Hilton Head Island has long been celebrated as a destination where pristine beaches, world-class golf courses, and a welcoming family-friendly atmosphere blend seamlessly. But, Hilton Head is America’s favorite island year-round and doesn’t only shine in the summer season!
If this is the white Christmas you’re dreaming of this year, trade in white snow for white sandy beaches on Hilton Head Island this holiday season. From sunny beaches, world-class golf, and outdoor adventures in nature to alfresco oceanfront dining, one-of-a-kind shopping, and coastal homes for the holidays, Hilton Head Island offers a smorgasbord of fun to celebrate the holiday season.
From winter markets, cultural celebrations, and unique culinary experiences to heartwarming holiday traditions, we invite you to embrace the winter season in true Lowcountry style on Hilton Head Island.
Whether you’re seeking private access to miles of uncrowded beaches, heated pools, spacious gourmet kitchens to host family feasts – or a combination of it all – you’ll find your coastal home for the holidays and peace of mind with Sunset Rentals.
HILTON HEAD ISLAND HOLIDAY EVENTS
HARBOUR TOWN LIGHTS
Date: November 29, 2024 – January 1, 2025
Time: All Day
Location: 149 Lighthouse RoadHilton Head Island, SC 29928
Cost: Free!
Stroll along the harbour and enjoy the illuminated seasonal figures, including the centerpiece attraction –a towering Christmas tree! The perfect place to spend the holiday season with your
family, Harbour Town will be bustling with activities and live entertainment. The official tree lighting will take place just prior to the Gregg Russell concert at 7:30pm Friday, November 29.
While you’re enjoying the holiday season, help the Deep Well Project make a difference in someone’s life. Drop off a couple of canned goods or a new, unwrapped child’s toy in the well by the Liberty Oak stage.
LIGHT UP THE HARBOUR
Date: December 1 – December 31, 2024
Time: 5 PM
Location: 1 Shelter Cove Lane, Hilton Head
Cost: Free!
The holiday lights at Shelter Cove Harbour & Marina are a must-see during your winter vacation on Hilton Head. As the sun sets, the harbour transforms into a colorful coastal winter wonderland with brightly lit boats, local holiday shopping, and waterfront restaurants along the marina.
Local’s Tip: Reservations are always recommended for dinner.
Shelter Cove Harbour & Marina is beautifully lit with over 100,000 holiday lights, brightly decorated boats in the marina, and waterfront shops and restaurants adorned in festive décor. Take a stroll along the waterfront promenade to soak up the sights and be sure to stop by Francesca’s at Shelter Cove Town Center for a visit with Santa and Mrs. Claus.
HILTON HEAD COMMUNITY MARKET
Date: Weekly on Saturday
Time: 9 AM – 12 PM
Location: 39 Shelter Cove Lane, Hilton Head
Cost: Free!
Start your winter adventures with a stroll through the Hilton Head Community Market at Shelter Cove Community Park. Browse and shop an array of handcrafted goods, locally sourced produce, and unique artisanal creations.
Upcoming Dates:
November 9, 2024 9:30 am – 12:30 pm
November 16, 2024 9:30 am – 12:30 pm
November 23, 2024 9:30 am – 12:30 pm
November 30, 2024 9:30 am – 12:30 pm
December 7, 2024 9:30 am – 12:30 pm
December 14, 2024 9:30 am – 12:30 pm
December 21, 2024 9:30 am – 12:30 pm
December 28, 2024 9:30 am – 12:30 pm
HILTON HEAD FARMERS MARKET
Date: Weekly on Tuesday
Time: 9 AM to 1 PM
Location: 70 Honey Horn Dr, Hilton Head
Cost: Free!
The Hilton Head Farmers Market at the Coastal Discovery Museum is a quintessential Lowcountry experience. Here, you can wander through rows of colorful market stalls, stroll around the Museum’s majestic 68-acre property, discover the island’s rich Gullah culture, or book a tour to explore Hilton Head Island, on land or water!
TASTY TUESDAY WINE TASTING
Date: Weekly on Tuesday
Time: 3 PM – 5 PM
Location: 9 Palmetto Bay Rd, Hilton Head
Cost: Between $25-$35 per person, food not included!
Tasty Tuesday at Roller Wine & Spirits invites wine enthusiasts and novices alike to sample a carefully curated selection of wines, led by expert sommeliers and often the winemakers themselves! Call (843) 842-1200 or book online.
