Golf, Tennis, Festivals, Fine Dining, Shopping, Comedy, Magic, & Seasonal Weather Await Vacationers After the End of Summer 

Jeff Walker,  Entertainment Writer / Travel Writer

While Charleston continues to draw most of the attention when it comes to tourism in South Carolina, there are a few select destinations inside the palmetto state that are equally attractive. Myrtle Beach with its theatres, amusement areas, and mini-golf seem to be ideal for family vacations during the summer.

However, Hilton Head Island (HHI) in the fall with its favorable beach weather, smaller crowds, and prime seasonal activities makes for a perfect week long or three day weekend. Encompassing 42 square miles, including 12 miles of beachfront, HHI aka Hilton Head is a South Carolina resort community like no other in the palmetto state.

Quick History Lesson:

But first let's start our journey on some lesser known, yet interesting facts about this South Carolina low country getaway. HHI is one of the few sea islands where the Gullah culture began to take shape. Cut off from the mainland, the Sea Islands freedmen developed their own culture, creating their own foods, language, art and more. Want to learn more about Gullah and Hilton Head's rich history, check out https://www.coastaldiscovery.org/

Additionally, to maintain the overall serenity and harmony of the natural environment Hilton Head has to offer, there is not a single neon sign on the island, rather signage comes in neutral or natural colors to complement surrounding habitats. Much like Italy is often referred to as a boot because of its shape, Hilton Head is called a 'foot' with the south end where Sea Pines Resort is located as the 'toe'. I guess you could say the island has a lot of 'soul' (pun intended). 

If you want to take a trip back in time, remnants of Daufuskie Island still reflect decades, as well as centuries old environmental preserves where oysters farming was the main economy. Located midway between Hilton Head Island and Savannah surrounded by the waters of Calibogue Sound, (intracoastal waterway) and the Atlantic Ocean, Daufuskie is only accessible by boat or public ferry. Retreat to https://www.daufuskieisland.com/

Once home to late SC author Pat Conroy, approximately 500 residents, reside on Daufuskie, most living in private communities, including Haig Point Club with its membership only golf club. Longing to get far away, even for just a day, consider Daufuskie. Maybe check out the Daufuskie Island Distillery where they've been creating distinctive rums and bourbons from handcrafted copper stills sine 2013. Let the spirits lead you to https://daufuskieislanddistillery.com/

Recreation:

As summer humidity fades and daytime temps hover from the high 70s to the low 80s, HHI is especially appealing to golfers and tennis players, as well as those who enjoy biking and being out on the water. 

Including neighboring Bluffton, there are roughly 40 public golf courses, with around 10 to 12 public or resort-accessible championship layouts located directly on the HHI proper. Easily, Harbour Town Golf Links at Sea Pines Resort, host of the PGA Tour's RBC Heritage is perhaps the most preferred by the serious golfers. 

Tee it up here first at https://www.seapines.com/golf/courses/harbour-town-golf-links and for access to all their courses, as well as book tee times visit https://www.hiltonheadisland.org/golf/book-tee-times Depending on where you stay, most are within a 15-20 minute drive.

Spread across public complexes, as well as resort and private communities HHI is home to six major tennis facilities, sporting 300 plus tennis and pickleball courts. Whether you're a beginner or want to take your game to the next level, Van Der Meer Tennis offers week long and weekend clinics, alongside private and group lessons. Game, set, and match at https://vandermeertennis.com/

Unless you're staying at a beachside resort, Coligny Beach Park is the island's most popular oceanfront park, providing access to miles of beautiful beach from 6am-10pm. This city owned park is an ideal choice for spending a day at the beach. Amenities include free parking (always a bonus), beach chair rentals, restrooms, outdoor showers, swings, bicycling, seasonal lifeguards, and accessible wi-fi (in case you can' t totally tune out). Your boardwalk journey begins at https://hiltonheadislandsc.gov/parks/ColignyBeach/

Pampering Yourself on HHI:

Though there are various resorts situated on HHI, the recently renovated award winning Sonesta Resort Hilton Head Island inside the gated Shipyard Plantation includes everything vacationers want and more. Set among lush, manicured gardens, palm trees, and oak trees with direct access to the beach, Sonesta sits adjacent to the Shipyard Golf Course, Van Der Meer Tennis, and Coligny Plaza. All within two miles of the resort. 

