Hilton Head Island
Sailing Trips & Tours

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Our most recommended Hilton Head Island Sailing Trips & Tours

Hilton Head Island: Guided Dolphin Tour

1. Hilton Head Island: Guided Dolphin Tour

Take in the beauty of Hilton Head from the perspective of the water on a 1.5-hour, fully narrated boat tour. Delight in up-close encounters with dolphins, and find out about their habits, eating patterns, and more with a local guide. As you explore the island's waterways, learn about the history of the area and the surrounding islands from your guide's narration. Hear about oysters, spartina grass, tides, mud, and more. As well as dolphins, keep on the lookout for other wildlife including pelicans, osprey, stingrays, herons, turtles, and many more besides.

Hilton Head Island: Pirate Cruise on the Black Dagger

2. Hilton Head Island: Pirate Cruise on the Black Dagger

Search for sunken treasure with this incredible pirate cruise. Head to the docks, where you'll be given a new name and learn to speak like a real pirate. Then board the Black Dagger and set sail on the Calibogue Sound. Stinky Pete, the island’s smelliest pirate, knows about the treasure map and he stole the key. The race is on, to find Stinky Pete before he gets to the treasure. The crew will man the water cannons and blast Stinky Pete until he gives back the key.

Hilton Head Island: Dolphin Nature Cruise

3. Hilton Head Island: Dolphin Nature Cruise

Take a sightseeing cruise to explore the incredible nature around Hilton Head Island and the surrounding waterways. Hear about the island’s history from your expert crew as you search for Atlantic bottlenose dolphins. Admire the coastal landscape as you learn about the lifecycle of these mammals. Discover why this region is the perfect place for dolphins to settle. With sightings guaranteed, this tour is sure to be a highlight of your vacation.

Hilton Head Island: Sunset Dolphin Cruise

4. Hilton Head Island: Sunset Dolphin Cruise

Sail towards the open ocean in search of Atlantic bottlenose dolphins on an amazing sightseeing cruise. After seeing these animals in open water, travel to Daufuskie Island and up Bull Creek to Dolphin Hole to watch the setting sun. Admire the incredible landscape of salt estuaries at sunset. Listen to live commentary from your expert captain, and ask the crew any questions you might have. Beer, wine, snacks, and drinks are available for purchase throughout the trip.

Hilton Head Island: Dolphin Tour at Sunset & Fireworks Show

5. Hilton Head Island: Dolphin Tour at Sunset & Fireworks Show

Once you've met your group at the meeting point, travel first around the Hilton Head coast and take in stunning views of the shoreline. Look out for resident Atlantic bottlenose dolphins as they play, feed, and swim around the boat, and make the most of this incredible opportunity to see these friendly creatures in their natural habitat. Along the way, pass by the iconic Harbour Town Lighthouse, an impressive, 90-foot (27.4-meter) tall beacon renowned for its candy-striped exterior. Learn about the rich history and diverse ecosystem of the island from your expert tour guides as you soak in the scenic views and sail past breathtaking landmarks. Then, sit back and relax as the sun begins to set, painting the water’s surface in a vibrant array of hues. Find out why Hilton Head has been named one of the best destinations for sunset viewing along the East Coast of the USA. Finally, after the sun has fully sunk below the horizon, get ready for Hilton Head’s weekly fireworks.

Hilton Head Island: America’s Cup Sailing Yacht Cruise

6. Hilton Head Island: America’s Cup Sailing Yacht Cruise

Step aboard a former America’s Cup sailing yacht for an afternoon cruise. Discover what it takes to sail a racing yacht as you help the crew, or simply sit back and enjoy the ride. See the sights of the Calibogue Sound and learn about the history of these waters. Have your camera ready as you keep an eye out for dolphins. Drinks and merchandise are available for purchase on board.

Hilton Head Island: 75-Minute Jet Ski Tour

7. Hilton Head Island: 75-Minute Jet Ski Tour

Discover Hilton Head on a thrilling 75-minute jet ski adventure. Depart from Palmetto Bay Marina`with your guide and cruise past beautiful mansions, spartina grass, oyster beds, and luxury boats on the way to your free riding area. Once in the designated area, let loose and zoom around on your very own jet ski or simply take in the beautiful surroundings. Try to spot some of Hilton Head's wildlife including dolphins, birds, and the occasional sea turtle.

Hilton Head Island: Round-Trip Daufuskie Island Ferry

8. Hilton Head Island: Round-Trip Daufuskie Island Ferry

Step back in time with a trip to Daufuskie Island and get a feel for the Low Country. This express ferry service departs from the Sea Pines Resort and arrives in Daufuskie just 30 minutes later, giving you more time to explore. Learn the island’s history from your captain and hear about interesting landmarks and sights to see. Bring your bike on board the ferry at no extra cost, or rent a golf cart on arrival. After exploring the island, hop back on the ferry to return to Hilton Head.

Hilton Head Island: 1.5-Hour Guided Small-Group Kayak Tour

9. Hilton Head Island: 1.5-Hour Guided Small-Group Kayak Tour

Learn about the rich history and diverse ecosystem of Hilton Head Island from an expert guide as you paddle on this 1.5-hour kayak tour. As you cruise through these pristine saltwater marshlands, your guide will tell you about spartina grass/cordgrass, oysters, and other local wildlife, while answering any questions you may have. Enjoy the opportunity to observe many indigenous bird species, including egrets, herons, ospreys, brown pelicans, and bald eagles. Also, make sure to keep an eye out for the beloved Atlantic bottlenose dolphins swimming playfully. Benefit from a small-group experience for up to 10 people.

Hilton Head Island: Dolphin and Nature Tour

10. Hilton Head Island: Dolphin and Nature Tour

Bring inquisitive minds and cameras on this private dolphin tour with a Master Captain and Low Country Master Naturalist. Explore the Calibogue Sound by boat and have the opportunity to observe wild Atlantic bottlenose dolphins swimming, feeding, and socializing. See these beautiful creatures in their natural habitat, and learn about the history of the island, the ecology of the low country, and particularly the salt marsh. Watch the dolphins and learn about their social habits, physiology, diet, and more. Enjoy an opportunity to view other marine animals like rays, sea turtles, manatees, and sharks, who make cameos throughout the season.

Frequently asked questions about Hilton Head Island Sailing Trips & Tours

What are other things to do than Sailing Trips & Tours that are worth visiting in Hilton Head Island?

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Other Sightseeing Options in Hilton Head Island

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What people are saying about Hilton Head Island

Captain Mark was knowledgeable, kept us fully engaged, and helped guide us to numerous bottlenose dolphin sitings, including a nursery with young dolphins, and we saw a sting ray breach the water and skim the surface. Highly recommended.

We had a great time on this tour and Jackson did a great job guiding. You do get much wetter than I had anticipated. We were soaked by the time it was over. We saw several dolphins and a sting ray jump out of the water!

Great way to get a view of Hilton Head from the water and excellent narration about dolphins.

Wonderful, laid back experience. Captain provided great knowledge about the area.

Relaxing and enjoyable ride across the water. Friendly staff!