For the 50+ Traveler

Live oaks dripping with gracefully draped Spanish moss mingle with tropical palm trees to line-wide parkways tastefully hiding the shops, restaurants, and golf courses. Finely manicured gardens mark the entrances to gracious plantations that house all the amenities any visitor could desire.

As you pass over the J. Wilton Graves Bridge that rises about the intracoastal highway, you can feel the relaxing island vibe switch on your vacation mode.

Note: Some information in this piece was obtained during a sponsored press trip, but all recommendations are my own.

Things To Do On Hilton Head Island

Hilton Head Island is synonymous with golf, and there are plenty of golf options available for golf fanatics. There are plenty of fun options when you are off the links, too. The wide sandy beaches, the beautiful scenery, unique shopping opportunities, and a wide selection of dining options round out your getaway stay.

Oyster Reef Golf Club on Hilton Head island.

Golf, Golf, And More Golf

The Heritage Golf Collection on Hilton Head Island features three prestigious golf clubs: Port Royal Golf and Racquet Club, Oyster Reef Golf Club, and Shipyard Golf Club. Offering 81 holes of golf, there are play options for the beginner to the avid golfer. The Heritage Golf Collection offers a selection of golf packages giving you the freedom to kick back and enjoy your golf getaway.

Port Royal Golf and Racquet Club is home to two spectacular golf courses, Robber’s Row and Barony. The courses are quintessentially Southern. The Robber’s Row course is a challenging course where the holes are hemmed in by stands of Magnolia trees and live oaks dripping with airy Spanish moss. Each hole gives you the feeling of being on your own private course. The small greens and tree-lined fairways prove challenging and will require you to straighten out your slice. The Barony Course will challenge your short game. Approaching the greens surrounded by multiple bunkers requires concentration and shot control to make par.

Oyster Reef Golf Club is on Hilton Head Plantation and is a classic course with wide fairways and large greens. The holes vary between hemmed in and wide open, providing a nice variety. When you round the turn to the 6th hole, you are treated to the most gorgeous view, a reachable par-3 with Port Royal Sound providing the backdrop to the green.

The Shipyard Golf Club offers three excellent courses to challenge your golf game: the Clipper Course, the Galleon Course, and the Brigantine Course. Each 9-hole course is designed to provide gorgeous views to enhance your vacation vibe and challenging holes to test your golf prowess. You can play 9, 18, or 27 holes at Shipyard to satisfy your daily golf enjoyment.

One of the many beaches on Hilton Head island.

Hit The Beach Or The Pool

Grab a towel, lounger, and a good book; relaxing by the pool is a perfect vacation pastime. The South Carolina sun does not disappoint, and most resorts on Hilton Head offer several pool options within a short distance from your rental villa.

However, the 13 miles of Hilton Head beaches are expansive, with soft sand and warm water. Hilton Head beaches include Coligny, Driessen, Folly Field, Alder Lane, Burkes, Fish Haul, Mitchelville, and Islander. Public parking is available at most beaches, and many are wheelchair accessible. Most of the beaches have seasonal lifeguards and designated swimming areas.

Aerial view of Harbour Town on Hilton Head island.

Visit Harbour Town

Beautiful Harbour Town on Hilton Head Island overlooks a snug, picturesque harbor with views of Daufuskie Island and the surrounding area. Stroll along the pier and admire the stunning yachts docked in the harbor. You can climb the lighthouse for a spectacular view. Grab a cocktail to-go and find a seat with a view.

To visit Harbour Town you need to pass through the gate at Sea Pines Resort, a stunning resort community. There is a fee to enter the resort.

Vagabond's Shrimp Trawling Expedition on Hilton Head.

Take A Tour

There are multiple tour options available to explore the island and surrounding area. Whether your interest is food, sea life, or adventure, there is a Hilton Head tour for you.

If you love sampling fun food and finding local restaurants try the Coligny Beach Walking Food Tour. This mid-morning tour visits establishments in the Coligny Beach Plaza, where you can explore fresh, expertly prepared island cuisine.

Vagabond Cruise offers a selection of wonderful cruises. Their 1.5-hour Ocean Dolphin Cruise and Sunset Dolphin Cruise are exciting expeditions where you search for playful dolphins. A dolphin cruise is a fun and exciting way to spend a few hours out on the water. As you pass through Calibogue Sound, you may spot pelicans, egrets, herons, cormorants, and other waterfowl while you are hunting for dolphins.

The Carolina shores are known for the sweet, succulent shrimp. Hop aboard Vagabond’s Shrimp Trawling Expedition. Become part of the fishing crew as you search for a hefty day’s catch. At the end of your 2-hour shift, head home with some of the freshest shrimp you will ever cook for dinner.

