Explore the Florida Keys on a road trip to queer Key West

Kevin Theriault, executive director of the Key West LGBTQ Visitor’s Center.
Kevin Theriault, executive director of the Key West LGBTQ Visitor’s Center.
Heather Cassell

Sunglasses. Check. Sunscreen. Check. Music. Check. I was ready to hit the road to Key West through the Florida Keys from Miami. I was rolling down the Overseas Highway solo as the warm sun, humid wind, and salty air kissed my skin through the open window. My girlfriend, who is usually at the wheel, stayed home in California.

Florida has been a complicated destination long before the NAACP and the Human Rights Campaign issued a travel advisory along with a coalition of civil rights organizations at the beginning of this year’s summer travel season. The organizations warned of Florida’s hostile policies toward LGBTQ people, immigrants, and Black and brown people. Ms. Magazine reported about how the Sunshine State’s policies were weakening women’s rights, too.

However, the sun-kissed destination — while a thorn in LGBTQ activists’ sides since the 1970s with the likes of Anita Bryant’s “Save Our Children” campaign — is also very popular for LGBTQ travelers. Florida’s Republican Governor Ron DeSantis is intent on repackaging the same anti-LGBTQ hype with potentially more dangerous consequences than in the past. In my imagination, I would love a busload of drag artists to drive to these destinations spreading queer joy and love, but fun antics like that might be more dangerous than ever now with armed groups like the Proud Boys. Plus, queens and transgender people have and continue to put themselves on the line for the rest of us more so than most care to admit.

Like many people, I’m nostalgic for the boycotts that changed the world nearly 60 years ago, but I’m not convinced these actions have the same impact for creating major cultural and political shifts in today’s world. I’m suspicious that these actions hurt local queer and progressive communities in the conservative destinations LGBTQ and human rights activists target, making their lives harder in the current political climate. 

Instead of staying away, I decided to head straight into the heat months before things really got hot. I got to know Floridians and transplants from other places who now claim the Sunshine State as home. I supported local queer, BIPOC (Black, brown, indigenous, and people of color), and progressive women-owned businesses. Locals pretty much told me they are struggling to recover from the pandemic and inflation. They didn’t appreciate DeSantis’ “anti-woke” policies and are concerned about the negative impact they are having on keeping travelers, especially LGBTQ people, from seeking sun and beaches on Florida’s shores.

Seeking summer beaches and fun

The end of summer, especially this year is a great time to head to the Florida Keys to Key West. The highway provides plenty of opportunities to pull off the road for a fun break. The drive is dotted with small sandy beaches shaded by palm trees, perfect for snorkeling and other water sports, tours, and dining experiences in small towns. At the end of the highway, there are plenty of queer celebrations waiting in the Conch Republic.

Kevin Theriault, executive director of the Key West LGBTQ Visitor’s Center, told Gay City News that “gay Key West” hosts so many different events every year to “make sure that people” know, no matter what the political situation is, that “you are always still welcome here.”

“We have a great, very vibrant LGBT community,” Theriault said.

Theriault, 46, explained that Key West has been open to the LGBTQ community way before it was popular anywhere else. It started when Tennessee Williams visited, took up residence, and died on the island from 1941 to 1983, according to the Key West Art and Historical Society.

“We’ve held on to that ever since,” Theriault said.

Beginning in August there are usually a string of parties starting with Tropical Heat (August 9 – 13). The five-day all-men’s party gives gay men reasons to drag up and strip down with drag shows, pool parties, and clothing-optional events. In September, women take over Key West for Womenfest (September 6-10). For more than 20 years, women have flocked to the Southernmost point in the United States for the three-day event filled with beach and pool parties, cruises on the water, dinner parties and shows, music and art, and more. In October, there’s Fantasy Fest (October 20-29) and Headdress Ball (October 26). The popular 10-day event gives queers and allies permission to get freaky in the spirit of Halloween.

