Sunsets with entertainment, live music, literary history, pirates, roosters, pie, drag queens, Cuba – what’s the common thread running through all of these things? If you don’t know then you’ve never had the fun of visiting the southernmost point in the United States, located in Key West, Florida. Settled in the early 1800’s and valued at one time for it’s position on the shipping lane known as the Straights of Florida and as a stronghold during the Civil War, Key West, originally known as Cayo Hueso, is rich in history and culture and is incredibly popular as a tourist destination, particularly in the winter. The island is probably the only place in the US that has somewhat lightheartedly declared itself an independent nation and that has it’s own passport, calling itself the “Conch Republic” (the story is too long for this post, but here is a link). It’s only 90 miles from Cuba, the many refugee boat trips over the years described lightheartedly by Jimmy Buffet in his lyrics to “Everybody’s Got a Cousin in Miami”

It was ninety miles to freedom but they took the risk

Though the ocean was all motion and the wind was brisk

The deadly gunboats never saw them in the pale moonlight

They were off to Cayo Hueso by the dawns early light

The gringo in the garden called the customs man

They answered all his questions, were allowed to land

The ladies shared a hairbrush and their husbands had a coke

Then they were taken up to Krome to meet with their kin folk

In spite of the fact that my fellow Jimmy Buffet friends and I consider Key West our mental mecca, I’ve actually only visited once about 20 years ago on a girls’ trip before I was married, when 4 of us planned a trip inadvertently during Fantasy Fest. Think of this as Key West’s version of Mardi Gras, where virtually anything goes – and I do mean anything! How does one do this inadvertently? Well, you begin by purchasing airline tickets first, THEN reserving your hotel room…or trying to. This was back in the day when I barely had e-mail, and we had no idea Fantasy Fest was planned until we tried to get a hotel room and all we could get was the last suite in Key West (at three times the price!) Anyway, I always wanted to go back and just never did, until last week. Yep, it took me 17 years, but I finally talked my husband into going. And while we had a great time, it wasn’t the same Key West that I remembered.

We did some of the  ‘must do’ touristy things like  watching the sunset at Mallory Square, seeing Ernest Hemingway’s home, and going to have your photo taken at the southernmost point marker. I wasn’t sure what to expect at Mallory Square, but it sure was fun people watching, and I think the entertainers were as much fun as the tourists! There was a crazy Frenchman with his flying stunt cats, and watching his odd little show as he hollered at the cats’ butts and the tourists with an accent as think as peanut butter was simultaneously creepy and hilarious. Jugglers with fire sticks, accordion players, a guitar playing mermaid, acrobats and all kinds of other stuff was happening all along the waterfront. Just keep walking back and forth. Mike and I just kept looking at each other feeling a little like we’d fallen through the looking glass.  I really can’t make this crap up, Google it. Especially Dominique and his flying cats.

One of the things we did, that almost didn’t turn out well, was an evening sunset sailing cruise. (Note to self, next time check the forecast first.) I love sailing, and have been on 4 Windjammer sailing cruises in the Caribbean (think of 3 and 4 masted pirate ships, and you have the right idea!)

We decided to go for a sail on the Jolly Rover, a 2 masted boat, and with a crew of 3. The guy who sold us our tickets used to sail with Windjammer, so it was fun comparing notes with him. The first part of the cruise was fine, and as we set sail they asked if anyone wanted to help raise the sails. Of course my hand was the first (and only!) one up in the air. I helped haul up the sheets which you see in the picture on the left (pull the rigging on the sails for you landlubbers) which I’ve done on other sailing trips, and think is fun, and off we went – sort of. Unfortunately there wasn’t much wind so while the sails filled, we moved awfully slowly. That’s ok though, I mean come on, I’m on the ocean, it’s warm, I’m on a boat, who cares?

We took some photos at the helm (beware of sailing hair!), then our captain checked the radar and noticed that there was a squall line coming in and there were wind warnings issued. Interestingly it still wasn’t particularly windy, but time to get the sails down and get back to harbor, fast. Out of nowhere, it seemed, the clouds came in, and we barely made it just outside the harbor when the winds picked up, and essentially blew us the last couple hundred yards back into the slip. We hustled off the boat and into shelter. Got a little rain for maybe 30 min, and then it was over as quick as it started. But it sure was a bummer to ruin the sail and the sunset!

As a writer, there was no way I was going to miss the chance to go over to Hemingway House and see how dear old Ernie lived on Key West for 8 years while he did some of his best writing. There are still  descendants of his infamous 6-toed cats and the penny his 2nd wife embedded in the concrete by the swimming pool (look up the story about how she got his last cent).

Just for the record, I loved his writing room that overlooked the pool, and I want a sanctuary just like it. Imagine a room to dream, loose yourself in like that, be at your most creative. Sigh. I might have to redo my craft room. (I think I just sensed my husband cringing.)

The thing that surprised us the most was probably the age of the people we saw. During the daytime there were people of all ages but the highest percentage were over 65, which neither of us expected. Because the bars are open until 4 am, we figure most of the younger ‘kids’ were sleeping it off during the daytime, then as sunset drew closer most of the over 65 crowd disappeared and the younger people showed up, filling the bars on Duvall, all of which have their doors open to the street, and many also have windows that are open as well, or have musicians outside on a patio, so no matter where you are you can hear music. Walking back to our hotel after dark was an interesting experience, too. We had to walk past a couple of clubs with drag queens, who would station themselves outside to try to get people to come in and watch the show. So as we would approach, we would hear “Hi there honey, how are you?” or “Hi, having fun tonight?” They were perfectly nice and polite, and the easiest thing to do was to greet them back nicely, and just say “yes”. If they asked if we wanted to come in and see the show, I just smiled and gently said “no thanks” and kept going. It’s really not fair, that they look better in a dress and makeup than I do though.

It was fantastic to get away though, from 35 degrees in Minnesota, to 80 degrees in Key West, even if the ocean water was colder than I would like. I suppose if I were laying on the beach and getting all toasty, the chilly water would feel great, but I’m not much of a sun goddess, so dipping my toes in the water it felt pretty chilly to me, but heck, it was still the ocean, which I love and miss!! I can’t wait to go back and hope I don’t wait so long for the next trip to see it.

Oh yeah, did I mention the Key Lime Pie?