Joe Maria Jorge told me about Seabird marina on Long Key as a great place to start my sailing trip there in 2009. They have a good boat ramp, and Iocked up my trailer in a fenced area so didn't have to worry about it not being there when I got back (though that was not exactly cheap). Spent the next week taking my time sailing by day and anchoring off at night till arriving at Key West. I found shallow (3 to 4 feet), small coves that protected against wind and waves to anchor each night. Very thin layer of sand over solid and surprisingly smooth bottom to anchor in most places. The danforth anchor did ok but I did set my GPS anchor drift alarm if it was windy. The prevailing winds in May allowed a great broad reach to a run all the way to Key West, but would have been a LOT of tacking and beating against the waves of Hawk Channel to return sail to Long Key. Would have taken way too long! You may have different wind direction options in January. I stayed in Key West Marina for a few days, next to John Edwards in his M17. It was great to run into another Monty sailor down there! The daily slip rental was $40, I think, but a lot cheaper than a motel and they had 30A service, fresh water and showers and laundry room. Restaurants in walking distance. I rented a bike for $15 and toured the town, otherwise city buses run right by the marina. Plenty to do and see in KW, especially Mallory Square. I took an inter-island bus that runs the length of the keys, back to Long Key ($5), picked up the truck and trailer, and hauled out at Key West. Only catch is lowering the mast and motoring a short distance under a low bridge, that is within the protected marina area. No big problem. Hope this helps and your trip goes well! George M17 #600