Top Hilton Head Island Private Sightseeing Tours

End your day in Hilton Head aboard a relaxing sunset cruise around the island and waterways. Board your private vessel and enjoy a calm ride on Calibogue Sound with views of Harbour Town and the area is awash in golden light. While you sail, keep your eyes peeled for several species of wildlife including the playful Atlantic bottlenose dolphin.

Our tour will take you through the city's National Historic Landmark District, showcasing beautiful historic homes, churches, and sites that have witnessed centuries of American history. You’ll see sites from the Filming of Forest Gump, hear stories of the civil war, Harriet Tubman, the Succession, the Jewish settlers, local history and so much more. Go at your own pace. Stop anytime and continue whenever you want. The tour is all outside, location aware, plays as you walk, and can be taken 24/7/365. It never expires.

Enjoy an immersive way to discover Hilton Head Island's aquatic scenery—and give yourself the best chance of spotting local marine life, including dolphins—on this guided boat tour. Choose a departure time that works best for you, greet your United States Coast Guard-licensed captain, and hop aboard. Learn more about the island's ecosystem along the way, and look out for wildlife as you head into nature.

Experience Hilton Head Island in a way that few travelers get to: On a small, motorized "creek cat" boat during this guided tour. Operate your own vessel under your guide’s supervision while taking in views of all the quintessential sights, as well as access to some smaller marshes and wildlife-rich areas.

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.

Located south of Hilton Head Island, Vanishing Mile Isle can only be visited when it’s briefly exposed during low tide. With this private charter, you can easily access this unique location and spend time beachcombing for sand dollars, seashells, and more, with a master naturalist onhand to provide more information. Along the way, look for dolphins and other wildlife in Calibogue Sound.

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.

Voted Best of Hilton Head year after year, Hilton Head Island Boat Rentals 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 for large groups. The quality and craftsmanship of this Bennington screams luxury! We guarantee enjoyment for everyone, combining comfort, style and function to create the perfect atmosphere for a great experience on the water. This luxury group pontoon rental allows you to see Hilton Head by water. Whether you want to anchor in a quiet cover or see the sites this boat is perfect for your group. The destinations pre-marked includes Daufuskie Island, Harbourtown LightHouse, Sandbar, Skull Creek BoatHouse and Fishing Holes.

Voted Best of Hilton Head year after year, Hilton Head Island Boat Rentals 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 for large groups. The quality and craftsmanship of this Bennington screams luxury! We guarantee enjoyment for everyone, combining comfort, style and function to create the perfect atmosphere for a great experience on the water. This luxury group pontoon rental allows you to see Hilton Head by water. Whether you want to anchor in a quiet cover or see the sites this boat is perfect for your group. The destinations pre-marked includes Daufuskie Island, Harbourtown LightHouse, Sandbar, Skull Creek BoatHouse and Fishing Holes.

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-minute cruise in one of our stable and comfortable powerboats. We will explore the Broad Creek Wildlife Area, Calibogue Sound and nearby marshes. Your Captain will guide you to points of interest, while explaining the unique connections between history, culture and nature in the Lowcountry. This tour is great for families!

This trip is completely customizable and based on your preferences. At Outside Hilton Head, we specialize in unforgettable outdoor adventures in the Lowcountry. Our team of expert guides, including master naturalists and USCG licensed Captains, is dedicated to providing exceptional experiences. From kayaking and paddleboarding to dolphin tours and custom watersport adventures, we offer something for everyone.

Combine an excursion to see Atlantic bottlenose dolphins in their natural environment with personalized attention on this private tour. Depart from the Palmetto Bay Marina in a boat headed for the dolphins' swimming and hunting grounds with a guide, who will teach you all about their biology and behavior. Having a dedicated guide means you can ask plenty of questions as you travel.

Embark on an unforgettable private boat tour for up to six people, departing from Hilton Head Island and taking you on a journey through the pristine waters of the Lowcountry. Learn about the marsh grasses and wildlife. Your journey will be escorted by dolphins. Cut across the Calibogue Sound and head to Daufuskie Island; an exclusive spot only accessible by boat. Visit Freeport Marina and Old Daufuskie Crab Company at your leisure and own expense. Once you've had your fill, board the boat and continue on your journey back to the mainland enjoying dolphin spotting along the way.

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 boat 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.

Tucked between Hilton Head Island and Savannah, and accessible only by boat, Daufuskie Island is a real gem. This private 4.5 hour Daufuskie Island trip provides a glimpse into a fascinating chapter of Lowcountry history on the undeveloped side of the island. Visit local artisans and learn the rich history of the Native Americans, European settlers, the cotton trade, and the Gullah culture. We encourage you to wear weather-appropriate clothing and bring water, snacks, and sunscreen.

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 everyone, combining comfort, style and function to create the perfect atmosphere for a great experience on the water. This rental allows you to see Hilton Head by water. Whether you want to anchor in a quiet cover or see the sites this boat is perfect for your group. The destinations pre-marked includes Daufuskie Island, Harbourtown Light House, Sandbar, Skull Creek Boat House and Fishing Holes.

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.

Bring the whole family to watch the sunset at Hilton Head on this new, private boat tour. You’ll easily meet your captain in plenty of time to get on the water before sunset. Feel free to rent this boat for parties, birthdays, anniversaries, or other functions, as the boat was made to host entertaining events.

Set out on a 2-hour private cruise from Hilton Head Island, South Carolina, in search of Atlantic bottlenose dolphins. Board your vessel and cruise past the Harbour Town Lighthouse and Daufuskie Island. While you sail, watch for playful dolphins and other local wildlife like bald eagles.

End another wonderful day on Hilton Head Island with a private sunset cruise around its waterways. Board your vessel at Broad Creek Marina and enjoy a relaxing cruise customized to your group's interests. Sail along Calibogue Sound and see the Harbour Town Lighthouse while watching for local wildlife.

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.

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 boats. In just two hours, you’ll enjoy guaranteed dolphin sightings, shaded seating, and plenty of room so kids, parents, and grandparents all feel comfortable. Every trip is flexible — spend more time with dolphins, visit a quiet sandbar, or simply enjoy cruising the Lowcountry waterways. Guided by friendly, USCG-certified captains who know how to keep all ages engaged, this is the rare activity that makes three generations smile at once. With over 900 five-star reviews, families say this is the highlight of their Hilton Head vacation — the kind of bonding experience you’ll remember for years.

This trip is completely customizable and based on your preferences. At Outside Hilton Head, we specialize in unforgettable outdoor adventures in the Lowcountry. Our team of expert guides, including master naturalists and USCG licensed Captains, is dedicated to providing exceptional experiences. From kayaking and paddleboarding to dolphin tours and custom watersport adventures, we offer something for everyone.