DAY TRIPS TO HAVANA – Experiencing a day trip to Cuba has never been easier

DAY TRIPS TO HAVANA – Experiencing a day trip to Cuba has never been easier - A group of people posing for the camera - Varadero
OKW allows visitors an authentic Cuban experience during days trips. CONTRIBUTED

It was only a few short years ago that Americans had to lumber through layers of red tape to visit Cuba — even as Havana acted as the closest major city to Key West (only 90 miles from the Southernmost Point). And while the lure of Cuba’s rich history, rums, cigars and nightlife were only minutes away, Cuba became the elusive holiday destination for almost everyone other than U.S. citizens.  That was … until now. 

Robin Smith-Martin, who began his upscale concierge service (OKW or Our Key West) over a year ago, now offers weekly trips to Cuba for tourists and local residents in the Keys. OKW, which partners with Air Key West, provides day trips to Havana that allow visitors to spend the day in Havana with the ability to return to Key West “in time for your dinner reservation.” 

“Havana is our sister city,” said Smith-Martin. “People forget that Key West was Spanish before it became part of America and I hope we can continue and improve the dialogue between our two cities.” 

Although OKW plans to expand into a series of themed day trips in the fall, the current expedition is a “Hemingway Excursion.” According to Smith-Martin, Hemingway embodies the symbol of the relationship between Key West and Havana. 

“The Hemingway Excursion, or experience, allows our guests to explore [Hemingway’s] relationship between Key West and Cuba,” said Smith-Martin. “We all know about Hemingway’s impact and life in Key West, but much of his day-to-day life and writing occurred while he was in Cuba.” 

Four to nine guests are invited on the bi-weekly day trip, with a 50-minute flight from Key West to Cuba that departs at 8 a.m. And by 9:30 a.m., the excursion to Hemingway’s home (about 30 minutes outside of Havana) is underway. From there, participants can enjoy rum, lunch and other cultural interactions in and around Havana—returning to Key West by 7 p.m. 

The costs of the trips vary, but at the time of our interview Smith-Martin said the average price is affordable for the Key West traveler, which includes airfare, travel visa, tax, fees, guide-service, lunch and a stop for rum.  And for those fretting over the hassle of obtaining a visa, Smith-Martin says the typical turnaround time is about two business days. 

“We like to remind people they still need their passports,” said Smith-Martin. “But the visa process is typically smooth. We just ask people to contact us a few days in advance to be safe.”

Like most Key West based businesses, Smith-Martin says that interested locals should take advantage of the Hemingway Experience in the summer months to avoid heavy bookings. However, OKW also plans to expand their air service and themed day trips this fall. 

“We are planning to launch a series next fall around Cuban history, art and culture,” said Smith-Martin. “And we also hope to provide regular flight service to Cuba, which will include the visa.” 

For more on OKW and Havana day trips, visit or call 305-290-2049

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Britt Myers traded in a life of monetary success, a chiseled body and intellectual enlightenment for a piece of the pie of the Keys Weekly newspapers. He is also the proud parent of an incredible six-year-old and a sucker for Michael Mann movies and convenience store hot dogs.