Warm sunshine. Balmy breezes. Wide, sandy beaches. Meandering bike trails underneath a canopy of live oaks and Spanish moss. Al-fresco dining. Effortless adventures for the entire family. Happiness. Have we just described your perfect summer day? Now imagine it with mild temperatures, fewer vacationers, and off-season pricing. You’ve just glimpsed Hilton Head Island during the fall. Read on to find out why there’s no place we’d rather be, and what we love most about this relaxed Southern isle.

Hilton Head Island Light House

Photo: S. Massey

The Great Outdoors

With average daily temperatures in Hilton Head in the 70s and the lowest precipitation during the year in October, your family can still enjoy the beaches on Hilton Head Island long after you’ve traded in your sandals for sneakers at home. But don’t mistake a trip to this 5,000-acre oceanfront vacation destination as a mere trip to the beach. You’ll also find a 15-mile network of leisure paths perfect for biking, and a 605-acre forest preserve where you’ll see 130 species of birds, wildflowers, and wetlands.

Insider Info: Thrill your little naturalists with a trip to the Coastal Discovery Museum, a 68-acre property dedicated to educating visitors about the Low Country of South Carolina. Enjoy the Museum’s trails, gardens, live oaks, butterfly enclosure and Marsh Tacky horses, or register for a Museum-lead excursion into marshes, waterways, and historic sites. Coastal Discovery Museum (70 Honey Horn Dr., 843-689-6767, online: http://www.coastaldiscovery.org)

Sea Pines Beach Club Exterior C30A3638

Photo: Sea Pines Resort

Resort Amenities

As one of the first eco-planned destination in the U.S., Sea Pines Resort seamlessly combines the natural beauty of Hilton Head with world-class amenities that make family vacations a breeze. The new Sea Pines Beach Club includes clean, well-appointed outdoor showers, public restrooms, plenty of parking (for bikes, that is!), family changing rooms, and dining options for beach-goers. If you’re a family that golfs together, you’ll find three world-class courses at practically every bend in the trail. And don’t forget your rackets, because the Sea Pines Racquet Club offers instructional programs and clinics for all ages. Sea Pines Resort (32 Greenwood Dr., 1-866-561-8802, online: https://www.seapines.com).

Pirates of Hilton Head Island

Photo: S. Massey

All-Ages Activities

In addition to miles of nature trails, sunny days, and sandy beaches, Hilton Head Island offers the small set plenty of thrills. Don’t miss an adventure with Pirates of Hilton Head, where kiddos become Pirate Crew on a custom pirate ship in search of hidden treasure. And every trip must include a trip to the top of the Harbour Town Lighthouse and Museum, which affords incredible views of the harbor and an aerial view of the island. Individual watercraft, including kayaks, sailboats, paddle boards, and jet skis, are all available to rent at nearby H2O Sports. And for those who like to keep their feet on the ground, the Gregg Russell Harbour Town Playground, built into a grove of Spanish moss-dripping live oaks, provides endless hours of fun. Pirates of Hilton Head (843-363-7000, online: http://www.piratesofhiltonhead.com), Harbour Town Lighthouse and Museum (866-305-9814, online: http://harbourtownlighthouse.com), H2O Sports (1-877-290-4386, online: http://www.h2osports.com), and Gregg Russell Harbour Town Playground are all located at 149 Lighthouse Rd., in Harbour Town at Sea Pines Resort. 

Insider Info: Hilton Head’s shopping is stellar, and you’ll find delightful boutiques throughout the Sea Pines Resort – all with bike racks for an easy (and fast) shopping stop. And if you’re looking to swing a club but your putters aren’t quite ready for prime time, head to Pirate’s Island Golf, where you can play 18 holes in an hour and cap off your evening with ice cream! Pirate’s Island Golf (8 Marina Side Dr., 843-686-4001, online: http://www.piratesislandgolf.com/hilton-head-sc-pirates-island).

Hilton Head Tree

Photo: S. Massey


Lodging options abound on Hilton Head, with an array of accommodations at Sea Pines Resort including 300 villas, 100 rental homes and the luxurious 60-room Inn at Harbour Town. If you opt to stay outside of the Sea Pines Resort, Hilton Head’s hotel scene has recently undergone a renaissance of renovations and you’ll find fresh, convenient, and updated options throughout the island. We particularly love the zero-entry pool and kid’s club at Sonesta Resort Hilton Head Island. Sea Pines Resort (32 Greenwood Dr., 843-785-3333, online: https://www.seapines.com/vacation-rentals/villas-condos/), Sonesta Resort Hilton Head Island (130 Shipyard Dr., 843-842-2400, online: http://www.sonesta.com/hiltonheadisland).

Insider Info: Looking for easy access to the playground, light house, and Pirates of Hilton Head cruise? We recommend the recently updated Villas at Sea Pines Resort at Harbour Town. Not only are they situated within walking or biking distance to some of the island’s main attractions, but they’re also equipped with elevators, kitchens, and spacious rooms (score!).

Ice Cream

Photo: S. Massey


Family dining at restaurants may typically conjure as much anxiety as anticipation for vacationers, but Hilton Head’s relaxed vibe extends to its dining options. Island staples, like the Salty Dog Cafe and Hudson’s on the Docks, offer al-fresco seating options, fresh and delicious adult menus, and kids menus that include local seafood. Hudson’s owns one of the island’s two fishing fleets, which you can check out from your dockside table. Or head to The Scull Creek Boathouse, where life size Connect 4 and corn hole will entertain everyone before they tuck in to local favorites like shrimp and grits and frogmore stew. Salty Dog Cafe (232 S. Sea Pines Dr., 843-671-2233, online: http://saltydog.com), Hudson’s Seafood House on the Docks (1 Hudson Rd., 843-681-2772, online: http://hudsonsonthedocks.com), The Scull Creek Boathouse (397 Squire Pope Rd., 843-681-3663, online: http://www.skullcreekboathouse.com).

Insider Info: If you’re looking to incorporate a date night on your family vacation, call Hilton Head Nannies & Companions and enjoy oceanfront dining at Coast for a relaxing adult evening. Coast Oceanfront Dining, located in the Sea Pines Beach Club, 87 N. Sea Pines Dr., 866-561-8802. 

Getting to Hilton Head: Hilton Head Airport, located approximately 5 miles from all Island resorts, and Savannah/Hilton Head International Airport, located approximately 45 miles south of the Island service flights to Hilton Head daily. It is approximately a 5 hour drive from Atlanta, Georgia.

Have you been to Hilton Head Island? What’s your favorite thing to do there?

-Shelley Massey