WINe dinners at the sea pines Resort
Location: 100 N Sea Pines Dr, Hilton Head
Links, an American Grill invites you to join us for the return of our wine dinner season. At our wine dinners, you will meet The Sea Pines Resort chefs as well as winemakers from around the country while enjoying fine dining and outstanding wines. Check out a list of our upcoming wine dinners and reserve your spot today while space is still available.
Shafer Vineyards Wine Dinner
Shafer Vineyards Wine Dinner – Friday, November 22, 6:30pm
Learn More
An Evening with Rob Mondavi Jr
An Evening with Rob Mondavi Jr – Friday, December 13, 6:30pm
Learn More
OYSTER ROASTS AT COAST, OCEANFRONT DINING
Date: Weekly Saturday until February 22, 2025
Time: 1:00PM – 4:00PM
Location: 87 N Sea Pines Dr, Hilton Head
Oyster roasts are celebrations of community and the bounty of the sea — two of South Carolina’s most enduring traits. Coast, Oceanfront Dining at The Sea Pines Resort invites you to enjoy a special menu of fresh, local and roasted-on-site oysters from Maggioni Oyster Company on St. Helena Island along with live music performed by Mark Husbands and drink specials with Fisher’s Island Lemonade. Completing the coastal culinary feast: Peel-and-eat shrimp, available by the half pound or pound. Join in on the fun at Coast Oceanfront Dining located at the Sea Pines Beach club every Saturday from 1-4pm, weather permitting.
Prime Rib Night at Links
Date: Weekly Wednesday until December 18, 2024
Time: 5:00PM – 9:00PM
Location: 11 Lighthouse Lane, Hilton Head
Links’ Signature Slow-Roasted Prime Rib is available every Wednesday night from 5-9pm. Subject to availability, reservations recommended.
HILTON HEAD DISTILLERY TOURS
Date: Weekly from Monday to Saturday
Time: Noon – 6:30 PM
Location: 14 Cardinal Rd, Hilton Head
Cost:
– Distillery Tours: $40 per person
– Cocktail Classes: $95 per person
– Holiday Cocktails & Cookies Class (12/6 & 12/13): $125 per person
** Pricing is subject to change
At Hilton Head Distillery, you’ll embark on an immersive journey through the art of distillation. Tour the production facilities, sample the distillery’s signature spirits, book a cocktail class with a master mixologist, or simply drop in for a drink. Non-alcoholic options are also available.
Dewars Whisky Dinner
Date: December 4, 2024
Time: Starts at 6:30PM
Price: $150
Location: 87 N Sea Pines Dr
Hilton Head Island, SC 29928
Join in on the fun for an evening of whisky tastings with Dewars and a delicious multi-course dinner at the Sea Pines Beach Club on December 4! To enhance your experience, a distillery representative will be present to share insights about each whisky including: Dewars White Label, Dewars 12 Year, 15 Year, 19 Year, and finally, 21 Year. Savor the unique flavors and notes of these exceptional spirits, starting with a welcome cocktail, followed by neat pours paired with each of the four expertly crafted courses crafted by Executive Chef Clinton Barabas and his culinary team. To conclude the night, enjoy a delectable dessert created by our Resort Executive Pastry Chef, Iain Jones!
All ticket prices include admission, tax and gratuity. Please note any food allergies for the chef when purchasing tickets. Allergies noted less than 24 hours before the event cannot be guaranteed.
WINTER WONDERLAND
Date: December 6, 2024
Time: 4 PM – 7 PM
Location: 39 Shelter Cove Lane, Hilton Head
Cost: Free!
Bring the whole family for a day of festive fun at Winter Wonderland at Shelter Cove Park. This one day event features carnival games, candy cane huts, inflatables, live DJs, and a festive children’s parade to celebrate the season. Admission is free with food, drinks, and some paid family activities available too!
Tap Takeover at Fraser’s Tavern
Date: Nov 19, 2024 – Feb 18 2025
Time: Monthly on the third Tuesday / 5:00PM – 8:00PM
Location: 100 N Sea Pines Dr. Hilton Head Island, SC 29928
Come out to Fraser’s Tavern every third Tuesday of the month for the Tap Takeover! Come out from 5-8pm for a special craft brewery takeover to try out local and regional beers! “The Art of the Brew” is an opportunity for the brewer and guests to interact, ask questions and giveaways!
