Dr. Jillian T. Weiss

What I Did On My Winter Vacation: Pearl's Rainbow, Key West's Lesbian Paradise

Filed By Dr. Jillian T. Weiss | January 13, 2009 2:30 PM | comments

Filed in: Entertainment, Entertainment
Tags: Florida, inn, Key West, lesbian B&B, lesbian hotel, lesbian resort, pearl's rainbow, vacation

I'm writing in from sunny Key West, Florida to recommend the most incredible resort: Pearl's Rainbow. If you're a woman considering a vacation, you must consider a stay here.

Pearls 1.jpgShayna and I have escaped NYC to these sunnier climes for our annual winter school break vacation. It's our first time in the Keys. We had heard a lot about how wonderful the weather is and how LGBT-friendly it is, but even so, I must say, the weather here is extremely gay. The whole island is LGBT-friendly, and gay tourism is one of the major sources of income on the island. One of the owners of the resort, Heather Carruthers, was just elected a county commissioner, and we befriended one of the other county commissioners in one of the many gay bars on Duval Street, aptly named the main drag. There are three gay bars (though a lot of patrons are straight) and drag shows nightly.

Rainbow flags are everywhere, and a major event here at this time of year, broadcast by CNN to a grateful nation for the past several years (bless Anderson Cooper's little heart), is the New Year's eve lowering of a giant ruby slipper, occupied by drag queen Sushi, from atop the tower at the Bourbon Street Pub.


Pearls Rainbow house.jpgThere are a dozen gender-specific resorts here for gay men, including Big Ruby's, Coconut Grove Guesthouse, Coral Tree Inn, Equator Resort, Island House, New Orleans House, and the Oasis Guesthouse. There is only one for women.

I wasn't sure when Shayna first suggested Pearl's, wondering whether it would be as comfortable as the condo we had last year in Ft. Lauderdale, and whether I would like sharing my vacation with all these people I didn't know, and whether an all-women environment would feel welcoming or restrictive. Gosh, was I wrong. Pearl's provides an atmosphere that we're reluctant to leave. Especially to come back to the frozen north.

Pearl's has won all kinds of awards -- Planet Out's "Best Inn/Hotel for Women," the 2006 Out & About "4 Palms" Award, the 2005 Lodging Association of the Florida Keys "Property of the Year" Award and more. The property is beautiful and comfortable in that B&B sort of way, but super-sized, with two pools, an outdoor bar, and our suite is quite luxurious. Free wireless internet access (thank goodness - I'm teaching an online course here to pay for this) and they also have a public computer. Breakfast is included with the price of your stay, and Chef Irene makes the best omelets. I didn't try the pancakes and such, as that stuff isn't on my diet, but gosh it looked great. The breakfast menu is actually quite large. The wait staff, Ingrid and Tammy, made every morning feel like breakfast at the Plaza. Cynthia, Justine and Nikki at the front desk have gone out of their way to accommodate us and our peccadilloes. Lorraine, the general manager, was very generous in helping us with our many unusual requests. She's got a major green initiative going, and the place is going out of its way to make sure it's eco-friendly. It's also reasonably-priced, compared to the outrageous prices for local vacation rentals. What alternate universe are those realtors living in? We managed to find flights at a very reasonable price. (After much work, we managed to get it down to about $500 per person round trip.)

There's also a level of comfort here that goes way beyond the amenities, however. It's holding my wife's hand and giving her a kiss on the lips, and getting the distinct feeling that the other people around us are thinking...nothing about us at all. I am kind of surprised at myself. I had thought I had dealt with all that "oh my god I'm queer" stuff years ago, only to realize that there is, in fact, a large part of my computing apparatus consumed with what other people think. Even walking down the street in New York City, where gay people and gay consciousness are everywhere, and we often hold hands...there's always that concern about who's looking and who's thinking what. Impression management. Be nonchalant. Don't notice the stares. They say you only know what you've got when it's gone, and walking in here is a totally different experience because the double consciousness is gone. Remarkably, the same thing is true for the rest of the island as well.

It's been wonderful to sit by the pool, with other women from all over the world. There was usually a nice group of women sitting by the pool during the day, and most of them were quite friendly. It's a clothing optional resort, and some people had their tops down. Pretty much every day is sunny and warm. It rarely rains or is cloudy. We've made friends with people from Philadelphia, San Francisco, Chicago, Wisconsin, Ft. Lauderdale, England and Wales. The staff is friendly and down-to-earth, and they know everything there is to know about events on this island. We've been to the theater, the symphony and the sunset women's cruise. We've skipped the snorkeling and kayaking, but it sure looks like fun.

Every week there are also activities in-house here and they have been fun rather than hokey -- poker night (Cynthia is a great dealer), karaoke night (Irene was good at cajoling), and L-Word night (nuff said). They're just put in a Wii at the Patio bar with bowling, golf and boxing. Women who live in the area come in for events - there was a rockin "New Year's Eve Eve" party with a great DJ. This was the first time that Shayna and I got to dance together in our 3 years+ together. There's an upcoming Super bowl party. The place is happenin', in an understated sort of way.


Kelly McGillis.jpgThe area has incredible restaurants. We've had some really good meals, on a par with the best that New York City has to offer. (Personally, I recommend Camille's, Mangoes, La Ti Da, and Sarabeth) We enjoyed walking down Duval Street, being tourists and buying tchotchkes and T-Shirts, and noticing lots of other gay couples. We've ridden our bikes around town, and Shayna has played a lot of tennis with friendly locals.

I understand that a lot of people come in for Spring Break in March/April, summer vacations in July/August and Women's Fest in September. The place is surprisingly busy, but not at all crowded. If you are a woman considering a vacation, you must check this place out. 800-749-6696. More pics are available here. They have a blog, too. And they have an email list to keep you updated on events, like the party with Kelly McGillis (!) coming up. All I have to say is Oh. My. Goddess.


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I've been and it's definitely fabulous. Highly recommended.

Jerame's been to Key West and still talks about how much he enjoyed his stay too.

But I do feel obligated to point out that Key West's Tourism Commission is a current advertiser on the site. There was no connection made between Jillian's vacation and the advertiser though.