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A Three-Day Work Retreat on Hilton Head Island Way Beyond the Boardroom

Smiling business people outdoors in the street on coffee break

Itinerary: Way Beyond the Boardroom

By Hilton Head Insider

Go beyond the boardroom during your next business trip to Hilton Head Island.

Day One

Your first day in the Lowcountry is all about getting into that “island time” frame of mind. Here, we always mix business with pleasure, whether it be networking on the fairways, indulging in some local flavor, or simply relaxing oceanside when the day is done.


Get settled into your guest rooms at the Omni Hilton Head Oceanfront Resort. Your home away from home for the next 72 hours, this elegant seaside retreat offers a range of unique event spaces, along with private balconies, ocean views, and airy coastal beach décor to perfectly set the tone for working on island time.

Tee Time

Nothing says Hilton Head Island like a round of golf played on an award-winning course, so head on over to the scenic Robert Trent Jones course at Palmetto Dunes Oceanfront Resort. A fun and challenging round for players of all skill levels, the inspiring par-five 10th hole is one of only two oceanfront holes on the island.

Sip and Savor

Cap off your first day on Hilton Head Island with an evening of unforgettable coastal dining at Poseidon. Dig into Lowcountry favorites like fresh-caught local shrimp and oysters in the half-shell, then head upstairs to their famous Rooftop Bar for crafted cocktails and live entertainment to close out the evening.


Day Two

Today is an opportunity to get creative, step outside your comfort zone, and take team-building to dizzying new heights — literally. From the leafy canopy above Broad Creek to the one-of-a-kind Shorehouse event space, your team will find inspiration and excitement around every corner on Hilton Head Island.

Go Sky High

Forget ice-breakers or trust falls in a stuffy hotel ballroom and take to the treetops at Adventure Hilton Head’s zipline ropes course. Professionally trained guides lead your team on a thrilling, two-and-a-half-hour treetop adventure to face their fears and find their nerve, all while enjoying some of the most spectacular views on the island.

Comfort Food

Flying through the air at 75 feet sure works up an appetite, so stroll on over to nearby Up the Creek Pub & Grill and snag a table on the outdoor deck overlooking scenic Broad Creek. Here, you and your team can relax and debrief while indulging in local favorites like fried oysters and conch fritters in a casual, welcoming environment.

Heads Together

Harness the momentum of your adventurous morning with a brainstorming session in a setting that’s guaranteed to get your team’s creative juices flowing: The Shorehouse at the Omni Oceanfront Resort. This spectacular indoor-outdoor space offers an inspiring seaside backdrop with thoughtful and professional staff to take care of every detail.

Day Three

Your final day on Hilton Head is a chance to slow things down — to take in the sights, appreciate the island's natural beauty, and savor the flavors of the Lowcountry. Until next time, of course.

Come Sail Away

Take to the high seas — while fostering team cohesion and leadership skills — on a once-in-a-lifetime dolphin encounter with Island Skiff Adventure Tours. Local guides will help you pilot your own skiff on a 25-to-30-mile adventure through the scenic marshes and incredible marine wildlife of Hilton Head, Bluffton, and Daufuskie Island.

Local Flavor

Make the most of your last day in the Lowcountry by digging into a delicious seafood lunch at The Crazy Crab. Overlooking the Harbour Town Marina, this beloved local institution serves up a menu of tried-and-true local favorites, including their famous fresh-caught Lowcountry Shrimp Boil.

Say Cheese

No trip to Hilton Head would be complete without a visit to the island’s most recognizable landmark, the iconic red-and-white-striped Harbour Town Lighthouse. A short stroll from The Crazy Crab, it’s the perfect place to snap that perfect team photo — or, if you’re up for the challenge, head inside and climb the 114 steps to the top for breathtaking views of Calibogue Sound.

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