Celebrate the Holidays on Hilton Head Island

Want to visit Santa, go on a festive train ride, and get your holiday shopping done all in the same day? With the wide array of Hilton Head Island holiday celebrations, activities, and experiences, you absolutely can.

Shelter Cove Harbour & Marina
When: November 28, 2025, 12:00 pm–2:30 pm 
Where: Neptune Statue, Shelter Cove Harbour & Marina

Santa will be visiting Shelter Cove Harbour & Marina first on November 28, 2025, so make sure your Christmas wish lists are finalized and ready for The Big Guy when he comes to town. He arrives at noon aboard a local fire truck and will stay until 2:30 pm at the Neptune Statue. The kids can share their Christmas lists, and you can snap a few photos. There will also be shopping, bounce houses, and train rides around the marina throughout the day. Each activity is $5, with donations accepted at entry for The Hilton Head Island Deep Well Project.

Polar Pines Express Holiday Wagon Ride
When: December 10, 2025, 10:00 am - 11:00 am
Where: Heritage Farm

Live the real-life story of The Polar Express at Heritage Farm with their festive wagon rides and storytelling experience. On December 10, 2025, they are hosting a Polar Pines Express Holiday Wagon Ride and invite you to a full day of holiday fun with crafts and activities, hot chocolate, and treats for your kids. Reservations are required in advance for this adventure, so make sure you book ahead of time.

Holiday Fun in Harbour Town
When: December 27, 2025 - December 28, 2025, 5:30 pm - 7:30 pm
Where: Harbour Town

The Hilton Head Island holiday lineup continues with Holiday Fun in Harbour Town on December 27 and 28, 2025, at the Liberty Oak tree. Watch classic holiday movies, roast marshmallows, and enjoy a train ride! Just bring a canned food donation for The Deep Well Project, and free entry is all yours.

Paws and Claus Parade
When: December 29, 2025, 1:00 pm - 3:00 pm
Where: Harbour Town

Santa will also be hanging out in Harbour Town for a little while after Christmas (probably to recover from all that traveling) and will lead the beloved annual Paws and Claus Parade on December 29, 2025. This may just be the cutest event of the season! Bring your furry friends dressed in their best holiday attire, snap a photo with Santa, and enjoy dog games afterward on the Liberty Oak stage.

Brunch with Santa
When: December 21, 2025, 10:15 am - 12:00 pm
Where: Alexander’s Restaurant & Wine Bar

Don’t worry, Santa is making his rounds more than once this season! You can even have Brunch with Santa at Alexander’s Restaurant & Wine Bar on December 21, 2025 — a beloved annual event made for the whole family. Help yourselves to a buffet during one of their two scheduled seatings (make sure you reserve in advance) and get complimentary photos with Santa. They will also be accepting donations of new, unwrapped toys at the restaurant to benefit The Deep Well Project, so spread the joy this Christmas and help a family in need while you dine.

Santa’s Holiday Breakfast in The Carolina Room
When: December 14, 2025, 11:00 am - 2:00 pm
Where: The Westin Hilton Head Island Resort & Spa

Staying at The Westin Hilton Head Island Resort & Spa over the holidays? Enjoy Santa’s Holiday Breakfast in The Carolina Room on Sunday, December 14, 2025. This is a joyful holiday breakfast with a visit from Santa, festive crafts for kids, and complimentary photos to start the season off with some holiday magic and cheer!

Holiday Bling & Wine Tasting Party
When: December 6, 2025, 4:00 pm - 6:00 pm
Where: Nunzio Restaurant and Bar

If you’re searching for a more elevated experience, enjoy signature holiday cocktails, festive wine tastings, and delicious Italian light bites at Nunzio Restaurant and Bar’s Holiday Bling & Wine Tasting Party on December 6, 2025, from 4–6 pm. It’s a festive way to toast the start of the holiday season and celebrate the reopening of their patio. 

Insider Tip: This one will fill up quickly, so be sure to reserve your space at the party ahead of time by registering on their website.

Our arts and culture scene comes alive in the winter months, and the holiday season is no exception. With holiday concerts and winter shows for kids and adults alike, there’s no better time to take in our local productions by choral groups and performing artists.

Holiday Pops
When: November 20, 2025, at 4 pm, and December 1, 2025, at 7:30 pm
Where: First Presbyterian Church

The holiday productions begin with Holiday Pops, a joyful, soulful performance at the First Presbyterian Church. A Hilton Head Island holiday tradition featuring conductor John Morris Russell, the Hilton Head Symphony Orchestra Chorus, and deep tones from renowned baritone Michael Preacely, this is a heartwarming holiday event for the whole family. They will be performing festive favorites, as well as jazz and gospel numbers.

Hilton Head Choral Society’s “Celebrate the Holidays” Concert
When: December 5, 2025, at 7:00 pm
Where: First Presbyterian Church

Hilton Head Choral Society’s “Celebrate the Holidays” Concert is a celebration of traditional classics blended with seasonal selections for all ages to enjoy.

Gregg Russell Christmas Concert
When: December 23, 2025, at 7:30 pm
Where: Liberty Oak Tree in Harbour Town

The beloved outdoor Gregg Russell Christmas Concert is an evening of festive guitar and songs for children and adults alike in Harbour Town. Stick around, Gregg might even bring out Santa for his encore. 

We may not have a white Christmas here in South Carolina, but our pristine white-sand beaches, protected wilderness areas, and sprawling golf links are all we need for a beautiful family day out in nature over the holidays.

Our beaches are gorgeous in the off-season, and you may just get the whole stretch of sandy shore to yourself during these quieter months. Go for a stroll or a bike ride at sunrise to check off one of our visitors’ favorite Hilton Head Island experiences. And with the backdrop of holiday light displays, your quiet beach or trail walk just got a whole lot more beautiful.

On the first day of Christmas, we’re giving you birdies on a world-class golf course instead of partridges in a pear tree. Although we can only really provide the golf course, which means the birdies are up to you. Book tee times whenever you like over the holidays with fewer crowds and shorter wait times on our 23 world-class golf courses on Hilton Head Island. You can even spend Christmas Day golfing.

Our nature preserves will also be quiet and teeming with wildlife over the holidays, so if you’re into birdwatching, nature tours, or wildlife photography, this is the best time to get out into the woods.

The Sea Pines Forest Preserve, Audubon-Newhall Nature Preserve, and Whooping Crane Pond Conservancy are some great options with walking and biking trails to explore during the holidays. If you’re on the Island on December 15, 2025, you can take part in the Audubon Christmas Bird Count 2025 and be part of this global citizen science project. There’s also an evening Holiday Lights Wagon Ride through the Sea Pines Forest Preserve for kids and adults on December 29, 2025 — a magical way to finish off the holiday celebrations.

Our cozy, white-sand wonderland is the perfect place for connection and family time this holiday season. Now that you have our recommendations for events, gift shopping, and family-friendly activities, you’re ready to plan the Christmas escape of your dreams. View our full list of events for more exciting additions to your holiday stay, and check out our offers for discounts on accommodations and experiences during the holidays.