Once we decided on Key West everything else fell into place pretty easily. Hotel? Check. Flight? Check. Ummm... okay, that's it!
The island is only a mile and a half wide and about 4 miles long, so we really didn't need to plan anything ahead of time. We figured we'd stumble upon the interesting stuff just by walking around.
We came in on an evening flight and grabbed a bite to eat at the beachfront restaurant next to our hotel. They were closing up at 10, so we just ordered appetizers and a couple beers. We then decided to take a walk up Duval Street to relax and stretch our legs. A block or two up we saw a crowded open-air restaurant/bar. Oh! If we'd known we could've come here for dinner and drinks! Then, a half block later, another one. And another one. And ten more. And, ummm... I thought this was a sleepy little beach town?
Okay, don't laugh all those who have been to Key West before. We didn't know!
All those who don't know anything about Key West: it is a party town. A loud drunken party town.
And just like any respectable touristy party town it had tacky T-shirt shops galore all up and down Duval. My favorites: "I got Duval faced on Shit Street" (does it get more poignant than that?) and "I'm not drunk, I'm just naturally a loud, clumsy, friendly person" (Oh! The insight!). I am easily amused.
Anyway, we proceeded to avoid this aspect of Key West as much as possible, which was kinda easy since we got up early and went to bed early like old people.
Instead, we concentrated on Key West's historical sites, and enjoying a wonderful little thing we like to call "physical exercise"! We visited Hemingway's house, the Customs House, the Lighthouse, and we took a trolley tour. We went kayaking, snorkeling, swimming, and did the glass bottom boat tour (word of warning: glass bottom boat=horribly sea sick). We also rented bikes for a day.
And, we visited the Key West farmers market! Which... was just one table. But it was a table filled with an abundance of tomatoes, zucchini, and all sorts of stuff we won't be seeing here until July or August. And they told us that this would be the last farmers market of the season: their growing season ends in April! I love finding out about the odd little regional differences in farmers markets around the country (for example, they sell snow cones at the Reno farmers market. Which would so not fly in NYC).
All in all we had an amazing time. We found that most activities were very affordable, but that ALL of the "guides" would ask very humbly for tips at the end. But only after giving AMAZING service, of course. An example: on our kayaking tour, our guide at one point spotted something in the water, DOVE in head first, came up with a conch shell in hand, and passed it around so we could all admire the cute little conch creature inside. Wow! Every guide had an endless stream of warm and witty banter. Every tour they gave seemed like it was given just for us. They were all knowledgeable, friendly, and funny! That said, we tended to tip generously and I began to see what their angle was. Low prices up front, knock-your-socks-off service, and humble requests for tips that probably produced windfalls for them at the end. Brilliant. Hats off.
One last thing. Apparently, there ain't no party like the Key West party 'cause the Key West party don't stop. I counted about 5 visibly drunk people on our flight out. Visibly because they were stumbling and slurring but also because they, separately, had to each be told that no, they couldn't bring their drinks from the airport bar onto the plane, and so I watched as each one chugged said drink and then deposited it in the trash before being allowed to board the plane. Oh, and one of them was wearing a T-shirt that said "I'm not drunk, I'm just naturally a loud, clumsy, friendly person."
Key West out.