Hilton Head Winter Events Calendar '23/'24 - Sunset Rentals Vacation Blog

Hilton Head Winter Events Calendar ’23/’24

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. 



Date: November 24, 2023 – January 1, 2024
Time: All Day
Location: 160 Lighthouse Rd, Hilton Head
Cost: Free!

The iconic Harbour Town Lighthouse shines even brighter during the holiday season! Get in the holiday spirit with a stroll along the waterfront at Sea Pines adorned with festive décor, thousands of twinkling lights, and eateries to sit down and soak up the views. The official tree lighting takes place on November 24th at the Gregg Russell Thanksgiving Concert, and the festivities end with the New Year’s Eve Ball Drop on December 31st.

The Harbour Town Lights at Sea Pines Resort is Hilton Head’s favorite holiday tradition. Take a stroll around the harbour illuminated with dazzling holiday light displays, glowing Santas and snowmen, a towering 30-ft Christmas tree, and stores decked out in holiday décor for Christmas shopping. Make a difference this holiday season by donating canned goods or new toys to the Deep Well Project – simply drop them in the well by the Liberty Oak Stage.


Date: December 1 – December 31, 2023
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.


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.


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!  


Date: Weekly on Tuesday
Time: 3 PM – 5 PM
Location: 9 Palmetto Bay Rd, Hilton Head
Cost: Between $25-$30 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.


Date: Weekly on Sunday until February 11, 2024
Time: 1 PM – 4 PM
Location: 100 N Sea Pines Dr, Hilton Head

Fraser’s Tavern in Sea Pines transforms into a sports lover’s paradise during NFL football season. With large screens broadcasting the games, a menu packed with game-day favorites, and a lively atmosphere, it’s the perfect place to cheer on your team for game day on Hilton Head Island.

* Please note guests staying outside of the Sea Pines Resort area are required to pay a $9 cash entry fee per vehicle at the Greenwood Gate or Ocean Gate into Sea Pines.


Date: Weekly on Saturday until February 24, 2024
Time: 1 PM – 4 PM
Location: 87 N Sea Pines Dr, Hilton Head 

– Bucket of oysters: $27
– Peel-and-eat shrimp: half pound $16 half pound, pound $29

The Oyster Roasts at Coast in Sea Pines deliver a genuine taste of Lowcountry cuisine! Indulge in freshly roasted local oysters and peel-and-eat shrimp by the bucket complemented by stunning oceanfront views and laid-back island vibes!  


December 4 Super Tuscan vs Bordeaux
December 15 Pahlmeyer Wine Dinner
December 18 NYE Bubbly
January 18 Larry O’Brien Wine Dinner
February 8 – Honig Vineyards Wine Dinner
February 12 Nickel & Nickel Cabernet Immersion

Location: 11 Lighthouse Lane, Hilton Head
Cost: View ticket pricing and availability HERE

Elevate your Hilton Head winter vacation with a unique dining experience on the iconic Harbour Town Golf Links. Links, an American Grill hosts casual wine tastings with expert Sommeliers and  intimate wine dinners featuring five course menus paired with fine wines. Limited seating is available so book well in advance.


Date: Weekly from Monday to Saturday
Time: Click HERE for real-time availability
Location: 14 Cardinal Rd, Hilton Head 

– Distillery Tours: $35 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.


Date: December 8, 2023
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!


Date: December 9, 2023
Time: 6 PM – 8 PM
Location: Click HERE for the parade route
Cost: Free!

Deck the Hulls is a beloved Hilton Head tradition where beautifully decorated boats glide along the shoreline of Skull Creek. The parade starts at Safe Harbor Skull Creek Marina and ends at Hilton Head Harbor RV. There are many waterfront restaurants to reserve a front row seat to the Deck the Hulls Christmas Boat Parade.


Date: December 10, 2023
Time: Two seatings at 10:15 AM and 12 PM
Location: 76 Queens Folly Road, Hilton Head
Cost: $43 for adults and $25 for kids

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.


Date: December 14, 2023
Time: 6 PM – 8:30 PM
Location: 76 Queens Folly Road, Hilton Head
Cost: $135 per person

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.


Date: December 16, 2023
Time: 1 PM – 2:15 PM
Location: Heritage Farms, Hilton Head

Delight the kids with a Sea Pines Forest Preserve wagon ride! Climb aboard the Polar Pines Express Holiday Wagon Ride for a narrated journey to the North Pole. This festive ride through Sea Pines Forest features storytelling, holiday songs, crafts, activities, hot chocolate, and heartwarming memories of your holiday happenings on Hilton Head Island.


Date: December 17, 2023
Time: 2 PM – 3 PM
Location: 76 Queens Folly Road, Hilton Head
Cost: $25 per person

Learn the rich culinary traditions and deep history of Lowcountry cooking with Alexander’s Executive Chef Charles Pejeau and his culinary team. This event covers the art of preparing a traditional Southern New Year’s Day “good luck brunch” of skillet cornbread and potlikker, a quintessential Southern dish.


Date: December 23, 2023
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.


Date: December 27-28, 2024
Time: 5:30 PM – 7:30 PM
Location: 147 Lighthouse Rd, Hilton Head
Cost: Free! Train rides $6

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.


Date: December 29, 2024
Time: 2 PM – 3:30 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.  


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.


Date: January 27, 2024
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!


January 21-22 | Grieg and Brahms
February 4-5 | Bach, Mozart, and Brandon Leonard
February 18-19 | John Williams Birthday Celebration
March 17-18 | Symphonic Dances of Rachmaninoff and Coleridge-Taylor
April 7-8 | Tessa Lark and Piazzolla’s Four Seasons of Buenos Aires 

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.


Date: February 10, 2024 

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!


Date: February 19 – 25, 2024
Location: Various Locations 

2024 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.


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!

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