In the summer of the 1970s, amid the golden sands of Hilton Head Island, a young Mike Overton embarked on a journey that would change the landscape of outdoor adventure on the East Coast. While on break from the University of Vermont, Mike’s passion for the wind and water led him to start a modest windsurfing company. What began as a small endeavor on the beach soon moved to South Beach, at the island’s southern tip, where it rapidly gained momentum. The company became the largest windsurfing school on the East Coast, attracting enthusiasts from far and wide and hosting some of the most popular windsurfing events of the era. In an age when the thrill of outdoor sports was just beginning to capture the collective imagination, Mike’s school became a beacon for adventure seekers.

As the 1980s brought growth and change to Hilton Head Island, so too did Mike Overton’s vision expand. Windsurfing Hilton Head evolved into Outside Hilton Head, and eventually, simply Outside, as it embraced a broader spectrum of outdoor activities. During these formative years, the focus shifted towards offering interpretive kayak tours, allowing both residents and visitors to explore the island’s intricate waterways and untouched natural beauty. In 1986, Outside opened its flagship store in the Plaza at Shelter Cove, where the selection of top-tier outdoor wear and gear rivaled the bold fashion statements of the decade. Just as MTV redefined music culture in the ’80s, Outside redefined outdoor adventure on Hilton Head Island, creating a new way for people to connect with nature.

The 1990s marked a decade of expansion and innovation for Outside. The acquisition of Page Island, a serene 40-acre chain of hammock islands nestled behind Daufuskie, opened up new horizons. Here, Outside established a series of team and leadership development courses, transforming the tranquil island into a hub for growth and exploration. Boating programs were introduced, allowing guests to embark on journeys to and from Page Island, adding a new dimension to the outdoor experience. This era, characterized by rapid technological advancements and the rise of the internet, saw Outside pioneering its own brand of adventure.

As the new millennium dawned, Outside’s growth showed no signs of slowing. The company outgrew its original facilities and established new operations at Shelter Cove Marina and Palmetto Bluff, solidifying its position as the most comprehensive outdoor outfitter in the region. The 2000s saw an explosion of offerings: unique kayak tours, extensive boating programs, fishing trips, children and teen camps, history tours, scavenger hunts, and more. The decade was marked by a spirit of exploration and adventure, with Outside guiding locals and visitors alike through the wonders of the Lowcountry.

The 2010s presented new challenges and opportunities, and ever the optimist, Outside seized the moment to expand its horizons. In the wake of an economic downturn, the company refocused and added Destinations DMC, a full-service destination management company, to its repertoire. This new venture allowed Outside to create exclusive experiences for groups, offering services that ranged from transportation and activities to team-building programs and event planning. As Savannah, Georgia, began to flourish, Outside expanded its presence there, offering leisure boating experiences and destination management services. In 2019, as the company celebrated its 40th anniversary, it stood as a testament to four decades of innovation, resilience, and a relentless pursuit of adventure.

The 2020s began with challenges that tested the world’s resilience, but Outside met them with perseverance and creativity. As the world navigated through the unprecedented changes of 2020, Outside introduced The Ohana, a 47-foot vessel that became the perfect venue for hosting private groups and parties, adding a new chapter to their legacy of unique offerings. Expansion continued in Savannah, Georgia, with the opening of a new retail location in the burgeoning Plant Riverside District, a symbol of the city’s revival and growth. As the decade unfolds, Outside remains committed to innovation, continuously introducing new and exciting ways for people to “Get Outside” across all three of its locations. The spirit of exploration and connection that has defined Outside for over four decades continues to thrive, reflecting the adaptability and creativity that the 2020s demand.