Alexander’s Guest House in Key West, Florida.
Womenfest in Key West..Key West Tourism

Heading to the rainbow’s end

The four-hour road trip can be taken fast or slow. I suggest taking your time along the Overseas Highway.

Similar to the Pacific Coast Highway drive, the Overseas Highway drive is an iconic scenic route built by visionary developer known as “The Father of Modern Florida,” Henry Morrison Flagler, in 1938. The highway passes through Key Largo, the gateway to the five major keys — Key Largo, Marathon, Islamorada, the Lower Keys, and Key West — and North America’s only living coral barrier reef.

The drive between Miami and Key West is 160 miles. The reef is approximately 360 linear miles, according to the Florida Department of Environmental Protection. It is worth doing at least once in a lifetime. The keys offer many outdoor activities with four national parks and 10 state parks, multiple ways to enjoy the water (boating, snorkeling, etc.), and plenty of opportunities to relax.

Life slowed the further I drove away from Miami. I passed over 42 bridges, beaches filled with families in swimsuits under umbrellas, and through small fishing villages on the single-lane highway.

Stopping in Key Largo, I was taken out into the canals and onto the Atlantic Ocean aboard the African Queen. The African Queen is the boat used in the Oscar winning film of the same name starting Hollywood legends Humphrey Bogart and Katharine Hepburn. The legendary steamboat offers small tours and at certain times of the year sightings of manatees. It is a must-do excursion, especially for movie buffs, seeking to learn the stories behind the boat and the movie.

The cameras also rolled at nearby The Fish House. The eatery and market appeared on the Food Network’s, “Diners, Drive-ins, and Dives.” I was not disappointed when I stopped in for lunch. The fish was fresh off the boat and seasoned and cooked perfectly. They also had a decent key lime pie. Another good lunch stop further down the highway in Islamorada is Robbie’s of Islamorada. It’s a nice semi-midway point right off the highway when you are driving to Key West or on your way back to Miami. You can also feed the tarpon (beware of the aggressive brown pelicans) and grab some last-minute beachy souvenirs at the open-air booths.

I spent the night in Islamorada as a guest in an oceanfront room at La Siesta Resort and Villas. I arrived in time to catch some sun on the beach before heading out for dinner at Morada Bay Beach Café and enjoying local craft beer and a live band at Florida Keys Brewing Co.

The next day, I enjoyed a slow and relaxing morning before I continued down the single-lane highway to Key West. By early afternoon, I was in Key West hanging out at the Alexander’s Guesthouse’s pool with a group of the LGBTQ inn’s longtime regular guests.

Alexander’s Guest House in Key West, Florida.
Alexander’s Guest House in Key West, Florida.Key West Tourism

I was a guest of the charming historical inn perfectly situated from Duval Street, where the action is. The street is home to many popular restaurants, such as Mangoes Key West and Poke in the Rear, located behind the Aquaplex Key West, that has the best drag show on the island. Toward Key West’s docks is Half Shell Raw Bar, an institution on the island and is popular with locals.

I fueled my days with the inn’s breakfast. The main dish changed daily and was always accompanied by a variety of pastries, cereals, and fresh fruits. I spent my three days on the island visiting the six-toed cats at the Ernest Hemingway Home and Museum, checking out the lighthouse museum climbing to the top of the lighthouse to get a view of Key West, and stopping at the Tennessee Williams Museum.

Alexander’s Guest House in Key West, Florida.
The Tennessee Williams Museum in Key West.Heather Cassell

I wasn’t able to enjoy heading out onto the water due to a hurricane level storm heading toward Florida at the time, nixing kayaking and other boating and water activities. Despite that, there wasn’t a lack of things to do. I perused the art galleries and boutiques along Duval Street and on side streets and enjoyed pool time at the inn.

The most popular way to get around Key West is by foot, bike, or scooter, which is part of the island’s charm.

While I road tripped it this time, flying into Key West International Airport is another option.