History of Hilton Head Island


Situated only 45 minutes from historic Savannah, Hilton Head is the largest of the South Carolina islands stretching 12 miles along the Atlantic Coastline. Hilton Head Island offers the ultimate in Lowcountry island living – miles of unspoiled beaches, nature preserves and biking trails, world-class golf and tennis, upscale shopping and dining, and luxury Lowcountry coastal retreats. 

Hilton Head Island also offers visitors a glimpse into the fascinating history of South Carolina’s Lowcountry, a destination that has survived three wars, multiple hurricanes, and eras of feast, famine – and fame. In 2021, Travel+Leisure ranked Hilton Head #1 in World’s Best Islands but what lies behind the fame of America’s favorite island. Journey with us as we explore the fascinating history behind Hilton Head Island.


2000 BC to 1500 AD

Evidence of life over 4,000 years ago remains on Hilton Head Island today. The well-preserved Native American Indian Shell Ring is located in Sea Pines Preserve and is the oldest known archaeological site on Hilton Head Island, and one of only 50 shell rings known to still exist today. This iconic remnant of Hilton Head Island’s history measures 150 feet in diameter and is one of the most pristine examples of a shell ring remaining in the USA. 

Later, in 1335 A.D, the Native American tribes built a fortified village covering two acres along the banks of Skull Creek. This shell ring is also open to the public on a short and easy trail at the Green’s Shell Enclosure Heritage Preserve. Both these historic shell rings are today listed in the National Register of Historic Places.


1500 to 1700: EARLY EUROPEAN EXPLORERS

Historical records show the first Spanish explorers making contact with local Native Americans in 1521, nearly two hundred years later. In 1566, the Spanish explorers built Santa Elena, a permanent settlement and Fort across the Port Royal Sound on Parris Island. They abandoned Santa Elena in 1587 to colonize further south in St Augustine, Florida. By 1663, the island was largely uninhabited except for a small population of Native Americans living off the land. 

In August 1663, English Captain William Hilton set sail from Barbados to explore land granted to the Lords Proprietors, eight Englishmen to whom King Charles II had granted power of Carolina. His original landing site was the Port Royal Sound and, on gaining first sight of the headlands, he claimed the land for Britain. 

In the spring of 1670, Captain Robert Sandford together with over 150 colonists, servants and slaves sailed into what is today Charleston Harbor claiming the land and naming it Charles Town, in honor of King Charles II. By 1672, the expanding settlement had relocated on a peninsula between the Cooper and Ashley River and …. the rest is history! Today, Charleston ranks as the #1 City in the USA

On 16 August 1698, the Lords Proprietors granted John Bayley of Ireland a barony which included most of Hilton Head Island, excluding Port Royal Sound and Skull Creek. John Bayley never once visited Hilton Head Island, instead appointed Alexander Trench as an agent to sell the property. The bulk of the barony remained in the Bayley family until after the Revolutionary War.


1700 to 1860: HILTON HEAD PLANTATION HISTORY

In 1717, Colonel John Barnwell was granted 1,000 acres of land on the NW corner of the island (now Hilton Head Plantation) and became the first white settler on Hilton Head. There was still hostility between the Spanish and British and, in 1733, the City of Savannah was founded as a barrier between Spanish Florida and British Carolina. 

By the 1750s, most of the plantations on the island were successfully growing indigo, which was being sold to the English – until the Revolutionary War. During the Revolutionary War (1775 to 1783), the British successfully took the city of Savannah (after failing to take Charleston!) and frequently raided the island, burning plantations and capturing slaves. Aside from rice, indigo was South Carolina’s most second valuable export, however trading with England had now ceased. 

It wasn’t until 1790 when William Elliott planted the first crop of Sea Island long-staple cotton that the island once again began to gain recognition. William Elliott teamed up with neighbor Will Seabrook to pioneer a new fertilizer for the cotton crops and the Lowcountry sea islands began to boom. 

The War of 1812 brought more devastation by British forces to the island, but the economy quickly resumed and, by 1860, the cotton industry on the island was lucrative with nearly two dozen working plantations.


