Outside Hilton Head at Westin Beachfront Outpost

Outside Hilton Head is your source for private and small group boating, kayaking, paddle boarding, biking and fishing excursions on Hilton Head. We have trips available throughout each day as well as rentals of kayaks, paddle boards, bikes and boats. All of our quality equipment is sanitized between each party. Start your adventure now by clicking a category below! Back in 1979, we were a windsurfing school operating off of the beach in Sea Pines. Since then, Outside has grown to become the Lowcountry’s leading outdoor outfitter. In addition to providing a multitude of excellent programs 365 days a year, Outside has two retail locations and offers group adventures, destination management, and team building programs in Hilton Head. The staff at Outside is made up of experienced, knowledgeable, and personable retail associates, reservationists, interpretive naturalist guides, and USCG licensed Captains.

Waves R Us Jet Ski Rentals

Shelter Cove Harbour & Marina

Shelter Cove Harbour & Marina is situated in the middle of Hilton Head Island across from Palmetto Dunes Oceanfront Resort, just off the Intracoastal Waterway. Shelter Cove Harbour offers year round waterfront dining, shopping and entertainment, and water sports, activities and tours. All kinds of water sports and activities may be enjoyed at our Hilton Head Island marina, from inshore and offshore fishing charters to sport crabbing, sailing and dolphin tours, sightseeing and nature excursions. Shelter Cove Marina is your #1 destination for Hilton Head Island water adventures. With 178 slip rentals, Shelter Cove Marina is the largest award-winning deep water marina on Hilton Head Island.

Hilton Head Outfitters & Bike Rentals

Hilton Head Outfitters & Bike Rentals provides outdoor activities and fun-filled adventures, like biking, kayaking, canoeing, and fishing, that the whole family can enjoy. We are located inside Palmetto Dunes Oceanfront Resort and situated right on the banks of an 11 mile lagoon. Our convenient location to nature and the resort on Hilton Head Island allows guests and visitors to be as active as they want to be. Hilton Head Outfitters & Bike Rentals is surrounded by beautiful beaches, 3 world-class golf courses, tennis courts, and plenty of biking trails! View our lagoon and bike trails map here!

Lowcountry Watersports

Located in Palmetto Bay Marina, Lowcountry Watersports is an outdoor adventure company offering unique ways to experience Hilton Head Island from the water. From thrilling Pirate Adventures to high-speed Creek Cat boats, these family activities are sure to amaze. For a more leisurely and up-close visit with nature, set sail on our popular dolphin tour, guided kayak tour, or try your hand at stand-up paddle boarding. No experience required, and all ages welcome. Private group excursions are available by request.

Hilton Head Boat Rentals

Hilton Head Boat Rentals offers luxury pontoons and boats for use in Hilton Head and the surrounding areas, including Savannah, Tybee Island, Beaufort, Port Royal, Garden City, and many more!

Saltmarsh Paddle Tours

Lowcountry life has treated us well and now we want to share it with you. Family owned and operated. With more than 60 years of combined Lowcountry living, our love for the water continues to grow. Our families have been in this area since the 1920s, visiting the Bluffton Fish Camps and Rose Dew Landing for recreation and fishing. Our grandfather, an avid fisherman, always taught us to appreciate the water. As kids, if we complained about eating seafood, our grandfather told us, “Well, you better learn to like it because if times get hard, that might be all we have to eat”. We listened and learned to respect our waterways for all they give.

H2O Sports

H2O Sports is located at the Harbour Town Marina on Hilton Head Island, South Carolina. Our number one priority is offering guests the very best experience they can have on the water! Our water activities are designed all ages so bring the whole family out for a day of great fun! We have so many AWESOME water activities to choose from that you won't know which to try first! We love being one of the top Hilton Head attractions and for good reason... FUN is our specialty! Safety is also a top priority at H2O Sports and we want everyone to have fun and feel safe. All of our captains are USCG licensed and trained in their specific area of expertise. You can feel confident knowing that you are using the best and most current equipment as well as having knowledgeable guides and captains who are there to help. All you need to do is relax, have fun, and enjoy your time on the water with H2O Sports.

Island Water Sports

We are located in South Beach Marina at the southern tip of Hilton Head Island. Water activities for all ages! Enjoy a day on the water with our USCG certified captains and state-of-the-art vessels equipped with everything to ensure an extremely safe and memorable experience on the waters of Hilton Head Island. We are passionate about providing our guests with a special and memorable experience while visiting Hilton Head Island, South Carolina. Our water activities and rentals in South Beach Marina provide a fun and convenient way to enjoy the coastal waters of Hilton Head Island. You and your family and friends will have a blast riding the waves on a waverunner, soaring above the water in a parasail, or exploring the calmer waters on a kayak or paddleboard. Whether you are looking for a relaxing activity or an exhilarating adventure, you can find all of the fun you're looking for at Island Water Sports.

Sky Pirate Parasail

Welcome to the #1 Parasail destination on Hilton Head Island, South Carolina!! Sky Pirate Parasail and Watersports will be the thrill of your Hilton Head Island vacation!! We offer a Parasailing experience like no other!! Our USCG certified 12 passenger boat will take you high above the Island offering views you can only get by Parasailing. As far as the eye can see, you will view our South Carolina coast like never before!! Not only Hilton Head, but Beaufort, Savannah, Tybee Island and even Parris Island Marine Training Depot will be viewed while soaring under our beautiful blue parasail with our signature, trademarked, Skull and Bones Logo! (see our Gallery). We offer a boating and flying combo unmatched by any sightseeing tour or trip available!!