Hilton Head, South Carolina, is a special island where the Tree Lady is the most important person in town — and visitors have it made in the shade.

When the air turns crisp and carries the scent of burning leaves, I turn my attention to the coming winter and begin planning an escape to a warm place full of possibilities. Without fail, Hilton Head Island makes my short list. I consult my criteria. Mild weather? Beautiful beaches? Outdoor sports to cure cabin fever? Check, check, and check.

And then there are the intangibles that make the island stand out: Southern hospitality, rich cultural heritage, and — most important of all — an extraordinary commitment to nature over commerce. While some beach destinations are blemished by high-rise buildings blocking views of the sea, Hilton Head is different. Charles Fraser, an environmentalist who envisioned a community that harmonized with its surroundings, set the standard in the 1950s when he built Sea Pines Plantation, a resort and golf community spanning 5,000 acres. Nearly 60 years later, Hilton Head remains true to Fraser’s mission: No buildings are more than five stories high, and trees rule. Locals joke that the Tree Lady — the woman at town hall who decides which trees can be cut down — is one of the most powerful people on the island.

This doesn’t mean that progress is stifled; it’s just made carefully. The area is home to 24 renowned golf courses, more than 200 restaurants, and countless shops, but you’ll find many businesses tucked back from the street in the shade of the ubiquitous trees.

Deep Roots

The landscape is an undeniable draw for vacationers, but a curious traveler also learns to see the forest and the trees. Explore the 5-by-12-mile barrier island, and you’ll experience an area steeped in Lowcountry culture. Indeed, all along this part of the South Carolina coast, you’ll find distinct art, food, and agriculture, thanks in large part to the Gullah community. The Gullah people are descendants of African slaves who came from Angola and Sierra Leone. Following the abolition of slavery in 1865 — and, ultimately, the demise of Hilton Head’s rice and cotton plantations — the Gullahs eked out livings as hunters, fishermen, and farmers, while retaining the traditions of their ancestors’ homelands.

Today, despite encroaching development along the southeastern seaboard and a shift to tourist-driven industries, the Gullahs have steadfastly preserved their customs, language, stories, and art forms. Around Hilton Head, you’ll still find Gullahs engaged in timeless traditions like basket weaving, quilting, and wood carving. However, for a true taste of their island contributions, I suggest you start with dinner.

Garden of Delights

Zesty dishes blending rice with greens, okra, and a gumbo of fish, tomatoes, and peppers are trademarks of Gullah cooking. Lowcountry specialties, such as shrimp and grits, she-crab soup, and Frogmore stew (shrimp and sausage with corn, potatoes, and other vegetables, all steamed in a big pot) display Gullah hallmarks. Vegetables and flavorings tend to be whatever is homegrown and in season.

There’s no lack of well-known chefs around the island as well. Orchid Paulmeier, a past finalist on the show Food Network Star, features family-friendly barbecue at her One Hot Mama’s American Grille. Wash down your plate of ribs with a refreshing Arnold Palmer, a favorite Southern beverage blending lemonade and sweet tea.

Fresh seafood takes top billing on many of the island’s restaurant menus. Hudson’s Seafood House on the Docks, serving shrimp right off the boat, is one of my favorites. The owners, Brian and Gloria Carmines, support sustainable fishing practices and most of their catch comes from local waters.

As good as Hudson’s is, I find that the most satisfying Lowcountry meals can be prepared right in your resort’s kitchen. Swing by a local fish market, gather local greens, and add rice and simple seasonings such as ground bay leaf, paprika, oregano, garlic, and pepper. Voilà — you have the perfect family dinner.

Family Tree

Come daytime, when temperatures can reach the low 60s, it won’t be hard to shuffle your clan for some outdoor fun. It’s also seasonable enough for water sports such as canoeing, kayaking, paddleboarding, and sailing. Or let a boat captain do the steering on a guided tour. More than 200 Atlantic bottlenose dolphins live here year-round, and some tour guides can spot a few by name and personality.

You’ll also find more than 300 tennis courts with every surface, including grass. Biking is more than a casual pursuit; many families never touch their cars until it’s time to go home. Over 100 miles of trails make it possible to cover the entire island on two wheels, and you can also ride on the firm sand right on the water’s edge.

Glorious Greens

Only the golf cart rivals the bicycle in popularity here. There are more than 20 world-class courses in the area — all but four are open to the public — and most encourage beginning golfers.

It was Charles Fraser who introduced the sport to the island, incorporating the Ocean Course (a George Cobb–designed layout later renovated by Mark McCumber) into the real estate plan for Sea Pines. Today the enclave is home to four courses, and hosts the PGA Tour’s RBC Heritage, established in 1969.

Two other notable courses are Harbour Town Golf Links (created in the late 1960s by Pete Dye and Jack Nicklaus), and Palmetto Dunes Oceanfront Resort (home to layouts by Arthur Hills, George Fazio, and Robert Trent Jones Sr.). Harbour Town boasts huge waste bunkers, narrow fairways, small greens, and the railroad ties that would become Dye’s signature. The backdrop of the challenging par-4 18th hole is the iconic candy-striped lighthouse overlooking Calibogue Sound and the Harbour Town Yacht Basin. Fazio’s Dunes design is heavily bunkered throughout, while Hills’ intimidation factors include elevation changes and carries over wetlands. The Jones course is a family-friendly option (it offers junior tees and lessons), and is known for its scenic 10th green overlooking the ocean.

Trunk Show

If art collecting or souvenir shopping is your preferred choice of exercise, Hilton Head’s extensive offerings will test your endurance. The island is home to numerous galleries, and many artists are full-time residents. One of the best-known is Walter Palmer, famous for his unusual and highly amusing bird sculptures. His commissions can be seen all over the island, as well as other parts of the U.S. and abroad.

Sculptures, paintings, and photos make wonderful keepsakes, but the most coveted item is a Gullah sweetgrass basket — pricey, but unique. The skills have been handed down through generations, and families have signature weaves that distinguish their work. The pride in work and environmental stewardship expressed by artisans and storekeepers is shared by the greater community, from the Tree Lady and farmers to the local chefs and fishermen. And it’s threaded through the tenacious legacy of the Gullah families who like to say “you’re either a bin yah (a Lowcountry native) or a come yah (a visitor or resident who originated elsewhere).” I’m content to be a come yah, because I know that the next time I return, there will always be trails, links, and galleries I’ve yet to discover. But the things I treasure most about Hilton Head — its sweeping shoreline and verdant landscapes — are almost certain to stay the same.