Dive Shops and Dive Boats in Islamorada

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I've dove with Key Dives in Islamorada.
I highly recommend Abyss Dive Center in Marathon. My wife and I just dove with them a couple of weeks ago. They have a 34 foot boat and take a maximum of 6 divers.
 
Since your from Boca you probably already know this but.....You will be hungry and thirsty after diving!

Try Bentleys, Marker 88 and the Islamorada fish company behind Bass Pro Shops.
 
In the upper keys, Conch Republic is my all around favorite dive operator. Big Boat, good crew, nice folks in the office, good service, gear storage, good fills on tanks, good prices when you bring your own tanks, they visit some sites other don't like Conch Wall, etc. It's likely they will always be my primary choice.

This summer I also tried Rainbow Reef with a buddy and would go out with them again under the right circumstances. Their boats are big, crews are nice and they provide a guide if you want one (my buddy and I didn't use one). The only thing I didn't like was the light fills on my HP 120 and 100 tanks.

I also tried Horizon this summer when I visited the keys alone and liked the captain/crew and this operator is one of the more flexible in allowing you to dive to your certification level. I'm solo certified and they allowed me to dive so on the S. Grove without a hassle when it was obvious that an insta-buddy was not going to work out (no one had similar tank sizes or Nitrox mix). I would use this operator again. The main downside is that they don't offer a discount if you bring your own tanks like most operators: you pay the full fare whether you use their tanks or your own tanks. I didn't really like the island hopper boat either, I puked but had no problem in Conch's newton the next day in worse marine conditions.

Silent World is also very flexible around diving to your certification level. On the double dips on wrecks, they've allowed tech guys to do a long decompression dive while rec divers do two dives with a SI between. They also allow solo diving if your certified. I don't really like their old boat but hear they have a bigger island hopper now.

Quiescence has a six pack fleet and a very nice group of captains and crews. They're also very flexible on dive site selection as a result of having smaller boats. I don't really like small boats, but would use them again if I were sure marine conditions would be flat.
 
https://www.shearwater.com/products/perdix-ai/
https://xf2.scubaboard.com/community/forums/cave-diving.45/

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