Hi, I'm headed down to the Keys, with my wife and another couple, in the middle of February.  Along the way, we are stopping in Islamorade. My buddy and I are looking to take a guide, to go fishing, either bay fishing or fresh water. Can anyone offer me some suggestions on a good guide or maybe what's the best fishing there.                                                                                       Thank you

Have fun.  Islamorada is a great place to vacation.  Great fishing, really good local captains and some of my favorite keys restaurants.  You need to decide between inshore or offshore.  Wintertime offshore means you have shots at catching big fish (sailfish, kingfish, amberjack..) but it can be windy and rough.  If its too windy they'll take you a shallow reef to pull on little snappers.  Check out the boats here http://budnmarys.com/

 

Inshore is more like bass fishing (usually).  You are in a open flats skiff either sight fishing (bonefish, snook, redfish), blind casting for seatrout or soaking bait for all of the above.  Most guys run north into Everglades National Park but the bonefish are caught within sight of the keys.  This guy is good https://blackflycharters.wordpress.com/ as are many others that work out the Lorelei https://www.loreleicabanabar.com/marina-and-fishing/

Thank you. My buddy gets sea sick, so we're going to fish inshore

Growing up, we took yearly family fishing trips there. Bonefish and barracuda are a blast on the flats there. There is a creek cut that leads to Robbies Marina where you can hand feed tarpon. That creek has an offshoot that has been great for snook and snapper. Offshore fishing spots aren't that far from shore and dolphin are fun to catch. But as a previous post said...this time a year gets pretty windy. You will also want to check the lobster seasons and avoid going during them because traffic will be bad. If you like snorkeling, Lignumvitae Key is awesome on the west side. lot's of deep holes in the rock shorline to see eels and parrot fish.

Thank you