BRUNCH WITH SANTA
Date: Sunday, December 15, 2024
Time: Two seatings: 10:30 AM & 12:30 PM
Location: 76 Queens Folly Road, Hilton Head
Cost: $43 for adults | $25 for kids
**Reservations are required.
Bring your wish list to the annual Brunch with Santa at Alexander’s Restaurant in Palmetto Dunes. Tuck into a tasty breakfast brunch and delicious holiday desserts, take a family photo with Santa fireside, and bring along an unwrapped gift to support the local Deep Well Project on Hilton Head.
Local’s Tip: Book online or call (866) 921-6639 for reservations.
ALEXANDER’S FREEMARK ABBEY WINE DINNER
Location: 76 Queens Folly Road, Hilton Head
Cost: $135 per person
2024 WINE DINNERS:
Date: Thursday, November 21
Time: 6 PM – 9 PM
Cakebread Cellars & Sequoia Grove Winery
Wine Dinner
Date: Thursday, December 12
Time: 6 PM – 9 PM
Chappellet Wine Dinner
Make a Wine Dinner Reservation here
Alexander’s, an upscale restaurant and wine bar in Hilton Head, SC, is delighted to offer wine dinners featuring a selection of wonderful wine, spectacular food, and lively conversation. Alexander’s Wine Dinners pair a specialty crafted multi-course dinner with award-winning wines in an elegant ambiance. Enjoy the chef’s finest creations while exploring the timeless craftsmanship of Freemark Abbey wines sourced from the Napa Valley.
Local’s Tip: Book online or call (866) 921-6639 for reservations.
Audubon Christmas Bird Count
Date: December 16, 2024
Time: All Day!
Location: 175 Greenwood DriveHilton Head Island, SC 29928
Cost: Free!
Help the Hilton Head Island Audubon Society as it works with communities across America, including Sea Pines, to conduct the annual Audubon Christmas Bird Count. To register, email hhicbc@gmail.com or visit hiltonheadaudubon.org.
Polar Pines Express Holiday Wagon Ride
Date: December 21, 2024
Time: Starts at 1:00PM
All aboard our festive wagon full of holiday fun. Join in on the fun as we travel to our version of the “North Pole” for crafts, activities, hot chocolate and treats. Along the way sing along to some holiday tunes and listen to the famous story “The Polar Express”. $17/adult, $19/child.
GREGG RUSSELL CHRISTMAS CONCERT
Date: December 23, 2024
Time: 7:30 PM – 9 PM
Location: 147 Lighthouse Rd, Hilton Head
Cost: Free!
Gather friends and family under the iconic Liberty Oak for a spirit holiday performance by acclaimed Hilton Head entertainer Gregg Russell. This heartwarming Hilton Head tradition is filled with festive tunes, sing-alongs, and hilarious humor with a special visit from Santa Claus for the kids.
SANDY SLEDDING AT SEA PINES
Date: December 27, 2024
Time: 1 PM – 2:15 PM
Location: 87 N Sea Pines Dr, Hilton Head
Cost: $40/team up to 6 people
Trade snowy slopes and frozen toes for sandy sledding on Hilton Head Island. You’ve still got time to reserve your space, build your team, and design your dream holiday themed sand sled! The event takes place in front of the Sea Pines Beach Club with an oceanfront restaurant, rooftop bar, and beach bar to make a day of it.
HOLIDAY FUN IN HARBOUR TOWN
Date: Daily Friday and Saturday until Sat, Dec 28 2024
Time: 5:30 PM – 7:30 PM
Location: 147 Lighthouse Rd, Hilton Head
Cost: Free!
Tickets: Train rides – $6/passenger, starting at 5:30pm
The festive fun in Harbour Town extends beyond the holiday lights! Enjoy a day of rest after Christmas then head to Holiday Fun in Harbour Town for two days of holiday movies, marshmallow roasting, family activities, and train rides around Hilton Head’s most famous marina. Entry is free with the donation of a canned food item.
PAWS AND CLAUS PARADE
Date: December 29, 2024
Time: 1 PM – 3 PM
Cost: Free!
Join in on the fun for the Paws and Claus Parade in Harbour Town! After Christmas, your furry friends can show off their best holiday attire in a parade led by Santa himself. Enjoy a festive day filled with holiday cheer and a photo op with Santa! All breeds and sizes are welcome—bring your pups and celebrate the season together! Registration begins at 12:15pm in front of Quarterdeck Market. Parade begins at 1pm also starting at Quarterdeck Market and ending near the Liberty Oak Stage. After the parade enjoy dog games around the Liberty Oak stage.
