Sailing into Second Chances

For SailFuture, cruising is all about second chances, presenting sailing as a learning experience and life-changing experience for at-risk youth.

The SailFuture crew poses for a photo in the Canary Islands before sailing to Agadir, Morocco.SailFuture

Life is all about ­cruising into second chances for Capt. Michael Long. Without a second chance of his own, this 20-something who once journeyed through Florida’s juvenile justice system wouldn’t have landed in Sarasota’s New College as a public policy/economics major in need of cheap housing.

In 2010, Long swapped his Jeep for a 30-foot sailboat and became an anchored liveaboard without a clue about sailing. The self-taught sailor, with friends as crew, eventually realized the positive impact sailing was having on his life. This sparked the idea for a program that would utilize the life-changing potential of sailing to navigate off-course kids into entirely new worlds. The foundation of SailFuture was laid. Today it’s a well-respected youth intervention program for society’s highest-risk teens.

The success of the initial pairing of college kids with at-risk high-schoolers aboard 420s and FJs inspired Long and co-founders Mark Hunter and Hunter Thompson to gain needed agencies’ permission to test three-day liveaboard cruises. This winning formula resulted in charter school certification, with three months cruising alternating with shore time in SailFuture group homes. Youth referred by the Florida Department of Children and Families are guided by teachers, mental-health counselors and captains. Community service projects, like teaching policemen to sail, are performed in each port of call.

Defy the Odds is a 65-foot McGregor fixer-upper that was donated to the organization.SailFuture

Via connections with the U.S. Merchant Marine Academy's boat donation program, SailFuture then became the owner of a 65-foot McGregor fixer-upper. The staff aptly named the vessel Defy the Odds. Their challenge: getting it from Turkey, where it was docked, to Florida. To raise money, Long, Hunter and Thompson launched Vacations with Purpose, a donation-based international charter business, through which they invited donors to come for weeklong sailing adventures in the Med. They raised enough money to make the vessel seaworthy and cover expenses for the delivery home. The boat sailed from Turkey to the Canary Islands in the summer of 2015. A group of eight youth sailed throughout the Canary Islands and Morocco, completing service projects in Casablanca and Rabat. The kids flew home, and the captain and staff made the transatlantic journey in December.

A SailFuture grad recently told a crowd at a Sarasota Yacht Club fundraiser that he was in charge of washing the crew's logo T-shirts in buckets on the bow of Defy the Odds. When they docked in Casablanca sporting clean shirts, he felt enormous pride, as locals knew the guys were part of a team. At that moment he realized how much the team meant to him — they were his new family.

The Moroccan people affected him, too. Back in his childhood neighborhood, drug dealers had taught him that money meant power, but he realized a wad of cash doesn’t bring you the heart-warming happiness he witnessed among the poverty-ridden people of Casablanca. Another transformed graduate posted on Facebook: “I woke up this morning missing the boat. How can something that isn’t human evoke so many emotions?”

For information about SailFuture and Vacations with Purpose, visit