Recent Searches
Clear

Top Hilton Head Island Cruises & Sailing

Saved to wishlist!

COVID-19: Check local travel restrictions and learn what we're doing to help keep you safe and your plans flexible. Learn more.

Read More
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
These experiences are highly rated by travelers and have met our top quality standards.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in Hilton Head Island. See more Virtual Experiences around the globe. 🌎

Price
$0
$500+
Duration
Time of Day
RatingClear
Specials

COVID-19: Check local travel restrictions and learn what we're doing to help keep you safe and your plans flexible. Learn more.

Read More
Select Dates
Today
Tomorrow

22 Hilton Head Island Cruises & Sailing | All Hilton Head Island Tours

Sort by:Featured

Hilton Head Shrimp Trawling Boat Cruise

Hilton Head Shrimp Trawling Boat Cruise

star-4.5
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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$43.44
From
$43.44
Taking safety measures

Hilton Head Sunset Dolphin Watching Cruise

Hilton Head Sunset Dolphin Watching Cruise

star-4.5
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$42.35
From
$42.35
Taking safety measures

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

star-5
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$35.90
From
$35.90

Hey, nice badge.
Experiences with this badge meet our highest quality standards and are loved by travelers like you.
Learn more
Hilton Head Island Dolphin Boat Cruise

Hilton Head Island Dolphin Boat Cruise

star-5
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$38.15
From
$38.15
Taking safety measures

2-Hour Private Hilton Head Sunset Cruise

2-Hour Private Hilton Head Sunset Cruise

star-5
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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$325.00
per group
From
$325.00
per group
Taking safety measures

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

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

star-4.5
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$52.95
From
$52.95
Taking safety measures

Hilton Head Island Dolphin Watching Nature Cruise

Hilton Head Island Dolphin Watching Nature Cruise

star-4.5
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$32.57
From
$32.57
Taking safety measures

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

star-5
This 2.5 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy with some good sailing. Perfect way to wind down and enjoy the ending of a great day. We will take the sails down to peacefully enjoy the beautiful show of an amazing Hilton Head Sunset. After the sun sets, we motor back to the marina and usually dock right around last light for the day. Sunset tours are usually full of wildlife such as dolphins, birds, sting ray and manatee which are some of the great wildlife that are often very prevalent in the evening. You will also have some great scenic views of Hilton Head, Pickney island and Parris island to mention a few. All of our sail trips we encourage our guests to be as involved in the sailing process as they would like. If you would instead like a relaxing trip, we then encourage you to relax and let the crew do the work.
More
  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$375.00
per group
From
$375.00
per group
Taking safety measures

2.5-Hour Private Hilton Head Afternoon Dolphin Watching Sail

2.5-Hour Private Hilton Head Afternoon Dolphin Watching Sail

star-5
This 2.5 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for great sailing along with the beautiful scenery and wildlife such as dolphins, birds, sting ray and Manatee are some of the great things we get to see on a very regular basis. This is a Monohull Sailboat which means it will heal over (completely normal but very exciting - designed not to tip over!). All this without the noise of the motor in the back ground - we like to sail not motor sail!!! We want our guest to be very comfortable on board our vessel known as "Knot the Office" and therefore if anyone is uncomfortable with the healing we can significantly reduce the healing to ensure everyone is comfortable. This is a fun and exciting activity but yet very relaxing and rewarding at the same time. Please call us directly to discuss other sail trip options
More
  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$355.00
per group
From
$355.00
per group
Taking safety measures

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

star-5
This 2.5 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions for sailing). During the MORNING, this is generally a calm - light wind relaxing sail, a great way to start off the morning or a great day of vacation. The morning tours are usually full with wildlife such as dolphins, birds, sting ray and Manatee which are some of the great wildlife that are often very prevalent in the morning. You will also have some great scenic views of Hilton head, Pickney island, Paris island, Lady's island and Bay island to mention a few. This sail trip is typically more on the calm side of things and would recommend for individuals that don't know how they would handle the more adventurous and exciting winds of the afternoon sail trips. This is also a great opportunity to anchor and swim off the boat if your group would like. Please call us directly to discuss other sail trip options such as Half Day trips / Sunset
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$324.00
per group
From
$324.00
per group
Taking safety measures

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

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

star-5
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.
More
  • 2 hours
  • Free Cancellation
From
$450.00
per group
From
$450.00
per group

