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The Southern Sun: A Key West Trip

Kw1_1 Kw4_1

I headed down to Key West from Miami with my boyfriend Dave just after Thanksgiving. I hadn't been to Key West in eleven years. I was hoping, above all, to just relax, so last Monday we headed down to stay with our friends Jon and Martin at the Island House. I'm always up for a good road trip, so I was looking forward to the drive down, much of which is on a two-lane highway. If there's a car accident along that stretch, as there was the first time I drove down years ago, you're seriously screwed and may spend a few hours idling on the road while they clean it up. Above, our first (sort of) sunset as we approached Key West on Highway 1.


Kw6_2 Kw7_1
Pepe's is my favorite restaurant in Key West. It's also the oldest. It was opened in 1909 (and looks it) and its rickety wooden walls are filled with old Key West memorabilia, photos and maps. One wall is painted with carnival masks through which you can peer, and the bill is served on a converted mousetrap (above). Perhaps that's a message that they (or the preponderance of cats) have done away with any rodent problem. The food is delicious, so I'd recommend at least stopping in for some oysters on the half shell if you get a chance. (MAP)


The brunch crowd last Thursday at Pepe's...

A period film shoot was going on next door. I think I saw Reese Witherspoon run out on the balcony and scream "the gays are being driven from Key West!" But then again, it could have been my imagination.

Walking toward downtown one night Dave and I stumbled upon the Key West cemetery, gridlocked with above-ground tombs. Walking beside it late at night is an eerie experience as many of the pretty wooden houses on Olivia Street seemed either boarded up or abandoned.

This is some of Key West's higher ground (the cemetery was moved here in 1847 after a hurricane disinterred most of the graves in its earlier location). It has an interesting history, which can be read about here. Among the more humorous tombs are one which reads "I Told You I Was Sick."

I only actually remember taking one shot of the cemetery, so you can interpret this shot (which showed up on my memory card unexpectedly) any way you want.

On a side note, right after we walked by the cemetery we passed Seven Fish, a restaurant we wanted to try but couldn't because the night we wanted to go they were holding a private party (MAP). It looked great though. When we passed Seven Fish this night, the Real World Key West cast were eating there while their very hot crew waited outside. I think the new season starts soon. I've already seen ads for it.

We ended up eating at a great Italian place on Duval Street called La Trattoria (MAP).

My boyfriend Dave checking out a biopic at the (roped-in) Tropic...

Islandhouseent Islandhousepool
Dave and I stayed at the Island House, a clothing-optional guesthouse that has supported Towleroad for many months. I'm happy to say that even if they weren't staunch supporters of this site I'd give them a first class rating since most gay guesthouses I've been to in the past have been sorely lacking in a lot of areas. Great service, a masculine, comfortable room (that's ours below) with feather mattresses, warm clean outdoor and indoor jacuzzis, a gym, and a spacious pool surrounded by a delicious restaurant and bar. I'm not the clothing optional type but felt totally comfortable here (in my swimsuit) and the staff is great (thanks Alan!) The attention they pay to detail is really commendable, and the broadband wireless internet access that blankets the entire property is a huge bonus in this blogger's book! (MAP)

Nightpool Islandhouserm

The Island House also has a free happy hour for hotel guests every evening for an hour and a half so you can get your night started...

If anyone tells you that it's hard to find cock in Key West, don't believe them. These things are everywhere, and they're loud. This is the same rooster in passive (above) and active modes.


Bourbon Street, Kwest, and Aqua are the big spots to hit on Duval Street and don't seem to be experiencing any lack of activity even during the middle of the week. The Bourbon Street complex is currently expanding beyond its borders. Now, instead of a mega-complex, I suppose it'll be a super-mega-complex. Sushi the drag queen drops in a high heel pump here on New Year's Eve, an event, as I remember, Anderson Cooper has not neglected to cover on CNN. (MAP)

The glazed look I get after downing several shots of Jagermeister.

Duval Street late at night. Don't forget to eat some Key Lime Pie while you're here. I prefer the kind covered in chocolate on a stick at the Blond Giraffe.

