You can fly into Hilton Head Island Airport from Charlotte, North Carolina, via U.S. Airways Express, but more likely you'll drive the forty-five minutes up I-95 from Savannah/Hilton Head International Airport. The island itself is shaped like a foot, and it's an easy place to navigate during the day, with most everything connecting to two main roads, William Hilton Parkway (Highway 278) and the Cross Island Parkway. But at night the paucity of streetlights (a local ordinance to allow for better stargazing) can make road signs quite difficult to see.
The twelve miles of beaches are a lovely place to start, and boaters could hardly find a nicer spot to cast about. The Harbour Town Yacht Basin (843-671-2704) offers fishing charters, cruising and sailing.
Your credit card can get a nice workout at Hilton Head Factory Stores 1 & 2 (shophiltonhead.com), found just off the island and with a wide range of stores. Fans of golf art should seek either counseling or the Linda Hartough Gallery (843-671-6500) in Harbour Town, where you'll find "golf landscapes" from one of the game's preeminent artists.
There are plenty of loftier pursuits within an hour of Hilton Head. You can check out historic Beaufort and its antebellum homes, tour the unspoiled beauty of Daufuskie Island with Outside Hilton Head (800-686-6996; also the place for outdoor enthusiasts), or take in all the charms of America's charm capital, Savannah, Georgia. You can even get there by boat on the Spirit of Harbour Town (843-842-7179).
There's something on Hilton Head in every style and price range. Marriott alone has eleven properties on the island (talk about being all over it), with a strong supply of family-friendly suites, cottages and villas.
DAUFUSKIE ISLAND RESORT & SPA Avenue of the Oaks, Daufuskie Island; 800-648-6778, daufuskieresort.com. Rooms: $89-$255. Cottages: $199-$499.
One nautical mile by private passenger ferry from Hilton Head and the setting for Pat Conroy's The Water Is Wide, Daufuskie Island Resort is the getaway from the getaway. The elegant antebellum inn has fifty-two rooms, all overlooking the Atlantic, as well as the brand-new Breathe Spa, with eight treatment rooms and so many spa services to choose from you may get stressed out trying to decide.
DISNEY'S HILTON HEAD ISLAND RESORT 22 Harbourside Lane; 407-934-7639, disneyvacationclub.com. Studios: $105-$275. Villas: $150-$710.
No, there are no Mickey Mouse courses to be found on this property, a rustic compound of Goofy fun set on a fifteen-acre island. What you will find are the three Palmetto Dunes courses just down the street, as well as a healthy dollop of family-oriented amusements centered around the 13,000-square-foot beach house.
HILTON OCEANFRONT RESORT 23 Ocean Lane; 800-845-8001, hiltonheadhilton.com. Studios: $99-$275; One-Bedrooms: $199-$499.
Located in Palmetto Dunes, this beachfront resort offers 303 studio suites and twenty oceanfront one-bedroom suites, all of which have minikitchens and balconies. Two pools are available for those who can't drag themselves the additional few feet to the private beach access. There's live entertainment five nights a week in the Regatta Lounge, which a fifty-something playing partner swore to me was "hopping with ladies, mostly my age, but still."
THE INN AT HARBOUR TOWN One Lighthouse Lane; 800-732-7463, seapines.com. Rooms: $146-$295.
The rather bland cream exterior of this sixty-room inn set adjacent to the golf links quickly gives way to an intimate, comfortable interior. There is a butler on call at all times whose duties range from recommendations to reservations; activities include tennis at the Sea Pines Racquet Club, whose twenty-three clay courts helped the resort garner the status of Tennis Magazine's number-two American tennis resort.
MARRIOTT'S HERITAGE CLUB AT HARBOUR TOWN & MARRIOTT'S HARBOUR CLUB 1044 William Hilton Parkway; 800-228-9290, vacationclub.com. Villas: $190-$330 (Heritage); $140-$280 (Harbour).
These get the nod among the island's copious Marriotts for their intimacy (there are only seventy villas) and proximity to the Calibogue Sound and Harbour Town (obviating the need for on-site restaurants). Each of their big two-bedroom-two-bath villas has all the goodies and gizmos you could want, from whirlpool tubs to balcony patios.
More than 200 eateries offer enough seafood to remind you you're on vacation, but there's ample cuisine for those who like meals to have legs.
CHARLEY'S CRAB (Seafood) Two Hudson Road; 843-342-9066. $$$
Sophisticated dining in a relaxed waterfront setting where the voices rarely rise above a contented murmur. Follow the waiter's tip and focus on the house specialties: luscious she-crab soup, teeming seafood chowder and truly crabby crab cakes that make Tim "Lumpy" Herron seem merely chubby by comparison.
HAROLD'S DINER (Diner) 641 William Hilton Parkway; 843-842-9292. $
The kind of authentic greasy spoon every golf destination should be required by law to have. You order at the counter from a guy who tells a loudmouth, "If you want to talk, go eat at Barnes & Noble." Someone (okay, me) who forgot to write his name on the bottom of the paper menu on which you check off your selection was asked, "What am I, your mother?" By the way, said menu fails to indicate that the "Big 'H' Burger" is one entire heart-stopping pound of meat.
OLD FORT PUB (Southern) 65 Skull Creek Drive; 843-681-2386. $$$
Generally regarded as the best place in Hilton Head to take a date—even if that date happens to be your spouse—this romantic eatery serves up succulent Southern fare along with more than 250 wines. Panoramic windows afford each diner a view of the spectacular sunsets from the banks of Skull Creek.
SANTA FE CAFE (Southwestern) 700 Plantation Center; 843-785-3838. $$$
Weather permitting, eat on the upstairs patio, where a roaring fireplace cuts the evening chill. The high vaulted ceiling and dark wood inside help create a cozy, clubby atmosphere, and the menu does equally well with the common (the "Outrageous Chimichanga") and the uncommon (wood-roasted quail).
TRUFFLES CAFE (Café) 71 Lighthouse Road; 843-671-6136. $$
There's a pleasant buzz here; Truffles serves the kind of food, including gourmet pizza, pasta and steaks, that you can enjoy and talk through at the same time—it's a nice spot for a postround lunch in particular. The "Chicken New Orleans" is a standout; if eaten for dinner, its thick, spicy cream sauce should preclude the need for breakfast the next morning. More than thirty wines are available by the glass.
TWO ELEVEN PARK WINE BAR & BISTRO (Fusion) 211 Park Plaza; 843-686-5212. $$$
This rollicking upscale bistro has perhaps the island's most bustling bar scene (excluding the nearby "Barmuda Triangle," located outside the gates of Sea Pines). Once you've made it to your table, you'll enjoy a convergence of American, Southern and international influences in dishes like "Rasta Pasta" and "Smothered Shrimp." The sprawling wine list spans 100 by the glass and 300 by the bottle.