Greet new mornings in one of 340 spacious rooms and suites featuring stylish and subtle earth toned coastal decor. Bask in views of the garden or the Atlantic Ocean from private balconies or patios. Love to kickstart the day with a healthy workout, drop in their 24-hour fitness center or perhaps rent a bike for a ride along hard-packed beach sand as the sun continues to rise.

Spending the entire day at Sonesta, enjoy one of several pool areas including their zero entry lagoon style or an adults only area with new hot tubs and private cabanas. The Sweet Cane Bar and Grille offers up refreshing frozen drinks and light bites daily from 11-3pm, with menu options for children.

After sunning yourself poolside maybe you're ready for a little me time. Take advantage of Sonesta's full-service spa offering massages, body wraps, and aromatherapy. Located on the second floor the Spa at Sonesta is designed to rejuvenate your body and your soul. Unwind at https://www.sonesta.com/sonesta-hotels-resorts/sc/hilton-head-island/sonesta-resort-hilton-head-island#hoteldetails_the-spa-at-sonesta

Serving breakfast (6:30-11am) and dinner (5-9pm) daily, Seacrest Restaurant & Terrace is Sonesta's main dining room. Whether it's early morning or early evening feast on regional cuisine and locally inspired dishes designed to please every palate. When mother nature allows ask to sit on the terrace where you can further enjoy panoramic views of the property including the sunrise. 

Located just off the main lobby, Driftwood Rum Bar is the latest addition to Sonesta's food & beverage Hilton Head empire. Open 3-11pm, Driftwood is the perfect place savor Rum Bites such as pineapple-rum glazed wings or Truffle Popcorn while sipping classic craft cocktails or over a dozen rum concoctions.

With multiple TVs and a rotating selection of draft beers the Patio Bar & Deck overlooks the courtyard and main pool and is an ideal hangout to watch the game. Open noon until 10pm daily the lounge serves up signature dishes including a Southern Smash Burger, alongside Chef Jake’s award-winning short rib chili. The Patio Bar & Deck is your classic gastropub. For all their dining options visit https://hiltonheadresort.sonesta.com/dining/

Further amenities include a well-manicured tropical courtyard complete with two gas firepits, with an oversized pit ideal for friends and family to gather around to unwind at the end of the day. Additionally, Sonesta's property backs up to a pristine white sandy beach. And when mother nature is not cooperating, the resort's expansive atrium converts into an activity room, allowing guests not only to play games but opportunities to make new friends.

Golf, tennis, and the beach just outside their doorstep, with shopping less than 10 minutes away, and several dining options and an awesome spa under one roof, Sonesta Resort Hilton Head embodies R&R, aka 'rest and relaxation', or as their website proclaims 'coastal chic serenity'.  Awarded a AAA Four Diamond Inspected Clean designation, a 2025 Stella Award Silver Medal, and a Tripadvisor Travelers' Choice Award, Sonesta is a clear choice on HHI. It's their little things that make the difference. Enjoy your stay at https://hiltonheadresort.sonesta.com/

Fine Dining Options:

Should Sonesta Resort be your central island lodging you're within 10 minutes of some of the most preferred eateries on HHI. From budget friendly to premium, and from burger bars to high-end steakhouses, and everything in between, there are price ranges and menus to fit every member of your party.

Without question, if you want to revel in one of the most exquisite culinary journeys on HHI, than I strongly urge you to make reservations at Alexander's Restaurant & Wine Bar. Tucked in the heart of the Palmetto Dunes community, Alexander's features a sophisticated, airy, and quiet indoor space with views overlooking a tranquil lagoon. 

Situated nicely at 76 Queens Folly Rd. Alexander's is akin to a rare clam. While its exterior entryway is modest, opening the front door exposes guests to a pearl of a restaurant, featuring three separate dining areas including one with a quaint pub. Aside from killer Maine lobsters, their menu leans heavily on seasonally inspired dishes created from locally caught seafood and regionally sourced ingredients.

While their starter and main menus offer up a variety of seafood dishes including New England Crab Cakes, Oysters Alexander, Shrimp & Grits, and Fresh Local Catch, for carnivores they do serve a Plum Wine Braised Short Ribs, a hearty and succulent choice of beef atop a medley of yukon gold mashed potatoes, and baby carrots under a plum wine demi-glace, crispy shallots and pickled ginger. Freakin' awazing!

