Hilton Head Island Cruises, Sailing & Water Tours

63 Results
Private Water Ski Adventure Day (2 Hours)

Come enjoy a day on the water with Island Head! This private experience includes a USCG captain to drive the boat and assist in the …More

Come enjoy a day on the water with Island Head! This private experience includes a USCG captain to drive the boat and assist in the...

2 hours Free Cancellation
5.0 (2)
from
$408
5 Hour Private Hilton Head Boat Rental 22 ft. Luxury Pontoon

Voted Best of Hilton Head year after year, Hilton Head Island Boat Rentals welcomes you to explore Hilton Head by boat! The new 2024 Luxury …More

Voted Best of Hilton Head year after year, Hilton Head Island Boat Rentals welcomes you to explore Hilton Head by boat! The new 2024 Luxury...

5 hours Free Cancellation
5.0 (2)
from
$775
4 Hour Private Hilton Head Boat Rental 22 ft. Luxury Pontoon

Voted Best of Hilton Head year after year, Hilton Head Island Boat Rentals welcomes you to explore Hilton Head by boat! The new 2024 Luxury …More

Voted Best of Hilton Head year after year, Hilton Head Island Boat Rentals welcomes you to explore Hilton Head by boat! The new 2024 Luxury...

4 hours Free Cancellation
5.0 (2)
from
$675
8 Hour Private Hilton Head Boat Rental 22 ft. Luxury Pontoon

Voted Best of Hilton Head year after year, we welcomes you to explore Hilton Head by boat! The new 2024 Luxury Group Pontoon is recommended …More

Voted Best of Hilton Head year after year, we welcomes you to explore Hilton Head by boat! The new 2024 Luxury Group Pontoon is recommended...

8 hours Free Cancellation
5.0 (1)
from
$950
7 Hour Ultimate Lowcountry Day Up to 6 Guests

This trip is completely customizable and based on your preferences. At Outside Hilton Head, we specialize in unforgettable outdoor adventures in the Lowcountry. Our team …More

This trip is completely customizable and based on your preferences. At Outside Hilton Head, we specialize in unforgettable outdoor adventures in the Lowcountry. Our team...

7 hours Free Cancellation
5.0 (1)
from
$1,092
5 Hour Ultimate Lowcountry Day: Up To 6 Guests

This trip is completely customizable and based on your preferences. At Outside Hilton Head, we specialize in unforgettable outdoor adventures in the Lowcountry. Our team …More

This trip is completely customizable and based on your preferences. At Outside Hilton Head, we specialize in unforgettable outdoor adventures in the Lowcountry. Our team...

5 hours Free Cancellation
5.0 (1)
from
$815
6 Hour Private Hilton Head Boat Rental 22 ft. Luxury Pontoon

Voted Best of Hilton Head year after year, we welcome you to explore Hilton Head by boat! The new 2024 Luxury Group Pontoon is recommended …More

Voted Best of Hilton Head year after year, we welcome you to explore Hilton Head by boat! The new 2024 Luxury Group Pontoon is recommended...

6 hours Free Cancellation
5.0 (1)
from
$850
Private Dolphin Tour up to 24 passengers

This is an exclusive private trip where your group of up to 24 passengers (including all infants and children) will get to enjoy our Dolphin …More

This is an exclusive private trip where your group of up to 24 passengers (including all infants and children) will get to enjoy our Dolphin...

1 hour 30 minutes Free Cancellation
5.0 (1)
from
$625
Private 17 Passenger Boat Charter in Hilton Head

Rent a 17-passenger boat for an unforgettable adventure on the Lowcountry waters. With your own captain, enjoy personalized activities tailored to your group's interests. Our …More

Rent a 17-passenger boat for an unforgettable adventure on the Lowcountry waters. With your own captain, enjoy personalized activities tailored to your group's interests. Our...

1 hour 30 minutes Free Cancellation
5.0 (1)
from
$615
Hilton Head to Savannah Round-Trip Ferry Ticket

Leave the driving to us! Cruise from Hilton Head Island to Savannah, Georgia (1hr 45-min each way), for a day trip that will allow you …More

Likely to Sell Out
Likely to Sell Out

Leave the driving to us! Cruise from Hilton Head Island to Savannah, Georgia (1hr 45-min each way), for a day trip that will allow you...

8 hours Free Cancellation
4.5 (574)
from
$80
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by …More

Likely to Sell Out
Likely to Sell Out

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by...

