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Top Hilton Head Island Cruises & Sailing

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

Hilton Head Sunset Dolphin Watching Cruise

star-4.5
169
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 Watching Nature Cruise

Hilton Head Island Dolphin Watching Nature Cruise

star-4.5
236
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
$42.35
From
$42.35

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
164
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.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$52.95
From
$52.95

Hilton Head Island Dolphin Boat Cruise

Hilton Head Island Dolphin Boat Cruise

star-5
496
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
$35.00
From
$35.00

Hilton Head to Savannah Round-Trip Ferry Ticket

Hilton Head to Savannah Round-Trip Ferry Ticket

star-4.5
155
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.
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  • 8 hours
  • Free Cancellation
From
$84.75
From
$84.75

2-Hour Private Hilton Head Sunset Cruise

2-Hour Private Hilton Head Sunset Cruise

star-5
181
Kick back and relax on your own private sunset cruise and experience Hilton Head in it's best light. Premium private tour accommodations are provided on board our brand new 2019 23' Key West - you won't find a newer or nicer charter boat available on the island. On your cruise you will take in breathtaking views of Harbour Town and the Calibogue Sound, encounter some of our resident Atlantic Bottlenose Dolphin, and drink in the spectacular sunset - all in two hours.
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  • 2 hours
  • Free Cancellation
From
$345.00
per group
From
$345.00
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
45
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 30 minutes
  • Free Cancellation
From
$375.00
per group
From
$375.00
per group

2.5-Hour Private Hilton Head Afternoon Dolphin Watching Sail

2.5-Hour Private Hilton Head Afternoon Dolphin Watching Sail

star-5
72
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 30 minutes
  • Free Cancellation
From
$375.00
per group
From
$375.00
per group

Daufuskie Island Guided History Tour from Hilton Head

Daufuskie Island Guided History Tour from Hilton Head

star-5
248
Remote Daufuskie Island is accessible only by boat and remains largely undeveloped, despite its fame as the setting of Pat Conroy’s novel “The Water is Wide.” A guided tour makes the trip a cinch—this 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
$95.00
From
$95.00

Private Hilton Head Sunset Boat Cruise (Up to 14 Passengers)

Private Hilton Head Sunset Boat Cruise (Up to 14 Passengers)

star-5
30
The private sunset cruise is the perfect way to end a day on Hilton Head Island. There is nothing quite like a low country sunset, especially seeing one from the water were you can see the broad spectrum of colors such as vibrant oranges, reds, and multiple shades of pink. This sunset cruise is perfect for a romantic evening, family time, friends gathering, bachelor or bachelorette parties, team bonding, the possibilities are endless. The boat holds up to 14 passengers.. The captain will show you what the low country has to offer on this 2 hours private cruise.
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  • 2 hours
  • Free Cancellation
From
$529.00
per group
From
$529.00
per group

Hilton Head Shrimp Trawling Boat Cruise
Likely to Sell OutLikely to Sell Out

Hilton Head Shrimp Trawling Boat Cruise

star-4.5
144
Take part in an authentic Lowcountry travel experience with this shrimping tour from Hilton Head Island. Join a crew on board a fishing boat and head out on the salt marshes for a chance to catch shrimp and fish, and learn about the environment and wildlife as you go. After the trip, hang out and enjoy a day pass to the Sea Pines Resort.
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  • 2 hours
  • Free Cancellation
From
$43.44
From
$43.44

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

star-5
436
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
$35.00
From
$35.00

Disappearing Island Dolphin Tour

Disappearing Island Dolphin Tour

star-4.5
40
Increase your odds of seeing dolphins in the wild on this dolphin watching cruise from Hilton Head. Sail out from easy-to-find Palmetto Bay Marina at your selected departure time: admire views of the shore, look for wildlife, and learn about the local ecosystem. Plus, take a quick stop to look for shells, starfish, and sand dollars at “Disappearing Island,” a strip of land only accessible at low tide.
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  • 2 hours
  • Free Cancellation
From
$55.00
From
$55.00

3-hour Private group tour with Fishing and Dolphin Watching

3-hour Private group tour with Fishing and Dolphin Watching

star-5
7
Whether your tour is a family vacation activity, experienced fishermen planned event, or the nights dinner, Captain Steve with Always Angling Charters will provide a memorable and safe experience!
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  • 3 hours
  • Free Cancellation
From
$497.44
per group
From
$497.44
per group

Turtle Beach Power Snorkeling Adventure
Likely to Sell OutLikely to Sell Out

Turtle Beach Power Snorkeling Adventure

star-5
116
Sea scooter snorkeling tours are popular shore excursion for visitors docked at St. John cruise ports. After your guide and captain provide a sea scooter tutorial, dive in and propel through the water, taking in diverse ocean life around you along the way. In addition to souvenir photos, light snacks and beverages are included.
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  • 2 hours
  • Free Cancellation
From
$125.00
From
$125.00

Hilton Head to Daufuskie Island Round-Trip Ferry Ticket

Hilton Head to Daufuskie Island Round-Trip Ferry Ticket

star-4.5
25
If you're looking for an authentic lowcounty experience look no further than Daufuskie Island on your next trip to Hilton Head. It's only a 30 minute Ferry ride from Harbour Town but it will feel like you stepped back in time when you arrive! Along the way to Daufuskie Island you will hear tails of this sea islands past from your naturalist captain. This trip allows 3-hours on Daufuskie Island. One of the most popular things to do when arrive is a self guided golf cart tour. 3-hour golf cart rentals will be available for purchase upon arrival to the island. There are both 4-seater and 6-seater golf carts available. Make sure to visit the Daufuskie Island Crab Company for lunch before you leave.
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  • 30 minutes
  • Free Cancellation
From
$42.35
From
$42.35

