Frank Sobchak ’88 Sets Sail

This summer, Frank Sobchak ’88 added a stunning accomplishment to his resume. “We just won the Finisterre division of the Newport Bermuda Race (sailing),” he said. One of the top three most prestigious amateur offshore sailing races, Frank and his crew completed the race in three and a half days.  

A retired Special Forces colonel, Frank’s career began at West Point where he earned his Bachelor of Science degree in military history. He spent 26 years in the U.S. Army between military intelligence and special forces assignments, while earning a Master of Arts degree in Arab studies from Georgetown University and a doctoral degree in international relations from Tufts University’s Fletcher School of Law and Diplomacy.   

“I don’t come from a military family,” said Frank. “At the time, my family was surprised that I chose this career path. I enjoyed it and worked to become a Green Beret and eventually a liaison between U.S. Special Operations Command and Congress. During my career, I was deployed to Iraq, Kosovo, Kuwait, Jordan and the U.S./Mexico border as part of a counter-narcotics task force training law enforcement.” 

Now living outside of Boston, Frank is the Chair of Irregular Warfare Studies at the Modern War Institute at the U.S. Military Academy, a Senior Fellow at the Global and National Security Institute at the University of South Florida and a Fellow (contributor) for the MirYam Institute.

Recently, Frank has had more time to return to a hobby he enjoyed with his family as a child: sailing. “My dad was always a big sailor,” he said. “He had raced sailing in Chicago, where I was born, and has stories of taking me and my mom sailing while I was still a baby. They would take out a drawer from a chest of drawers, put it on the boat and take me sailing!” 

As Frank’s military career came to an end in 2018, his dad offered him the sailboat that they used growing up in Fort Lauderdale. To get it to his new home in Massachusetts, Frank and one of his children sailed it up the Atlantic coast. “It gave me a chance to sail again,” Frank said. “One thing led to another, and we ended up buying a second boat during the pandemic that was bigger and more comfortable.” 

The new boat, a 48-foot sailboat is more modern, has air conditioning, a generator and is generally sturdier; it can go longer distances and handle tougher conditions. “Purchasing that vessel prompted me to revisit one of my bucket list items—the Newport Bermuda Race. It is an approximately 650-mile race, and is one of the six big off-shore amateur races and one of only two where the entire race is out of sight from land. It is well-known in sailing circles as a tough event and an accomplishment to finish.”

Having a bigger boat opened the possibility of Frank putting together a team to compete in the race. He called an old friend with connections in the racing community and put together a team. 

“The Bermuda Race, in particular, is perilous,” continued Frank, “because Coast Guard helicopters can only go so far without refueling. There is a point on the map where you are briefed ‘once you get past this point you are on your own unless another boat rescues you.’ At that point, rescue would require a special helicopter, so you need to be well equipped for any situation—long-range flares, life rafts for everyone, beacons that will go off if someone falls in the water, secure floorboards on the boat that don’t fall out if you capsize. When you are at sea for three to four days or longer, you can face serious weather and you have to be ready.” 

The week before the race, Frank’s team began making preparations. However, they didn’t actually get on the water until the day before the race. “That day, we noticed the top part of the rudder post (the rudder turns the boat) was moving when it shouldn't move at all,” Frank said. “We had two engineers on our team and they came up with a solution, so between multiple trips to West Marine and Home Depot, we got the parts to secure the top of the rudder post; it wasn’t pretty, but it held!” 

Frank’s race spanned three days and 17 hours. “It was kind of amazing,” Frank said. “On the way down, we could see many of the other boats. They’d be on the horizon, and we’d move ahead or fall back.”

“It was an interesting course; you go through the Gulfstream, the same one off of Fort Lauderdale. Tactically, you have to pick where you’re going to enter it. It’s like a moving walkway, and if you hit it wrong you can be working against it. If you merge into it just right, you get a massive kick. There was a lot of strategy planned and meteorology used in the days preceding the race. Racers are peering over satellite images from NOAA and other weather prediction agencies.”

Frank and the crew relied on a satellite phone and two satellite data sources, which included a map, the weather, and downloadable wind predictions for up to 72 hours ahead. “We would download it every six to eight hours, try to pick the most accurate forecast and make the decision on where to sail accordingly.” 

Over the course of the race, the team divided itself into two watches, critical for continuous sailing. “We never slept more than four hours at a time,” Frank said. “Really, at times it can be closer to three, because there may be an issue that requires everyone to help. This is also the time that we would cook and eat. Sailing like this is hard and exhausting, but then afterward you think, ‘Wow, that was really fun and rewarding!’”

Wrapping up the race experience, Frank explains how race sailing works when it is time to select winners. “There is an award for the first boat to cross the line, but we were not even close to being in contention for that. But there are also competitions within different categories of boats, such as our boat raced in the racing cruiser division. To make those races fair, each boat is measured either with computer mapping or with a measuring tape and weights to determine its handicap. That handicap provides a fair way to have different types of boats compete against each other.”

“We knew how our handicap compared to others, and during the race we were consistently ahead of boats that had less of a handicap than we had.  Knowing that we began to think, ‘hey we might win this!’ As we approached the finish, it was an electric feeling knowing that we were definitely doing well! When we realized we had won, we had to pinch ourselves. The prize for winning our division is a silver cup with an inscription of the name of your boat, and you also get a trophy to take home. It was truly an amazing experience,” Frank exclaimed.

After this experience, Frank says he is now addicted to sailing. “I am working on getting a team together for another race, one from Marblehead, Massachusetts to Halifax, Canada that will take place in 2025.”

“Sailing fulfills some of the void from what I miss about my life in the military,” Frank said. “Your world becomes simpler on a sailboat—you only have 48 feet to move on, and there are no emails or texts. You are cut off from civilization and it is just you and some friends against the cruel sea.”