1 hour 30 minutes Free Cancellation
4.7 (565)
from
$55
Hilton Head Sunset Dolphin Watching Cruise

Set sail from the iconic Harbour Town Yacht Basin, right beneath Hilton Head’s famous lighthouse, for an unforgettable evening on the water! Aboard the Vagabond, …More

Likely to Sell Out
Likely to Sell Out

Set sail from the iconic Harbour Town Yacht Basin, right beneath Hilton Head’s famous lighthouse, for an unforgettable evening on the water! Aboard the Vagabond,...

1 hour 30 minutes Free Cancellation
4.6 (476)
from
$45
Hilton Head Island Ocean Dolphin Cruise

This isn’t just another boat ride—it’s Hilton Head’s original dolphin cruise, operating for over 50 years on Hilton Head Island! Step aboard the iconic Vagabond …More

Likely to Sell Out
Likely to Sell Out

This isn’t just another boat ride—it’s Hilton Head’s original dolphin cruise, operating for over 50 years on Hilton Head Island! Step aboard the iconic Vagabond...

1 hour 30 minutes Free Cancellation
4.6 (422)
from
$39
Hilton Head Shrimp Trawling Boat Cruise

Come join the crew aboard the Tammy Jane for a 2-hour educational and picturesque low-country experience as we take you out Shrimping! We invite you …More

Likely to Sell Out
Likely to Sell Out

Come join the crew aboard the Tammy Jane for a 2-hour educational and picturesque low-country experience as we take you out Shrimping! We invite you...

2 hours Free Cancellation
4.7 (371)
from
$50
Hilton Head Sunset Dinner Cruise

Come aboard the Spirit of Harbour Town for a 3 course dinner cruise prepared by the chefs of Sea Pines Resort *SHARE YOUR MEAL PREFERENCES …More

Likely to Sell Out
Likely to Sell Out

Come aboard the Spirit of Harbour Town for a 3 course dinner cruise prepared by the chefs of Sea Pines Resort *SHARE YOUR MEAL PREFERENCES...

2 hours Free Cancellation
4.5 (260)
from
$109
90 Minute Hilton Head Dolphin Tour

Come explore the low country on a 90 minute dolphin tour with Island Head. We depart from Broad Creek Marina in the center of Hilton …More

Likely to Sell Out
Likely to Sell Out

Come explore the low country on a 90 minute dolphin tour with Island Head. We depart from Broad Creek Marina in the center of Hilton...

1 hour 30 minutes Free Cancellation
4.7 (193)
from
$45
Hilton Head Firework Cruise

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 …More

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...

1 hour 30 minutes Free Cancellation
4.3 (23)
from
$50
Hilton Head Sunday Brunch Buffet Cruise

What sets the Sunday Brunch Cruise apart is the unique opportunity to enjoy a relaxing meal while cruising through the scenic waterways of Hilton Head …More

What sets the Sunday Brunch Cruise apart is the unique opportunity to enjoy a relaxing meal while cruising through the scenic waterways of Hilton Head...

1 hour 30 minutes Free Cancellation
4.4 (20)
from
$83
Mini Boat Tour with stop at Disappearing Island

Embark on the extraordinary Mini Boat Disappearing Island Tour on Hilton Head Island, SC, and unlock a hidden paradise that only reveals itself at low …More

Likely to Sell Out
Likely to Sell Out

Embark on the extraordinary Mini Boat Disappearing Island Tour on Hilton Head Island, SC, and unlock a hidden paradise that only reveals itself at low...

2 hours Free Cancellation
4.7 (15)
from
$249
Sip & Sunset - BYOB Adults Only Dolphin Cruise

Experience the magic of a Sip & Sunset - BYOB Adults only Dolphin Cruise on Hilton Head Island, where breathtaking coastal views meet great music …More

Experience the magic of a Sip & Sunset - BYOB Adults only Dolphin Cruise on Hilton Head Island, where breathtaking coastal views meet great music...

1 hour 30 minutes Free Cancellation
4.6 (11)
from
$50
Hilton Head Sunrise Kayak Tour

Experience the serene beauty of Hilton Head Island’s Lowcountry on a guided sunrise kayak eco tour. As the first rays of light illuminate the marshlands, …More

Experience the serene beauty of Hilton Head Island’s Lowcountry on a guided sunrise kayak eco tour. As the first rays of light illuminate the marshlands,...

1 hour 30 minutes Free Cancellation
4.6 (5)
from
$45

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These answers are based on answers previously given to Key West Private Charters customers' questions.

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