1860 to 1940: SLAVERY & THE CIVIL WAR

South Carolina was the first US state to withdraw from the Union in December 1860, and, in April 1861, the Civil War began. After the Battle of Port Royal Sound in November 1861, more than 12,000 soldiers captured Fort Walker and Hilton Head Island fell into the hands of the Federal troops. Hilton Head Island became the headquarters for the blockade of the South Atlantic coast with an estimated forty thousand soldiers, prisoners of war, and former slaves settling on the island. The prospering rice, indigo and cotton plantations were abandoned, yet this victory meant freedom for the African Americans that remained. 

In 1862, Union General Ormsby Mitchel built the town of Mitchelville, the first self-governing town of formerly enslaved African Americans with nearly 1,500 Gullah residents. Land was confiscated, northern missionaries opened one room schools, and homes were built for the former slaves, known locally as “contrabands of war”. 

In 1864, as the troops began to move out of the area, Fort Howell was built to protect the town of Mitchelville. In 1865, the 13th Amendment to abolish slavery was signed and the Gullah community of Mitchelville were legally freed. Many moved on, others stayed on the island farming in the summer, oyster harvesting in the winter, and remaining true to the rich legacy of the Gullah culture. 

Hilton Head Island returned to nature and from the 1900s to 1950s was primarily used as a destination for wealthy private hunting groups. Today, visitors to Hilton Head can walk the quiet trails leading through historic Mitchelville Freedom Park with the original site of Battle of Port Royal, historical remnants of the town and Fort Howell, and access to an off the beaten path beach overlooking the passage taken by Captain William Hilton in 1663. 

The Baynard Plantation, built by Revolutionary War hero Captain Jack Stoney in 1793, was used as the HQ for the Union troops and was later burned to the ground. Visitors to the island today can still tour the ruins of the grand antebellum home and slave quarters on a short hike through Sea Pines Preserve.


1950 to 2000: MODERN AGE OF HILTON HEAD ISLAND

By early 1950, Georgia timberman Fred Hack had discovered the acres of loblolly pine and live oak trees on Hilton Head and, along with JB Fraser and other investors, set up the Hilton Head Company and began to buy up acres of land to harvest lumber. Lumber mills were built and, after harvesting millions of feet of lumber, Hilton Head Company began selling off lots along the beach for vacation cottages.

The modern age of Hilton Head Island began with Charles Fraser, son of J. B Fraser. Charles had a vision to preserve the plantation history and natural beauty of the island and build an eco-friendly, resort community on his family land dominating the southern tip of the island. The first car ferry arrived in 1953, a grocery store opened at Coligny Circle in Forest Beach, and the James F. Byrnes swinging bridge was built in 1956, finally connecting Hilton Head Island to the mainland. 

Fraser’s vision for a world-class resort became a reality and a model for future resort communities across the US. Sea Pines Plantation was a stunning natural oasis with classic Lowcountry architecture and beach homes, untouched forest preserves, 5-miles of sandy beaches, championship golf courses, and the signature candy-cane Harbour Town Lighthouse. Shipyard was the second plantation to be developed on Hilton Head, followed by Port Royal and Palmetto Dunes


EXPERIENCE HILTON HEAD ISLAND’S HISTORY

Harbour Town Lighthouse

Hilton Head Island is home to two lighthouses: The historic Leamington Lighthouse built by Union Troops in 1879 which overlooks the Arthur Hills Golf Course in Palmetto Dunes and the iconic Harbour Town Lighthouse in Sea Pines Plantation, built by Charles Fraser as a fun and memorable landmark and museum dedicated to the history of Hilton Head Island. The 90-ft lighthouse features ten levels of fascinating photos and artifacts, a Coast Guard Exhibit, a one-of-a-kind gift shop and views all the way to Tybee Island!

Coastal Discovery Museum

The Coastal Discovery Museum is situated on the historic Honey Horn plantation, dating back to before the Civil War. The museum is home to nine historical buildings, the Santa Elena Center highlighting the history of 16th century Hilton Head, and 68 acres of beautiful grounds with nature trails, butterfly gardens, and an ancient 500-year old Southern Red Cedar. The Coastal Discovery Museum offers guided history tours of Hilton Head Island, the Forts of Port Royal and the habitats and history of Pinckney Island.

