Gay Travel in Key West: Sun-Drenched Days, Tropical Nights

    By Gary McKechnie

    The Sunshine State is widely known for its outlet malls and unique beach boutiques -- but there's another side to Florida's shopping scene. Flea markets.

    What can you find at flea markets in Florida? Just about anything. Does the world have a shopping capital? I'd argue it does, and it's Florida.

    Not even 100 mega malls or 1,000 garage sales could display the varied inventory you'll discover at Florida's flea markets. Hawked by itinerant dealers, working farmers, part-time collectors, and professional merchants from across the Southeast (and, in the winter, from across America), a curious collection of super-affordable merchandise fills indoor booths and outdoor fields.

    To discover the mother lode of merchandise, just unfold your road map, grab your wallet, and prepare for some fantastic retail road trips.

    Waldo Farmers and Flea Market

    17805 U.S. Highway 301, Waldo
    (352) 468-2255

    Where's Waldo? It's about 15 minutes northeast of Gainesville and it's where more than 900 dealers set up shop at “The Old-Fashioned Flea Market” each weekend. As a result, more than 40,000 shoppers flood into this small town, combing through six large buildings as they search for leather goods, DVDs, tools, clothing, kitchen gadgets, appliances, linens, produce -- and really anything else they think they need. If you're more inclined toward antiques, head next door to the Waldo Antiques Village. Open seven days a week, the village showcases 20,000 square feet of antique furniture, collectibles and knick-knacks.

    Sumter County Flea Market

    516 NW 3rd Street, Webster
    (352) 793-2021

    How does a one-day-a-week market manage? Quite well, actually. In the small town of Webster, an influx of visiting shoppers swells the local population from 800 to more than 50,000 every Monday. Established in 1937, this is actually two markets in one. The first is a massive flea and farmers market with 2,000 spaces and 1,500 dealers specializing in standard flea fare and farm fresh produce. Across the street, Webster WestSide showcases the goods of approximately 500 antiques and collectible dealers. This is where you can find anything from a Lone Ranger lunchbox to original 1920s silent movie advertising slides, as well as Coke collectibles, pottery, militaria, 1940s kitchenware, patio furniture, African masks… and many other things your mom probably threw away.

    St. Augustine Flea Market 

    2495 SR 207 at I-95, St. Augustine
    (904) 824-4210

    Midway between Daytona and Jacksonville, the St. Augustine Flea Market features 300 permanent dealers (and up to 100 drop-in dealers) who peddle rare books, records, and rustic hardware alongside Indian collectibles, beads, fishing poles, citrus, instruments, sporting goods, computers, and Art Deco furniture. You'll also find Cajun-boiled peanuts, pets, clothing, tools and anything that has room for a price tag. Tired? This is the rare market that includes an RV park. Hungry? In addition to restaurants, this market features a U-pick farm.

    The Market of Marion

    12888 SE U.S. Highway 441, Belleview
    (352) 245-6766

    Many Central Floridians have added this clean and well-stocked flea market to their weekly shopping schedule. Close to popular retirement community of The Villages, the MoM in  Belleview features approximately 400 dealers at more than 1,100 booths filled with impressive (and affordable) inventory. Drop by any Friday, Saturday or Sunday ad you can stock up on tools, T-shirts, fashion, cell phones, office and home furnishings, artwork, produce, books and more. Be sure to check their calendar for special weekend swap and/or shop events that focus on a variety of subjects including military vehicles, guns, stamps, antique engines and – believe it or not – gourds. There's plentiful parking beside the covered pavilions so weather will never interfere with a good day of shopping.

    Flea World

    4311 S. Orlando Dr., Sanford
    (407) 330-3976

    Claiming the mantle "America's Largest Flea Market," Sanford's Flea World is a legend among enthusiasts of flea markets in Florida. This Sanford flea market broke ground with services such as hair stylists, tax preparers, psychics and wedding reception rentals. With 1,700 booths, vendors deal in that unusual region between Florida flea market and bargain store with about eight "dollar stores," selling everyday wares like bungee cords, tools, and cell phone covers. Flea World also has a pet store, plenty of electronics, and a "Garage Sale Row." Want to bring the kids? Flea World's "Fun World" features go-karts, bumper cars, miniature golf and other kid-friendly activities.

    Daytona Flea & Farmers Market

    1425 Tomoka Farms Rd., Daytona Beach
    (386) 253-3330

    Located at the junction of Highway 92 and Interstate 4, this Friday-Sunday market should be on the list of every sun worshipper and NASCAR fan. Not only will you find deals on sunglasses and beachwear, the market's "Speedway" area features souvenirs honoring the legends and heritage of nearby Daytona International Speedway. More than 800 vendors spread across the market's 30 acres pitching produce, pickles, antiques and collectibles, tires, spices and rubs, New Age gifts, custom jewelry, Avon products, darts, vacuums, knives, landscape plants and garden supplies. After getting a trim at the barbershop, dine in air-conditioned comfort – then get a tattoo (that's here, too). Check their calendar – the market hosts monthly car cruise-ins and craft shows.

