July 6, 2017:  Connected And Separated by the Straits:  Keys Mariners Wonder What’s Next

May 25, 2017:  Key West, Cuba collide in celebration

May 10, 2016: Second Havana Challenge Departs Across Straits

May 3, 2016 Salt Life presents the historic Havana Challenge on May 10

April 13, 2016: Havana Challenge 2016 (KONK Life)

October 19, 2015: Havana Thunder Challenge gears up (Key West Citizen)

September 16, 2015: Quick travel to Cuba for boat racers (Examiner)

Fall, 2015: Jolly Rover Sails to Cuba (Cruising Outpost)

September, 2015: Cuba Invasion (Men’s Journal Magazine)

August, 2015: The Havana Challenge (

August 11, 2015: Revved up flotilla planned for Cuba in November (Key West Citizen)

August 6, 2015: Havana Challenge To Cross Straits Again, Under Power (WLRN)

August 4, 2015: The First Government Sanctioned Boat Race to Cuba Was a Total Sh*tshow (Outside Online)

July, 2015: Havana Challenge 2015, Hobie 16s Race from Key West to Cuba, May 16 (Southwinds Magazine)

July 1, 2015: Hobie-ing to Havana (Sailing Magazine)

May 29, 2015:  Cuba Formally Removed From U.S. List of State Sponsors of Terrorism  (Associated Press)

May 25, 2015:  Americans find ways to visit Cuba despite tourism ban (The Kansas City Star)

May 24, 2015:  Getting to Cuba is getting easier, but … (Key West Citizen)

May 22, 2015:  Key West to Cuba: Racing toward new relations (Key West Citizen)

May 23, 2015:  Time for Regattas and Tourism in Cuba (Prensa Latina News Agency)

May 21, 2015:  Crowds welcome American Sailors (Key West Citizen)

May 21, 2015:  Havana Challenge Ends, More Regattas to Cuba on the Horizon (Prensa Latina News Agency)

May 21, 2015:  Key West in Favor of Links with Cuba, says Mayor (Prensa Latina News Agency)

May 20, 2015:  Ten Hours from Key West to Havana (NY Havana Blogging)

May 20, 2015: “Havana Challenge”, Regattas are back in Cuba (PanAmerican World)

May 19, 2015:  US and Cuban sailors in friendly race amid warming relations (The San Diego Union-Tribune)

May 18, 2015:  US Havana Challenge Yacht race in Cuba (Cuba News Agency)

May 18, 2015:  Havana Challenge features five American sailracers (Soundings Trade Only Today)

May 17, 2015:  U.S. sailboats arrive in Cuba for Havana Challenge regatta (FOX News Latino)

May 17, 2015:  George Bellenger, Havana Challenge race organizer, talks to the media at the Marina Hemingway in Havana May 16, 2015 (Yahoo News)

May 16, 2015:  Historic race sets sail from Key West to Cuba (Local

May 16, 2015:  Sailboat race is latest sign of better US-Cuba relations (AP Wire)

May 6, 2015 10:15 AM:  First Sanctioned Key West-To-Cuba Sailing Race In 50 Years Set For May 16 (Miami, CBS Local)



Sailing race to Cuba gets OK2015-04-23_0837

Citizen Staff 4/23/15

An adventure sailing trip and Hobie Cat race between Key West and Havana has been resurrected, with a group of
sailors set to make the roughly 90 mile trek on May 16.

The race, called  the Havana Challenge, has been in the works for the past year. Late last week, the U.S. Department of Commerce issued the necessary permits, called temporary export licenses, for at least 10 boats to participate in the regatta. The organizers have requested permits for at least 22 boats and are hoping to receive the remaining permits by May 16, event organizers said.

In addition to racing across the Florida Straits to Marina Hemingway in Cuba, the sailing crews will be racing against the Cuban national team in front of the historic Malecon roadway and seawall in downtown Havana. Also, organizers will host youth sailing trips with Cubans.

The event is the brainchild of Key West-based Capt. George Bellenger and is organized by him, his wife Capt. Carla Bellenger and Capt. Joe Weatherby. The three captains started making the trek via Hobie catamarans in the late 1990s as part of their personal adventure sailing trips. The last trip made by any of the crew was in 2001, after which the annual event was put on hold.

The event is being sponsored by the nonprofit Key West Community Sailing Center. A portion of the proceeds from the event will go to youth sailing scholarships at the sailing center, organizers said.

The Bellengers, who run kayak, sail and ecotours in Key West, decided to resurrect the trip last year, and along with Weatherby, have been working with the U.S. State Department, Coast Guard, Department of Commerce and other federal agencies to obtain the proper licenses and permits.  The commerce permit was the last major hurdle they had to clear.

Key West Community Sailing Center hosted the commodore of the Marina Hemingway while he was visiting South Florida for the annual Miami boat show earlier this year. The commodore has been very supportive of the event, organizers said.

The Bellengers and Weatherby also have been holding regular meetings with a group of captains and sailors who want to participate in the event. They met Wednesday night at the Key West Community Sailing Center to hammer out some of the details and logistics.

Weatherby and the Bellengers also have been working with Key Westers Tom and Nancy Coward, who organized a youth soccer trip that took Key West youngsters to Cuba.

The Havana Challenge falls under the sport and culture categories of the 12 allowable “people to people” exchanges, the Bellengers and Weatherby said.

“We are bridging cultures through traditional maritime heritage,” George Bellenger said. “We just want to sail and have a cool trip. We want to race the Cuban Oylmpic team in a beautiful place.”

“There are cultural and personal relationships between Key West and Havana that date back more than 100 years,” added Weatherby, an organizer of the USNS General Hoyt S. Vandenberg artificial reef project off Key West. “We are just trying to re-establish that relationship.”

The group’s earlier treks were much different and much more of an adventure than what is planned for the May trip. The early trips were just a small group sailing with primitive GPS equipment, which often didn’t work and required the crews to use small hand-held compasses to navigate the treacherous Florida Straits.

On one trip in 1997, the Bellengers’ Hobie Cat began sinking six miles offshore. They had to navigate around Cuba’s coral reef to beach the boat on land. Also, Carla Bellenger had to tie a bandana around one of the riggings to help them navigate to shore. Despite the perils, they have successfully made the crossing each time and have had amazing experiences, which included watching a humpback whale give birth to a calf, they said.

“We have had all kinds of adventures,” Carla Bellenger said.  For the May race, there will be chase boats carrying emergency medical equipment. Other boats will be fitted with salvage equipment so in the event one of the Hobie Cats breaks down, it can be towed or lifted out of the water and repaired, organizers said.  The organizers are hoping to make the Havana Challenge an annual event.

Sailboats race through the Florida Straits on their way to Cuba in the 1990s. The early incarnation of the Havana Challenge started among a group of Key Westers in the late ’90s. After a lengthy hiatus, the event will return next month when teams of Key West sailors head from the Southernmost City to the island nation.

Sailboats race through the Florida Straits on their way to Cuba in the 1990s. The early incarnation of the Havana Challenge started among a group of Key Westers in the late ’90s. After a lengthy hiatus, the event will return next month when teams of Key West sailors head from the Southernmost City to the island nation.