Outside Hilton Head

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In 1979, Mike Overton was living in Burlington, Vermont, on the shores of Lake Champlain — one of North America’s best inland windsurfing locales. One chilly spring evening, he and a friend hatched a plan to leave wintry New England and start a windsurfing school on Hilton Head Island. In early summer, Overton loaded up a truck and headed south to establish Sailin’ Shoes Windsurfing. Named after a Little Feat song, the school later became Windsurfing Hilton Head.

Four decades on, Overton’s youthful notion has expanded into Outside Hilton Head, the Lowcountry’s go-to source for outdoor adventure, from stand-up paddle boarding and kayaking to bike tours, dol-phin cruises, fishing, boat rentals and adventures on its own 30-acre chain of private islands.

“For 40 years, Outside has been driven by a mission to enrich lives by connecting people to exceptional places, products and experiences,” Overton said. “The Hilton Head community and its remarkable and unique blend of nature, history and cul-ture have made the achievement of this goal very attainable.”

Outside Hilton Head2

Today, the company includes four major divisions, four retail locations and nine activity outposts. There is also a sep-arate nonprofit foundation.

The retail locations and activity out-posts offer the best in outdoor adventure, while Destinations DMC creates fully customized experiences for groups of any size as well as corporate transpor-tation and special events. The Team and Leadership Development Department does team-building programs, including philanthropic programs and “team-bond-ing” experiences, as well as strategic planning and leadership consulting.

The Outside Foundation, established in 2013, seeks to connect kids to the out-doors and protect and preserve the natural environment through water-based activ-ities, environmental-education programs and sustainable practices.

“The foundation’s biggest environmen-tal initiative is the Oyster Recycling and Reef Building Initiative, started with funds from Patagonia’s Environmental Grant Program,” said Jessie Renew, director of marketing. “The foundation also does a lot of beach cleanups and waterway clean-ups. We did two beach cleanups a week this summer and collected a lot of trash.”In 2020, the company will celebrate the 25th anniversary of its Recycle Your Jacket campaign, collecting gently used coats and jackets for donation to The Deep Well Project, which provides emergency assistance to local communities in need; in return, customers get a great deal on a new jacket. In addition, customers who don’t bag their purchases at the retail stores receive a wooden nickel to donate to one of three local nonprofit groups.

At peak season, the company has more than 100 employees, from retail associ-ates, and reservationists to instructors, guides and U.S. Coast Guard-licensed boat captains.

“The Outside leadership team is now mostly female, with seven director-level and nine managerial-level positions held by females, including the COO,” Renew said. “That’s pretty unusual for the out-door industry, and even for Hilton Head.”

The company has been celebrating the anniversary with a variety of special events and initiatives, including:

  • Public parties in the retail space. The final party of the year will be Dec. 12.
  • A special logo incorporating the com-pany’s first logo.
  • Sailing Shoes Lager, created in honor of the anniversary by Hilton Head Brewing. The beer has been served at company parties and events through-out the year; the December party may be your last chance for a taste.

Looking ahead, Outside will continue to focus on its mission “to enrich lives by connecting people to exceptional places, products and experiences.”

“We want to reach more people and enrich more lives,” Renew said. “We love making people’s lives better.”


50 Shelter Cove Ln, Hilton Head Island, SC 29928 | 843-686-6996 | www.outsidehiltonhead.com