Hilton Head, SC Road Trips

Hilton Head Island was first occupied by Native Americans, with Europeans first making contact in 1521. In 1663, Captain William Hilton came to the island and named it for himself, "Hilton's Head". The island was later settled, and activity on the island primarily consisted of farming, with the island serving as a base of operations for the Union blockade of the Confederacy. After the war, ex-slaves flocked to the island to work on plantations, with this legacy most prominent in the naming of communities on the island, which are known as plantations (though this naming convention is controversial given the ties the word "plantation" has with slavery). The first resort development occurred in 1956 with the development of Sea Pines Resort, with additional development coming over the following decades. Hilton Head Island remains a popular resort destination, and now boasts several resorts and other tourist accommodation. Hilton Head Island website

1 Harbour Town. Visit to see how the upper class lives. Admire the multi-million dollar yachts in many different marinas and sailing in the Atlantic Ocean. (updated Sep 2025) Jenkins Island. Right between the bridges from Bluffton to Hilton Head Island. Shelter Cove. The Island's largest deepwater marina. During the summer enjoy live music and weekly fireworks.

Biking. The Hilton Head Island area offers over 25 crossing bike paths, and many shops rent bikes. Palmetto Dunes Tennis Center. Regarded as one of the best in “The 50 Greatest U.S. Tennis Resorts” by Tennis Magazine, this resort offers 25 courts, instructional programs, and tournaments. Beaches - Nearly 9 miles of Atlantic Ocean surf and beautiful beaches, all publicly accessible. There are several public parks that provide beach access. From there, you can walk or bike the length of the island. Recommended spots are South Beach, Disney's Hilton Head Island Resort area. Golf courses - There are almost too many to count. Among the best: 1 Harbour Town Golf Links. While it has one of the most expensive greens fees in the Hilton Head area, here you can play the same course as the pros, as Harbour Town hosts the Verizon Heritage golf tournament every April. Among the best public golf courses is Hilton Head National in Bluffton one mile from the bridge to Hilton Head. Greens fees and rates are very affordable for all. (updated Sep 2025) George Fazio Golf Course. Designed by the revered golf designer, George Fazio, this 18-hole course is the only par-70 course on Hilton Head Island. Arthur Hills Golf Course. Ranked 4.5 by Fodor’s Golf Digest, this course takes advantage of the natural beauty of Hilton Head Island’s marshland and ocean surroundings. Robert Trent Jones Course. Golfweek readers regard this course as one of the best in the region. This course was named 2003 Golf Course of the Year by South Carolina Board of Directors of the NGCOA.

Ask some service employees for their recommendations for great Hilton Head restaurants. Well-known or busy does not necessarily mean good food. Coupons and menus are available in local tourism magazines. To get started: HH Prime, 23 Ocean Lane (in Omni Hilton Head Oceanfront Resort at Palmetto Dunes), ☏ +1 843-842-8000. Provides beachside dining with culinary flair including USDA Prime Grade beef selections and fresh seafood along with decadent dessert creations, serving up classics like New York Strip to a savory Filet. For a lighter fare, enjoy island seafood. The grand interior and exterior fireplaces, dinner hour music, and the island's ultimate wine room, offering the island's largest collection -- more than 100 selections. Kenny B's, 70 Pope Avenue Suite A, ☏ +1 843 785-3315. New Orleans-style cuisine. Great for lunch. (updated Sep 2022) Amigos Cafe Y Cantina, 70 Pope Ave Suite I, ☏ +1 843 785-8226. Great burritos and BBQ Grilled Chicken salad. (updated Sep 2022) Santa Fe Cafe, 807 William Hilton Pkwy #700, ☏ +1 843 785-3838. Mexican/American. Nice lunch combos. Try the Painted Desert Soup. If you're feeling flush (and haven't eaten for two days), the Cowboy cut rib of Aberdeen Angus beef takes some beating. (updated Sep 2022) British Open Pub, 1000 William Hilton Pkwy D3, ☏ +1 843 686-6736. Excellent overall menu. (updated Sep 2022) The Sea Shack, 6 Executive Park Rd, ☏ +1 843 785-2464. Tasty seafood, cheap prices. Arrive early. (updated Sep 2022) Palmetto Bay Sunrise Cafe, 86 Helmsman Way, ☏ +1 843 686-3232. Great breakfasts.

