Still Crazy for Key West

By Anne Stockwell

Originally published on Advocate.com May 23 2006 12:00 AM ET

Two summers ago I
went to Key West, Fla., for the first time, and
honestly I’ve wanted to go back ever since.
It’s not like we often go back to reminisce on
this site, but pictures keep coming to mind. For
instance, my room at Pearl’s Rainbow.

When I stepped
off the pint-size plane at the Key West airport in July
2004 I was on the job, being shown the gay and lesbian
sights so that I could recommend the island to
Advocate readers. Nice work if you can get it, you may
say—and indeed it is. But just between you and me,
not every site that’s said to be charming
actually charms. And making up pleasantries for days
at a time can start to feel like very heavy lifting.

I mention this
now because at the time I wasn’t sure I wanted to
stay in a women-only hotel. So sue me: I stereotype as
much as the next dyke. I was picturing something
genteelly underfunded and overpoliced. Like that
lesbian-owned bed and breakfast I once visited that had
little brass signs all over: “Please do not sit
on the eiderdown.” “Please do not put
jiggle the handle on the toilet.” Hoo-hah. Party
time.

Pearl’s
Rainbow is nothing, nothing like that. It’s luxe to
the perfect degree—no expense spared, yet not
so formal you want to tiptoe. The fixtures are
handsome, the towels thick, the air conditioning fierce, the
staff queer as queer can be. It’s bliss. The main
building started its life, like many in Key West, as a
cigar factory. (Remember, Key West is just 90 miles
from Cuba. The whole time I was there I saw planes and
helicopters circling a point on the horizon headed, I was
told, to Guantánamo Bay.) At the rear an
extravagantly landscaped patio shelters two pools, a
hot tub, and a laid-back bar where they’ll grill you
a burger whenever you want. I watched women arrive
and, over the next few days, melt into puddings of
lesbian contentment. One of the staffers told me that
women cry when they leave and go back to their everyday
lives. I believe it.

Pearl's Rainbow | Advocate.com

Pearl's: Something marvelous

So, two years
later, I want to send a continued shout-out to
Pearl’s proprietors, Heather Carruthers and
Leslie Leonelli. If you’re a lesbian looking
for a wonderful time away, call these women and get a move
on. They’ve created something marvelous.

Not to be all
grrrl-centric—if you’re a guy visiting Key
West there are a number of gay lodgings where
you’ll feel at home, in your clothes or in the
altogether. Before I ever arrived, my delightful gay tourism
contact, Steve Smith, assured me that there’s
no friction on Key West between gays and straights.
That point was repeated by Carol Shaughnessy, the gracious
(hetero) PR rep assigned to facilitate my stay.

I mean, come on,
you think to yourself when you hear that kind of thing.
But a few days later, I was well on the way to being a
believer. Gay and straight, Key West puts out some
major hospitality. (More shout-outs to realtor supreme
Martha Robinson and lesbian scooter pilot Laurie
Thibaud.)

Another place I
keep wishing to revisit is Subtropic Dive Center. After a
morning refresher course with unflappable instructor Jan
Henry, I got underwater for a reef dive, cruising
along at an easy depth and surrounded by a riot of
underwater life. Favorite “gotcha” moment:
When I first got down to the bottom, I swiveled my
head and found I was face to face with a cobalt blue
fish the size of a bathtub. I laughed so hard I
shipped a little water in my mask. The fish blinked and swam
off.

Other major
hoots: The Gay Trolley Tour, which kicks off every Saturday
at 11 a.m., mixes lots of humor with a considerable helping
of gay pride. At Alice’s Restaurant, I had one
of the best meals of my life and got to say so in
person to Alice herself, who appeared in a leopard-print
toque. La Te Da, the pleasingly upscale
hotel-restaurant-cabaret-bar that dominates the gay
end of main drag Duval Street, was perpetually filled
with tanned and windblown gay folk, tourists and locals,
sharing vital dirt and powerful libations.

La Te Da | Advocate.com

La Te Da, the pleasingly upscale
hotel-restaurant-cabaret-bar that dominates the gay end
of main drag Duval Street.

Speaking of La Te
Da, drag is huge on Key West. We forget out here in Los
Angeles how freeing drag can be for a crowd of queer
vacationers who spend 51 weeks of the year trying to
act straight. One of my favorite mental snapshots is
of a vacationing crowd of lesbians at the dance club
Aqua, genially stuffing dollar bills into the G-string of a
burly drag queen lip-synching novelty songs like
“Hot Pussy.” John Waters would have been
proud. On the other end of the drag spectrum, La Te
Da’s Christopher Peterson is the
island’s Eleanora Duse. He does his own singing and
at least a dozen quick changes too, and the night I
saw him he had the audience on its feet.

There’s
lots more to tell: Hemingway’s house—that
scandalous old homophobe—and Tennessee
Williams’s too. A visit with gay travel pioneer
Hanns Ebensten, who received me with his majestic black cat
in his arms. Everywhere, tropical vegetation that
flourishes in gigantic proportion, like something out
of a dream. Homemade ice cream in Cuban flavors. The
gay-owned Key West Butterfly Museum, a spectacular
experience that deserves a column to itself. And
finally, the fun of tooling around the island on a
rented scooter, zipping along fast enough to cut through the
humid air and become your own cool breeze.