Top Hilton Head Island On the Water

Explore Hilton Head Island's beautiful coastal habitat in the seat of a comfortable and stable kayak. A trained interpretive naturalist will lead you through the ever-changing tidal creeks and salt marsh estuaries so you can witness it for yourself. Observe herons and osprey flying gracefully above the sea grasses...perhaps some dolphin dining on menhaden in the shallows...fiddler crabs scurrying in unison across the glistening mud flats. NO EXPERIENCE IS NECESSARY to enjoy a kayak tour with us! Tours depart daily from Shelter Cove Marina, conveniently located mid-island. We also offer full and half-day tours.

Enjoy the beautiful views of Daufuskie Island, Calibogue Sound, Harbour Town Lighthouse, Harbour Town Yacht Basin, South Beach Marina, and all the other breathtaking views the Lowcountry has to offer. Don’t forget to keep your eyes open for Hilton Head Island’s famous bottlenose dolphins. Flyers get to take off and land on the flight deck of our 31′ Ocean Pro parasail boat powered by a diesel Volvo Penta engine. Tandem and triple flights are available based on weather conditions. Flyers also have the option to stay dry or get wet – will you make a splash? Time on board is approximately one hour and 30 minutes with a full boat of 12 passengers. Each flight lasts between 8-10 minutes.

Hop on a Jet Ski and explore Hilton Head Island on this scenic tour. Leave from Palmetto Bay Marina, past gorgeous mansions, until you reach the designated area where you can zoom around as you like. Enjoy the beautiful surroundings and get the chance to observe birds, dolphins, and maybe even a sea turtle in their natural habitat.

Paddle the ins and outs of Hilton Head Island on this kayaking tour. Explore the waterways and inlets with a small group of 16 people and a guide in the lead. Choose the best departure time to fit your personal schedule; choice of single or double kayaks available.

Take a break from the beaches and entertainment of Hilton Head and get closer to nature on a guided kayak tours. In a small group of no more than 15, glide through the waters of Skull Creek, paddle through the rich ecosystem of the saltwater marshlands, and spot such wildlife as brown pelicans, egrets, herons, osprey, bald eagles, and Atlantic bottlenose dolphins.

Explore the inlets and rivulets around Hilton Head Island on this stand up paddleboard tour. Travel to secluded spots along with your guide, who leads you through the warm waters to places with good views and plenty of wildlife. This tour offers multiple departure times throughout the day so you can leave at your convenience.

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. Bring your friends and family along for an awesome day on the water!

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!

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!

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!

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.

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.

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.

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.

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.

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!

Rent your own pontoon boat for a fun family day out on the water! Relax, take vacation in, and explore the beautiful island of HHI by water! Our guides will instruct you on the waterways, where you can go, and be available at all times if you have questions!

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.

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 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

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. Bring your friends and family along for an awesome day on the water!

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

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.

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.