Winter time fishing in Key West can be very good. You get wide variety of options in winter as long as you get the weather.
The wind tends to blow more in the winter, and that fluctuates every year, some winters are windier then others.
Sailfish show up around November and December and they tend to like it the windier the better.
Black fin tuna also start to show, often on the deeper wrecks such as the sub and airplane wreck.
The wahoo run begins somewhere in this time, depending on reports the whole key west fleet will be at the end of the bar targeting these fish, along with king mackerel, amber jacks and other offshore fish that congregate there.
The bar in Key West is second dead reef that is outside the main barrier reef. This bar comes up to 50 feet deep on the top, to the north and south this bar drops off to 100+. In the winter when the currents are right, this bar will be bathed in dark blue water and often ripping currents. These conditions will cause upwellings, which will make huge schools of bait congregate out there, speedos, bar jacks and blue runners primarily. This bait attracts the predators.
The most sought after fish out there will be the wahoo which can grow to over 80#. They will not be the only fish shadowing these bait schools, mackerel will be out there in force both king and cero. Yellow jacks, amber jacks sometimes crevelle jacks. Sailfish and the occasionally a dolphin as well.
Numerous sharks will be cruising this area as well.
The colder water turns on the reef big time. Grouper will suddenly be everywhere and you will catch nice reef fish in very shallow water. There will also be a lot more pelagic fish on the reef such as mackerel and jacks.
Big yellow tails will congregate on the bar and deeper reef, these are commonly called flags. They are harder to catch then the smaller versions but once you can get them biting it’s really blast catching them.
The inshore patch reefs can be very productive at this time, and often will have a lot of mutton snappers along with red grouper.