Most of the weekly/monthly rentals in old town barely have parking just for your car, let alone a trailer as well. Sometimes we leave our trailer up in Sarasota then just car top the TI while in Key West, the crazy boat is up on the roof sometimes weeks at a time, the downside to that is you have to get the boat down from the stupid car every day (that gets old fast). We have motorcycle locks thru the mirage drive slots, then thru the roof rack, nobody has ever messed with our stuff in 7 yrs of going down a week or two at a time every couple months. Of course the mirage drives, sails, and anything valuable goes in the house. I hate to be the bearer of bad news but KW is a pretty seedy place with a lot of homeless. Fortunately you have a built in theft deterent designed into your TI that is 18.5 ft long and 250 lbs. Car topping solved our parking problems (the parking lots don't care whats on your roof), so it's a bargain, it only costs you $2.25/hr to park most anyplace in KW.
Of course you can always go north and launch pretty much anyplace you desire all the way up US-1 along side the road. There are several Marinas up on Stock Island, but it's a pretty long haul down to KW from up there. One of the main reasons we have big ole twin outboards on our TI is because of the great distances to anything of interest down there.... Most everyplace near shore is just shallow bare sand for miles around (we are mostly divers and snorklers).
Even with all the downsides, KW is our favorite place to take our TI, the warm crystal clear water everywhere year round is unequaled anywhere else. South of the Island you can stop and snorkel pretty much anyplace and have a blast.
90 percent of the time when we go out down there we normally have 5-6 people, we usually pull all our gear and coolers behind our TI on our inflatable 6 person inflatable, then have the extra people in the dingy or in their own kayaks hanging onto the dingy (we call it our party barge lol), then go out and anchor just offshore and snorkel and dive. Obviously we only do this when it's very flat and calm. Our TI with 4 adults on board is usually overloaded so don't bother trying to stow anything inside the hatches (just sayin).
PS if you spear fish, know the areas spear fishing is allowed, you don't even want a spear gun on board in the protected areas (just FYI).
Hope this helps
FE
and pictures.
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