Venture beyond Hilton Head Island to learn more about the history of the Gullah culture on a boat tour of Daufuskie Island or take a cruise of Savannah’s historic port and riverfront.

Local Tip: For traditional Gullah-Geechee cuisine, soulful blues, and warm southern hospitality, stop by Ruby Lee’s situated just across William Hilton Parkway!

Port Royal Golf Club

Tee off for a round of golf at the Robber’s Row Course set atop former civil war grounds with interpretive markers on several holes describing the historic events that took place at Port Royal.

Gullah Heritage Tours

Travel through the communities of Hilton Head Island on a two-hour narrated bus tour with native Gullah residents. The tour is fun, interactive and covers the top historic Gullah attractions on the island including the Gullah Museum, a tiny museum dedicated to preserving the Gullah-Geechee heritage and culture. 


Locally serving Hilton Head since 1993, Sunset Rentals are one of the most experienced vacation rental companies on Hilton Head Island. Our portfolio of 220+ vacation homes and villas are situated in the top resort areas of Hilton Head Island with luxury vacation amenities and a 24/7 guest concierge from our local team. 

Take a tour of the resort areas of Hilton Head Island, browse our collection of luxury rentals (many including bike & beach gear credit valued up to $350!), and book your vacation with confidence and ease with Sunset Rentals.


Top Summer Tours on Hilton Head Island

A summer vacation on Hilton Head Island offers the best of both worlds – serenity and quiet seclusion away from the crowds and action-packed activities and adventures on land, along the Calibogue Sound, and in the warm Atlantic waters, that beckon you to dive right in! 

Hilton Head is “The South’s Best Beach Town” and is consistently ranked the “#1 Island in the US” in the World’s Best Awards. While Hilton Head’s 12-miles of unspoiled, natural beaches and Lowcountry landscapes are the top summer attractions, an abundance of unique experiences await on our small slice of paradise. 

Hilton Head Island was one of the top-booked summer destinations in 2021 so don’t leave your vacation planning to the last minute! Here’s our team’s favorite tours and experiences to add to your summer vacation itinerary on Hilton Head Island.


Dolphin Discovery Tours

Hilton Head Island is rated one of the 10 Best Dolphin Sighting Destinations in North America. The waters surrounding Hilton Head are home to a year-round population of over 170 inquisitive and friendly Atlantic Bottlenose Dolphins cruising the sounds, creeks, Atlantic waters, and strand feeding along the muddy banks.

Experience our favorite locals up close and in the wild on a Dolphin Tour of Hilton Head Island, with chance encounters of manatees, otters, and sea turtles along the way. You’ll find dolphin encounters for every occasion on Hilton Head Island – pirate cruises for the kids, regular cruise boats departing the marinas, or small boats with freedom to follow the pods and engage in intimate encounters with Hilton Head’s dolphin pods in their natural habitat.


Kayak & Paddle Tours of the Waterways

Navigate the hidden creeks and pristine waterways and head off the beaten path on a kayak or SUP tour of Hilton Head. Hilton Head Island boasts 25 miles of back creeks, tidal salt marshes, and serene waterways teeming with wildlife, marine life, and beautiful shore birds. Surrounded only by the sounds of nature, Lowcountry serenity, and your travel tribe, nothing quite matches a Hilton Head eco-adventure along Calibogue Sound.

Get out in nature on a guided eco-tour with Outside Hilton Head, Hilton Head’s outdoor experts. With unique experiences ranging from guided tours with a naturalist and family SUP classes, to full moon kayak tours and fireworks paddles at Shelter Cove, there’s a tour for every traveler.


Boat Tours & Fishing Charters

If paddling your own boat is not your style, hop on a boat tour of Hilton Head Island and let someone else take the helm. Outside Hilton Head offers a wide variety of boat tours, cruises, fishing charters, and family water skiing adventures from Shelter Cove Marina, or head to Harbour Town in Sea Pines Resort Area.  

There are more unique boat tours operating from the Harbour Town Marina. Learn to sail the America’s Cup Stars & Stripes, trawl for shrimp aboard the Tammy Jane, take a sightseeing tour on the Vagabond, or take a luxury cruise on the Spirit of Harbour Town to experience the beauty of the Lowcountry in style.