Their Dry-Aged Bone-In Pork Chop or Joyce Farms Half Chicken are just two of a half dozen gluten free options. Maybe kick start your meal with southern panache and savor a bowl of Lowcountry Crab Soup or a serving of Fried Green Tomatoes topped with pimento cheese and a side of tangy bacon rémoulade (mayo based sauce). Absolutely the best way to arouse the tastebuds!

Poured by the glass and by the bottle, Alexander's wine list is among the islands most exclusive, https://www.alexandersrestaurant.com/wine-menu carrying fruit of the vine from regions around the world. Whether it's an old school red Louis Jadot Santenay Clos de Malte from France, Spain's A Veira Do Mar Albariño white, or Taylor Fladgate 30 Year Old Tawny Port, a Portuguese dessert wine, Alexander's has vino to complement every entrée from start to finish. Visiting HHI mid month, check out Alexander's third Thursday wine dinners.

Bestowed both the Diners' Choice for Best Seafood in South Carolina and the Wine Spectator Award of Excellence for 2026, Alexander's is exceptionally 'RUDE' without being over the 'TOP', meaning it's a 'Really Upscale Dining Experience' that's not 'Too Overly Pretentious'. Whether it's a couple's romantic date night or cause for celebration, Alexander's is not only the perfect host site, but will provide memories for years to come. For impeccable service combined with top notch food & drink begin here at https://www.alexandersrestaurant.com/wine-menu

If you're visiting from NY, NJ, or Chicago and craving old school Italian food, than make your way to Coastal Capri (841 William Hilton Pkwy) where Chef Johnny Rovito carries on the family tradition of serving up authentic entrées inspired by Italy's rich heritage. 

Enjoy over a dozen time honored Pasta Di Casa (home-made pasta) dishes alongside veal, pollo (chicken), and perfectly seasoned seafood plates. Awarded the Lowcountry's Best in 2025, Coastal Capri received a Gold for Best Italian Restaurant and Silver for both Best Fine Dining and Best All-Around Restaurant.

While the food is off the charts amazing, they pair their dishes with equally compelling wines and signature cocktails. Savor Italian vinos and select martinis while dining on Pappadella Bolognese (flat, ribbon-like egg pasta) under beef ragu (slow cooked meat sauce). Magnifico! Even their dining room screams traditional Italian. For an unforgettable Italian meal visit Coastal Capri at https://coastalcapri.com/

Sonesta Resort is literally 10 minutes away from Shelter Cove Towne Center, offering ten very different dining options. If you're just out browsing their retail shops and develop a sweet tooth then Crumbl Cookies or Kilwin's Ice Cream & made-in-store confections might satisfy. Shelter Cove Towne Centre has almost everything you need including local specialty shops and a supermarket. For a full list begin here at https://www.sheltercovetownecentre.com/

Want to step back in time, then plan to dine at Chophouse 119, where the ambiance, decor, and exemplary table service resembles a 1950's era New York City supper club, with songs of Frank Sinatra and his fellow crooners playing softly in the background.

Since opening at Shelter Cove in 2022, Chophouse 119 have become the go to destination for prime steaks sourced from the finest meat purveyors, served up alongside extensive wines from around the globe, as well as distinct signature cocktails. Begin your culinary journey to yesteryear at https://www.chophouse119.com/

Seasonal Happenings On HHI:

Traditionally held in late October, the annual Hilton Head Island Concours d’Elegance & Motoring Festival at the Port Royal Golf Club celebrates classic collector vehicles, luxury experiences, and automotive art. Widely recognized as South Carolina’s premier Concours d’Elegance, the weekend attracts enthusiasts, collectors, and travelers from across the country. 

The kick off event includes the Flights & Fancy Aero Expo showcasing vintage and exotic aircraft at the Hilton Head Island Airport. Set against the beauty of the Lowcountry and featuring over 500 rare and classic machines including antique automobiles, motorcycles, boats, and historic aircraft, this is where beauty and excellence becomes personal. Combining automotive perfection with southern hospitality. Start your engine at https://www.hhiconcours.com/

If your travels bring you to HHI anytime around mid November the Sea Turtle Patrol light up the island during their annual Lantern Parade! Established for acclaimed lantern artist Chantelle Rytter the parade showcases hundreds of colorful lanterns crafted by residents, visitors, school groups, and local organizations. 

