If you’re wishing to charter, you need to hone in on where you want to do your sailing as that will dictate from where you’ll want to charter the vessel. People tend to think that getting from Virginia Key to Key West is no big trip or problem, but I’m sure you don’t want to spend your entire 6 days/5 nights going in circles and then have to get the boat back on time. Weather can change. Tides need to be considered. You need a plan. So, recommending you look at charts of the Keys (you can find them online) and figure out from where you wish to charter. Then you can branch out your sail and overnighting (be it on the hook or at a marina) from there.
“Mod cons,” you say? Modern conveniences… have mercy. That’s like telling a realtor you want a house with modern conveniences. That’s quite relative and subjective to each individual. It depends. I had satellite phone, satellite television, watermaker, inboard diesel generator, freezer, etc., things that many others would not want on a charter but that some others wouldn’t leave the dock without them. LOL Okay, so I admit to being somewhat of a prima donna when it came to “mod cons.” Bottom line: please be specific in requesting what you desire.
A draft of 5’ or more is probably too drafty for someone on a 6 day vacation and never having sailed the Keys. That is, not unless there is a solid plan of where and how one wishes to sail. People come down to the Keys all the time from up north where there’s deep water everywhere (especially Canada) and run aground constantly. They are used to having lots of water beneath them and are not adept at chartplotting. It’s necessary in the Keys to either know the lay of the land beneath the water or know how to read charts! The only way you know the seafloor is by reading charts.
You’d be surprised how the adage, “ignorance is bliss” gets tested time and time again when people come down to sail the shallower waters of the Keys. It can be a rude wakeup call to those who thought they knew all the ins and outs of sailing. Getting in and out can be a problem too, depending where you are! But it can be done. One simply needs do some homework.
You’ve made it clear you wish to sail both sides of the Keys: Florida Bay/the Gulf of Mexico and the Atlantic sides. Most locals of the Keys rarely take their sailboats on the Bay/Gulf Side, though I did all the time during my eleven years there. It’s actually some of the most pristine and fabulous backwaters in all of the Keys. However, it comes down to reading charts and having your course plotted BEFORE you leave the dock or hook (depending on where you wish to go)… tides and currents can move you around and some areas are very tight for passage if you have much of a draft beneath you. Hurricanes have changed the seafloor and areas get silted in… before you know it you’re hailing Tow Boat U.S. No one wants to spend much time on their vacation doing that!
You want have to fun on your vacation and do all the sailing you can. And that, with due preparation, can most certainly happen! And when it does, it is a glorious thing!
Fair Winds and Calm Seas!
Charmaine Smith Ladd
Hard Aground in West Central FL (Yikes! I’m a Landlubber!)
CSmithLadd.com (Author of “Shake Hands with Yourself” Amazon Books)