The mrs and I went to KW for 3 days at the beginning of May. It was a great kid-free R&R vacation. One of our friends frequents KW and provided us a list of places with some notes. We went to two places on this list, which I'll call out.
Not on the list though, was Sloppy Joe's (probably the most famous bar in KW). We went here every night. They had a great live band and the drinks were plentiful. Outside of that it's just fun to find a seat in the corner and people watch, which was excellent to do here.
Blue Heaven http://www.blueheavenkw.com/
729 Thomas St
Kick *** breakfast DO NOT MISS! It's a converted house. Make sure to sit outside if you can. There's a bar outside, usually a dude playing guitar. Awesome lobster eggs benedict. If you want to drink order a Greyhound. Vodka, lime, grapefruit, orange juice. Get the morning off on the right foot!
El Meson De Pepe's http://www.elmesondepepe.com/
410 Wall St
Awesome Cuban restaurant on Mallory Square. Check out the sunset and then eat here. They have inside and outside seating. The best Mojito I ever had was here. (chrismar's take: We went to mallory square for the sunset, which was quite spectacular, then to El Meson for dinner after. Nothing spectacular. Not even the mojito, in my opinion.)
Pepe's Café http://www.pepescafe.net
806 Caroline St
Key West's oldest restaurant. I've had really good breakfast and great coffee here. Also known for their steaks. I've never had dinner here but my brother did, said it was excellent. Looks like a hole in the wall.
El Siboney Restaurant www.elsiboneyrestaurant.com
900 Catherine St
This is a Cuban place off the beaten path and pretty close to your hotel. It's in a regular neighborhood, but the food is EXCELLENT. Get the chimichurri steak. Skirt steak with a garlic/parsley sauce. AWESOME!
Conch Republic Seafood Company http://www.conchrepublicseafood.com
631 Greene St
This is a big place overlooking the Key West Seaport. Great drinks and seafood.
Schooner Wharf www.schoonerwharf.com
202 William St Key West
Not exactly a classy restaurant, it's a dive bar on the Wharf that I love. Typical key west Bar food, oysters and fish sandwiches are great. The location is good and you can sit on the roof, listen to live music and get a good view of the wharf and the boats. Again, it's a dive, but you'll like it.
428 Greene St,
Just a bar, but definitely my #1 bar. Sit close to street, people watch. One of Jimmy Buffet's favorites too. The bands are usually good too.
400 Front St,
Key West staple. Good for lunch, but very popular and gets crowded from cruise ship visitors. Not bad, but if you miss it you won't be disappointed. (chrismar's take: We had a nice lunch here. The conch fritters were pretty good.)
Other things besides eating and drinking:
Duvall Street - Shopping
Mallory Square - 400 Wall St - Don't miss the sunset and freak show
Conch Tour Train - Mallory Square area - Good tour of the island. You'll see these yellow trains all over the roads. Very good way to get your bearings.
Ghost Tours of Key West - Leaves from same place as Conch Tour. Interesting, campy, fun.
Sebago Catamaran Sunset Cruise - 205 Elizabeth Street in the historic seaport - another great way to see the sunset. Costs covers boose. About $50 each I think.
Southernmost Point - Whitehead Street - The name says it all. 90 miles to Cuba from here. Great Cuban coffee down the street at Ana's Cuban Café
Key West Lighthouse - 938 Whitehead St - Good way to kill an hour. Climb lighthouse, great views, I almost fell down the steps and died here.
Audubon House & Tropical Gardens - 205 Whitehead St - I went here because it was across from our hotel. A lot of drawings of birds, but the gardens were pretty impressive
I went there probably 20 years ago with the ex wife and her family, I don't remember too much from it though except all the bridges we had to drive over to get there. I know that's not a whole lot of help but so be it. Oh, we did go by and see Hemmingway's house as we had 2 Hemmingway cats at the time.
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