When planning a visit to Hilton Head’s Harbour Town, you might wonder what activities there are to do during your stay. Luckily, there are a multitude of activities available, meaning your vacation will be completely booked from day ‘till night!

In this guide, you’ll find a detailed rundown of the most exciting must-try activities that Harbour Town has to offer — all within reach of any Beachside Hilton Head vacation rental you book. Get ready for an unforgettable trip.

Daytime Harbour Town Activities

When visiting Harbour Town, water sports are a must-try and make for great daytime activities. H2O Sports, a water sports equipment rental service provider located in Harbour Town Marina, has everything you need to enjoy Hilton Head Island.

Take a Boat Tour on Freshwater Lakes

H2O Sports offers guided tours through the freshwater lakes of the Sea Pines Forest Preserve. This 60-minute excursion offers an intimate encounter with Hilton Head Island’s native flora and fauna. You might even spot the American alligator if you’re lucky! Rest assured that your guide will keep you safe as you encounter the island’s biodiversity.

Go on Kayak Tours

If you want to explore local waters longer, H2O Sports has kayak tours that last for 90 minutes. The guided tour of the Calibogue Sound exposes you to exciting and diverse wildlife as you paddle along the channel. If you’ve never ridden a kayak before, don’t worry —  each tour comes with a short training session. You’ll get the hang of paddling in no time.

Join a Daytime Dolphin Tour

You can get up close and personal with some of the most playful animals in Harbour Town. H2O Sports offers daytime dolphin tours where you can witness the Atlantic Bottlenose dolphin as closely as possible. Each tour can accommodate 15 passengers comfortably aboard a robust C-Hawk center console boat. Shorebirds occasionally fly around as well as an extra visual treat.

Go on a Parasailing Adventure

Do you want to soar high above the sparkling waters? For the adventure-seekers and thrill enthusiasts, parasailing with H2O Sports promises an adrenaline-pumping experience. Picture yourself with the wind in your hair and the vast ocean stretching beneath you. This is a heart-pounding adventure that will leave you feeling invigorated and exhilarated. Parasailing adventures in Harbour Town provide a newfound appreciation for the natural beauty surrounding you. Keep an eye out for marine life that may reveal itself from your lofty vantage point.

Take a Vagabond Cruise

All voyages with Vagabond Cruise are conducted under full sail, with afternoon and sunset sails available. Immerse yourself in the unique opportunity to sail aboard the Stars & Stripes, an authentic 12-meter yacht that once sailed under the command of Dennis Conner during the America’s Cup. The cruise provides an exclusive chance to absorb the breathtaking scenery, learn the art of sailing, and even take the helm. Take this chance to embrace sailing like a seasoned pro, an experience exclusive to Harbour Town.

Nighttime Harbour Town Activities

After spending the day on the water, you might be ready to head back to your Beachside Hilton Head rental, but there’s still more to do! As the sun sets over Hilton Head Island, Harbour Town undergoes a breathtaking transformation, emerging as a vibrant and enchanting nightlife destination. Here, a dazzling collection of hotspots awaits, promising to keep the night alive and brimming with energy.

Kickstart Your Night at CQ’s Restaurant

To launch your unforgettable night in Harbour Town, start with a culinary adventure at CQ’s Restaurant. This upscale eatery offers more than just delicious food — it creates an inviting atmosphere that sets the tone for your evening. Enjoy delectable cuisine in a cozy ambiance while sipping on your favorite libations. Whether you’re in the mood for appetizers or full-course dining, CQ’s provides the perfect prelude to an exciting night of entertainment.

Head to the Rooftop Bar

If your night is far from over and you want to elevate your Harbour Town experience, the Rooftop Bar is open. This sophisticated establishment offers breathtaking panoramic views of the marina and the vast ocean beyond. Here, you can indulge in signature cocktails while mingling with fellow night owls. The gentle ocean breeze complements the views and adds an extra layer of charm to your evening. Savor the beauty of the night, elevated to new heights.

Stroll the Starlit Marina

As the night descends and the excitement mellows, the marina in Harbour Town transforms into a mesmerizing haven, inviting you to relax and unwind. Take a leisurely, starlit stroll along the waterfront. The soft glow of harbor lights and their shimmering reflections on the tranquil waters provide a picturesque backdrop, an ideal setting for a romantic interlude, a moment of quiet contemplation beneath the celestial tapestry of the starry sky, or a chance to simply enjoy the serenity of the marina at night.

Satisfy Late-Night Cravings at Street Meet

After an evening filled with dancing, rooftop revelry, and tranquil marina moments, your appetite is likely to stir. Street Meet is here to satisfy your late-night cravings with its mouthwatering late-night menu. Choose from a delectable array of dishes, including succulent burgers, fresh seafood, and sweet desserts — the perfect way to wrap up your night in Harbour Town, ensuring your taste buds are as satisfied as your sense of adventure.

Family Activities in Harbour Town

Are you considering a family vacation to Harbour Town? You’re in for a fantastic adventure with an array of exciting activities that cater to everyone in your family. No matter the age or interests, you’ll find something to create unforgettable moments and lasting memories for all. Whether you have kids who love playground adventures or adults eager for historic exploration, Harbour Town has something to offer everyone.