A bike path on Hilton Head island.

Ride A Bike

There are over 80 miles of mostly flat biking paths; it is an easy and efficient way to get around. The bike paths meander through plantations and alongside main roads for a pleasurable get-around-town.

Most villa rentals come with cruiser bikes. If you need to rent, Hilton Head Outfitters offers a selection of bike options, including cruisers, tandem, tag-a-longs, adult 3-wheelers, and geared bikes.

Daufuskie Island near Hilton Head island.

Daufuskie Island

Pat Conroy’s The Water Is Wide: A Memoir is about Conroy’s time teaching on Daufuskie Island. There is still not much on the island, but it is a popular spot to visit, and there are some overnight accommodations. It can only be reached by boat, and there are several options available. Once on the island, renting a golf cart or riding your bike to get around is the easiest mode of transportation. The Daufuskie Ferry will get you to the island and is a good resource for golf cart rentals.

The Skull Creek Boathouse on Hilton Head.

Best Restaurants On Hilton Head

From hands-on low country boils to fine dining cuisine, the variety of independent restaurants on Hilton Head Island offers you a wide variety of choices to suit your needs and culinary desires.

Skull Creek Boathouse

Skull Creek Boathouse is more than just a waterfront restaurant. They offer expertly prepared classic Southern dishes. The menu offerings include sushi, ceviche, nigiri, and other raw dishes that transition seamlessly into southern specialties. Skull Creek Boathouse is the perfect spot to try a Lowcountry Boil, Carolina Shrimp and Grits, or Blackened Carolina Classic Catfish. Make sure to order the Green Tomatoes with shrimp, goat cheese, and 5-pepper jelly; they are spectacular.

Ombra Cucina Italiana

Ombra Cucina Italiana is a top fine dining choice on Hilton Head Island. Tucked away in the corner of a shopping mall, the restaurant offers indoor and outdoor seating, white tablecloths, expertly trained service staff, and classic Italian dishes. Begin with a Prosecco and Prosciutto di Parma with arugula and shaved Parmigiano. Follow with Tagliatelle alla Bolognese, homemade spinach tagliatelle with a classic meat sauce. For an entree, you can’t go wrong with their Filetto di Manzo, a filet mignonette wrapped in prosciutto, Gorgonzola butter, and a Barolo wine sauce. Mangiare!

Enjoy their early bird, prix fixe menu option, a great dining value.

Tio’s Latin American Kitchen

Tio’s Latin American Kitchen is a fun dining adventure and a great take-away option for the nights you want to eat in. Offering classic tacos, fajitas, quesadillas, burritos, and chimichangas, Tio’s has a taste sensation for the spice adventurers and mild seasoning lovers alike. Create your own tapas-style meal by ordering several appetizers. Try the Poblano Pepper Poppers with cotija cheese and cilantro lime sauce, the Tostones -- twice-fried plantains with a delicious house sauce -- and Camarones -- coastal shrimp in a spicy garlic sauce with toasted Cuban bread.

A seafood bowl from Fish on Hilton Head island.


Fish is a casual spot in the Coligny Plaza offering great food and entertainment most nights. Their classic Coconut Shrimp with Chili Mango Sauce paired with Bowl O’ Puppies (hush puppies with honey butter) are perfectly washed down with your favorite libation. Fish’s patio is a fun place to meet up with friends for a casual night out.

Where To Shop On Hilton Head Island

Hilton Head Island is a shoppers paradise. High-end outlet stores and unique local shops line the main streets and back roads, just waiting to be discovered.

Coligny Plaza functions as Hilton Head’s downtown area. Offering a selection of restaurants, cute specialty shops, and grocers, Coligny Plaza is a maze of nooks and crannies with a fun surprise around each corner.

The Tanger Outlets brings all the name brand outlet shopping to the island. If you love classic brands with a discounted price tag, Tanger Outlets is the place to shop.

Best Accommodations On Hilton Head Island

There are multiple options available for your Hilton Head Island stays. The most popular way to visit is a private villa rental, particularly if you plan to golf at the villa’s course.

The Hilton Head Island destination website outlines a variety of villa, hotel, and resort options.

Pro Tip

During the season, golf courses, restaurants, and tours book up quickly. If you want to experience the best of Hilton Head, book some or all of your excursions or golf packages before you arrive.

Hilton Head Island isn’t the only beautiful stretch of shoreline in South Carolina. Kiawah and Myrtle Beach are both worth a visit as well!