Birdwatching Tours

With miles of Lowcountry coastal habitats and 300+ species of birds, Hilton Head Island is a prime destination for birding enthusiasts. Top birding destinations on Hilton Head include the Audubon Newhall Preserve, Sea Pines Forest Preserve, Fish Haul Beach Park, Pinckney Island National Wildlife Refuge, and the Coastal Discovery Museum at Honey Horn. 

Birders have miles of trails to explore alone but Hilton Head Island’s birdlife is best experienced under the guide of a local, knowledgeable birdwatcher! The Coastal Discovery Museum offers walking tours of Pinckney Island at the northern tip of Hilton Head. The 4,000 acre preserve lies along the Atlantic Flyway with three unique birding habitats (salt marshes, maritime forests and freshwater lagoons), and an abundance of birdlife including duck, egret, pelicans, ibis, and the iconic Great Blue Heron. 


Hilton Head Bike Tours

Get ready to pedal! Hilton Head Island is a gold level bicycle friendly community with designated bike lanes, more than 60 miles of public trails, and 12-miles of hard-packed beaches to explore by bike. You can literally bike everywhere on Hilton Head Island and Sunset Rentals make it easy to get on the trails with an exclusive bike and beach gear credit program with Vayk Gear and complimentary rentals on select Sunset Rentals.

The Hilton Head Pedego Tour is always a hit with visitors to Hilton Head. Departing from Shelter Cove Plaza, the 2-hour tour cruises the Hilton Head bike trails highlighting the top attractions, history and culture of Hilton Head Island. Join a group tour or book a private bike tour just for the family!


Touring Sea Pines Preserve on Horseback

From the saddle of a Pedego to a western saddle! The 605-acre Sea Pines Forest Preserve is one of the most scenic settings on Hilton Head Island with secluded forests of Palmettos and moss-draped Oaks, lakes and fishing docks, wetland boardwalks, and historic ruins dating back over 4,000 years.

Visitors to Hilton Head can tour this protected wildlife habitat on horseback with Lawton Stables, a local equestrian center and top attraction on Hilton Head Island. Saddle up for a western style trail ride through the preserve (minimum age 8-years) or if you’re visiting Hilton Head Island with kids, the Shetland pony rides and petting zoo are always a hit with the kids.


Nature Tours at The Coastal Discovery Museum

The Coastal Discovery Museum at historic Honey Horn is not only a bird watcher’s paradise, it is a top Hilton Head destination for nature lovers with a museum in an original Hilton Head plantation house, historical landmarks, an interactive Kids Zone, and endless tours, nature programs, and on-site and off-site eco-activities for the whole family to enjoy.  

Guided tours include the marsh critters and creatures of the Lowcountry, the Marsh Tacky horses of Honey Horn, and tours of the historic plantation grounds and butterfly gardens. Coastal Discovery Museum tours extend beyond the Honey Horn plantation with off-site turtle tours, beach discovery tours, boat tours, and guided history tours of Hilton Head Island.


Guided History Tours of Hilton Head Island

Hilton Head Island lies in the Gullah Geechee Corridor, a National Heritage Area recognizing the authentic West African culture, traditions and customs of the South Carolina sea islands. The Gullah culture survived centuries of slavery and today visitors to Hilton Head can embark on a historic adventure with Gullah guides, born and raised on Hilton Head Island.

The Gullah Heritage Trail Tours at the Coastal Discovery Museum is an immersive experience of the Gullah communities on Hilton Head Island, the Gullah language, traditional foods, music, and more. Tour highlights include Gullah family compounds, plantation ruins and First Freedom Village, where freedom began in 1862 for Hilton Head. The Coastal Discovery Museum also offers tours of the Forts of Port Royal, occupied by the union forces during the civil war.


Tours of Daufuskie Island

Touring Daufuskie Island is a bucket-list day trip from Hilton Head Island. Daufuskie Island is a small (five by two miles) and remote island nestled between Hilton Head Island and Savannah, and only accessible by boat or ferry. 

