Hop aboard the "Black Sparrow" and set sail on the pirate cruise for an amazing family adventure! The fun starts at the dock as we transform your little one with pirate vests, face paint and tattoos. Learn how to walk and talk l... More

This is our most popular boat trip! Hilton Head and surrounding areas boast a large and active population of Atlantic Bottlenose Dolphin, with great viewing opportunities year-round! Join Outside Hilton Head for a PRIVATE 90-minut... More

This is our most popular boat trip! Hilton Head and surrounding areas boast a large and active population of Atlantic Bottlenose Dolphin, with great viewing opportunities year-round! Join Outside Hilton Head for a 90-minute cruise... More

This morning kayak tour is the perfect time to get on the water - quiet, calm, less boat traffic, coffee and picturesque views! Upon check in, our staff will hook you up with a speciality brewed coffee - a portion of the proceed... More

Experience the magic of a Sip & Sunset - BYOB Adults only Dolphin Cruise on Hilton Head Island, where breathtaking coastal views meet great music for an unforgettable evening on the water. As the sun dips below the horizon, castin... 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, paddle through calm, winding waterways rich with natural wonders. Your j... More

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!... More

Photograph Hilton Head Island in a way most visitors never experience — on a guided, small-group photo expedition shaped by light, timing, and the quiet moments that define the Lowcountry. This experience is designed for anyone... More

Enjoy a two-and-a-half-hour adventure on your own private boat. Your Master Captain will guide you safely through the Calibogue on a falling tide to the isle. This mile long sandbar is exposed for only a couple of hours per day, a... More

This rental is recommended for parties 8 or more. It is without a doubt the best rental boat on Hilton Head Island for large groups. The quality and craftmanship of this Bennington screams luxury! We guarantee enjoyment for everyo... More

Explore the captivating history of Beaufort on a charming 50-55 minute horse-drawn carriage tour. Discover the elegance of the past as you glide past moss-covered Live Oaks, stunning Antebellum homes, historic churches, and iconic... 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 for parties 8 or more. It is without a doubt the best rental boat on Hilton Head Island fo... More

Come relax & enjoy Beaufort the way it was meant to be seen, listen to the Clippity-Clop of our gentle horses while our tour guides share their love of Beaufort & its History with you. * Completely Narrated Tour of Old Beaufort S... More

Rent a 16-passenger boat for an unforgettable adventure on the Lowcountry waters. With your own captain, enjoy personalized activities tailored to your group's interests. Our USCG licensed captains are also interpretive naturalist... More

Skip crowded tour boats and enjoy a private Hilton Head sunset cruise for groups of 7–15, often about the same per-person cost as shared tours. Our extra-wide boat offers 30–40% more space, giving your group room to relax, pla... More

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 goo... More

Make this the family memory everyone talks about. Our private large-group dolphin tours are designed for multi-generational families of up to 20 passengers, giving you the space to relax together without the stress of crowded boat... More

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 gre... More

This unique tour starts with an exciting boat ride to beautiful Page Island, Outside's private paradise. Along the way, your captain will find tell entertaining stories and help spot interesting wildlife. Watch for dolphins and bi... More

Voted Best of Hilton Head year after year, Hilton Head Island Boat Rentals welcomes you to explore Hilton Head by boat! The new Luxury Group Pontoon is recommended for parties 8 or more. It is without a doubt the best rental boat ... More