1. Sing Along at a Classic Gregg Russell Concert

One of the most beloved family-friendly activities in Harbour Town, the Gregg Russell Concert under the Liberty Oak has been entertaining guests for decades. This interactive evening event brings together families, couples, and kids of all ages for music, laughter, and unforgettable memories.

It’s more than a concert—it’s a Sea Pines Resort tradition. Children love being part of the show, while parents enjoy the nostalgic charm that defines summer nights in Hilton Head Island.

2. Relax Poolside at The Sea Pines Resort

If you’re dreaming of a relaxing Hilton Head Island vacation, poolside time is essential—and at The Sea Pines Resort, you have options to suit every style of stay.

Many of our vacation homes feature backyard pools, offering ultimate comfort, privacy, and convenience for families and groups. Guests staying at The Inn & Club at Harbour Town enjoy access to a private pool just steps from their room—perfect for a quiet, elevated experience.

In addition, Sea Pines Resort guests can enjoy the Harbour Town Pool, located in the heart of Harbour Town, making it easy to combine a swim with shopping, dining, and evening entertainment.

Whether you prefer a secluded retreat or a centrally located pool experience, it’s easy to unwind in the sunshine and enjoy the laid-back pace of island life.

3. Tee Off at World-Class Hilton Head Island Golf Courses

Known as a top golf destination in Hilton Head Island, The Sea Pines Resort is home to legendary courses set among breathtaking coastal landscapes. Golfers of all skill levels can enjoy scenic fairways surrounded by maritime forests and marsh views.

Whether you’re booking a full golf getaway or fitting in one round, this is your chance to experience some of the best golf courses in South Carolina.
 

4. Climb the Iconic Harbour Town Lighthouse

No visit to the Sea Pines Resort is complete without climbing the Harbour Town Lighthouse, one of the most recognizable landmarks on Hilton Head Island. As you ascend, you’ll explore exhibits on local history and culture before reaching the top for panoramic coastal views.

From the observation deck, you’ll see the Calibogue Sound, the marina, and miles of stunning coastline—making it one of the best photo opportunities on the island. 

5. Enjoy Beach Chair Service at the Sea Pines Beach Club

For an effortless day on the sand, the Sea Pines Beach Club offers a convenient beach chair service—marked by its signature orange chairs and umbrellas—so you can settle in and enjoy the coast without the extra work.

With comfortable seating, umbrellas for shade, and beachside food and beverage service, everything you need is right at your fingertips. Guests of The Inn & Club at Harbour Town enjoy this experience complimentary as part of their stay, while resort guests may access it based on availability. 

It’s one of the simplest ways to experience the beauty of Hilton Head’s beaches—just arrive, unwind, and let the ocean set the pace.

6. Enjoy Ice Cream and a Harbour Town Sunset

Few experiences capture the essence of a Hilton Head summer evening quite like enjoying ice cream while watching the sunset over Harbour Town. Stop by the Quarterdeck Market for a sweet treat, then head toward the marina for one of the most scenic sunset views on the island.

As the sky turns shades of gold and pink, the harbour creates a picture-perfect backdrop—ideal for photos and quiet moments alike. 

7. Browse Boutiques and Coastal Finds in Harbour Town

For a more leisurely outdoor activity, spend time browsing the boutiques and shops in Harbour Town. This charming marina village features coastal-inspired apparel, unique gifts, and local artisan goods.

Strolling along the shaded pathways, you’ll discover that shopping here is as much about the experience as the items themselves, complete with waterfront views and a laid-back atmosphere. 

8. Explore the Sea Pines Forest Preserve by Bike

For a peaceful yet active outdoor experience, head to the Sea Pines Forest Preserve, a protected natural area spanning more than 600 acres of wetlands, forests, and scenic trails. The best way to explore is by bike—easily rented from the Sea Pines Resort Bike Shop, where you’ll find everything you need for a comfortable ride.

From there, set out along the resort’s extensive network of leisure paths, pedaling beneath towering pines and moss-draped oaks. Along the way, discover boardwalks, freshwater lakes, and historic sites like the Native American Shell Ring, while keeping an eye out for local wildlife.

9. Discover Outdoor Adventures on Land and Water

From horseback riding to coastal excursions, The Sea Pines Resort offers countless ways to experience the outdoors from new perspectives.

At Lawton Stables, enjoy guided horseback trail rides through shaded pathways, or visit the animal farm—home to goats, alpacas, miniature donkeys, and more—for a fun, family-friendly experience.

For those drawn to the water, choose from a variety of watersports and excursions including kayaking, paddleboarding, fishing charters, and dolphin-watching tours departing from Harbour Town. These experiences offer a closer look at the Lowcountry’s unique ecosystem and coastal beauty.

Whether on land or on the water, these guided adventures add unforgettable moments to your island getaway.