Best fish sandwich in North America: BO's fishwagon, fresh everyday, don't let the appearence scare ya. If you're feeling freaky visit the Garden of eden. Best Bar (my opinion) Schooner's Wharf Bar. The ride through the keys is unique, I ride down at least 5 or 6 times a year and never get tired of it.
ya gotta park the truck and trailer on the mainland and take the run down with the Fla Crew, nothing like the Keys ride in Jan. Drop a PM when you are coming, we can find a place for the truck.
Definitely get your picture taken at the Southernmost Point. We rode from Florida City/Homestead to Key West and back to Florida City/Homestead in the same day. Key West was PACKED with tourists ... hard to even find a parking spot! We decided not to fight the restaurant crowds on Key West and stopped at the Square Grouper Bar & Grill on Cudjoe Key on the way back. EXCELLENT FOOD, perhaps a little pricey but what the heck, you'll be on vacation. Live a little! $12 for the absolute best grouper sandwich ever. The Key Lime Pie was well worth the price, too.
KW on New Years is otta hand, personally I like it there in the summer, not a whole bunch of tourist, you can ride your bike down Duval and park in front of any bar you want. New Years is wall to wall people.