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Some old, some new, but all places that I found worth returning to in the future.
I would imagine this place is on most go-lists. For me, it's a can't miss. If you're looking for a relaxing meal that typifies the old Key West, this is where you want to be. Breakfasts are second to none.
Another great breakfast nook. Eat outdoors while you watch the sun come up over the Atlantic. The service and atmosphere are better than the food, which still ain't bad.
A must for Buffett fans, but non-fans will get an interesting taste of recent Key West history as well. Fun stories of Jimmy's years on the island, and the location of Jimmy's Key West recording studio is revealed. Really? That's it? I've walked past it a hundred times and never knew!
Frankly, I have a hunch that you'll hear some semi-true stories, believe it or not, but they're entertaining nonetheless.
Where the aforementioned tour ends. If you're looking for good food, this may not be the first choice in Key West. However, you have to have the obligatory drink. And the t-shirts are some of the better quality you'll find on the island.
A kind of out-of-the-way place (unless you're staying on way up on the wrong "resort" end of the island). Hurricane Joe's is just across the bridge to Stock Island on your right. The outside pier restaurant is a great getaway for lunch and the peel and eat shrimp may be the best value in Key West. As a bonus, my wife and I happened to glimpse a manatee up close next to the docks. Way cool!
Either you "get" this place, or you don't. If you get it, good for you. You'll have a one-of-a-kind dining experience. The conch fritters are very good and the fish sandwich won't leave you hungry. Have a brew or two while you're having your lunch. It will make the place more palatable.
If it comes in key lime, it's in this shop. Choose from the obligatory Key Lime pie to cookies, candy, coconut patties, barbecue sauces, salsas, beverages, soaps, candles, jams, etc. etc. Lot's of limery going on.
Perhaps my favorite watering hole in a town full of them. Capt. Tony's never seems to be overly crowded, but the entertainment is usually entertaining, and some of the patrons are as well. I have yet to see the Captain (although he was supposed to be there on our last visit) and I have yet to get a stupid quarter into that fish's mouth. One of these days! Bring a business card if you go.
Edit: On our November 2007 trip, I met the Captain AND immediately afterward landed a quarter in the fish. What a night!
The first (or last, depending on your direction of travel) bar on US 1. Also the oldest bar in Key West. The Green Parrot isn't your typical tourist bar. The entertainment leans more toward blues and jazz than rock, but if that's your thing, you'll love this place - and especially its jukebox. How about finding Clapton, Rundgren and the Velvet Underground in the same lineup as John Lee Hooker, Tinsley Ellis and Jimmy Vaughan? Nice!
Make sure you get a Bloody Mary to cure what ails you in the morning.
Not much for atmosphere, but the best seafood in Key West! If you can enjoy excellent food while sitting in a bus station, you won't be disappointed. If you need to have the right ambience to make your dining experience a pleasant one, pay twice as much for the same food at Cafe Marquesa.
You have to watch just one Key West sunset on Mallory Square. Sure, there's an entire circus going on around you, but when it comes time for the sun to set and you can actually watch it descend over the horizon, well... you just have to see it.
Surprisingly good fried chicken from a gas station. Dion's are up and down the Overseas Highway, but if you're looking for a late-night snack or something to absorb some adult beverages the next day, you can't beat their quality or price.
Sadly, the Ocean Breeze has been sold. I stayed there once since it was taken over by an out-of-town investment group and will no longer recommend it.