    Opa-Locka Hialeah Flea Market

    12705 NW 42nd Avenue, Miami
    (305) 688-0500

    Busy on the weekend? No matter. This multicultural market, located northwest of Miami, is open seven days a week from 6 a.m. to 6 p.m. The highlight may be the 200,000-square-foot farmers market that features a cornucopia of freshly harvested items from fields and groves in nearby Homestead. To accommodate a steady stream of shoppers (about 100,000 each week), a 10,000-space parking lot gives customers easy access to eight restaurants and merchandise that includes appliances, pets, ceramics, shoes, handbags, luggage, sportswear, watches, auto accessories, toys, wigs, a barbershop -- and a dentist!

    B&A Flea Market

    2885 SE US 1, Stuart
    (772) 288-4915

    Sure, you can find plenty of new flea market merchandise inside B&A, but as you stroll past the outdoor vendors you may detect a feeling similar to one you'd experience in a Middle East bazaar. Rugs and fortunetellers are among the standouts at the largest and oldest Florida flea market on the Treasure Coast. The market's 500-plus dealers are also keen to strike a bargain on golf equipment, produce, ladies' fashions, antiques, estate jewelry, furniture and tools. When in Stuart, you can also save some gas: Instead of combing the town in search of far-flung garage sales, "Garage Sale Alley" offers novice dealers a centralized place to clear out their clutter (and gives shoppers a shot at more bargains).

    Enjoy sun-drenched days and tropical nights in a place where closets are only for your clothes.

    Heading South

    The drive south through the Keys is breathtaking. The brilliant blue-green ocean is dotted with sailboats, catamarans and wave runners; it's obvious that people are out to have an exhilarating day on (and in) the balmy waters.

    You will find shells, corals and other nautical items crowding the shelves at many of the local shops that line Highway 1, including The Shell Man in Key Largo where you can purchase big, colorful shells at a really good price.

    After meandering through Key Largo, Islamorada, Marathon, Big Pine Key and all the other small keys in-between, you’ll arrive in Key West with still plenty to explore and uncover.

    Getting Settled & Exploring Old Town Key West

    Alexander’s Guesthouse, a gay-owned and operated retreat that primarily serves the gay and lesbian community, is the perfect place to settle for your gay travel trip to Key West. Michael, one of Alexander’s attentive and helpful personnel, helps with your bags and gives a tour of the grounds. Your balcony overlooks the pool and hot tub, which are nestled among blooming plants, banana trees and other shade trees – the perfect garden sanctuary. 

    After getting settled in, set off on foot to find a late lunch – you can walk everywhere in Old Town Key West. The crew at Alexander’s recommends when asked by guests to go to Pepe’s Cafe, a small bar and grill offering the catch of the day, raw oysters and a chowder that is out-of-this-world. There, you will get in on a local favorite – the Oyster Race. It's simple: patrons get a number one through five. A shucker begins to shuck five oysters while another person keeps time. The fastest time wins. Each patron with a number matching the number on the fastest shucked oyster gets to choose a key. If the key opens a locked box, the patron wins the money inside

    Sunset Celebration & Out on Duval Street

    There is no better place to watch the sunset than at Mallory Square. It’s a romantic sight. Gay and lesbian couples stroll hand in hand alongside straight couples. Walking around, you’ll meet lots of friendly and open people. In the Keys, no one really cares if you’re gay or straight, making gay travel to Key West an enjoyable experience.

    Mallory Square hosts a Sunset Celebration every eveningThe square is buzzing with musicians, acrobats, mimes and unicyclists. We peruse vendors selling their wares – jewelry, artwork and hand-painted t-shirts just to name a few.

    The sun may be calling it a day, but the night is just beginning.

    Walk down Duval Street towards what the locals call the Pink Triangle. Rainbow flags are easy to spot on Duval. Many of the establishments in Key West are gay-owned or gay-friendly, and they let you know it.

    If you’re in the mood for a fun night outing, check out the nightly drag show at a nightclub called Aqua. The crowd at Aqua is mixed, not just gay men and lesbian women, but straight singles and couples also. Patrons vary in age from young adults to retirement-age folks. The drag show is astounding. The performers do more than sing and dance – they delighted the crowd with outrageous and comedic numbers.

    Some other places to visit for great entertainment are 801 Bourbon Street, which also has nightly drag shows at 9 and 11, and Bourbon Street Pub, which has sexy male dancers. Both are popular spots on the gay Key West circuit. 

    Duval Street is also a shopping haven offering everything from beach gear to small, fashionable boutiques. If you enjoy a good cigar, you can get a hand-rolled stogie at one of the many tobacco shops. And on Duval, you’ll have no problems finding a good place to eat.

    But Key West isn’t all about late nights.

    Out on the Water

    Hop on the boat for an all-day, do-it-all water sports adventure on the Party Cat with Sunset Watersports. The day includes jet skiing, snorkeling, water skiing, banana boat rides, wind surfing, kayaking and more.

    Professional photographers on board will capture your best moments. You can purchase the photos on CD for a nominal fee. Lunch is available, which is the perfect time to meet the friendly staff. During the last hour of the day, draft beer is free and everyone sits together and shares their fun stories.

    Heading Back Home

    Leaving Key West is a glum day – you’ll come to know and love the locals and other visitors.  It’s easy to feel so “at home” and accepted in Key West where "One Human Family" is their official philosophy. There are plenty of opportunities to return for one of the many festivals like Pride Fest, WomenFest and Fantasy Fest.