Fun Things to Do in a Weekend on Hilton Head Island

Sometimes you just need a few days to recharge and spending an extended weekend in Hilton Head, South Carolina was just the thing after a busy summer. If you have not been to Hilton Head Island, you might be interested to know that the island has earned the top spot for islands in the continental US in the Condé Nast Traveler Awards for several years in a row! It’s the type of place where families come back year after year, and after two visits in the past few years I see why. There are so many fun things to do on Hilton Head Island that a weekend is definitely not long enough, but it was certainly a fun way to get a flavor for many of  the activities the island has to offer. 

*Post Updated December, 2024

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How to Get to Hilton Head Island & Where to Stay
Things to Do on Hilton Head Island
What to Eat on the Island
When to Visit 

How to Get to Hilton Head Island & Where to Stay

First, you need to figure out how to get there and where to stay. The exit for Hilton Head Island is less than a dozen miles north of the Georgia/South Carolina border, easily reached from Interstate 95. Although most visitors probably drive to Hilton Head, since we were only there for a long weekend, we took advantage of a direct flight from DC  to the convenient Hilton Head Island Airport (the larger Savannah/Hilton Head International Airport is less than an hour away). This seasonal flight option, offered by United Airlines, along with several big carriers who now offer service on select days throughout the year, makes it easier to plan a long weekend visit.

As far as accommodations, there are plenty of choices, from resort hotels like the Sonesta Resort Hilton Head Island to beach front houses large enough to accommodate extended family, and everything in between. I recently had the chance to visit again for a December long weekend, with a stay at the Beach House. Even with the cooler weather, I loved the outdoor Tiki Hut with live music, easy beach access, and proximity to restaurants. The island is also home to gated communities like Sea Pines, that require a fee to enter if you are not staying there. I enjoyed staying within Sea Pines, with easy bike access to get around.

Things to Do on Hilton Head Island

So what are some fun things to do in Hilton Head? It would be easy to just plant yourself in a beach chair with a good book on a beautiful stretch of beach and be perfectly happy! But then you would miss out on all the other wonderful things to do that make this island special. So first, I suggest you get up early to see the sunrise. To me, one big advantage to staying on or close to the beach is the ability to get up before the sun rises. We were staying in a home in Sea Pines close to the beach, so it was an easy stroll down to the sand to catch the beautiful morning sky. The colors at sunrise were spectacular! Be sure to head out at least 20 minutes prior to actual sunrise, when you can really catch the sky in all its pink and orange glory. Plus the early morning is a perfect time for a long walk on the beach before the weather warms up. Find out more about Hilton Head’s beaches, including those that are wheelchair accessible. ​

Next, ride a bike! One of the things I loved about Sea Pines, was the miles and miles of bike trails. Fun fact—the American League of Bicyclists has awarded Hilton Head Island the rating of Gold Level Bicycle Community—one of just 21 in the entire country. So no matter where you stay on the island, expect biking to be a popular activity and a fun way to get around. It’s easy to rent bikes on the island, and I have since learned that many bike shops will deliver directly to your rental. We were fortunate to be staying with a friend who had beach cruiser bikes, which are perfect for both the paved trails and along the sand. With a long, flat stretch of beach, we saw lots of riders on the hard packed sand, especially early in the morning. In the gated community of Sea Pines, we used the bike trails to get to shopping, food, and the very cool Sea Pines Forest Preserve. We took advantage of the post-Labor Day season to take a leisurely bike ride through the preserve. Another thing not to miss in Sea Pines is the Legacy Oaks Program, highlighting 15 oak trees, some dating as far back as the late 1600’s. Follow the tour by walking or bicycle.  ​

Of course, if you are a golf, tennis, or pickleball lover, you won’t be disappointed, as the island offers two dozen world class golf courses along with both private and public courts. Plus, there are opportunities for kayaking, water sports, tours, and climbing to the top of the iconic Harbour Town Lighthouse while learning about the Island’s history.

One of the other cool things about Hilton Head is being able to view wildlife in all shapes and sizes. Because Hilton Head is in the South Carolina Lowcountry region, don’t be surprised to find signs warning about alligators scattered throughout the island.  During our short visit, we spotted a few alligators lazily floating along in the water, along with egrets, a Great Blue Heron, and pelicans. 

Recently, I had the chance to enjoy a stroll around the smaller Audubon Newhall Preserve (put in the street address to avoid entering through Sea Pines), and a longer walk at the Pinckney Island National Wildlife Refuge (having a bike here would have made it faster to get around). Both offer a good opportunity to enjoy quiet time in nature.  Read more about some of the wildlife on the island.  ​

What to Eat on the Island

With all the outdoor activities available on Hilton Head Island, it’s easy to work up an appetite, and fortunately there are plenty of opportunities to sample local cuisine. Seafood lovers will find plenty of restaurants serving Lowcountry specialties, fresh oysters and shrimp. For lunch, we headed over to Skullcreek Boathouse, a nice spot for outdoor, waterfront dining. Seafood lovers are sure to find something on the extensive menu. Don't forget to try anything with pimento cheese and hush puppies, two southern favorites. The location of the restaurant makes it popular for sunset happy hour.

During our recent visit, we ate the highly-rated Shrimp and Grits at A Lowcountry Backyard Restaurant, lunch at the Salty Dog Cafe, and breakfast at the cute Watusi Cafe. The Shrimp and Grits were my favorite! All are popular dining options during the busier months, so it was nice to visit during a less-crowded time. ​

If you would rather cook it yourself, Barnacle Bill’s Fresh Seafood Market is a popular option for fresh seafood.  And no trip to the beach would be complete without a stop for ice cream, and you can't go wrong at the popular Salty Dog Ice Cream Shop!

When to Visit

So when is the best time to plan a trip to Hilton Head Island? Personally, the fall has always been a favorite time of year for me for a beach visit, with smaller crowds and generally sunny weather, but with a mild year-round climate, Hilton Head Island is perfect for a weekend getaway all year long. Seeing the island all lit up for the holidays was also fun! 

If you do visit in the fall, definitely keep in mind the risk of hurricane activity. One way to get some peace of mind is to purchase travel insurance, which I certainly would have done if we were staying longer or in a rental house. Our trip did get delayed overnight as Hurricane Dorian churned up the east coast, but fortunately, our airline re-booked us on the next available flight so we didn’t lose any money on the flight.   
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​A long weekend is never long enough! Still on the list to do on Hilton Head Island is a cooking class at Michael Anthony’s Cucina Italiana, climbing to the top of the Harbour Town Lighthouse, and a kayaking or dolphin tour. Find suggestions for weekend fun all year long from the Hilton Head Island Chamber of Commerce and Visitor Convention Bureau.