The Unofficial yet Undeniably Gay Guide to St. Augustine

No other city in America is as gay as St. Augustine, Florida, perhaps because this place had a head start (or a “leg up,” as we like to say) as the nation’s oldest European settlement.  Sporting flamboyantly gay points of interest (including a pink jailhouse), antiques stores galore, gay-friendy Victorian B&B’s, men dressed as pirates or undressed as surfers, show tunes ringing from bell towers, and a strongly Greek population (the Greeks invented homosexuality, don’t you know?), St. Augustine is nothing short of a gay paradise.  Here are the nine gayest hotspots:

Gay Icons Everywhere

Sebastian painting

Plausibly the earliest gay icon was Saint Sebastian, a Christian saint and martyr, whose strong and shirtless physique, symbolic arrow-pierced flesh, and rapturous look of pain combined have intrigued artists, both gay and straight, for centuries and began the first explicitly gay cult in the nineteenth century.  Sebastian pops up everywhere around St. Augustine, though perhaps most prominently at the San Sebastian Winery.  Essential streaming: Derek Jarman’s controversial gay landmark film Sebastiane (1976).

Chiseled and Massive

Michelangelo's David sculpture at Ripley's Museum

A veritable synonym for masculine beauty, Michelangelo’s statue of David is the world’s best-known celebration of the male form.  Art critic Michael Bronski notes that beginning in the 1950s, gay men displayed Michelangelo’s David in their homes to signal their sexuality to visitors.  A massive statue of David towers over St. Augustine from the courtyard of Ripley’s Believe It or Not museum.  There are benches below the statue so one can gaze up at one’s leisure.  A tall hedge (David’s crotch level) ensures privacy as you ogle.

The Ultimate 5 o'clock Shadow

Lighthouse Moustache
St. Augustine Lighthouse shadow at 5:00 p.m.

Standing proudly erect, the lighthouse is a phallic symbol if there ever was one.  (Sometimes ours even sports a dapper moustache!)  St. Augustine’s lighthouse is an inspirational beacon for lovers both day and night.  With 219 steps to the top, the tower offers a great workout in addition to a panoramic view of the ocean and historic downtown waterfront.  Every Wednesday is the unofficial Gay Day at the Lighthouse.  The place is so friendly and comfortable that we’ve seen guys holding hands as they strolled about.

A Pride of Lions

Sunrise at the Bridge of Lions

The iconic Bridge of Lions is guarded on both sides of the mainland mouth by St. Augustine's most chiseled gay couple: two proud male lions, their paws holding their balls.

A Pink Prison

The Old St. John's County Jail

Extravagantly painted in gay-pride-pink and sporting white picket fences, the Old Jail is a strong contender for St. Augustine’s gayest point of interest.  The jail was designed by a man of exquisite taste, Henry Flagler, whose castle-like Ponce de Leon Hotel (now Flagler College) is a St. Augustine landmark.  Essential streaming: Jean Genet’s homoerotic prison fantasy Un Chant D’Amour (1950).

Life is a Cabaret

Sundial at Memorial Presbyterian Church

Classically gay showtunes like "Cabaret" and "Somewhere Over the Rainbow" fill the air as the carillon marks the hours from the tower of the Memorial Presbyterian Church, adjacent to Flagler College.  Essential streaming: Liza Minelli in Cabaret (1972).

The Fountain of Youth

Sundial at the Fountain of Youth Park

The Fountain of Youth is the epicenter of the gay world’s cult of youth and beauty.  Judging by the landscaping throughout this archeological park, no homosexuals were employed.  However, the colorful peacocks dotting the grounds are charming and quite photogenic.  Sips from the world-famous fountain are free with paid admission, and cannon loads are shot into the water throughout the day.  Essential viewing: Pirates of the Caribbean: On Stranger Tides (2011).

Buccaneer Buddies

Pirate Statue

The tightly-bound brotherhood of men who roved together on the high seas for years at a time, uninhibited by the rules of mainstream society, obviously found fulfillment in each other.  St. Augustine’s multi-million-dollar Pirate Museum celebrates buccaneer buddies.  The theming and attention to detail throughout are nothing short of fabulous.  Essential reading: Sodomy and the Pirate Tradition by Barry R. Burg (second edition, 1995).

Just For Swingers

Romantic Swing at Mission of Nobre de Dios

St. Augustine’s best-kept secret is the town’s equivalent of Plymouth Rock — the very spot where the Spanish first set foot in America.  The scenic and exquisitely peaceful spot is on the grounds of the historic Mission of Nombre de Dios.  Just a stone’s throw from the giant cross (the largest in the world) is a romantic swing for two, looking over the salt marshes of the Matanzas River and toward the grand mansions on Anastasia Island.

Glistening Cock

Glistening Cock

This flamboyant rooster, the mascot of The Mellow Mushroom on Anastasia Island, is surely a contender for the gayest thing in town as it combines a cock with a disco ball.  Essential reading: How to Tip the Pizza Guy (stranger first time gay erotica).

In the Limelight

Limelight Theater

“Theatrical” types invariably congregate at the Limelight Theater.  The lobby is decorated with a statue of Michaelangelo’s David under stag horns — seems unambiguous to us!  Essential reading: The Queerest Art: Essays on Lesbian and Gay Theater.


Jay ♥ David graffiti

While we’re happy that a certain Jay and David are in love and want the world to know it (see graffiti in photo), they gave homosexuality a bad name when they defaced a wall at the Dow Museum of Historic Houses.


Your faithful webmasters had an absolute blast during our extended visit to St. Augustine!  Here’s a gallery of our gay-old-time in the oldest city, where we comfortably ventured out and about as an openly gay couple.