Cuba! The name evokes romantic images of Spanish conquistadors, swashbuckling pirates, bearded guerrillas, expensive cigars and pulsating salsa music.
However, the most recent impression is one of a mysterious island locked away behind decades of U.S. economic sanctions. That view is beginning to clear now, following negotiations between the two nations’ governments.

For American sailors, the timing could not have been more perfect. The Pensacola Yacht Club (PYC) is well known for sponsoring the Regata al Sol, an offshore race to Isla Mujeres off the Yucatán Peninsula. With the Mexican race on a biannual schedule, PYC officials have been searching for another destination in the alternating seasons.

(Photo/Submitted) The local crew of the Daedalus, will be competing against at least 22 other boats in the inaugural Pensacola a la Habana race beginning Sunday.

(Photo/Submitted) The local crew of the Daedalus, will be competing against at least 22 other boats in the inaugural Pensacola a la Habana race beginning Sunday.

“When President Obama announced in January about allowing travel to Cuba, we jumped on that as a possible venue for our off-year Mexico race,” Bob Kriegel said. Kriegel is serving as chairman of the Pensacola a la Habana race (, which begins on Sunday. “We have looked at the notion to do something else, but not distract from the race to Mexico. This was just an incredible opportunity.”

The PYC group first approached José Miguel Díaz Escrich, commodore of the Hemingway International Yacht Club in Havana. Once a mutual agreement was reached, the major hurdle of gaining U.S. approval came up.

“It took a tremendous amount of work to identify and reduce to terms that could be handled by individual race participants,” Kriegel said. “Each competitor has to be identified and get a license. Then you had to deal with the Department of the Treasury, the Department of Commerce and finally the U.S. Coast Guard.

“These were significant and tough hurdles. Going to Mexico is not even in the mix when compared to sailing to Cuba.”

Despite the struggles, sailors are ecstatic about this historic event. The most recent count has 23 boats for the race, which will cover approximately 500 nautical miles.

“We have boats from all over,” Kriegel said. He is a former winner of the Mexico event who will again be at the helm for the race to Havana. “We will have boats from New York to Key West coming to Pensacola.”

A Bermuda-style start is planned, which will allow for a staggered departure based on a handicap system. The slowest boats go first, with the vessels crossing paths in the Gulf. This will allow the first boat at the finish line in Havana to be declared the winner.

The classes include Classic Cruisers (older than 25 years, with a sail area/displacement ratio of less than or equal to 16), Modern Cruisers (newer than 25 years old, with a SA/D of less than or equal to 20), Race Cruisers and Multi-hull Cruisers.

“I have done the Mexico race before, but I am really looking forward to Cuba,” Krieger said. “This is not just a race. This is a way to promote and improve relations between two countries.”

(Photo/Submitted) The local crew of the Daedalus, will be competing against at least 22 other boats in the inaugural Pensacola a la Habana race beginning Sunday.

(Photo/Submitted) The local crew of the Daedalus, will be competing against at least 22 other boats in the inaugural Pensacola a la Habana race beginning Sunday.

Locals to join the adventure
A sailboat that has become an icon along the Alabama Coast is expected to take part. B.J. Roberts, captain of the Daedalus, has announced plans to set sail for Cuba.

“When we heard about the race, we knew we had to do it,” Roberts said. “It is a step back into time. This is a big-history moment.”

The vessel, built by Fred Saas in 1976, has been an attraction since helping to popularize the “dolphin tours” in Orange Beach and Gulf Shores in the early 1980s ( Although currently rigged for short tours, its original mission was to sail around the world.

“Captain Fred had the Daedalus custom built,” said Roberts, who has been running the boat for seven years. “He was an architect, and he built it for himself. It is sharp in the bow and stern. It cannot be mistaken for any other boat.”

Saas, who is still alive, salvaged many parts from a 1920s sloop called the Last Straw that hit the rocks near Santa Barbara, California. Roberts said those parts are still functioning today.

Another unique feature for the 50-foot-long ship is its mizzenmast. Because of its placement over the rudder, Roberts said the Daedalus is not technically a ketch or a yawl.

After making the solo journey through the Panama Canal, Saas had the boat in Elberta at Pirate’s Cove for many years. It is now moored across the Intracoastal Waterway at Bear Point Marina in Orange Beach.

Roberts has made some modifications to upgrade the Daedalus from a day-trip boat to an offshore racer.

“We don’t use an autopilot for a two-to-three-hour cruise, but for a 500-mile run it is necessary,” he said. “We must upgrade the solar panels, because you do not want the battery to die. We also have to add appliances to cook, because the boat is not currently set up for that.”

Roberts is also looking to purchase a new mainsail, the most expensive item for this trip.

At the time of the interview for this article, Roberts was still looking for a fourth person to join the crew. On board at this time are David Smith, who was featured in a previous Lagniappe column for his work reconditioning fishing reels, and Leroy McMillan.

“Four is the perfect number,” Roberts said. “You have four-hour shifts, and this keeps everyone fresh and strong. You can rotate cooking and sailing.”

Roberts said the Baldwin County sailing community has been quite excited about the race. He said the staff at Bear Point Marina is putting up a flat-screen television in its Tiki bar to keep track of the racers. Those wishing to follow from a computer can do so by visiting

“Bear Point Marina will have a system where we log in and it marks our location,” Roberts said. “They will be able to track our position. We can also send a message back to our friends and family.

“We are going to be a part of history. This is something else.”