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Top Hilton Head Island Sailing

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America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
Likely to Sell OutLikely to Sell Out

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

star-4.5
206
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 AmericaÔÇÖs CupÔÇöhead 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.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$52.95
From
$52.95

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail
Likely to Sell OutLikely to Sell Out

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

star-5
75
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.
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  • 2 hours
  • Free Cancellation
From
$465.00
per group
From
$465.00
per group

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail
Likely to Sell OutLikely to Sell Out

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

star-5
17
Explore the waters around Hilton Head, South Carolina aboard your own vessel during this morning excursion. Meet your dedicated captain and sail to Port Royal Sound to begin your tour. Take in the views of Hilton Head, Pickney Island, Paris Island, and many other landmarks while you keep your eyes peeled for playful dolphins that play in the wake of the boat.
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  • 2 hours
  • Free Cancellation
From
$425.00
per group
From
$425.00
per group

Private Hilton Head Sunset Sailing Tour with Dolphin Watching
Likely to Sell OutLikely to Sell Out

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

star-5
60
Go sailing at sunset in Hilton Head Island with this private dolphin-watching tour. Climb aboard a sailboat and cruise out into Port Royal Sound during this tour. Keep an eye out for wildlife including dolphins, manatees, sting rays, and more. Learn about sailing if you choose or just sit back and enjoy the ride, complete with sunset views.
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  • 2 hours
  • Free Cancellation
From
$495.00
per group
From
$495.00
per group

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
Likely to Sell OutLikely to Sell Out

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

star-5
485
Embark on a nautical adventure aboard the Black Dagger pirate ship, which transforms kids into little pirates for a treasure hunt on the waters of Hilton Head. The crew provides kids with pirate costumes and pirate lessons before setting sail in search of treasure. This family-friendly cruise has a choice of several departures in the morning and afternoon, making it easy to fit into your schedule.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$40.95
From
$40.95

Hilton Head Sunset Dolphin Watching Cruise
Likely to Sell OutLikely to Sell Out

Hilton Head Sunset Dolphin Watching Cruise

star-4.5
198
Enjoy sunset views and scan the water for Atlantic bottlenose dolphins on this dolphin-watching cruise off the coast of South Carolina. The frequency of dolphin sightings makes this cruise ideal for those hoping to catch photos of the majestic sea creatures. Plus, throughout the cruise, you can learn about dolphins and your surroundings from an on-board naturalist.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$47.65
From
$47.65

Hilton Head Island Dolphin Boat Cruise

Hilton Head Island Dolphin Boat Cruise

star-5
558
Learn about the marine life populating the waters off the coast of Hilton Head Island on this dolphin watching cruise. Up your chances of spotting dolphins and other marine animals with the help of your professional guide, who will also provide information about the ecosystem as you go.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$39.00
From
$39.00

Hilton Head Island Dolphin Watching Nature Cruise

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Hilton Head Island Dolphin Watching Nature Cruise

star-4.5
253
On this dolphin watching cruise from Hilton Head, you have the chance to see wildlife, check out local landmarks, and admire the coastline as you cruise out on the Calibogue Sound and Atlantic Ocean. Your guide narrates the entire trip as you sail past Bull Island, the Haig Point Lighthouse, and more, all while looking out for dolphins, egrets, herons, and other animals in the wild.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$38.11
$42.35
$4.24 savings
From
$38.11
$42.35
$4.24 savings

2-Hour Private Hilton Head Sunset Cruise

2-Hour Private Hilton Head Sunset Cruise

star-5
191
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.
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  • 2 hours
  • Free Cancellation
From
$399.00
per group
From
$399.00
per group

Hilton Head to Savannah Round-Trip Ferry Ticket
Likely to Sell OutLikely to Sell Out

Hilton Head to Savannah Round-Trip Ferry Ticket

star-4.5
195
Cruise from Hilton Head to Savannah on this Lowcountry day trip thatÔÇÖs 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.
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  • 8 hours
  • Free Cancellation
From
$84.75
From
$84.75

Private Hilton Head Sunset Dolphin Tour

Private Hilton Head Sunset Dolphin Tour

star-5
11
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.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$399.00
per group
From
$399.00
per group

Daufuskie Island Guided History Tour from Hilton Head

Daufuskie Island Guided History Tour from Hilton Head

star-5
385
Remote Daufuskie Island is accessible only by boat and remains largely undeveloped, despite its fame as the setting of Pat ConroyÔÇÖs novel ÔÇťThe Water is Wide.ÔÇŁ A guided tour makes the trip a cinchÔÇöthis package includes round-trip ferry tickets, plus transportation between island attractions such as the First African Baptist Church and Mary Fields School, all visited with the benefit of commentary from your guide.
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  • 4 hours 30 minutes
  • Free Cancellation
From
$115.00
From
$115.00

Hilton Head Island Daytime or Sunset Creek Cat Boat Tour

Hilton Head Island Daytime or Sunset Creek Cat Boat Tour

star-5
295
Zoom around Hilton Head Island on a small, motorized "creek cat" boat during this guided tour. Get views of all the quintessential sights, as well as access to some smaller marshes and wildlife-rich areas. Enjoy the opportunity to operate your own creek cat under the supervision of a guide; multiple departure times available.
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  • 2 hours
  • Free Cancellation
From
$145.00
From
$145.00

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