A pair of Santa's helpers outside Aqua nightclub on Duval Street. (MAP)

Mallory Square (MAP) is the traditional sunset viewing spot in Key West but I'm a bit turned off by the tacky souvenir shops and cruise ship day trippers. I'd recommend one of the sunset cruises, which we did (more below). That said, a gorgeous sunset is hard to complain about from any vantage point.

Another shot from Mallory Square.

Here's one of the boats you can take out for the Sunset Cruise, but you might want to do what Dave and I did and take the Blu Q, a catamaran with an all gay crew.

Here are two of the Blu Q's crew, First Mate John and Captain Scott (right). In addition to just standing around looking sexy, they really do know how to sail a catamaran. They'll take you out and give you good sunset.

Here's John pulling up the sail.

On the far shore you can see some of the sailboats in the KW harbor that didn't fare too well during Hurricane Wilma. Not exactly where you want to see your boat parked.

The object of my affection.

Sunsetboat Sunsetboat2
If you're lucky, your voyage will end like this.

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Conchbarber Yellowhouse_1
Key West architecture is mostly ordinary, and mostly charming. There is plenty to talk about here, but these are just a few structures that caught my eye during our trip. I tend to gravitate toward things that are lit interestingly or have a damaged, antiquated charm about them. One place I'd also suggest visiting, which I didn't get to this time, is Ernest Hemingway's house, still very much the way it was when he lived here. Its grounds also house a huge number of housecats which may interest you or not, depending on your allergy situation.

One tropical night we came upon this old lady reading on her front porch. She was so perfectly framed in her peaceful island of light I wish I could have summoned Edward Hopper back from the dead to paint her.

Here's another shot of the Southernmost Point marker, which locals refer to as the Southernmost Buttplug. It's usually surrounded by tourists wanting a photo.

Here you have a local practicing her yoga on one side while a tourist poses for a picture on the other. I guess that symbolizes fairly well how the transients and the locals share this beautiful place. One other note. As you can see, they seem to be in the process of repainting the marker. I'm not exactly sure how frequently that happens but it usually has "southernmost point" painted on it, just so people know they're not posing for a photo with a giant...

Dave and I had a great little trip, short as it was. A few weeks ago there was an article in the NYT about how Key West was slowly being de-gayed due to rising real estate prices. While gentrification is obviously taking place, to me Key West seemed just as gay as I remembered, and definitely very friendly. We left just before the beginning of Fantasy Fest, which was moved this year due to the hurricane. I can't wait to make another trip. A special hello to those we met down there and a thanks to Stephen Smith from the Gay and Lesbian Center of Key West, which is a great resource (MAP) for LGBT travelers heading down to visit.

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  1. It looks and sounds like you had a fantastic trip. Thanks for sharing the photos. :)

    Posted by: Austin | Dec 3, 2005 5:20:40 PM

  2. Andy, your photo journalism talents have once again given us a great tour of Key West, the warm accommodations of the Island House and the its many offerings. A cruise on the Blu Q looks irresistible. Having never been there, you have convinced me to vacation there this winter! Looks like you were only two shots away from "crossing over".......

    Posted by: Johnny Lane | Dec 3, 2005 5:34:45 PM

  3. The southernmost point of the United States is Ka Lae (South Cape), in Hawaii, not Key West!

    Posted by: O. Johnson | Dec 3, 2005 5:49:49 PM

  4. I'm headed that way after the new year. I'll take your recommendations to heart and give'em a try.

    Posted by: moby | Dec 3, 2005 6:31:11 PM

  5. Thanks. I've often wondered what Key West is like. I think you caught the ambience of the place, and it was nice to see some personal shots in the mix, too. My best wishes to you and Dave.

    Posted by: Greg | Dec 3, 2005 6:35:54 PM

  6. the drive down and back is horrible
    fly next time

    Posted by: kuros | Dec 3, 2005 7:03:05 PM

  7. I miss Key West! Had a great time last year in June. The picture of Santa's helpers are Inga and Faith from the Aqua Lounge. Is Rodney still showing the goods at Bourbon St. Pub? Thanks for sharing these pictures....brings back fond memories. Love you guys and this blog.

