For boat rentals down there - look to Stock Island - it's the island just before Key West, and is considered part of Key West, although it is seperated by Cow Channel. You have three places worth renting boats from - Stock Island Marina on the ocean side, and then a marina on the bay side - sunshine or something - both high class places ... I know the guys at Stock Island Marina better - same marine that the Yankee Captain's boat heads out of for the Tortugas trips ... also there's Murray marine, it's right on A1A on stock island, can't miss it, the only caveat with this is getting to the ocean or gulf will take a bit longer as you have no motor zones, but not a big deal - all three of those marinas are excellent. If any of them no longer rent boats, as I have not been in contact with them over the past few years ... they can tell you where to go.
... as for guides - you have several choices at the end of February to consider - sailfish should still be around, unless it's a warm winter and they would have passed ... but other billfish may be coming in ... also king mackerel are real hot down there, and should still be good at that time, I think some of the big king mackerel tournaments are going on then - check the
www.fla-keys.com Web site for a listing of tournaments (this is important as it will give you an idea of what's the most abundant species around there at that time). Depending upon the temperature, during the winter - they used to get a good blackfin tuna run and even some yellow fin coming through, although those numbers dropped off during the last few years I was down there, could have come back up though since I left.
On the bottom fishing side - you have rock piles out front in the atlantic and wrecks in the gulf - can be hugely successful - ideally you will have chum and live baits that you can use sabiki rigs to catch - around bouy markers and piliings in the slightly deeper waters - and moving waters - 10 feet or better - chum and jig the sabikis and you can catch a bunch of small bait fish to live line ... or get frozen ballyhoo, mullet, etc. If you have the frozen bait, put them on jigs and drop to the bottom and hold on ... never know what can bite - snappers, grouper, ajs and more (within the grouper family are the goliath grouper I think they are called these days, used to be called Jewfish - get huge and they eat the small fish you catch and are pulling up, happens wiht AJs as well) ... but also shots at cobia, spanish mackerel, little tunny (which they call bonito, but they are the little tunny) ... as well as a variety of jacks and other species. You can never know.
Flats at the time of year - depending upon where you go and the temperature, often in late February if you get four days of warm weather, the tarpon will show up in the backcountry, the lakes and Marquesas ... check with the local guides and they can tell you. Typically in February down there because of the cold weather - you will get great shots at baraccuda on the flats - jumping minnows, any spooks the guys sell on the site here work great, although if you want to save the wood, use plastic, but also needlefish should work well moved fast and silver bombers wiht the lips broken off and skittered across the top. and again, weather dependent, on the atlantic side you may find bonefish and a variety of other species.
It's always a guess but exciting as there are so many opportunities to pursue. A few people to consider - Captain Mike Weinhoffer on the Compass Rose - he fishes wrecks, rock piles, offshore - great, great fisherman. As for the flats captains - check with the Key West angler - captain jeffry cardenas's shop - he can put you on a good flats guide, as can captain mike as well ... if you want to and can afford both.
As for the bridges - great options for night fishing, tarpon and snook as well as jacks and sometimes permit and sharks. live bait is always good, live crabs, metal, and an assortment of plugs. The action is not as hot as it was when I lived there in the 1990s, but still good.
If you want to travel up the island chain, there are so many flats to check out north of there in the big pine key, ohio key, bahia honda key, marathon key, long key, islamorada and others that have access to good wadable flats to find bonefish and cudas. Not always tailing, sometimes you either have to blind cast off the edges into the channels, or see if you can get a folding chair or a ladder from someone to stand up on a nd get the angle to look for cruising fish and muds .. which is when the fish are searching along the bottom a nd make little puffs of mud to blow bait out of holes in the sand.
Good luck and send pictures.