Frosty Frog, Coligny Plaza, ☏ +1 843-686-FROG (3764). Frozen drinks. 1 Tiki Hut, 1 S Forest Beach Dr, ☏ +1 843-785-5126. "Barefoot" bar at a resort offering sand volleyball, beach lounge chairs & live music. Located on Coligny beach and is the only bar on the beach on Hilton Head Island. The only contact for email is via the Facebook page for the bar. (updated Apr 2026)

Being such a popular vacation destination, Hilton Head has many lodging choices. There are several hotels on the island, however a great and widespread accommodation alternative is the vacation rental. Vacation rentals are available in many types, from large condo buildings to quaint homes, new and old. Holiday Inn Express Hilton Head Island, 2 Tanglewood Drive, ☏ +1 843-842-6662, fax: +1 843-842-6664. Check-in: 4PM, check-out: 11AM. This hotel sits on six acres of wooded land and is surrounded by three lagoons. Sonesta Resort Hilton Head Island, 130 Shipyard Dr, ☏ +1 843-842-2400. (updated Nov 2021) Omni Hilton Head Oceanfront Resort, 23 Ocean Ln, ☏ +1 843-842-8000. The hotel has 324 rooms with full mini-kitchens. Two in-resort restaurants. (updated May 2019) Palmetto Dunes Oceanfront Resort, toll-free: +1-866-380-1778. A family-friendly oceanfront resort featuring private home and villa rentals, and offering three public championship golf courses, 25 tennis courts, and various outdoor activities. 1 The Sea Pines Resort, 32 Greenwood Dr, toll-free: +1-866-561-8802. Check-in: 4PM, check-out: 11AM. Check out the gators! Seasonal rates, approximately $200-300/night. 2 Hilton Head Marriott Resort & Spa, One Hotel Circle, ☏ +1 843-686-8400. Check-in: 4PM, check-out: 11AM. Full-service resort with updated guest rooms, luxury spa, and 3 golf courses. (updated Dec 2015) Resort Rentals of Hilton Head Island by Vacasa, 32 Palmetto Bay Road, Suite 1-B, ☏ +1 843-686-6008, toll-free: +1-800-845-7017. Homes and villas, from 1 to 9 bedrooms.

US Route 278 is the only road on and off the island. An interchange with Interstate 95 is along US 278 about 40 minutes west of the island. Between the island and I-95, US 278 intersects with South Carolina Route 170, which provides access to and from Beaufort and Savannah. Traffic onto the island can be particularly heavy on the weekend, when many arrive to and leave the island, so consider arriving and leaving on weekdays if you'd like to avoid the heaviest of traffic. Hilton Head Island is served by two airports. 1 Hilton Head Island Airport (HHH IATA). The only airport on the island. American Airlines operates flights from Charlotte and Atlanta year round. A majority of the airport's operations are still general aviation. Savannah/Hilton Head International Airport (SAV IATA) is about an hour away from the island and served by seven airlines. The airport is directly connected to Interstate 95. Air taxi and air charter companies such as Jetset Charter fly a variety of private charter aircraft, such as pistons and turbo props, for small groups and individuals into Hilton Head Island Airport (KHXD). Generally, private jet aircraft must fly into Savannah/Hilton Head Int'l (KSAV). The nearest Amtrak stations are in Savannah and Yemassee.

Once entering the island, US 278 becomes known as the William Hilton Parkway. After traveling about a mile on the island, the road splits in two. William Hilton Parkway continues as US 278 Business, a surface road around the eastern end of the island. US 278 Business is a four-lane divided highway, but most businesses on the island are along the road, making for a slow, 25- to 30-minute drive to the southern end of the island. US 278 branches off onto the Cross Island Parkway, a grade-separated expressway. While the Cross Island Parkway is no longer a toll road; you can drive the entire length of the Parkway for free. The parkway reduces the journey from the split to the south end of the island to five minutes. US 278 and US 278 Business terminate at the Sea Pines Circle at the south end of the island. From this circle, cars can continue south on Greenwood Drive to enter the gated Sea Pines plantation, or east on Pope Avenue to head towards Coligny Beach, the major public beach on the island. Hilton Head is quite cycling-friendly. All main roads and most major roads in the resort plantations have a companion bicycle path, and there are a few miles of paths that cut their own trail away from the roads. Although not lit for night riding, they are the perfect way to traverse the island during the day time hours. Bicycle rental stores are plentiful, although they may be expensive. Some golf courses may open up their cart paths to bicycles during non-playing hours (in the morning and at night), but other than this it is generally not a good idea to stray off the paths.