Reply #15: I lived there for 12 years...

[SiobhanClancy]

That's exactly what happened to me...I went on vacation and stayed for awhile:)
I think November is one of the best months to go...the snowbirds usually descend after the holidays,and the weather is nice. Key West is a really fun place to go,but of course there is more to the Keys than just that. Duval Street is very touristy ...T-shirt shop heaven!

My KW picks:

Best bars:
Garden of Eden
Schooner Wharf
Flying Monkeys
Carolines
Green Parrot
Meteor
Half Shell Raw Bar
Crabby Bills
Capt. Tonys
The Bull
The Whistle

Tourist Traps:
Maragaritaville
Sloppy Joe's
Irish Kevin's
Hog's Breath Saloon(best rumrunners!)

Best Restaurants (expensive):
Michaels
A and B Lobster House
Louie's Backyard
Square One
Key West Seafood Co. and Beer Garden

Best Restaurants (moderate):
Half Shell Raw Bar
Turtle Kraals
Alonzos
Crabby Bills
Meteor Smoke House
Schooner Wharf for lunch
Pepe's
Blue Heaven(Bahama Village)

Best Restaurants (cheap):
No such thing

Best sightseeing:
Sunset any evening at Mallory Square
Hemingway House
The Lighthouse
Smathers Beach
The beach at Ft Zachary Taylor
Walking the Harbour Walk
Some of the harbor cruises
People watching

Best places to people watch while imbibing:
One of the outside seats at Ricks
The Tree Bar
Carolines
A sidewalk seat at Flying Monkeys/Fogartys

Marathon is about 50 miles north of Key West on US 1(or Overseas Highway). People in the Keys usually refer to locations as "MM 23"(for example).
Restaurants in Marathon:
Herbie's(moderate and casual)
Barracuda Grill($$$)
Shuckers
7 Mile Grill(by the 7 mile bridge,rustic)

Bahia Honda State Park is one of the most beautiful beaches in America,if you are into that sort of thing. You might be surprised that there are not as many beaches in the Keys as you expect. John Pennekamp State Park in Key Largo is wonderful for snorkeling. Big Pine Key has minature Key Deer and is a refuge with a strictly enforced and slow speed limit.

One cautionary word...there is an expression,"Arrive on vacation,leave on probation". There is every kind of law enforcement you can imagine down there,so just behave yourself:)