Hilton Head Classics Celebrate 30+ Years on the Island

Everyone knows of Hilton Head celebrities Shannon Tanner and Gregg Russell for their summer singing on the Island, but they’re not the only familiar faces who have built a name for themselves here on the Lowcountry’s loveable boot-shaped barrier island. From the 1970s to now, several businesses have not only kept up with the times, but also grown, evolved and continued to welcome generations of families to Hilton Head Island and serve the locals diligently. Share the love and congratulate the following businesses for their long-standing reputations and upcoming anniversaries!

Outside Hilton Head

Est. 1979

Outside Hilton Head KayakingWhat is now possibly one of the largest guide services on the Southeast Coast and encompasses several specialty retail shops and a non-profit called The Outside Foundation, all started as a windsurfing school in 1979 on the beach in Sea Pines.

By the mid-1980s, what was then Winsurfing Hilton Head opened the first outdoor clothing store in the area and started offering kayaking instruction. “Through the late ‘90s we ended up buying a 30-acre chain of islands behind Daufuskie Island, called Page Islands,” Mike Overton, Outside Hilton Head’s CEO and founder, said. “In the early 2000s we started our consulting business and consulted many of the off-island developments—such as Colleton River, Belfair, Rose Hill, Berkley Hall, Old Field, Hampton Lake and Palmetto Bluff—on about how they should set up a nature-based recreation business.”

In 2008, Outside Hilton Head started a destination management division, Destinations by Outside, and in 2014 formed The Outside Foundation, a non-profit with the mission to get kids outdoors and also protect and preserve the local environment. With a new shop in Palmetto Bluff that focuses on products that are directly connected to area nature, history and culture—such as scarves made with indigo from Daufuskie Island and sweetgrass baskets made by Michael Smalls—Outside Hilton Head’s growth continues.

“I remember Charles Fraser telling me that if you want to connect people to the area, you have to connect them to the tides. Everything here, all of the literature, all the culture, the history and nature revolved around tides,” Overton explained. “That kind of mission is very much why we’ve grown.”

Camp Hilton Head

Est. 1981

Camp Hilton Head in Harbour TownInspired by a business in Beverly Hills, Camp Hilton Head opened their first store in 1981 in Harbour Town. The merchandise was clothing and gifts and the concept was a camp for the whole family—a way visitors could “Take Hilton Head Home.”

Shortly thereafter, they opened their second store in Harbour Town and from there kept expanding, opening in key locations across the Island, including South Beach, Coligny Plaza, Shelter Cove Harbour and The Fresh Market Shoppes. They developed an efficient inventory tracking system between the stores and continued to update the stores each off-season, making improvements and renovations.

Today they have six locations and continue to carry an assortment of souvenirs and clothing, including popular brands, such as Simply Southern, Life is Good and Spirit Jerseys. Keep an eye out for their new store coming to South Beach—rumor has it, this will be more of a boutique with clothing for ladies and children.


Est. 1982

Reilley's Grill Hilton Head IslandIn 1982 Tom Reilley turned his vision of having an Irish-style restaurant without the “pub” label into a reality with Reilley’s Grill & Bar. Two years later, with his friends help, he arranged to get a small fire truck from the fire department, a trolley and 60 people to join him for the first St. Patrick’s Day Parade on Hilton Head, during which he was almost arrested for not applying for a permit to hold the parade. This became a tradition and word got around town about the delicious offerings his wife, Diane, was crafting in the kitchen at Reilley’s.

In 1988, Reilley’s North End Pub opened, and in the coming years, the restaurants became a staple on Hilton Head. Reilley’s Grill & Bar changed locations over the years before settling into the current location, which was remodeled about five times and grew from 53 seats and 14 bar stools, to now 180 seats and 40 bar stools at two bars.

The North End Pub got its own full-renovation about 10 years ago, expanding from a bar with dinning tables to a full dinning room and a separate bar area, also upgrading their dinner menu to more of a “fine dinning type food without the fine dinning prices.” In the upcoming months, they hope to move forward with plans to build an outside bar and dinning area adjacent to their current bar.

Adventure Cruises

Est. 1984

Adventure Cruises The HolidaySince 1984, the Maurer family has been in Hilton Head Island’s boating business, serving locals and visitors alike on dolphin tours, ferry rides and dinner cruises. The family business started even earlier, when Mark Maurer’s father decided to quit his teaching job in in Eerie, Pennsylvania. Before coming to Hilton Head, they lived in Florida, and after graduating from Florida State University, Mark decided to join his parents on Hilton Head Island in the late 1970s.

“My dad’s first boat that the built was the new Vagabond, which went into service in Harbour Town in about ’84. Then four or five years later, we built the Holiday to go in at Shelter Cove and after that, we got the Spirit of Harbour Town, which was a dinner cruise boat at the time and also ran ferry trips to Savannah, Georgia,” Mark Maurer said.

With two other boats in their arsenal, Adventure Cruises was at its peak in the 1980s and 1990s, with some of what were likely the biggest boats on the Island.

“I’ve been doing it so long, that we’ve got second and third generations coming on the boat now. I’ve had families come aboard and they’ll poke their head in the wheelhouse and say, ‘You know when I was a child, my family used to come vacation to Hilton Head and now I’ve got my own kids and we’re doing the same thing,’” he explained. “Everybody loves dolphins—it doesn’t matter which historical era you live in. The dolphins are out there and the people want to see them, so we are going to provide that service.”

The Crazy Crab

Est. 1984

The Crazy Crab Hilton Head RestaurantOut on Jarvis Creek, something else was brewing in 1984—a seafood restaurant! What was then a small 100-seat location called The Boilers known for local oysters soon became The Crazy Crab. Things were also in the works in Harbour Town, where the second Crazy Crab opened, and got major renovations in 1986. Only minor changes were made to the Jarvis Creek property, until 1998 when a devastating fire burned the old wooden structure at Jarvis Creek to the ground. The building was rebuilt and remains today with the largest saltwater aquarium on Hilton Head, as well as an onsite playground and outside deck.

Part of the Coastal Restaurants and Bars group, The Crazy Crab prides themselves on having 15 people on their team who have been working for the restaurant for over 20 years. This year, they are looking forward to, of course, seasonal menu changes, as well as an iconic new look for the classic menu.


Salty Dog and Forsythe Jewelers are both celebrating more than 30 years of business and have become somewhat iconic on the Hilton Head in two very different realms. While Salty Dog continues to grow, and has celebrated the recent opening a second cafe location in Tanger Outlets, Forsythe Jewelers upholds its reputation of bringing the world’s best designer jewelry and gifts to Hilton Head with Andrea Bragg taking over ownership. If you want to get in on the fun, Salty Dog will be celebrating with their 30th Birthday Bash on Saturday, May 13, 2017.