    Posted by: R. Ho | Dec 3, 2005 7:41:32 PM

  8. Brings back great memories. Thanks!

    Posted by: Tom | Dec 3, 2005 7:58:47 PM

  9. Nice pics! Looks like you had a great time!

    Posted by: Jeff | Dec 3, 2005 8:03:33 PM

  10. Really great pics and you're bf looks like such a hunny as yourself.

    Posted by: Semaphore J | Dec 3, 2005 9:11:05 PM

  11. Love is a many-splendoured thing.

    Posted by: max | Dec 3, 2005 9:12:14 PM

  12. Aww... that looks like a lot of fun. I wish my boyfriend and I could make a road trip there, but somehow the thought of driving from the west coast of Canada seems a little daunting.

    Thanks for sharing!

    Posted by: Jason | Dec 3, 2005 9:48:55 PM

  13. Andy, I fly 1600 miles just for the key lime pie on a stick!

    Posted by: midnight lounge | Dec 3, 2005 10:16:17 PM

  14. You show me yours, I'll show you mine! You are right about the pie on a stick.

    Posted by: Lee | Dec 3, 2005 10:48:47 PM

  15. Thanks for the pics and the memories!

    I was stationed at Key West for two years while I was in the Navy - back in 1996. I was on the honor guard, and performed many funerals (doing the 21 gun salutes) at that cemetary you sent pics of. It was creepy in the daytime too!

    Lots of great memories from KW - it really does feel like another country... and it's a great place to go and 'disappear'.

    Thanks again.

    Posted by: matty | Dec 4, 2005 2:03:52 AM

  16. What a wonderful update! I really enjoyed your photos and descriptions and am glad you had such aa great time. The Island House looks really nice, and Dave is a cute!

    Thanks for the update once again.

    Posted by: David | Dec 4, 2005 3:48:46 AM

  17. Andy... What have I told you about smuggling drugs into the U.S. from Cuba? Stop!

    Posted by: M@ | Dec 4, 2005 5:50:57 AM

  18. and Matty was in the Navy? He wasn't on the USS Independance, was he? *(the most predominantly gay flagship in the US NAVY)

    Posted by: M@ | Dec 4, 2005 5:51:44 AM

  19. On the day KW is no longer gay, J Lo will suddenly reveal talent. At anything.

    Seriously - seems like a cozy, fun trip. I haven't been down there in many years as well - is there still a Monster? Massive bar, good dance floor, and running slideshows on the wall of construction workers. What was odd is that they weren't hot construction workers. Just picture after picture of fat, unattractive, all-too-real, construction workers.

    Posted by: Giacomo | Dec 4, 2005 8:06:01 AM

  20. my partner and a couple of friends have been going to Key West and staying at Island house for the last 5 years. While this year we enjoyed our time at Island House as always(we ARE clothing optional boyz,,LOL) We found Key West a lot different this year. Its disapointing that not only the real estate prices but just the attitude that they want the "family crowd" and some changes that we saw on Duval are disapointing. We decided to do something different this February and are going on an Atlantis Cruise instead,,,hopefully the next year we go back it will be the way it used to be. Oh and by the Way,,,Seven Fish is FANTASTIC.

    Posted by: LeanOhioGuy | Dec 4, 2005 2:07:23 PM

  21. Putting that well defined map at the top really puts things in their proper perspective as i hadn't realized how far off the coast KW was until now.

    A few shots reminded me of flat portions of Bermuda but cocks the size of yours aren't to be found there and it looks like a marble piano in the graveyard?

    Perhaps your Captain Scotty can beam us down to his ship without us having to make that long dreadful drive? i prefer getting a rise at sunrise to going down at sunset.

    The population is a bit too old for me as i prefer young choir boys...

    Posted by: HisHolynessDPope | Dec 4, 2005 4:02:59 PM

  22. Brilliant summary of your trip. Great fotos and commentary... puts the rest of us to shame and well worth the wait. JB

    Posted by: J.B. | Dec 4, 2005 5:01:35 PM

  23. It really looks like you had a blast. Great pics too! What cam did you use?

    Posted by: towlefan | Dec 4, 2005 6:14:00 PM

  24. It must be nice to take a lavish vacation on the money that you get from companies advertising on the journal you get to use for free and just because you copy/paste stories from the internet.


    Posted by: Hunter | Dec 4, 2005 10:31:21 PM

  25. Jealous much?

    Posted by: Shorty | Dec 4, 2005 11:04:35 PM

  26. 1 2 »

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