Top Hilton Head Island Private and Luxury

Cruise from Hilton Head to Savannah on this Lowcountry day trip that’s packed with views. Relax on the open-air upper deck or air-conditioned lower cabin as you cruise through the Intracoastal Waterway, drink in hand from the onboard bar (own price). Then, dock in Savannah and spend a few hours of free time shopping, dining, and sightseeing before sailing back to Hilton Head.

A sailboat cruise from Hilton Head is a peaceful way to see stunning Lowcountry landscapes without the noise of a moor. Join a captain and crew aboard a 39-foot long (12 meter) sailboat that competed in America’s Cup—head through quiet waters and past gorgeous scenery without the roar of a motor. You can even try your hand on deck and help out with the sails.

Over 24 Hollywood films have been shot in the historic town of Beaufort, South Carolina. Explore Beaufort without the hassle of navigating on a tour of the area’s highlights, from scenic film locations to historic homes. Your small group size ensures the full attention of your guide, who navigates for you and provides little–known stories about Beaufort’s past. Morning and afternoon departure times are available for your convenience.

End your day in Hilton Head aboard a relaxing sunset cruise around the island and waterways. Board your private vessel and enjoy a calm ride on Calibogue Sound with views of Harbour Town and the area is awash in golden light. While you sail, keep your eyes peeled for several species of wildlife including the playful Atlantic bottlenose dolphin.

Discover the charming southern city of Beaufort on a walking tour through the historic district. Join a small group and explore the antebellum streets while listening to your guide regale you with the city’s 500-year history. Learn about Native Americans, pirates, the Revolutionary War, the Civil War, and more as you visit monuments, churches, and statues.

Skip the hassle of renting a car and explore the islands near Beaufort from the comfort of an air-conditioned coach during this sightseeing tour. See the Gullah plantation house, cemetery, and church ruins, and visit the praise house, which still hosts meetings for families on the island. Learn about Gullah heritage with commentary from your guide and experience island life in the South Carolina Lowcountry.

Set out on a cruise from Hilton Head Island, South Carolina in search of Atlantic bottlenose dolphins. Board your private vessel and cruise past the Harbour Town Lighthouse and Daufuskie Island. While you sail, keep your eyes peeled for the playful dolphins as well as other local wildlife like bald eagles.

Hilton Head Island is known as one of North America’s best spots for watching dolphins in the wild. Get out on the water and take in amazing views of these intelligent, playful creatures during this private boat tour. With a Lowcountry Master Naturalist as your captain and guide, you’ll learn all about the ecology of Hilton Head while watching the dolphins along with other wildlife including rays, sharks, and sea turtles. Just your group (up to six passengers) cruising the waters, watching dolphins eating, playing, and socializing.

Chase after a mermaid and look for dolphins in the wild on this fun-filled boat tour from Hilton Head. Mermaid Nina swims right up to your boat and shares tons of information about marine life and ocean conservation in a light-hearted way that kids are sure to love—you can ask her about life as a mermaid, too.

Discover Beaufort’s historic district without the hassle of navigating a tour that highlights the town’s Hollywood past. In addition to telling little–known stories about the town’s 300–year history, your guide brings you to landmarks often missed by visitors, from unmarked Forrest Gump film locations to the cemetery used in The Great Santini.

See Hilton Head Island from a fresh perspective with this private sunset dolphin tour. Meet your boat captain at Palmetto Bay Marina for a private tour that can accommodate up to six people. Keep an eye out for Atlantic bottlenose dolphins as you learn about their feeding patterns, social behavior, and more. Admire sunset views from the deck of the boat.

Explore Hilton Head Island by Segway with this small-group tour. Meet your guide for a quick safety tutorial and then head out to cruise through Shelter Cove and the Veteran’s Memorial. Learn about local history as you cover ground quickly on the Segway. Stop for photographs and to admire the landscape during the tour.

Cruise along the coastal waterways of Hilton Head Island aboard a private boat during this sunset cruise. Board your vessel and see as the sky changes from blue to shades of orange and pink as the sun begins to set. While you sail, keep your eyes peeled for local wildlife like dolphins, turtles, and even otters.

Go sailing in Hilton Head Island with this private dolphin-watching tour. Motor out to Port Royal Sound and then put up the sails for a true sailing adventure. Keep an eye out for a variety of wildlife including birds, dolphins, manatees, and sting rays during this boat tour. Maximize time with a private tour and learn about sailing from your guide.

Go deeper into flooded estuaries and see more fantastic wildlife! This is a birder and a photographer's dream.

Tucked between Hilton Head Island and Savannah, and accessible only by boat, Daufuskie Island is a real gem. This trip provides a glimpse into a fascinating chapter of Lowcountry history on the undeveloped side of the island. Visit several one-of-a-kind places, including the First African Baptist Church, the Praise House, Mary Fields School (memorialized in Pat Conroy’s ‘The Water is Wide’) and the site of the Bloody Point Lighthouse. Tour studios and meet local artisans at Silver Dew Pottery and The Iron Fish, home to Martha Stewart American Made winner Chase Allen. Learn the rich history of the Native Americans, European settlers, the cotton trade, the Gullah people and the locals who have chosen to make this remote island their home. Tour includes boat cruise from Hilton Head Island, USCG licensed Captain and interpretive naturalist/historian guide, golf cart, light snack and refreshment.