Key West Architecture and Lifestyle Showcased During Home Tours

From its cigar-makers’ cottages to its Victorian mansions, Key West’s architecture is as individualistic and historic as the island itself. Visitors can explore houses exemplifying that rich architectural tradition, as well as contemporary Keys design, during weekend home tours in December 2024 and January, February and March 2025.

Now in their 65th year, the long-running annual home tours are presented by the not-for-profit Old Island Restoration Foundation, which was established in 1960 to promote the preservation of Key West’s historic architecture and cultural heritage. The island city’s Old Town contains what is believed to be the largest predominantly wooden historic district in the United States, with some 3,000 structures.

The first tour is scheduled Friday and Saturday, Dec. 27-28, spotlighting five homes and the venerable St. Peter’s Episcopal Church — all festively dressed for the holidays. The self-guided explorations are set for 1-4 p.m. both days.

Subsequent tours are planned for 1-4 p.m. Friday and Saturday, Jan. 24-25, Feb. 14-15 and March 14-15. Each showcases multiple homes chosen for being significant historic buildings, creative renovations or examples of the Florida Keys lifestyle.

“We have gems each month,” said Barbara Span, director of the OIRF. “They include the former home of Ernest Hemingway’s carpenter, with artwork that goes back centuries, and Key West’s famed ‘wedding cake’ house dripping with lace-like wooden gingerbread.”

OIRF volunteers serve as guides at each tour stop, providing details to visitors about each featured property’s past, architecture and décor. Participants can discover unique interiors filled with quirky art and antiques as well as imaginatively designed outdoor living areas.

In great part because of the OIRF’s work, today scores of lovingly restored Key West structures still flourish as single-family homes, bed-and-breakfast guesthouses and museum attractions. The island’s historic district and its restorations have drawn attention and honors from organizations including the National Trust for Historic Preservation.

Tickets for each tour are $55 per person in advance ($45 for OIRF members) or $60 on tour days at a featured home. Ticketholders receive a list of homes and a map, and can proceed from house to house at their own pace using their own transportation.

Ticketing and tour information: oirf.org or 305-294-9501

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