My advice is "Go". Find lodging a few blocks off of Duval so you can walk to most of the activities. Best advice is "ask a local". Over the years I have visited my best "finds" have been those places where local dine and drink. For example, El Sibonet is a family Cuban food restaurant with excellent roast pork, black beans, yellow rice and onions served with fried plantains (making my mouth water just remembering)- got our morning Cuban coffee at a laundromat where all of the city workers get theirs- excellent cafe con leche y pan con mantequela (pardon the spelling but it is Cuban flat bread toasted with butter and strong coffee with hot milk and sugar) at Sandy's Cafe, which is a window to the street at the M&M Laundry 1026 White Street. Walk by get the grub then enjoy a sunrise in the beach with a Key West delight. Oh, their Cuban Sandwich is also very good so swing by for lunch too!
If you're interested in water sports or want a unique way to see the islands, consider this local tour group specializing in ecology trips. See crystal clear waters with tropical fish, reefs and mangroves inhabited by rare birds. They offer daily back country tours that depart from Key West in sea kayaks to explore the northern islands of Geiger Key and Sugar Key. Tours last approximately six hours. 9 AM to 3 PM (pack a brimmed hat, sunglasses and waterproof sunscreen) Mosquito Coast Outfitters 310 Duval Street.
No shortage of things to do and yummy delicacies to consume (or drink) during a visit to KW. I am headed back with a buddy in September for a few days to soak up some Conch Republic "culture", diving, drinking and dining.
Just go and have fun.
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