About Outside

We enrich lives by connecting people with exceptional places, products, and experiences


About Outside Hilton Head

Back in 1979, we were a windsurfing school operating off of the beach in Sea Pines. Since then, Outside has grown to become the Lowcountry’s leading outdoor outfitter. In addition to providing a multitude of excellent programs 365 days a year, Outside has two retail locations and offers group adventures, destination management, and team building programs in Hilton Head.
The staff at Outside is made up of experienced, knowledgeable, and personable retail associates, reservationists, interpretive naturalist guides, and USCG licensed Captains. We are committed to offering exceptional programs along with unparalleled customer service. Fueled by ongoing education and training of our staff, we take great pride in the quality of our programs and products.
Outside has over 35 years of experience in creating and customizing life-changing adventures.  Our programs include guided kayak tours, kayak fishing, boat based dolphin tours, charter fishing, tours of historic Bluffton and Daufuskie, kids and teens camps, stand-up paddleboarding programs, boat rentals, surf lessons, and much more.



The Outside Hilton Head story started on a crisp spring evening in Burlington, Vermont. There, Outside’s founder and CEO, Mike Overton, concocted a plan with a friend to start a windsurfing school on Hilton Head that summer. He loaded up a truck with windsurfing equipment, headed South and established Sailing Shoes Windsurfing.

  • Chevron down 1980s
  • Later renamed Windsurfing Hilton Head, the company grew through the ’80s to become the premier windsurfing school, destination, and race organizer on the East Coast. By the mid ’80s, Windsurfing Hilton Head had opened the only outdoor clothing store in the area and began offering instruction and outfitting for the growing sports of kayaking and rollerblading. In response to its expanding menu of operations, Windsurfing Hilton Head became Outside Hilton Head in 1992. The same year it received the award for Business of the Year from the Hilton Head Chamber of Commerce.

  • Chevron down 1990s
  • As Outside Hilton Head’s program offerings grew through the ’90s, Overton started to look for new ways to use the company’s resources to get locals, tourists and groups outside. The answer came in the form of a 30 acre chain of islands on the back side of Daufuskie. Named the Page Islands, this adventure outpost is a hub for backwater boating and paddlesports excursions, a challenge course site for teambuilding activities and an unbelievable special event venue.

  • Chevron down 2000s
  • In 2010, Outside Hilton Head branched out further still, establishing a full service destination management division. Later named Destinations by Outside, this arm of the company is charged with constructing fully customized experiences for groups of all sizes, including transportation, events, activities and teambuilding.

  • Chevron down Today
  • Today, Outside Hilton Head has retail locations at Shelter Cove Plaza and Palmetto Bluff, and has activity outposts at Shelter Cove Marina, Pinckney Island, The Westin Resort, Palmetto Bluff, Daufuskie Island and Page Island. Their program offerings include kayaking, paddleboarding, boating, dolphin tours, tubing and ski trips, bike tours, scavenger hunts, surf camps, kids programs, and all kinds of group offerings. At peak season, close to 60 people are employed by the company, each of whom shares the same passion for the outdoors that led Overton to Hilton Head in 1979.


Page Island

The Page Islands are a chain of Islands in the remote ‘outback’ behind Daufuskie Island. With its beautiful untouched scenery, Page Island offers visitors a chance to disconnect from the outside world and immerse themselves in the Lowcountry.
The Islands act as an adventure outpost and a hub for outdoor activities. Outside recreation programs including The Outback, Adventure Island and Ultimate Lowcountry Days include stops on Page Island.
Page Island is also outfitted with challenge courses designed for Outside Teambuilding Programs. This unique location facilitates the building of teams and leaders by offering a step away from the everyday.
The islands also make a truly memorable special event venue. Outside provides transportation for your guests to the island along with catering, music, and staffing.

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Giving Back

Since it’s inception, Outside has been dedicated to giving back to our local community. In 2013, our efforts led to the establishment of The Outside Foundation.
The Outside Foundation is charged with getting kids outside and protecting and preserving our local environment. The guiding principals of the Foundation are to provide outdoor experiences that will have a positive impact on people by creating awareness, expanding knowledge and developing a responsible understanding of nature and the environment. The Foundation is made up of people who share a passion for the outdoors and are committed to sharing this passion with others through water-based activities, environmental education programs and sustainable practices.

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