Daufuskie Island abounds in natural beauty and boasts a rich history dating back to the early 1700s. Today, the Gullah heritage still thrives, and visitors can hop on a ferry to explore the uncrowded beaches, scenic bike paths and Lowcountry landscapes by foot, bike, or golf cart.

The best way to experience Daufuskie Island is on a guided tour. Daufuskie Trail Rides offer exclusive beach rides of the historical trails and beaches of Daufuskie Island or embark on a guided tour from Shelter Cove Marina with Outside Hilton Head.


Pirates of Hilton Head

Ahoy Matey! For the young pirates, lads and lassies in tow, nothing beats a swashbuckling adventure on Hilton Head Island’s only custom pirate ship, the Black Dagger. Climb aboard the Black Dagger at Harbour Town in Sea Pines, sail the coastline, fight off Stinky Pete for treasure, and celebrate the defeat of the island’s stinkiest pirate with singing, dancing and a share of the buried pirate booty! If you’re planning a family vacation to Hilton Head Island, it’s a must-do attraction and nautical adventure of note.


Summer Bubblegum Cruise

If you’re a regular vacationer to Hilton Head Island, you’ll know all about Gregg Russell’s famous, family friendly summer concerts under the Liberty Oak Tree at Harbour Town. Every evening through the summer, Greg entertains families with sing-alongs and games under the oak tree – but by day, he has adventures of a different kind. For over 25 years, the Summer Bubble Gum Cruise has been a Hilton Head Island favorite!

Embark on a 90-minute cruise with the kids aboard the Vagabond (every Friday) for an interactive and educational experience with dolphin spotting, singing and games, haunted lighthouses and ghost stories, and a treasure hunt at Harbour Town.


Aerial Tours of Hilton Head

A birds eye view of Hilton Head Island is unbeatable. The Zipline Canopy Tour at Adventure Hilton Head offers the highest views of the island from Broad Creek. The tour includes 7 ziplines, a swinging sky bridge, a spiral staircase in the trees, and a 900-foot long finale on a dual racing zipline. Take it a step further on the high ropes challenge course with 6 high ropes courses and 4 levels of difficulty from beginner greens to double black diamond challenges.

For the ultimate aerial tour of Hilton Head Island, take a climb in altitude along the South Carolina coastline on a Hilton Head helicopter tour. These tours offer unmatched views of the top Hilton Head attractions all the way to the remote shoreline of Daufuskie Island.


Sightseeing Tours of Savannah

The historic city of Savannah, Georgia is only 33 miles from Hilton Head and is easily accessible by car or boat. Savannah is one of the most loved cities in the Lowcountry with historic architecture and attractions, cobblestone streets, tree lined walkways, and tranquil water views from Savannah’s historic riverfront.

Shop along famous River Street, picnic at the fountains in Forsyth Park, indulge in Savannah’s foodie hot spots, and embark on a local sightseeing tour of Savannah. Unique Savannah experiences include culinary tours, hop-on hop-off trolley tours, segway tours, Savannah harbor tours, and ghost tours of Savannah, one of the most haunted cities in the US!


Sunset Dinner Cruises

Sail into the sunset on a romantic dinner cruise aboard the Spirit of Harbour Town, Hilton Head Island’s only sunset dinner cruise. Dine alfresco on the top deck with the best restaurant views in Hilton Head, sip on specialty cocktails and watch the HarbourFest fireworks from the water. For an evening of fine dining with live entertainment, dancing and sightseeing, you’ll create forever memories from the moment you climb aboard a classic Savannah Riverboat for a dinner entertainment cruise along the scenic Savannah River.


Take a Tour of Hilton Head Island’s Top Summer Vacation Rentals

Take a tour of our luxury Hilton Head Island summer vacation homes in the top resort areas of Hilton Head. With a portfolio of 220+ Hilton Head Island rentals and first class service from our on-island team, you can book your Hilton Head vacation home with confidence and ease with Sunset Rentals.   

Stay with Sunset Rentals and receive complimentary beach and bike gear credit on select vacation homes and villas, up to the value of $350! Whether you’re seeking kayaks, SUPs or bike rentals to adventure alone or chairs, umbrellas and beach toys for a family beach day, we make it easy to spend summer on Hilton Head Island. Turn your summer dreams to reality with Sunset Rentals!