Key West restaurant where Hemingway refereed Friday-night boxing matches in a building that previously served as a cockfighting arena, gambling den, and bordello
729 Thomas St, Key West, FL 33040
Research updated June 2026
Age
All Ages
Cost
$$
Full-service restaurant; no cover charge. Menu prices typical for Key West dining.
Access
Wheelchair OK
Outdoor dining in a dirt-floored tropical yard; some uneven ground around the banyan tree and garden areas
Equipment
Photos OK
Est. 1890 · Ernest Hemingway Boxing Connection (1930s) · Cockfighting Arena History · Former Bordello with Surviving Peepholes · Dade County Pine Construction
The building at 729 Thomas St occupies a corner lot in Key West's Bahama Village neighborhood, the historically Bahamian-descended section of the island that developed independently from the Anglo-American commercial center. The structure is built of Dade County Pine — a virtually rot-proof native hardwood so dense it resists insects — which accounts for the building's survival through multiple Key West hurricanes and more than a century of hard use.
The property's history of uses reads as a compressed catalog of informal Key West commerce: cockfighting, billiards, gambling, and operation as a bordello. The cockfighting arena use is the most physically documented — the back yard retains a configuration consistent with organized bird fights, and the venue's own history confirms this use. The bordello operation appears to have been in the upper rooms; peepholes cut into the walls of those rooms, consistent with commercial voyeur arrangements of the era, remain visible and are pointed out on informal history tours of the property.
In the 1930s, the back yard hosted a boxing ring. Ernest Hemingway, then living on Whitehead Street about four blocks away, organized and sometimes refereed the Friday-night matches. Hemingway's interest in boxing was documented throughout his Key West years; he sparred regularly and is known to have attended and officiated bouts at several Key West venues during the period 1928–1939.
The property sat through various commercial uses in the mid-20th century before reopening as a restaurant. Blue Heaven as a restaurant opened in the early 1990s and has operated continuously since, becoming one of the more distinctive dining experiences in Key West for the combination of the outdoor yard, free-roaming roosters, live music, and the building's history.
Sources
Blue Heaven has no well-documented ghost. It appears in Key West dark-tourism discussions primarily because of what it was rather than what people have claimed to see there. The combination of cockfighting deaths, the economics of the bordello trade, and the boxing ring creates a site that fits the genre's expectations, though no specific entity or specific incident is consistently attached to it.
Some Key West ghost tours note the peepholes in the upstairs rooms as a physical relic of the building's commercial voyeur use — an architectural detail that connects visitors to the texture of early 20th-century Key West street-level economy in a way that no signage or narrative fully replicates. The peepholes are not paranormal in any documented sense; they are simply a surviving piece of a past use.
Hemingway's boxing connection is occasionally noted in the context of Key West's broader haunted-Hemingway tourism ecosystem, though Hemingway himself is more firmly associated with his home at 907 Whitehead Street, where he is the most consistently reported presence in the city's paranormal circuit. Blue Heaven's Hemingway story is a daylight story — boxing matches, Friday nights, the known friendship between Hemingway and the working-class Key West men who fought there.
Eat in the outdoor yard of a Dade County Pine building that cycled through uses as a cockfighting arena, billiards parlor, gambling den, and bordello. The 1930s-era boxing ring in the back of the property was where Ernest Hemingway organized and sometimes refereed Friday-night matches. Peepholes in the upstairs rooms from the bordello era remain visible.
Some links on this page may earn HauntBound a small commission when you book, at no extra cost to you. Our editorial picks are independent. Full disclosure
Every HauntBound history is researched from documented sources. We clearly separate verified historical fact from paranormal folklore.
Free Guide
11 verified stops, rated for families, mapped in order. Free.
One email to confirm, then the guide link. Unsubscribe anytime.
Rockledge, FL
Jack's Tavern opened at this site in 1933 and cycled through several names — Cooney's Tavern, the Mad Duchess, Gentleman Jim's — before becoming Ashley's Restaurant in 1985. The Tudor-style building features original stained-glass windows and antique photographs. The structure sits adjacent to the Indian River on US 1 in Rockledge, Brevard County.
Delray Beach, FL
The Blue Anchor's Victorian interior — bar fixtures, facade woodwork, and back bar — originated in a London pub established in the 1840s near Fleet Street. The fixtures were dismantled and shipped first to New York, then installed in Delray Beach in 1996. The Travel Channel named it Florida's Most Haunted Pub in a 2004 special. The current operator filed for Chapter 11 bankruptcy in April 2026; operating status should be verified before visiting.
Daytona Beach, FL
The building at 310 Main Street dates to the 1920s and previously housed the Kit Kat Club, one of Daytona Beach's most popular gathering spots of the era. As motorcycle culture expanded, the club changed hands; bartender Dennis MaGuire bought it and opened the Boot Hill Saloon in 1973, welcoming the biker community and naming the bar for the Pinewood Cemetery directly across the street.