The purpose of this blog-post is to provide our readers with an overview of the most reasonable practices for cruising the Florida Keys in a sailboat and it is especially intended to suggest the different options available to bareboaters for the best vacation experience in paradise. Apologies to Jimmy Buffett and yes, they fix some pretty good margaritas and burgers down here. Keys Disease!

Driving Overseas Hwy to Key West is slow and tedious with lots of traffic and an overdose of commercial billboards for restaurants, billboards for resorts, motels, diving experiences, day trips to the reef. Never ending. That said, sailing in the Keys is totally different and provides the un-rushed, and laid-back character of the chain of islands with its pristine waters and marine wildlife.

Cruising the Keys is a great option to avoid the weather-dependent Gulf Stream crossing to the Bahamas. You can cruise the Keys in virtually any weather because you have three basic route choices.
  • Outside the reef in the Gulf Stream with deep water but with a South to North current of about 2 to 3 Knots.
  • Inside the reef using Hawk Channel with minimal current effect.
  • The Intra-coastal waterway, which is slow going due to the zig-zag channel and its irregular markers.
The back-drop to cruising the Keys is always the DISTANCE and the SHALLOW waters. first-timers are always amazed at the distances involved in cruising these waters. We get many requests for boats to cruise from Miami to Key West and back, for example. Yes, it’s about 135 Nautical Miles, while this doesn’t seem a whole lot, if you break it down in to bite-sized chunks, things begin to make sense.

If you estimate an average of 5 Knots traveling South along the Hawk Channel, it would take you 27 hours of sailing non-stop to reach Key West.  Since you can only travel during daylight due to the shallow water and reefs, that gives you 8 or 9 hours of sailing a day that equates to basically, a three-day trip without stopping off anywhere. i.e. a week of hard sailing – no sight-seeing.  PLUS three days back to Miami, so 6 days of sailing non-stop. Not quite what you signed up for I imagine.

There are options however, that depend on your inclinations. Here are some of my own preferences.

1. Cruise the Upper Keys for a week. This includes starting your charter in Miami or Fort Lauderdale and heading South down Hawk channel inside the reef. The objective is to reach Key Largo on Day 2 of your charter. Continue down to Islamorada, Duck Key and maybe even Marathon and back to the base. You can return outside the reef and get some traction from the Gulf Stream current on the way back. OR, If the weather turns sour, you can always come back on the intracoastal waterway by ducking under the Channel 5 bridge (65’) or the Snake Creek bridge (opens on demand) to pick up the ICW.
2. Start your charter in Key West and visit the Dry Tortugas which are about 68 miles from KW. Very interesting trip to see Fort Jefferson which was constructed in 1849 shortly after The US purchased the State of Florida from Spain. At the time it was considered a strategic location for the defense of the Gulf of Mexico against foreign powers (sic). Fort Jefferson is the largest brick and masonry construction in the Americas and was used as a prison during the Civil War.
3. Do a one-way cruise from Miami to Key West, or vice versa, stopping off (anchoring or tying-up) along the way in different locations such as No-Name Harbor on the southern tip of Key Biscayne. Rodriguez Key, the Channel 5 Bridge, Duck Key, Marathon, and many others. For a very complete list of anchorages both on the inside and the outside, click here.
The Florida Keys are a great option for bareboaters especially in the iffy winter months when the risk of cold fronts coming across from the West are most prevalent. These fronts produce unsettled weather that would make a Gulf Stream crossing quite uncomfortable. The other issue with the Bahamas in Winter is the timing factor. Sometimes you can get across to the Bahamas pretty-much unscathed, but when time comes for the return crossing, you find that the weather conditions have changed and that you can’t get back! Bummer.

These are not things you can change. This is what the insurance companies call “acts of God”. The bareboat company will probably be unsympathetic and perhaps your boss will too….

44′ Wind’s Will Sun Odyssey 439
37’6″ Kitty Cat Leopard 39
In summary, I hope this blog has been of some use to you, not necessarily as a trip planner but simply to provide you with an overview of the Florida Keys option for a great bareboat vacation.  To find a great boat, please feel free to call us at +1-305-758-2500 or email us at charters@americanyacht.net or visit our website.
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