Tours & Activities in Hilton Head Island

Our luxurious 2021 30-foot Chaparral 307SSX has plenty of room to bask and enjoy your trip. We limit our groups to 6 guests in order to maximize your comfort. Our vessel has never been used for fishing so odor and cleanliness will never be an issue. Create your perfect playlist and connect to our premium sound system, while you sit by the teak cocktail table or lounge on the hand stitched, convertible sun lounger. Dual USB ports available with charging capabilities so you never have to worry about your phone dying and missing that perfect photo op. Our boat also offers plenty of storage space, two coolers, and a restroom. We provide water, soft drinks and light snacks for your convenience and you are always welcome to bring beverages and snacks aboard.

Our luxurious 2021 30-foot Chaparral 307SSX has plenty of room to bask and enjoy your trip. We limit our groups to 6 guests in order to maximize your comfort. Our vessel has never been used for fishing so odor and cleanliness will never be an issue. Create your perfect playlist and connect to our premium sound system, while you sit by the teak cocktail table or lounge on the hand stitched, convertible sun lounger. Dual USB ports available with charging capabilities so you never have to worry about your phone dying and missing that perfect photo op. Our boat also offers plenty of storage space, two coolers, and a restroom. We provide water, soft drinks and light snacks for your convenience and you are always welcome to bring beverages and snacks aboard.

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!

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!

Kick back and relax on your own private sunset cruise and experience Hilton Head in it's best light. We can accommodate in between 7 - 20 people total on our brand new boat. She's built to entertain, and fantastic for family get togethers, anniversaries, friendsaversaries, bachelorette parties, or any type of other group gathering occasion that you can dream up. On your cruise you will take in breathtaking views of Pinckney Island, Mackey Creek, Skull Creek, Harbour Town and the Calibogue Sound. While on your sunset tour, you will not only drink in the spectacular water views that Hilton Head is know for, but you will also encounter some of our resident Atlantic Bottlenose Dolphin as well. Please join us for your special occasion - and we'll be sure to help you create vacation memories that will last a lifetime!

Kick back and relax on your own private sunset cruise and experience Hilton Head in it's best light. We can accommodate in between 7 - 20 people total on our brand new boat. She's built to entertain, and fantastic for family get togethers, anniversaries, friendsaversaries, bachelorette parties, or any type of other group gathering occasion that you can dream up. On your cruise you will take in breathtaking views of Pinckney Island, Mackey Creek, Skull Creek, Harbour Town and the Calibogue Sound. While on your sunset tour, you will not only drink in the spectacular water views that Hilton Head is know for, but you will also encounter some of our resident Atlantic Bottlenose Dolphin as well. Please join us for your special occasion - and we'll be sure to help you create vacation memories that will last a lifetime!

Front-row seats to the fireworks display over the salt marsh of Broad Creek. 22' Bentley Luxury Pontoon with 115HP 4-Stroke Motor Be your own captain, cruising the beautiful lowcountry waterways! This pontoon offers spacious dual captain's chairs, comfortable sofa-style seating, and enhanced style. Can accommodate up to 12 passengers.

Front-row seats to the fireworks display over the salt marsh of Broad Creek. 22' Bentley Luxury Pontoon with 115HP 4-Stroke Motor Be your own captain, cruising the beautiful lowcountry waterways! This pontoon offers spacious dual captain's chairs, comfortable sofa-style seating, and enhanced style. Can accommodate up to 12 passengers.

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.

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.

While on your Large Group Dolphin Tour - you will get to experience first hand: Skull Creek, Mackey Creek, Pinckney Island Wildlife Refuge, Dolphin Head, the Port Royal Sound, "Cocktail Cove", and the Intracoastal Waterway. On your tour you will also experience our local wildlife - especially our local resident Atlantic Bottlenose Dolphin. Every tour is flexible - so we can customize our trip to meet whatever your needs may be within that two-hour span. In town with friends or family and celebrating something special? We can absolutely make sure that you have an amazing time. Just let us know what the occasion is and we will be sure to take care of you.

While on your Large Group Dolphin Tour - you will get to experience first hand: Skull Creek, Mackey Creek, Pinckney Island Wildlife Refuge, Dolphin Head, the Port Royal Sound, "Cocktail Cove", and the Intracoastal Waterway. On your tour you will also experience our local wildlife - especially our local resident Atlantic Bottlenose Dolphin. Every tour is flexible - so we can customize our trip to meet whatever your needs may be within that two-hour span. In town with friends or family and celebrating something special? We can absolutely make sure that you have an amazing time. Just let us know what the occasion is and we will be sure to take care of you.

Come aboard our custom ski boat rated for 6 passengers. This charter comes with a USCG captain to drive the boat so you and your group can sit back and enjoy the day hassle free. This is your charter to customize from water ski, tubing, wake boarding, and kneeboarding! This is fun for all ages, no experience required. Book your custom experience with Island Head today!

Come aboard our custom ski boat rated for 6 passengers. This charter comes with a USCG captain to drive the boat so you and your group can sit back and enjoy the day hassle free. This is your charter to customize from water ski, tubing, wake boarding, and kneeboarding! This is fun for all ages, no experience required. Book your custom experience with Island Head today!

Take in all the gorgeous sights as we offer one of the largest riding areas on the island. You will have a short idle time through the beautiful waters of Broad 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.

Take in all the gorgeous sights as we offer one of the largest riding areas on the island. You will have a short idle time through the beautiful waters of Broad 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.

This 2 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.

This 2 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.

Depart from Island Head's newest location at Broad Creek Marina. Enjoy the evening on a private sunset cruise on the waterways surrounding Hilton Head Island. This cruise if private to your party and the captain will customize the cruise to suit you and your group. Feel free to bring snacks and drinks as we enjoy a low country sunset from the water. Our boat holds up to 14 passengers. This is perfect for a romantic evening, bachelor parties, bachelorette parties, and a family and friends cruise. Book your evening with Island Head!

This 2 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

This 2 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

This is a great way to explore the water ways of Hilton Head. Our custom 25ft boat comes with an experienced captain to operate and show you around the waterways. Sit back and enjoy your custom trip on the water with Island Head!

This is a great way to explore the water ways of Hilton Head. Our custom 25ft boat comes with an experienced captain to operate and show you around the waterways. Sit back and enjoy your custom trip on the water with Island Head!

This 2 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

This 2 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

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!

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!

This tour will be the family memory you’ll always remember! You’ll depart from Palmetto Bay Marina and enjoy this fully narrated tour by our licensed captains explaining the ecosystem, wildlife, and Hilton Head in general! We’ll show you the beloved Atlantic Bottlenose Dolphins in their natural environment! Along the way, we will make 1-2 stops at exclusive waterfront restaurants! You will have time to sample local Hilton Head/Daufuskie Island cuisine!

This tour will be the family memory you’ll always remember! You’ll depart from Palmetto Bay Marina and enjoy this fully narrated tour by our licensed captains explaining the ecosystem, wildlife, and Hilton Head in general! We’ll show you the beloved Atlantic Bottlenose Dolphins in their natural environment! Along the way, we will make 1-2 stops at exclusive waterfront restaurants! You will have time to sample local Hilton Head/Daufuskie Island cuisine!

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 water sport of your choice. A tube, water skis, wakeboard, and knee board will be on board for your group to enjoy. This tour is private and custom to your group! The activities can be split up however you choose. Feel free to pack a lunch and drinks or we can pull off at a low country favorite (Old Daufuskie Crab Co. to grab lunch on the water. Our Parker ski boat maxes at 6 passengers. All skill levels welcome!