5 Great Key West Bars: Belly Up
By Chris King
Bob Leonard spent most of his adult life helping men like Dale Earnhardt Jr. and Sr. drive race cars as fast as possible. Now, he’s spending his golden years helping people slow down.
The man known as “Bahama Bob” traded the high-speed, high-stress world of auto racing for a bartender job at The Rum Bar at the Speakeasy Inn in Key West, where he listens, laughs and occasionally provides advice while handcrafting every cocktail.
The Rum Bar creates a sense of comfort. It’s small – with seating for 10-12 inside – but people who enter as strangers end up in conversation with folks from all parts of the country, swapping stories about their favorite Bahama Bob concoctions.
“It’s like being at a friend’s house,” said Karen Chrisman, an Ashburn, Va., resident who makes an annual visit to enjoy Leonard’s famed mojitos.
About Bob and The Rum Bar
The Rum Bar was once home to legendary Key West rum runner Raul Vasquez. The hardwood floors and bar, lined with more than 240 different types of rums, must have Vasquez salivating in his grave.
Leonard’s work would make the old bootlegger proud as he happily answers questions about the secrets to his cocktails, whose virtues are extolled far and wide on Trip Advisor and Yelp.
“There are busy days where I will make nearly 100 mojitos and that many Painkillers, but nobody’s drink gets shorted,” Leonard says. “If you want a drink made to the original recipe and made with care, then this is the right place for you. If you want a speed drink, you can go down the street and get that.”
Speed may no longer be a priority for Leonard, but the ability to help people acquire it led him to Key West.
The now 68-year-old opened an auto shop and started a race team in California in 1972. He used an engineering degree from Humboldt State to help create suspension and diagnostic acquisition systems that allowed stock car teams to improve performance.
In 1989, he moved cross country to North Carolina to work with NASCAR star Rusty Wallace and then launched the Leonard Company, which allowed him to sell his services to a number of teams, including the Earnhardts, NASCAR royalty.
With business thriving, Leonard began traveling to the Caribbean where his affinity for rum blossomed. He collected different rums and recipes along the way and built an island-style bar in his North Carolina home.
When he decided to get out of the NASCAR full-time in 2005 (he continued to work part-time until 2014), he did the most Key West thing imaginable; he bought a 51-foot houseboat and moved to the island.
Rum lovers have been the beneficiaries.
“People will come in and say, ‘I had drinks with Bob,’” said Anne Perina, owner of the Rum Bar and Speakeasy Inn. “You can tell he really enjoys what he does. He has a personality of his own and everyone loves that.”
Love for The Rum Bar started to soar in 2010 when Leonard was invited to be a member of RumXP, an international panel of rum experts. He began traveling domestically and internationally, judging rums and continuing to hone his new craft.
As the bar’s popularity surged, so did Leonard’s. He embraced social media, self-published two books featuring drink recipes, and launched a blog that he continues to update daily, rising at 6 a.m. to write.
“I’m just an old guy having fun with a group of people who come down and share my interest,” he says. “I tell people you will have to take a crow bar to pry me out of here. I love it.”
There are a lot of good Key West bars, but here are five that stand out from the Old Town crowd:
1. The Rum Bar
The Rum Bar has more than 240 rums -- and Leonard. It’s a cozy establishment with a friendly vibe and cocktails prepared with care. Don’t miss a chance to visit one of the world’s top 15 rum bars, according to Caribbean Journal.
Make a reservation in advance on the complimentary shuttle and take the ¼-mile boat ride across the Gulf of Mexico to Latitudes, located on the appropriately named Sunset Key. The view as the sun dives below the horizon is breathtaking, especially when enjoyed with a key lime colada. In case you are planning to stay over, Sunset Key Guest Cottages has some great deals.
3. Captain Tony's Saloon
Captain Tony’s Saloon provides a taste of Key West’s iconoclastic past. The building was home to the original Sloppy Joe’s and is the namesake bar of former Key West mayor, charter fisherman and local legend Tony Tarracino.
Bras and dollar bills adorn the walls and this is where Jimmy Buffet got his start in Key West.
The best value in Key West is happy hour at Alonzo’s, an oyster bar overlooking A&B Marina. Drinks and appetizers are half-price from 4 to 6 p.m., and a key lime martini or Bloody Mary is easy to enjoy while admiring the docked yachts.
5. Green Parrot
Proudly referring to itself as a dive bar, the Green Parrot has long been a favorite of locals and informed visitors. At the heart of the Green Parrot’s appeal are live music, an open-air bar, and an atmosphere that encapsulates the spirit of the island.