Voted the best island in the continental U.S. by Travel + Leisure readers for three consecutive years, Hilton Head is a great family destination year-round. But if you’re looking for cooler temps and quieter beaches, visit during the winter.
Growing up, I enjoyed spring and summer vacations on Hilton Head Island. But as an adult, I prefer to skip the touristy warmer months. Instead, I visit the island and its grand oak trees, swaying sea oats and sand dunes in the cooler — and calmer — fall and winter.
While you might not be able to take surfing lessons in the off-season, that’s pretty much the only activity you’ll miss out on, thanks to the 70-degree days that are so common in the heart of a Hilton Head winter.
Here are my favorite ways to enjoy everything Hilton Head offers in the off-season:
Hilton Head Golf
The heat and bugs that come with summer on a southern barrier island are long gone come fall and winter. The pleasant weather creates the perfect atmosphere for enjoying a round on one of the many Hilton Head golf courses.
If you’re a novice or simply seeking to enhance your game, take lessons at one of the island’s golf schools. Don’t miss the chance to play one of Hilton Head’s oceanfront courses, including the Robert Trent Jones course and Harbour Town Golf Links.
As you golf, take in the area’s natural beauty — many courses wind through marshes, palm trees and live oak trees draped with picture-perfect hanging moss. Just be wary of alligators sunning themselves along the way!
When visiting Hilton Head Island, make time for dinner at Hudson’s Seafood House on the Docks, established in 1967. The shrimp and hush puppies are mouthwatering.
Tennis and Pickleball Galore
Hilton Head Island is also a favorite destination for tennis enthusiasts. The area hosts many top tournaments and nationally ranked facilities, while the mild winter weather makes playing on one of the island’s clay courts much more enjoyable. Join in a round robin tournament, take a cardio tennis class or just enjoy a relaxing afternoon match.
Another unique form of recreation, pickleball, is popular among Hilton Head locals and visitors alike. The game, which combines tennis and ping pong, is played on a shortened court and is easy to learn, making it ideal for all ages, from families with young children to senior citizens.
Biking, Kayaking and More
Hilton Head Island has more than 60 miles of multi-use paths and has earned Gold Level recognition as a Bicycle Friendly Community. Everywhere you turn, folks are riding bikes to get from place to place or simply admire the island’s scenery.
For more outdoor fun, head to Shelter Cove Harbour & Marina, where you can rent kayaks and paddle across the water in search of dolphins, birds and other marine life. You can even rent a catamaran for a speedier way to navigate the harbour, as well as stand-up paddleboards, boats and water skis.
While summer offers plenty of fun festivals, winter in Hilton Head boasts its fair share of great events, too. In November, the island hosts the Hilton Head Island Concours d’Elegance & Motoring Festival, an exhibition of more than 500 cars, boats, motorcycles and aircraft. And December brings a range of holiday festivities, including Harbour Town’s holiday light display and outdoor seasonally themed movies, as well as visits from Santa at Shelter Cove Harbour.
And don’t miss an oyster roast while you’re in town! Traditionally, these take place during in any month that ends in “r” — meaning the delightful off-season months of September, October, November and December!
When in Hilton Head, you must visit the beach! With the summer high season over, you’ll find quiet stretches of sand perfect for a morning run, a shell-seeking excursion or an evening glass of wine as the sun sets.
During my visits, I’ve always enjoyed looking for sea creatures like horseshoe crabs and yes, even the occasional jellyfish, while strolling along the surf. One time, a dolphin even jumped right out of the inlet beside me! Hilton Head is also pet friendly in the off-season — dogs are allowed on the beach from Labor Day through Memorial Day, so bring Fido along for the fun.
Take Fido to Hilton Head’s local dog park at Chaplin Community Park off William Hilton Parkway.
Where to Stay: