Top Hilton Head Island Tours, Sightseeing & Cruises

Kick back and relax on your own private sunset cruise and experience Hilton Head in it's best light. Premium private tour accommodations are provided on board our brand new 2019 23' Key West - you won't find a newer or nicer charter boat available on the island. On your cruise you will take in breathtaking views of Harbour Town and the Calibogue Sound, encounter some of our resident Atlantic Bottlenose Dolphin, and drink in the spectacular sunset - all in two hours.

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.

Experience the Atlantic Bottlenose Dolphin of Hilton Head up close and personal on your own premium private boat tour. We have the newest boat you will find in the charter fleet (2019 Key West 23' DFS with hard top) that will protect you from all the elements Boat tours are limited to up to 6 guests total.

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.

Cruise from Hilton Head to Savannah on this Lowcountry day trip that’s packed with views. Relax on the open-air upper deck or air-conditioned lower cabin as you cruise through the Intracoastal Waterway, drink in hand from the onboard bar (own price). Then, dock in Savannah and spend a few hours of free time shopping, dining, and sightseeing before sailing back to Hilton Head.

Come explore the low country on a 90 minute dolphin tour with Island Head. We depart from Broad Creek Marina in the center of Hilton Head Island. We explore the beautiful water way of Broad Creek a rich eco system of wildlife including the famous bottle nose dolphin, a variety of birds, and so much more. We will also explore the Calibogue Sound where we will see from the water the famous Harbour Town Lighthouse, Daufuskie Island, Buck Island, Bull Island, and see Hilton Head Island from the water. Depending on the time of day and tides the captain will take the boat to the best spot off of these locations to increase our chances to find some wildlife. Enjoy a smooth ride aboard our comfortable custom tour boat. There are many different routes for our USCG captain to choose from based on the conditions. This is a great was to get up close with nature in the low country.

Travel along a forested bike trail without breaking a sweat on this Hilton Head Segway tour. Admire the scenery and the ride as you glide among live oaks, Spanish moss, and saw palmettos at a leisurely pace that’s ideal for teens and families. This fun ride doesn’t include any narration—just get rolling and enjoy the views.

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.

Travelers of all ages can see more of the lush Honey Horn landscapes in less time with this Hilton Head Island Segway adventure. Meet-up with your group, and follow your guide to explore this 70-acre (28.3-hectare) preserve. Marvel at meadows, glide along the trails and boardwalks, and check out the oldest tree in South Carolina. Along the way, you might even spot a few alligators lounging in the sunshine.

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.

Enjoy sunset views and scan the water for Atlantic bottlenose dolphins on this dolphin-watching cruise off the coast of South Carolina. The frequency of dolphin sightings makes this cruise ideal for those hoping to catch photos of the majestic sea creatures. Plus, throughout the cruise, you can learn about dolphins and your surroundings from an on-board naturalist.

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

Remote Daufuskie Island is accessible only by boat and remains largely undeveloped, despite its fame as the setting of Pat Conroy’s novel “The Water is Wide.” A guided tour makes the trip a cinch—this package includes round-trip ferry tickets, plus transportation between island attractions such as the First African Baptist Church and Mary Fields School, all visited with the benefit of commentary from your guide.

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!

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.

This private sunset tour will be an activity your family will always remember! Up to 6 people will enjoy this 1.5 hour tour complete with a licensed captain, eco narration, dolphin sightings, picturesque sunset views, water/soda, snacks, and pictures of your family. Meet us at Palmetto Bay Marina for your Private Sunset Tour. Depart for an exciting experience as you explore and search the waterways of Hilton Head Island for the extremely friendly Atlantic Bottlenose dolphin. Your small group will see these splendid Atlantic bottlenose dolphins feeding, playing, and simply cruising around the waters in their natural habitat as you learn about their social behavior, feeding habits, and much more.

Ride together as a couple, family or group at the same speed and duration, regardless of age or handicap. Learn to ride a Segway in just a few minutes--then have fun! You must book for at least 2 guests. Tours booked with less than two must unfortunately be cancelled.

Our extended tour takes you through the Shelter Cove and Veterans Memorial areas and for addition fun riding. You must book for at least 2 guests. Tours booked with less than two must unfortunately be cancelled.

Sunrise is the calmest, quietest time on the Hilton Head waterways! We will enjoy donuts/juice/water as we cruise and observe the Atlantic bottlenose dolphin in its natural habitat! Watch as they play, eat, or simply swim. This will surely be an event your family won't forget!

See the sunset, watch fireworks, and look out for dolphins swimming in the wild on this Hilton Head sailing tour. The boat comfortably holds up to 22 passengers for a not-too-crowded experience, and a guide helps you spot dolphins swimming through the waves as you go.

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 2-3 stops at exclusive waterfront restaurants! You will have time to sample local Hilton Head/Daufuskie Island cuisine!

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.

Ride together as a couple, family or group at the same speed and duration, regardless of age or handicap. Learn to ride a Segway in just a few minutes--then have fun! You must book for at least 2 guests. Tours booked with less than two must unfortunately be cancelled.

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.