Explore the Gregg Russell Playground

Nestled adjacent to Harbour Town’s main parking lot, the Gregg Russell Harbour Town Playground awaits, named in honor of the much-loved entertainer. This playground isn’t your typical play area — it’s a nature-inspired wonderland, and the highlight is a remarkable treehouse set amidst the embrace of a majestic Live Oak, creating a magical setting for young adventurers. In addition to the treehouse, the playground boasts a range of play centers with swings, slides, and climbing structures, guaranteeing hours of entertainment for the entire family. While the kids revel in their playful escapades, grownups can unwind and relax in the welcoming surroundings.

Observe Harbour Town From Atop Its Iconic Lighthouse

No visit to Harbour Town is complete without embarking on the thrilling journey of ascending the iconic Harbour Town Lighthouse. This experience is equally captivating for kids and adults, offering an adventure of climbing 114 steps to the observation deck. Once at the top, you’ll be greeted by awe-inspiring panoramic views of the harbor and the surrounding area. More than just a visual treat, it’s a great opportunity for your family to delve into the island’s rich history and maritime heritage. As you stand atop the lighthouse, the sense of achievement and the stunning vistas make the adventure a truly memorable family experience.

Enjoy Mini Golf at Harbour Town Golf Links

For families with a passion for golf, Harbour Town Golf Links Miniature Golf provides an enjoyable way to introduce kids to the sport. This thoughtfully designed mini-golf course offers an excellent balance between fun and challenge for family members of all ages. The course features stunning landscaping and imaginative obstacles, making each hole a delightful experience. It’s not just a game; it’s a perfect way to bond with your family while having a great time. If you’re feeling ambitious and want to test your skills on a full-size course, Harbour Town Golf Links also offers an 18-hole public course nearby.

Visit the Coastal Discovery Museum Gift Shop for Local Artisan Work

For those in your family who appreciate art and local craftsmanship, a visit to the Coastal Discovery Museum‘s gift shop is a must. Here, you can peruse and purchase locally crafted artwork and unique Hilton Head souvenirs. By shopping at the Coastal Discovery Museum’s gift shop, you’re not only acquiring beautiful art but also supporting local artisans. Your purchases help preserve the island’s cultural heritage. This ensures that future generations can admire and be inspired by the talents of Hilton Head’s creative community.

Navigate Hilton Head’s Dining Scene With Beachside Hilton Head

With a plethora of dining options across Hilton Head Island, finding the perfect place to enjoy a family meal can be overwhelming. That’s where our Beachside Hilton Head Dining Guide comes in handy. We’ve compiled a comprehensive dining guide tailored for all our guests staying in our vacation rental homes. You’ll find our top recommendations for breakfast, lunch, and dinner, all conveniently located near your rental property. You can access detailed information about these dining favorites in the online portal. We, and past guests, have personally vetted these places. Whether you’re looking for a beachfront breakfast, a leisurely lunch, or a gourmet dinner, trust us to direct you to the finest dining experiences in Hilton Head Island, ensuring that your family’s culinary journey is truly exceptional.

Upcoming Events at Harbour Town

Hilton Head Island is a vibrant hub of activity, with a calendar filled to the brim with exciting and diverse events that cater to every taste and interest. Whether you’re a sports enthusiast, a music lover, a foodie, or a cultural connoisseur, you’re bound to find something that piques your curiosity and gets you excited. Here are some events that you might be in time to experience when you visit.

November 3–5, 2023: Hilton Head Island Motoring Festival & Concours d’Elegance

From November 3–5, the Hilton Head Island Concours d’Elegance & Motoring Festival returns, bringing with it a rich tradition enriched with the unique flair of the South. This event curates a rare collection of automotive delights, setting them against the backdrop of the distinctive Lowcountry, creating an experience found nowhere else.

March 2024: Hilton Head Island Wine & Food Festival

March 2024 marks the momentous 38th anniversary of the celebrated Hilton Head Island Wine & Food Festival. Prepare to embark on a sensory journey that has become an annual rite of passage for those who appreciate the finer things in life. This year’s festival promises an even more enchanting experience, boasting a diverse array of events that will tantalize your taste buds, educate your palate, and ignite your senses.

April 2024: RBC Heritage at Harbour Town Golf Links

In April 2024, the illustrious 56th RBC HERITAGE presented by Boeing returns to the picturesque Harbour Town Golf Links on Hilton Head Island, SC. Get ready to immerse yourself in a world of golfing excellence and Southern charm as the tournament invites you to “Get Your Plaid On!” This year promises a thrilling showcase of skill and sportsmanship. Mark your calendars and prepare to witness the finest in golfing action against the stunning backdrop of Hilton Head Island.

Beachside Hilton Head: Find the Perfect Place To Stay in Harbour Town Now

Harbour Town on Hilton Head Island offers a wealth of activities for visitors of all ages, ensuring that your vacation is packed with excitement from day to night. From thrilling water adventures to enchanting nighttime experiences, there’s something for everyone to enjoy.

Families can create lasting memories through outdoor adventures, while food enthusiasts can explore the island’s dining scene with ease. And with a calendar full of exciting events, you might just be in time for a unique experience during your visit. So, book your Beachside Hilton Head vacation rental and get ready for an unforgettable trip to Harbour Town.