- Experience dolphins up close and in their natural environment - Fun for Families & Educational - Comfortable and completely shaded boat - Passionate local guides - Make memories with us... More

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, you’ll enjoy a 90-minute narrated cruise led by our Captain and ... More

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 and experience the magic of the Lowcountry the way it was mea... More

Our nature activities are a great way to experience Hilton Head Island by water. We get up close and personal with the salt marsh, oysters, and, by far, the vast number of our tours will see bottlenose dolphins. The dolphins are, ... More

Explore the salt marsh and take in views of the incredible Lowcountry sunset! On this 90-minute tour, learn about the salt marsh and try to spot local dolphins! Guests are welcome to bring snacks and beverages on board. Don't for... 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

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

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 Island. With stunning views, the chance to spot dolphins, and a laid-back atmos... More

The 2 Hour Disappearing Island Dolphin Tour is sure to be a Family Favorite! Enjoy searching for the Atlantic Bottlenose Dolphin and learning about the local ecoystem! Also, we'll make a 30 Minute stop at Disappearing Island - an ... 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

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 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... More

Enjoy an intimate sunset sailing experience aboard a cozy vessel with only six guests. Glide through the picturesque waters of Port Royal Sound as the sun dips below the horizon, painting the sky with brilliant colors. Keep an eye... More

Looking for a more personal sailing experience without the cost of a private charter? Our Afternoon Public Sail is the perfect balance. With a maximum of just 6 guests onboard, you’ll enjoy an intimate, relaxed atmosphere. Aboar... 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 & Nature Tour. Your boat is a comfortable pontoon boat with cushioned seats, a full top f... More

Looking for an intimate sunset sailing experience without booking an entire private charter? Your 2-Hour Sunset Public Sail offers the perfect balance. With a maximum of just six guests onboard, you’ll enjoy a peaceful, uncrowde... 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 USCG licensed captains are also interpretive naturalist... More