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Five activities for fall & winter family fun on hilton head island

By Hilton Head Insider

The air is cooling, the leaves have changed, and school is back in session, virtual or otherwise. Which means all the more reason to plan family fun activities outside the classroom. And here on Hilton Head Island, we have plenty of great ideas to make your getaway a great one. If you’re making your way to America’s Favorite Island® this fall or winter, these five must-do activities are sure to be fun for you and the kids! 

*Image on Left is by @alanhunt42


Photo by @nativegvlgirl
Photo by @nativegvlgirl

What better way to enjoy the fall than by spending it outside? On the next bright sunny day, we recommend you trade in four wheels for two and hit up the Hilton Head Bicycle Company. There’s just no better way to spend a weekend then by exploring the trails on Hilton Head Island while taking in all the beautiful fall foliage. Pack a lunch and make a special day of it — one full of fantastic biking, fresh air, and plenty of quality time. With more than 60 miles of leisure pathways and plenty of bike rental shops, you certainly won’t need to put the pedal to the metal to find everything you need for a memorable day.


Photo by @fo.odtrip

No great itinerary ever went without fantastic food, and you’re in luck because fall time in the Lowcountry means ‘oyster season’. It’s true, the months that end in ‘R’ offer the freshest and most delectable oysters you can imagine. Family favorites include Hudson’s Seafood on the Docks and the Skull Creek Boathouse. There is no shortage of places to enjoy sustainable local fare in inviting outdoor settings - usually with a spectacular sunset served gratis


Photo by @astro_tom_d
Photo by @astro_tom_d

The fun doesn’t stop at the shoreline, in fact, it’s only just beginning! If you’re looking for fun on the water, we suggest checking out the Outside Hilton Head private boat rentals. Whether you’re looking to cruise the open waves, or simply relax on deck and let the motion of the ocean soothe you, renting a boat is an amazing way for any family to spend the day. Oh, and if you want to take a dip, dive in! The water’s always wonderful here on America’s Favorite Island®!  


Everybody knows that Hilton Head Island is the golf island. After all, there are 33 traditional courses in the region and 24 here on the Island to challenge your game at every hole. But what if you and your family are not golfers? An easy and accessible sport that’s fun for players of all ages is Pickleball. Not just a funny name, Pickleball is a sport that is similar to tennis. The difference is that the game is played on a much smaller court, uses paddles instead of rackets, and a lightweight perforated ball. It’s easy to get the hang of and offers plenty of fun. Check out our Pickleball Infographic for more fun facts.

Did you know? Hilton Head Island’s own Palmetto Dunes Tennis & Pickleball Center was recently named #1 Tennis Resort in the Carolinas by Tennis Magazine. It’s the perfect place to try your hand at some sports on the courts!



Photo by @detailsinfabric
Photo by @detailsinfabric

Always a family-favorite, the Coastal Discovery Museum is not to be missed! The Smithsonian-Affiliate inspires people to care for the Lowcountry and teaches visitors about our beautiful yet fragile environment, the region’s history, culture and art, and our diverse wildlife. Most importantly, leave with the knowledge that you can make a difference by actively caring for our environment and heritage.

After enjoying their plentiful exhibits and/or spirited tours, take the family to explore the trail system which begins behind the museum. As you walk across this historic landscape, enjoy the magnificent live oaks and ancient cedars, take in the view from the boardwalk, see the Marsh Tacky horses grazing in the wide-open fields, and envision what the island was like before it was developed.

Photo by @hillerjcu04
Photo by @hillerjcu04

If you dream of spotting dolphins, then get ready for your dreams to come true at Dolphin Tours Hilton Head Island. There are four different types of tours to choose from here, including their one and two-hour discovery tours that offer plenty of opportunities to discover these wonderful creatures — as well as miles of scenery around Hilton Head Island. If you’re eager to see even more, join them on a 3-hour tour that will take you to Vanishing Island. This hidden island can only be seen at low tide, so catching a glimpse of it is a real treat. Educational, and exciting, these tours have everything a family could want for a day of fun.


From land to sea, there’s always something fun to do with the entire family here on Hilton Head Island. Whether you jump into these ideas or have some fall ideas of your own, we would love to hear about your vacation. Be sure to tag us on InstagramFacebook, or Twitter, and share all the fun you’re having during your time on America’s Favorite Island. Start planning your fall getaway today.  

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