Islamorada is a nice place to stop over for a day or two. The anchorage is pretty straightforward. Simply peal off the ICW and head towards the Lorelie on Upper Matecumbe Key. You’ll see anchored vessels fairly close to shore. We found the holding to be good in 8 feet of water, a few hundred yards offshore. Closer in the depth comes up to 6 feet, and there is thick grass. I suggest not getting any closer in than the closet boat you see already anchored.
There are two ways to access shore. First, you shouldn’t miss the Lorelei. It’s a great example of what a Florida Keys Bar/Restaurant can be. http://loreleicabanabar.com/
Dinghy up to their small beach or tie off to the dock and get lunch and/or a cocktail. Great sunset views can be had with a drink in hand. You can walk a short distance into town from here. You’ll be on US1 amongst the typical T-Shirt shops, art galleries, and souvenir stands.
Another way to get to shore is to look about two hundreds yards south of the Lorelei. There is a road that dead-ends into the water, serving as a ramp for small vessels, kayaks and the like. Tie off to the mangroves and you will one block from a grocery store. A few hundred more feet to the south and you’ll find a well stocked liquor store. Both are a short walk, convenient, and quite expensive.
One half mile to the south is The Worldwide Sportsman complex. It’s a well-equipped Bass Pro Shop featuring multiple restaurants, a marina, and a seafood market. There is a replica of Hemingway’s boat inside. Worth a look.
A few hundred more feet on the oceanside of US1 is the famous Green Turtle Restaurant. You shouldn’t pass this place by, but bring a full wallet.
We did not see a way to get water, but there is a dumpster at the ramp for your trash. There’s a Burger Kind 1/4 mile to the north if you have a fast-food craving. We enjoyed our stay, but after a few days we felt we’d seen all there is to see.
Of note: This anchorage is completely open to north winds. It gets very rolly when winds clock out of any direction with a north in it. It’s clear that some of the locals ride it out, but I wouldn’t advise it. It is not crowded. We counted less than twenty boats and it could hold twice that easily with plenty of swing room.
Enjoy your stay.