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Old 18-05-2021, 13:58   #1
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Upper and Middle Keys cruising advice needed

Hi All,

I’m planning on a 10 day upper/middle keys cruise from Stuart, leaving in a week or so. We’ll sail directly to Miami/No Name so that’s my first 24 hours. I’m hoping to go as far south as Marathon and stay there 2-3 nights before heading north.

Where would you stop along the way if you were inside or outside? I’m considering going inside south and outside north but not sure at this point. I draw 4.2 with the board up so I should be good to go. Any advice on must see Keys, bars, restaurants, anchorages, snorkel spots, etc. is most appreciated.

Also curious about sailing Hawk Channel at night. I’ve read that you shouldn’t due to lobster pots and I’ve read other threads that say it’s a non-issue. Thanks for any and all feedback.
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Old 18-05-2021, 14:09   #2
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Re: Upper and Middle Keys cruising advice needed

4.2 draft. Go inside. There isn't much to see, and no great anchorages going the Hawk Channel route. And, yeah, there can be a lot of crab trap buoys.

There are a lot of great places to stop going the inside route.

I'll catch hell for saying it, I imagine, but I love Alabama Jack's.
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Old 19-05-2021, 15:45   #3
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Re: Upper and Middle Keys cruising advice needed

Thanks for the response Group 9. Curious why you’d expect grief recommending Alabama Jacks.
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Old 19-05-2021, 16:20   #4
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Re: Upper and Middle Keys cruising advice needed

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Thanks for the response Group 9. Curious why you’d expect grief recommending Alabama Jacks.
Some would call it a "Tourist Trap". And, it kind of is, but it's a cool one.
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Old 19-05-2021, 16:23   #5
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Re: Upper and Middle Keys cruising advice needed

don't wait much longer. the mosquitos in the upper keys can be unbelievable in the warm weather.
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Old 19-05-2021, 16:52   #6
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Re: Upper and Middle Keys cruising advice needed

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4.2 draft. Go inside. There isn't much to see, and no great anchorages going the Hawk Channel route. And, yeah, there can be a lot of crab trap buoys.

There are a lot of great places to stop going the inside route.

I'll catch hell for saying it, I imagine, but I love Alabama Jack's.
Along the same lines is Gilberts Resort in Key Largo .. a little less of a tourist trap , but if you're looking for that side of the keys .. there it is !
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Old 19-05-2021, 17:16   #7
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Re: Upper and Middle Keys cruising advice needed

Agree that inside is the way to go with shallow draft. It's there you will find fresh seafood and great beer.



Try to stay away from the Miami area on weekends. There are tons of boats, and No Name is sometimes too crowded to get in. If so, try the anchorage near the old Miami Marine Stadium on the other side of the Rickenbacker Causeway.


Boca Chita Key has a keyhole harbor and is deserted during the week. (Also packed on the weekends.) You can have an island to yourself (and 10 million mosquitoes at night) during the week. Button up the boat before dark and put on the screens.



Anchor for free off Gilbert's at Jewfish Creek in Key Largo. Live music and lots of partying at Gilbert's. Alabama Jack's is kind of a long dinghy ride, but lots of fun.



Lorelei is not to be missed. One of the best tiki bars in the Keys. Also a free anchorage.


You can get a mooring at Boot Key Harbor in Marathon for $20-something a night. Keys Fisheries across the highway has fine, fresh seafood. Dockside is a fun dive and a dinghy ride away, as are several other places with live music sometimes.
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Old 19-05-2021, 19:04   #8
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Re: Upper and Middle Keys cruising advice needed

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Some would call it a "Tourist Trap". And, it kind of is, but it's a cool one.

Substantially all retail and service businesses in the Keys chiefly cater to tourists. It's part of the charm.


I like Alabama Jack's.



I have been up and down the Keys several times via car but have not sailed there.


Other favorite restaurants:

In Marathon, Sunset Grill and Raw Bar.
In Islamorada, Wahoo's Bar & Grill. Really good fish, service iffy, great view from many of the tables. In Key Largo, The Fish House or Snook's Bayside, both with more ambitious menus.



Key Largo has some of the best diving and snorkeling in the USA but access is difficult via sailboat. The best sites are along the continental shelf on the seaward side of Hawk Channel, about 3 miles from the coast. Typical sea state precludes a dinghy expedition that far from shore and the paucity of anchorages on Hawk Channel, and absence of convenient channels from the ICW to outside, complicate diving from the mothership.


There is good diving/snorkeling inside but I couldn't tell you where.


Perhaps someone will be along with advice on how to cruise Hawk Channel. There are anchorages but they typically offer only one or two sided protection and are shallow and small.
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Old 21-05-2021, 08:40   #9
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Re: Upper and Middle Keys cruising advice needed

Thank you all for your responses. Good information that I did not have. Seems like the inside heading south is the way to go. I look forward to hitting some of those tourist traps.
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