This casual, family-friendly outdoor gathering illuminates the beach with creative handmade lanterns. Festivities kick off around 3pm at Alder Lane Beach and include food trucks and live entertainment and bands. For more on this beloved seasonal attraction visit the city's website at https://culturehhi.org/portfolio/2026-hilton-head-island-lantern-parade/

If you're a seafood lover and a connoisseur of the arts, than perhaps it's best to schedule your stay on HHI around mid October when neighboring Bluffton host their Historic Bluffton Arts & Seafood Festival. For more than two decades the annual event showcases locally harvested seafood and Lowcountry cuisine as well embracing the community's rich history and culture.

The nine day festival culminates on a Saturday with a Street Fest, featuring over 100 artists displaying their handy-work combined with a culinary delights from area vendors, live music, and entertainment. To learn more about the festival and daily events visit https://blufftonartsandseafoodfestival.org/

For those who fancy symphony and jazz music, under Music Director John Morris Russell the Hilton Head Symphony Orchestra perfom regularly during the fall and holiday season. All concerts are at First Presbyterian Church 540 William Hilton Parkway on HHI. For specific shows and guest artists visit the series page at https://www.hhso.org/orchestra-series-2026-2027/

A Definite Bucket List Item:

Looking for something different to do. Do you love comedy and magic? If so, you don't have to look any further than Comedy Magic Cabaret at 843 William Hilton Pkwy. Owned and operated by veteran entertainers Kerry Pollock and his lovely wife Kelly, the couple have been wowing islanders since 2013, with their 'funny, not filthy' brand of comedy and magic. 

Having spent the better part of 30 years working in Vegas, Reno, Maui, and on cruise ships, Kerry knows how to captivate a crowd, and has found a permanent home and audience for his style of entertainment on HHI. When he's not acting as the headliner, Comedy Magic Cabaret plays host to seasoned stand-up comedians, with Kerry as the evening's emcee, with Kelly as the gracious 'hostess with the mostest'.

For those who appreciate clean comedy, similar to the very popular 'dry bar' comedy specials, Comedy Magic Cabaret is a welcome club, with many of Kerry's guest comics coming courtesy of Gutfeld!, the number one late night show on the Fox News Network. Kerry has hosted the likes of Joe DeVito, Jamie Lissoe, and Michael Loftus. In February of 2027 Joe Machi will make his first appearance at the club.

Enjoy handheld delights alongside specialty cocktails, beer, wine, and dessert coffees while laughing uncontrollably for two hours non-stop at Comedy Magic Cabaret. On select nights Kerry performs close-up magic in the club's hidden parlor. Illusions and jocularity begin at https://www.comedymagiccabaret.com/

Parting Shots:

An island destination since 1955, Coligny Plaza is home to 60 specialty stores, including a mix of apparel, accessories, and gift shops, as well as 20 different casual food & beverage locales. The Carolina Tasting Room pours up a variety of local craft beers and wine.

Open 7am-4pm, Sweet Al's is Hilton Head's beachside breakfast and brunch go to place serving NJ bagel, pastries, and sandwiches alongside bold coffee and dreamy espressos. Likewise Carolina Coffee & Crumbs offers up fresh brewed coffee, homemade pastries, omelets, sandwiches, and paninis, as well as beer, wine, and cocktails until 3pm daily.

Maybe don't leave the plaza without eating at Slowcountry BBQ & Grill where patrons dine on slow-smoked BBQ and hand-pattied burgers couples with southern sides.

The ladies might find a cute casual dress or beachwear at Island Girl Boutique, Tropical Styles, or Spartina. If you're feeling patriotic and love to support shops that give back to local charities, perhaps drop in Nine Line Apparel. Another 15 shops selling Christmas decor, high-end sunglasses, collectibles, and trinkets for kids of all ages.

Featuring weekly events and nightly entertainment throughout the fall Coligny Plaza is just minutes from the beach and Sonesta Resort. Shop Hilton Head's downtown area here first at https://colignyplaza.com/

The beauty of vacationing on Hilton Head Island during the fall is accessibility. The resort town boasts just under a 40K for year round population. However, during the summer months it increases to four times that number on any given day, which can make it hard to get reservations at several of the preferred spots.

Although HHI is home to many affluent people, when it comes to vacationing with its mix of outdoor recreation, accessible public beaches, and varied resort communities 'America's favorite island' welcomes travelers from all backgrounds and budgets. To learn more about Hilton Head Island check out their visitor's page at https://www.hiltonheadisland.org/