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.

    Guides were fun and very informative about not only the habits and lives of dolphins but about the coastal area around Hilton Head. We had a great time and saw lots of dolphins on a beautiful day to be on the water. Highly recommend this tour!

  • Hilton Head Island: Sunset Dolphin Cruise

    2. 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.

    The cruise was wonderful from start to finish. Checking in with seamless being greeted at the boat and welcome to board. The captain shared great information about the area and what we were looking out. The crew was wonderful.

  • Hilton Head Island: Pirate Cruise on the Black Dagger

    3. 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.

    It was a great experience for our 5 year old grandson. He loves pirates and especially shooting the water cannons at Stinky Pete.

  • Hilton Head Island: Dolphin Nature Cruise

    4. 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.

    My friends and I were able to see dolphins as soon as we got on the boat! The captain was very knowledgeable about the animals and beaches in that area. The scenery was wonderful and the boat ride was very relaxing. I recommend this trip to anybody visiting Hilton Head Island!

  • Hilton Head Island: High-Flying Parasail Experience

    5. Hilton Head Island: High-Flying Parasail Experience

    Enjoy beautiful views of Daufuskie Island, Calibogue Sound, Harbour Town Lighthouse, Harbour Town Yacht Basin, South Beach Marina, and all the other breathtaking sights the Lowcountry has to offer. Don’t forget to keep your eyes open for Hilton Head Island’s famous bottlenose dolphins. Flyers get to take off and land on the flight deck of the 31-foot Ocean Pro parasail boat powered by a diesel Volvo Penta engine. Tandem and triple flights are available based on weather conditions. Flyers also have the option to stay dry or get wet — will you make a splash? Time on board is approximately one hour and 30 minutes with a full boat of 12 passengers. Each flight lasts between 8-10 minutes.

    We had an awesome time. Our crew was so much fun and just treated us so special. It was the first time for several of the kids and they can’t stop talking about it and everybody enjoyed our pictures and why didn’t know where we went because we brag on the cruise so much. We definitely will be back

  • Hilton Head Island: Round-Trip Ferry Ticket to Savannah

    6. Hilton Head Island: Round-Trip Ferry Ticket to Savannah

    Cruise through stunning intracoastal waterways from Hilton Head Island to Savannah with this round-trip express ferry ticket. Board from inside the Sea Pines Resort, then travel to the city in a comfortable air-conditioned boat. Sit back and admire the view as you sail through old shipping channels. Enjoy over 4 hour in Savannah to explore the city, before heading back to the ferry. On the return trip, benefit from happy hour pricing on selected drinks.

  • Hilton Head Island: Mini Boat Dolphin Tour

    7. Hilton Head Island: Mini Boat Dolphin Tour

    Start the experience with a short safety briefing and instruction on how to use your mini boat. Set off and get a view of Harbourtown and Daufuskie Island. Try to spot a variety of wildlife including heron, pelican, dolphin, osprey, and turtles. With your experienced guide, try to spot some of the dolphin population up close. Have pictures taken of your trip for and take home the memories of your trip.

    The tour was a lot of fun, we actually saw several dolphins. Our tour guide was the best, very knowledgeable. If in the Hilton Head area, I would highly recommend using this tour group.

  • Hilton Head Island: 75-Minute Jet Ski Tour

    8. 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.

    This was my second attempt at jetski. Water here was more turbulent. Had fun. Kudos to staff.

  • 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: America’s Cup Sailing Yacht Cruise

    10. 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.

    This was a major hi light of our trip to Hilton Head! Captain Peter and his crew, Luke and Taylor, were amazing! They were all so personable and so interested in ensuring our trip exceeded our expectations. It certainly did! I highly recommend this sail for anyone interested in getting a water view of the island.

Other Sightseeing Options in Hilton Head Island

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What people are saying about Hilton Head Island

This was a major hi light of our trip to Hilton Head! Captain Peter and his crew, Luke and Taylor, were amazing! They were all so personable and so interested in ensuring our trip exceeded our expectations. It certainly did! I highly recommend this sail for anyone interested in getting a water view of the island.

The ride was wonderful. Make sure to check your receipt to make sure the right number of passengers are identified. There was a mix up at the check in point with my tickets. The attendant corrected everything quickly to my satisfaction. Everything else went well.

Guides were fun and very informative about not only the habits and lives of dolphins but about the coastal area around Hilton Head. We had a great time and saw lots of dolphins on a beautiful day to be on the water. Highly recommend this tour!

Had blast saw a lot of dolphins. Very knowledgeable guide with great attitude (Nick) will do again for sure.

The captain was very informative and the staff was friendly. We really enjoyed it!