AFTER A LONG, SCORCHING summer, September is finally upon us. Everywhere other than

Key West, the mere mention of this month sends shivers down every hot-blooded American’s spine. The advent of September means back-to-work, back-to-school, sharpened pencils and brand new backpacks and briefcases — that is to say, summer vacation is over and it’s back to the daily grind.

And somehow, despite all of our best efforts to make the most of every summer day, there are still untaken boat trips and squandered three-day weekends that will be haunting our dreams until winter break. But in Key West, there is no turning of the leaves, no chill in the air to usher in autumn. So how does a tropical island celebrate the changing of the seasons when the seasons don’t actually change all that much? With the ultimate end-of-summer girls’ weekend: Key West Womenfest, which runs from Sept. 4-8 this year.

For decades, Key West’s Womenfest weekend has drawn thousands of lesbians and their friends to what is arguably the premier gay vacation destination in the country (sorry, Provincetown, but the weather up north is already a little too nippy for our taste). Womenfest weekend has a simple goal: to serve as a gathering for women who want to mix, mingle, feel comfortable being themselves, soak up some rays and then party their faces off.

Past revelers on the Sunset Watersports Tea Dance and Dinner Cruise. COURTESY PHOTOS

Past revelers on the Sunset Watersports Tea Dance and Dinner Cruise. COURTESY PHOTOS

Since its debut over 20 years ago, Key West Womenfest has grown to become a worldwide standard for lesbian gatherings. Couples, singles and families arrive in the southernmost town each year to enjoy the famously gay-friendly atmosphere that the Key West Business Guild — the nation’s first ever gay-oriented chamber of commerce — works tirelessly to maintain.

With Lilith Fair a mere memory (I’m still mourning the lack of Alanis in my life) and Palm Springs’ Dinah Shore Weekend already come and gone, the streets of Key West (complete with LGBTQ-themed rainbow sidewalks) are guaranteed to be overrun with women looking to celebrate in all their Sapphic glory against the lushly tropical backdrop of our remarkable island paradise.

La Concha’s luxury pool (above) and Sister Funk (right).

La Concha’s luxury pool (above) and Sister Funk (right).

While this year’s schedule of events ranges from raucous pool parties to intimate art openings, much of the draw of Womenfest is the simple promise of lazy days spent poolside, or else strolling through the sun-dappled historic neighborhoods of Key West with the comfort of knowing you can hold your girlfriend’s hand without some psychopath yelling hateful slurs from across the street. Key West is a city where gay couples don’t just vacation; they settle down, procreate and then send their children to the local Montessori school.

While many arriving for Womenfest will invariably take advantage of Key West’s picturesque state park, its wide-ranging culinary scene, unique museums and world-famous watering holes, it’s the official Womenfest events that keep the ladies coming back year after year. This year’s schedule has been curated to appeal to a wide audience, with both family-friendly events and events that are decidedly adult in nature. We’ve got the full schedule, so read on to learn what’s happening when and plan your ideal itinerary for the weekend.


This year, Womenfest’s official host hotel is Alexander’s Guesthouse (1118 Fleming St.), one of Key West’s most charming inns. Alexander’s kicks off the festivities on Wednesday, Sept. 4, with a Welcome Party from 6-8 p.m.

The undisputed party headquarters of the weekend is the Aqua Nightclub complex (711 Duval St.), whose “Reality is a Drag” shows, satellite Sidebar (504 Angela St.) and open-air Back Bar make it the perfect spot to take in a drag show, catch a burlesque performance or enjoy cocktails under the stars. If you get into town a little early, stop by Sidebar for Women’s Wednesday, where drinks are 2-for-1 from 4-7 p.m. After the official Welcome Party at Alexander’s, the Aquanettes will host their official Womenfest Show at 9 p.m. at Aqua Nightclub. Entry is free for Womenfest attendees.

Alexander’s Guesthouse is the perfect host hotel for Womenfest.

Alexander’s Guesthouse is the perfect host hotel for Womenfest.

If you were a good girl and went to bed at a reasonable(ish) hour on Wednesday night, then you’ll be ready to hit the pool bright and early on Thursday. The day starts with La Concha Hotel & Spa’s women-only Womenfest Pool Party from noon until 4 p.m. (430 Duval St.). For four whole hours, the lucky ladies attending Womenfest can enjoy La Concha’s dazzling luxury pool, pool bar, comfortable daybeds and Blue Chair Bay rum specials while Local DJ Kyd spins by the pool all day long. For the girls who were a little more naughty Wednesday night, Hangover Hospital will be on hand with B12 shots to ensure the party doesn’t have to stop because your head is pounding louder than DJ Kyd’s speakers.