Hilton Head Pirate Ship Adventure Cruise aboard the Black Sparrow

Hilton Head Pirate Ship Adventure Cruise aboard the Black Sparrow

star-5
On this Hilton Head pirate cruise, let your inner buccaneer out to play as you set sail off the coast of Hilton Head Island. This cruise was specifically created for kids and includes fun details such as face paint, pirate gear, and fake tattoos so you can look the part, plus water cannons for a blast of entertainment.
More
  • 2 hours
  • Free Cancellation
From
$30.77
From
$30.77

Hilton Head to Savannah Round-Trip Ferry Ticket

Hilton Head to Savannah Round-Trip Ferry Ticket

star-4
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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$65.18
From
$65.18
Taking safety measures

Daufuskie Island Guided History Tour from Hilton Head with Ferry Transportation

Daufuskie Island Guided History Tour from Hilton Head with Ferry Transportation

star-5
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.
More
  • 4 hours 30 minutes
  • Free Cancellation
From
$95.00
From
$95.00

5-Hour Private Hilton Head Pontoon Boat Rental

5-Hour Private Hilton Head Pontoon Boat Rental

star-5
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!
More
  • 5 hours
  • Free Cancellation
From
$500.00
per group
From
$500.00
per group

Hilton Head to Daufuskie Island Round-Trip Ferry Ticket

Hilton Head to Daufuskie Island Round-Trip Ferry Ticket

star-4
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. Their are both 4-seater and 6-seater golf carts available. Make sure to visit the Daufuskie Island Crab Company for lunch before you leave.
More
  • 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$34.95
From
$34.95
Taking safety measures

4-Hour Private Hilton Head Pontoon Boat Rental

4-Hour Private Hilton Head Pontoon Boat Rental

star-5
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!
More
  • 4 hours
  • Free Cancellation
From
$425.00
per group
From
$425.00
per group

Hilton Head Vanishing Island Dolphin Watching Tour

Hilton Head Vanishing Island Dolphin Watching Tour

star-5
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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$47.89
From
$47.89
Taking safety measures

Hilton Head to Daufuskie Island Round-Trip Ferry with 2-Person Golf Cart Rental

Hilton Head to Daufuskie Island Round-Trip Ferry with 2-Person Golf Cart Rental

star-4
Discover the beauty of Daufuskie Island at your pace with a golf cart rental. This tour includes a round trip boat ferry from Hilton Head Harbor to Freeport Marina on Daufuskie Island. You will be dropped off at Freeport Marina where their staff with get you setup with your golf cart rental to explore Daufuskie Island for 3 hours. There is so much to see on Daufuskie Island from the secluded beaches, Daufuskie Island Rum Company, Bloody Point Lighthouse, Historic Gullah Homes, Maryfield School, The Iron Fish Studio, historic churches, Silver Dew Winery, and so much more. Once you finish exploring Daufuskie Island by golf cart, you will have about an hour at Old Daufuskie Crab Company to enjoy some food and drinks before boarding the return boat ferry back to Hilton Head. To rent golf cart you must provide a valid drivers license. Golf carts hold up to 4 passengers per cart.
More
  • 5 hours
  • Free Cancellation
From
$175.00
per group
From
$175.00
per group

3-Hour Private Customized Small-Group Fishing, Dolphin Watching, or Nature Tours

3-Hour Private Customized Small-Group Fishing, Dolphin Watching, or Nature Tours

star-5
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!
More
  • 3 hours
  • Free Cancellation
From
$497.44
per group
From
$497.44
per group

Hilton Head Fireworks Boat Cruise

Hilton Head Fireworks Boat Cruise

Take in the sights of the Shelter Cove Fireworks from the water. We depart just before sunset to enjoy the beautiful low country sky as the sun fades away. We will set up in Broad Creek to watch the firework show. Along the way you will see some beautiful homes, wildlife, and dolphin if you’re lucky! The firework cruise is available every Tuesday evening in the summer months. This trip sells out quick so make sure you sign up in advance.
More
  • 2 hours
  • Free Cancellation
From
$49.99
From
$49.99

6-Hour Private Hilton Head Pontoon Boat Rental

6-Hour Private Hilton Head Pontoon Boat Rental

star-5
Come enjoy our brand new pontoon boats. 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!
More
  • 6 hours
  • Free Cancellation
From
$575.00
per group
From
$575.00
per group

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Cruises & Sailing in Hilton Head Island?
Q:
What Cruises & Sailing in Hilton Head Island are taking additional safety precautions?
Q:
What Cruises & Sailing in Hilton Head Island are good for avoiding crowds?

Things to do near Hilton Head Island