4-Hour Private Hilton Head Pontoon Boat Rental

4-Hour Private Hilton Head Pontoon Boat Rental

star-5
12
We have brand new pontoon boats located at Hilton Head Harbor. Take in all the gorgeous sights as we offer one of the largest riding areas on the island. Enjoy a short idle time of four hours through the beautiful waters of Skull Creek, while keeping an eye out for our famous Atlantic bottlenose dolphins. From there on, it is smooth sailing, as we allow you to travel to the mouth of the Atlantic Ocean, behind Daufuskie Island, through the Cooper River, or up the May River to check out the sand bar and Palmetto Bluff. You will receive a professional orientation on navigating Hilton Head Island’s waterways, and don’t be afraid to ask for some superb lunch recommendations on the water. Pontoon boats have a capacity of 10 people, and the captain must be 18 years or older with a valid driver’s license and prior boating experience. Bring your friends and family along for an awesome day on the water!
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  • 4 hours
  • Free Cancellation
From
$480.00
per group
From
$480.00
per group

Hilton Head Dolphin Watching Cruise with Fireworks Display

Hilton Head Dolphin Watching Cruise with Fireworks Display

star-5
12
See the sunset, watch fireworks, and look out for dolphins swimming in the wild on this Hilton Head sailing tour. The boat comfortably holds up to 22 passengers for a not-too-crowded experience, and a guide helps you spot dolphins swimming through the waves as you go.
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  • 2 hours
  • Free Cancellation
From
$69.00
From
$69.00

2 Hour Private Sunset and Dolphin Watch Powerboat

2 Hour Private Sunset and Dolphin Watch Powerboat

star-5
8
This is a private power boat tour including only your group of up to 6 passengers plus our Captain. In this intimate setting, your group will see tons of wildlife, learn area information as well as information of wild life, dolphins and birds, Stingrays, and sharks
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  • 2 hours
  • Free Cancellation
From
$375.00
per group
From
$375.00
per group

5-Hour Private Hilton Head Pontoon Boat Rental

5-Hour Private Hilton Head Pontoon Boat Rental

star-4.5
7
Take in all the gorgeous sights as we offer one of the largest riding areas on the island. Enjoy a short idle time through the beautiful waters of Skull Creek, while keeping an eye out for our famous Atlantic bottlenose dolphins. From there on, it is smooth sailing, as we allow you to travel to the mouth of the Atlantic Ocean, behind Daufuskie Island, through the Cooper River, or up the May River to check out the sand bar and Palmetto Bluff. You will receive a professional orientation on navigating Hilton Head Island’s waterways, and don’t be afraid to ask for some superb lunch recommendations on the water. Pontoon boats have a capacity of 10 people, and the captain must be 18 years or older with a valid driver’s license and prior boating experience. Bring your friends and family along for an awesome day on the water!
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  • 5 hours
  • Free Cancellation
From
$565.00
per group
From
$565.00
per group

90-Minute Private Dolphin Tour in Hilton Head Island

90-Minute Private Dolphin Tour in Hilton Head Island

star-5
6
This is your private boat taking you on an intimate tour to see dolphins in the wild, up close and personal! Just your group (up to 6 passengers) comfortably cruising the waters, while your Captain provides you with in depth details of the life of the Atlantic bottle nose dolphin. Learn about their social habits, life cycle and mating patterns. You’ll get all the time you need to see these beautiful creatures as they spend their days cruising the Calibogue Sound. See Hilton Head’s storied landmark, the Harbourtown Lighthouse from the water. Cross over to the other side of the Sound and see Daufuskie Island. While on the Sound you’ll have a chance to glimpse other creatures that call the low country home; manta rays jumping out of the water, spinner sharks breaching the surface, sea turtles coming up for a breath of air. Hundreds of species of birds that make their way through their migratory periods. This trip is a wonderland of wildlife to behold.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$249.00
per group
From
$249.00
per group

Hilton Head Crabbing Expedition Boat Cruise

Hilton Head Crabbing Expedition Boat Cruise

star-5
1
Search for crabs alongside marine science students on this Lowcountry crabbing tour from Hilton Head. As you sail out on the Lowcountry’s famous salt marshes, your knowledgeable guides share tons of information about the rich local ecosystem and the wildlife that calls it home—see some of it for yourself, including whatever you pull up in your crabbing pots. Take home some of your catch if you get any.
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  • 2 hours
  • Free Cancellation
From
$43.44
From
$43.44

3 Hour Private Cruise in Hilton Head Island

3 Hour Private Cruise in Hilton Head Island

star-5
1
Discover the coast along Hilton Head Island with a private half-day boat tour. Set out on a family-friendly cruise around Pickney Island and anchor near a sandbar to go swimming. Keep an eye out for dolphins during the cruise and learn about local wildlife from your guide. This private cruise can accommodate up to six people plus the captain.
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  • 3 hours
  • Free Cancellation
From
$460.00
per group
From
$460.00
per group

6-Hour Private Hilton Head Pontoon Boat Rental

6-Hour Private Hilton Head Pontoon Boat Rental

star-5
1
Set out on a private adventure on Hilton Head Island’s waterways with this pontoon boat rental. Receive professional orientation on navigating and then choose an itinerary that matches your interests. Keep an eye out for dolphins as you cruise along Skull Creek and travel to the mouth of the Atlantic Ocean. Pontoons can comfortably fit up to 10 people.
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  • 6 hours
  • Free Cancellation
From
$650.00
per group
From
$650.00
per group

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