Key West
I am a regular there an considered something of a local because I stay a month at a time until recently.
I usually stay in the Truman annex. Villas to homes, pick your size, view number of bedrooms and price. Awesome Managament Company.
http://www.compass-realty.com/exec/...nex&template=_search_results_trumanannex.html
It has units on the water, walk to the State Park and visit Fort Zachory Tayler.
One block out the west gate is Mel Fishers, must see, tell Bill I told you watch the reaction, and the start of Duval St and Sloppy Joes.
Two blocks north from any gate is Duval St.
Kellys is one block out the north gate by the rental office.
Also, a Brazilian Steak house same street between Kelly's and Duval $50 each all you can eat.
Blue Heaven is good but I prefer Le Creperie across the street, Claudia and Sylvie and family run it and you watch them cook your food if you sit at the rail inside or you can sit outside. Every kind of Crepes and coffees or eggs, less wait if any and cheaply priced plus if you like a morning Cappucino they serve it in a cup the size of a bowl. They know we very well. I don't even order I wlak in and they put my Banana Lime Sugar crepe with a huge Cappucino down. Man I'm craving one right now! Out the front gate turn right immediately and Blue Heavan anCreperie are abouyt three blocks East on the left.
Antonio's (Italian) is on Duval about 2 blocks north out main gate then right half a block. Small, nice, excellent food.
Conch Republic is on the Harbor, out West gate to Fishers hang a right and walk about six blocks to the water. Ask for a table at the windows.
Half Raw Bar is a little further down the boarwalk that runs past Conch Republic but also a famous spot with good seafood and ask again for a window and watch the huge Tarpon swim by right below your window!
Fred Cabanas runs the Pitts sight seeing and sometimes the Waco. He is an airshow pilot and a heck of a lot of fun to fly with. I've logged acro training with him in the Pitts. Always fun with him.
The tortugas I fly in the DH3 DeHavilland with Turbine float plane. If you go take the tour and then walk around the inside then the outside perimeter moat wall. It's breautiful.
If you like Art most of the best Galleries are on East end of Duval maybe 2 mile from from easy walk. Greene St gallery are vintage posters most over a hundred years old ranging from cars and race posters to wine, food, and airplane races. Say hi to Betsy for me.
Southernmost marker is about three blocks past her place and a block right at the corner. Take you picture and walk back to Truman annex from that street if you dont want to double back on Duval.
I dont walk much around home area but there I put in about 5-6 miles a day inseveral short walk abouts. I eat lots of Seafood, Stone Crabs from Oct-May15! I usually come home after a month of that 10-15 lbs lighter even though I'm eating really well and just walking.
Hope this helps.
It's not everyones thing but Truman is semi gated, only one gate open at night but they give you keys to the others.
I like that its right in the middle of everything so walking is never far away unless you walk all the way to the far end of the island about 6 miles. I usually only do that to stock up at the big Grocery stores then take a cab home. I dont rent a car or electric buggy.
Closest grocery store is one block past Duval called Faustos, been there since the 30's I think and the locals use that one if they dont go to the far end. It's only 4-6 blocks from the villas and each one has a kitchen a fridge so you can stock up on food, snacks and beverages if you want. I never cook there.
If your dates are around Spring Break definitely book now if you can. Look on the website I linked to find a unit you like then call. If they dont have it they will tell you waht they have and you can look right at the unit while on the phone.
Also, a lot less of the Break crowd stays here compared to town.
La Concha is nice too, it's just right on Duval and that can get old if you stay too long.
Have fun, wish I was going.