My latest “for fun” adventure was biking to Key West with three buddies. The goal: reach Mile Marker Zero and the Southernmost Point in five days, preferably without incident. We covered about 155 miles, stayed in some memorable places—including a resort and a houseboat—and tagged 41 tiki bars (purely for research). This was our fourth Keys ride in seven years. We love it for the relatively safe cycling, the scenery, and the lingering taste of Old Florida. We also make it a point to find out-of-the-way spots to meet locals after each day’s ride. Once again, we were not disappointed.

 

After picking up one buddy flying in from San Diego via Miami, we started in Key Largo.

 

Key Largo favorites: Sharkey’s, Gilbert’s, and the Caribbean Club—one of the oldest bars in the Keys.

 

The ride from Key Largo to Islamorada was mostly bike lane with limited water views, but we did stop in Tavernier and at the old Postcard Inn.

 

Islamorada favorites: Lorelei, Robbie’s (to feed the tarpon), Wahoo’s, Lazy Days for happy hour, the OV Pub for music, and hands down the best steak in the Keys at Mad Dog’s. We treated ourselves to a night at the Islander Resort.

 

Biking to Marathon was more scenic, with smaller bike-only bridges. We stopped at Hawks Cay Resort for a drink at the famous Pilar Bar on the water, named after Hemingway’s boat and sponsored by Pilar Rum—clearly a historical necessity.

 

Marathon favorites: lunch and conch chowder at Island Fish House (a massive tiki hut with helipads), sunset cornhole at Sunset Grill at the start of the infamous Seven Mile Bridge, music at Dockside, and local BBQ at Porky’s.

 

Leaving Marathon meant crossing the Seven Mile Bridge—a two-lane highway with a very narrow bike lane. Only two of us chose to ride it, navigating bolts, pipes, tire strips, dead birds, and one barefoot Hare Krishna. Bahia Honda State Park was a very welcome reward.

 

Big Pine Key favorites: lunch at No Name Pub (open since 1925), sunset at Tonio’s, music at Kiki’s Tiki Bar, and of course, the Moose Lodge—a genuine step back in time. That night we stayed on a houseboat at the local marina.

 

The ride to Key West was our longest day, but also one of the prettiest, with bike paths off the main road that felt almost Everglades-like and several bridges reserved just for bikers and fishermen. We detoured to Geiger Key Marina for lunch—classic Old Florida and the perfect halfway break.

 

We rolled into Key West sunburned, windblown, and exhilarated. After the obligatory photos at Mile Marker Zero and the Southernmost Point, we celebrated properly at our post-ride favorite, rum tasting at the Pilar Rum Distillery. Life was good.

 

Five days, 155 miles, one flat tire, and one skinned knee later, the trip was complete. Next up: May, when we ride from Vienna to Passau along the Danube—250 miles, a few castles, and hopefully fewer bolts in the bike lane.