MERRY PINES WAGON RIDE
Date: December 29, 2024
Time: 5:30 PM – 6:30 PM
Location: 175 Greenwood DriveHilton Head Island, SC 29928
Cost: $22/adult, $18/child
Join in for a magical evening aboard our illuminated wagon as we journey through the Sea Pines Forest Preserve! Immerse yourself in the holiday spirit with a delightful sing-along featuring your favorite festive tunes. Cozy holiday attire recommended. Hot chocolate and treats provided.
POLAR BEAR SWIM
Date: December 30, 2024
Time: 10 AM
Location: 1 Lighthouse Lane, Hilton Head
Cost: Free!
While it’s not the Rocky Mountains, the winter water temperatures on Hilton Head still offer a refreshing, polar bear worthy chill for those seeking a New Year’s plunge! Come and embrace our island’s winter spirit with a polar bear plunge in the Harbour Town Pool in Sea Pines.
NEW YEARS EVE CELEBRATION
Date: December 31, 2024 – January 1, 2025
Time: 6 PM – 12:30AM
Location: 149 Lighthouse RoadHilton Head Island, SC 29928
Get ready for a festive New Year’s Eve ball drop from the top of the Harbour Town Lighthouse! Enjoy food, entertainment and live music throughout Harbour Town, then count down to the ball drop as we welcome the New Year! There will be two drops: 7pm and midnight.
SNOW DAY AT SHELTER COVE
Date: January 25, 2025
Time: 11 AM – 4 PM
Location: 39 Shelter Cove Lane, Hilton Head
Admission: $10 for ages 2-17
Experience the magic of “snowfall” without leaving the island! Snow Day at Shelter Cove is a rare delight in the South. The park transforms into a winter playground with falling snow, inflatables, and fun-filled entertainment for the whole family. Building a snowman near the beach should be a bucket-list adventure!
HILTON HEAD SYMPHONY ORCHESTRA SERIES
November 10-11 | THE AMERICAN EXPERIENCE
December 1-2 | HOLIDAY POPS
January 19-20 | JAIME AND FRIENDS
February 2-3 | THE SEVEN DEADLY SINS
February 16-17 | GET HAPPY! A JUDY GARLAND CELEBRATION
March 2-3 | CARL ORFF: CARMINA BURANA
April 6-7 | MENDELSSOHN AND VIVALDI
April 28-29 | LA MER AND ENRIQUE GRAF
Location: 540 William Hilton Pkwy, Hilton Head
Cost: View ticket pricing and availability HERE
The Hilton Head Symphony Orchestra Series showcases the island’s vibrant arts scene. Enjoy world-class performances featuring award-winning artists and conductors in the elegant setting of Hilton Head’s First Presbyterian Church.
HILTON HEAD marathon half MARATHON and 5K
Date: 5K – February 15, 2025
Date: Marathon & Half Marathon – February 16, 2026
Register Here
For fitness enthusiasts, the annual Hilton Head Marathon is an opportunity to run a scenic course that winds through the island’s natural beauty. With multiple race options, it caters to runners of all levels with a post-race party and complimentary local beer that’ll bring you back to Hilton Head year after year!
HILTON HEAD ISLAND SEAFOOD FESTIVAL
Date: February 17 – 23, 2025
Location: Various Locations
2025 Schedule of Events & Tickets
Wrap up your winter vacation in Hilton Head on a cultural and culinary high note at the Hilton Head Island Seafood Festival. This unique annual event celebrates the South’s rich heritage with award-winning chefs and the best seafood on the island. From pop-up dinners, pig pickin’, and oyster roasts to prestigious home tours of Hilton Head, this annual event is not to be missed.
HEAD HOME TO A SUNSET RENTAL
Our on-island team has been welcoming families to celebrate the holidays in our luxury homes on Hilton Head Island for more than 25 years. The holiday season kick-off festivals have begun and no matter how you like to celebrate the holidays, there are fun festivities for the whole family on Hilton Head Island.
The most important factor in planning events for your Hilton Head vacation is finding a home away from home, hosted by a local team that cares! Sunset Rentals has been proudly serving guests on the island for more than 25 years – come and experience the Sunset Advantage on Hilton Head!
