A leisurely bike ride through the shady lanes of Old Town Key West is one of the best ways to explore the history and architecture of the island. The Old Island Restoration Foundation provides an informative road map called the Pelican Path that courses through this national historic district. You can download the self-guided tour from their website or pick one up at the Key West Visitors Center.
Biking through Key West is one of the best ways to explore the island — Photo courtesy of Felipe Correa / Tours to You
Armed with your map, rent a bike from Eaton Bikes on Eaton Street. If it’s been a while since you’ve hopped on a bike, consider renting a three-wheeler. They’re more stable, and you’ll feel safer tooling along with the traffic.
As you set off on your adventure, you’ll cruise past notable landmarks like the 1891 Customs House (constructed from almost one million red bricks) and the Presidential Gates. The gates were installed in 1906 as the ceremonial entrance to the Navy base, and they open only for visiting dignitaries like Jimmy Carter, Colin Powell and Bill Clinton.
The Little White House is Florida's only presidential home site — Photo courtesy of Amber Nolan
Once you come to the Harry S. Truman Little White House, a presidential retreat since 1948, lock up your bike and take a closer look. The house is a living museum, impeccably restored down to the fabric on the couches and drapes. It seems like Truman himself could walk back through those doors any minute.
Starting to get a little peckish? Take a lunch break at Kelly's Caribbean Bar, known as the birthplace of Pan American Airlines. Pan American offered the first international flight service ever for passengers, taking visitors on the 90-mile journey from Key West to Cuba.
Now you can order beers like Havana Red from the wing of a plane at this restaurant and microbrewery once owned by Top Gun actress Kelly McGillis. Don’t miss their Mahi Po' Boy sandwich on Cuban bread with jicama-pineapple slaw.
After lunch, make your way into the residential neighborhoods, where you’ll find single-family homes from the 1800s that have been lovingly preserved. As you roll past white picket fences laced with red and purple bougainvillea, you’ll feel like you’ve returned to the 19th century.
Ornate millwork covers the balustrades, friezes and brackets at the Gingerbread House — Photo courtesy of Claudia Miller
Keep your eyes peeled for architectural details unique to Key West like metal roofs, widow’s walks, wrap-around porches and louvered shutters. The Artist House (534 Eaton Street) was built in 1887 in the Queen Anne tradition, and its purple turret soars three stories high. At the Richard Peacon House (712 Eaton Street), peek past the palm trees that partially obscure the unusual facade; it’s one of the two octagonal houses in Key West built in the 1890s.
The Edward Roberts House (643 William Street) features an architectural style unique to Key West called an “eyebrow” house. The eaves slope down low to shade the upper story windows (and catch cool breezes).
For an over-the-top example of the Victorian-style millwork that covers many of the homes, visit the Gingerbread House (615 Elizabeth Street). This frothy pink concoction was built by Benjamin Baker in 1872, and the explosion of ornate millwork covers the balustrades, friezes and brackets.
After pointing out 51 points of interest (all helpfully marked with pelican signage), the tour loops back around to Front Street, where you can easily return your bikes.