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Itinerary: Your Family Fall Getaway on Hilton Head Island

For a fall getaway that parents and kids alike will love, Hilton Head Island is the perfect destination. Fall on America’s Favorite Island brings warm days, comfortable evenings, and plenty of opportunities for outdoor activities, delectable dining, picture-perfect photo ops, and family-friendly festivals and events. There’s no better place to spend a long weekend or a full week (or more!) making unforgettable family memories and extending your summer just a little bit longer than on Travel+Leisure’s #1 Island in the Continental U.S. 

To make it easier than ever to experience the best of Hilton Head Island this fall, we’ve created a three-day family itinerary. Staying even longer? Check out these tips for Lowcountry family fun.

Day One – Hit the Beach

No matter how you’re traveling to Hilton Head Island, chances are, by the time you arrive, your kids will have plenty of pent-up energy to burn! For day one, keep it loose and ease into your vacation in true Lowcountry style and head to the beach. With miles upon miles of pristine sand and gentle waves, Hilton Head Island’s beaches are excellent for searching for shells, building sand castles, or simply soaking up the sun. As soon as you arrive, you’ll understand why we’ve been recognized as one of the top 10 family beaches in the country! Don’t worry about packing beach toys – there are shops and services which allow you to either buy or rent everything you need for a great day by the water.

Nothing works up an appetite quite like a day of sand, sun, and surf, so cap off your first day on Hilton Head Island with a longtime local favorite and grab dinner at the award-winning Hudson’s Seafood House on the Docks. With 365 seats, there’s plenty of room for the whole family to enjoy fresh, local shellfish, and a kids menu ensures even the most particular palates can enjoy a satisfying dinner. Stick around for the sunset, then make your way back to your hotel for an early night – there’s plenty of action coming up on day two!

Day Two – Explore the Lowcountry

Fuel up with a hearty breakfast at your hotel, because it’s time to spin your wheels and head out on a Lowcountry bike tour! Rated as a Gold Level Bicycle Friendly Community by the American League of Bicyclists, Hilton Head Island boasts more than 60 miles of multi-use trails. Bikes and bike equipment for all ages can be rented prior to your arrival – you can even grab a Kiddie Kart for the little ones in your family – and the flat, groomed trails are perfect for bikers of all abilities. Before you hit the trail, check out our Biking FAQ so you’re familiar with bicycling guidelines, then use our bike map to help you plan your route.

Family biking through the trees

Head to the Salty Dog Café for lunch. Located at Sea Pines Resort, this casual restaurant is both kid- and pet-friendly and serves up stunning water views alongside a full menu of seafood, salads, and sandwiches. At select times, kids’ activities like face painting and magicians will keep youngsters occupied while parents can enjoy a well-deserved frosty beverage on the deck.

After lunch, it’s time to hit a different kind of saddle. Lawton Stables’ trail rides give you a unique perspective on the Lowcountry landscape. Younger children will love Shetland pony rides and a small animal farm where they can interact with and feed critters like chickens, goats, sheep, potbelly pigs, and alpacas. 

Not into horses? For a fresh take on adventure, give ZipLine Hilton Head a try! Eight ziplines and six activity courses are guaranteed to thrill the whole family and provide gorgeous Island views at the same time!

Spend the rest of the afternoon unwinding at your hotel with a dip in the pool or some downtime in your room before heading out to dinner. When you’re recharged for the evening, The Dunes House at Palmetto Dunes Oceanfront Resort is a popular choice for parents and kids, with crowd-pleasing menu items like quesadillas, wraps, and burgers. This outdoor restaurant is located on the beach, so it’s perfect for an after-dinner stroll to wrap up the day.

Day Three – Discover Daufuskie Island

After such an active day, everyone in the family is probably ready to take it easy on day three. For a slower pace that everyone can appreciate, head to Daufuskie Island. You’ll feel like you’ve stepped back in time, and the kids will marvel at an island where there are no cars and very few paved roads! Spend the day strolling around Daufuskie Island, popping into colorful shops and boutiques, checking out the rum distillery and choosing a unique Lowcountry souvenir by one of the local artists.

Get lunch at the Old Daufuskie Crab Company, where you’ll find local shrimp, Daufuskie Deviled Crab, and other Lowcountry favorites on the menu. If your children aren’t adventurous eaters, don’t worry – a kids’ menu features grilled cheese, hot dogs, fish sandwiches, and other popular treats.

Wrap up your Daufuskie Island day at the volunteer-run Daufuskie Island Community Farm, where kids can get up close and personal with farm animals, including baby goats and their mothers. Or, roam the island’s beautiful beaches, hunting for shells, stones, and other found treasures to bring home.

Ready to start planning your fall family getaway on Hilton Head Island?

For a full list of all the family-friendly activities and attractions on Hilton Head Island, request your copy of the Hilton Head Island Vacation Planner now. And don’t forget to download our Island Compass App for even more trip ideas and to keep you on track once you arrive. We can’t wait for your whole family to experience fall on Hilton Head Island this year!

Family vacation dos and don'ts infographic
Hilton Head Island

Find Your Island Time

Hilton Head is America’s favorite island, offering 12 miles of pristine beaches and everything you need for the ultimate retreat. Enjoy easy days relaxing in the sun, sand and surf on some of the best beaches in the country.
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