After you’ve worked on your tan lines (or lack thereof), hitch a ride out to Suite Dreams Inn by the Beach (1001 Von Phister St.) for their Womenfest Cocktail Party. From 5:30-7:30 p.m., enjoy a Cuban buffet, beer, wine and cocktails by Suite Dreams Inn’s beautiful pool. Bring your swimsuit and take a dip with mermaids, or just chat it up with local mermaid Kristi Mills, owner of The Captain’s Mermaid Boutique (608 Front St.) and founder of the Key West Mermaid Festival. Or have your crystals read, meet Brandie Patrice (Ms. Gay Pride 2019) and peruse the beautiful work of local artist Pam Hobbs. There will be games, prizes and live music and then the night is yours to make as much mischief as you’d like (karaoke at Bobby’s Monkey Bar, anyone?).

We suggest you spend the next morning recharging your batteries, because Friday, Sept. 6, is chock full of great events and is going to require some stamina. If you’re feeling bright-eyed and bushy-tailed (and miraculously unhungover from Thursday’s antics), hit one of the IWFFA Flag Football Clinics held from 10 a.m. to noon at Bayview Park and get in some practice for Saturday morning’s “friendly” game.

After you work up a solid sweat (and maybe sweat out some of Thursday’s toxins), soak your tired muscles in the pool at Alexander’s Guesthouse during KAT’s R U Wet Yet? Pool Party with DJ Rude Girl from noon until 3 p.m. A $10 donation at the door goes directly towards the Gay-Straight Alliance High School Organization. Later that evening, enjoy a Sunset Tea Dance and Dinner Cruise hosted on one of Sunset Watersports’ deluxe catamarans, with a tropical buffet, unlimited beer, wine, champagne and mixed drinks and a pulse-pounding dance party with Sister Funk to round out the trip.

If you’d prefer to party without the ocean rolling beneath your feet, the Real Women Do Drag fundraiser kicks off at Aqua Nightclub at 6 p.m. Presented by Jodyrae Campbell and hosted by Aquanette Elle Taylor and emcee extraordinaire Laurie Thibaud, the second annual Real Women Do Drag is an all-candidate fundraiser for the Royal Campaign of Fantasy Fest to benefit AH Monroe, which provides vital support to members of the Key West community living with AIDS/HIV. After the show, roll around the corner to Sidebar for the White Party at 9 p.m, with DJ Citizen Jane behind the decks delivering her impossible-to-resist beat-murdering music. Your feet have been warned.

You can party all the way into the next morning, then sweat out the toxins by the pool at the Womenfest Pool Party from noon to 4 p.m. at the typically male-only Bourbon St. Pub (724 Duval St.). There will be games and prizes, and in true Key West spirit, clothing is completely optional. At 4 p.m., play a few rounds of Texas Hold ‘Em at Poker for a Cause at the Silver Palms Inn (830 Truman Ave.). A $40 buy-in gives you a chance at a $1,000 prize package, a live performance by indie folk singer/songwriter Britney Doyal and the knowledge that your money is taking care of all the precious puppies and kitties at the local SPCA of the Florida Keys.

If you get knocked out of the tournament early, head to Mangoes (700 Duval St.) for Brushes ‘n Booze. Co-hosted by Effusion Gallery Key West (701 Duval St.), the first annual Brushes ‘n Booze gives you the opportunity to paint alongside local artist Chris Hotham. Entry is a mere $30, which includes two drinks, appetizers and a painted canvas of your own work to take home. After you make a masterpiece (or a mess, but who’s judging?), pop across the street to Sidebar for Backroom Burlesque, where burlesque superstars Tatah DuJour, Minnie Tonka, the Key West Burlesque dancers and other surprise performers will put a little sizzle into your September.

If you’re anything like the rest of us (which means you need a long nap, a heavy meal and a Bloody Mary to make you feel whole again after a late night), you’ll be thrilled to know that Drunken Drag Brunch 2 at Mangoes doesn’t start until 1 p.m. If 1 p.m. is still pushing it, the Back Bar at Aqua is hosting Hot Dog Church, a weekly ladies’ tradition here in Key West. Hot dogs and hamburgers will be in ample supply starting at 3 p.m. and drinks will be two-for-one. A hot dog with a little hair of the dog? Sounds like a marriage made in hangover heaven.

From Back Bar, it’s a short skip to the traditional Sunday Tea Dance at Key West’s gay mainstay, La Te Da (1125 Duval St.), in the heart of Duval Street. DJ Rude Girl will be spinning by the pool and La Te Da’s professional mixologists will make sure you’re kept lubricated with their famous Key West cocktails and dangerously delicious martinis.

With such a wide variety of activities all weekend long, you’ll be forgiven if you return home on Monday a little worse for the wear. But the exhaustion is well worth the price of admission to Key West Womenfest.

For more information, ticket prices and contacts, visit ¦

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