Top Hilton Head Island Cruises & Sailing

Hilton Head is known for its stunning sunsets over the Lowcountry salt marsh, and this dinner cruise from Harbour Town sails up Bull Creek as the sun goes down. Along the way, enjoy a three-course, chef-prepared dinner. Cruise back after dark, when Harbour Town's red-and-white striped lighthouse is lit up above the marina.

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.

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.

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, making this the ultimate way to sightsee and keep kids entertained. This family-friendly cruise has a choice of several departures in the morning and afternoon, making it easy to fit into your schedule.

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.

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.

Experience Hilton Head’s wildlife-rich Broad Creek Estuary on this kayaking tour designed for all ages and experience levels—no need for prior experience or your own equipment. Glide through calm salt-marsh waters and keep an eye out for wild bottlenose dolphins, as well as manatees, sea turtles, otters, and shorebirds. Paddle past waterfront homes and learn about the local history and ecology from your guide.

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 atmosphere, it’s a perfect way to unwind and enjoy the beauty of the Lowcountry. Reserved seating, both indoor and shaded outdoor, ensures comfort for everyone, and $10 bottomless mimosas make it an extra special way to start your Sunday.

Climb aboard at Palmetto Bay Marina and kick off your evening Lowcountry-style. This two-hour Sunset Lowcountry Boil Cruise mixes everything Hilton Head does best—good food, good views, and that salty “I’m on vacation” feeling. As we drift through the calm waters, your crew will serve up a classic Lowcountry boil piled high with shrimp, sausage, corn, and potatoes —fresh and flavorful served with specialty butters and seasoning. While you feast, you’ll cruise past local wildlife, beautiful waterways, and the hidden corners of Hilton Head that look their best from the water. Then comes the main event: sunset. Watch the sky flip through golds, pinks, and fire-orange as we cruise back toward the marina. Food, views, and a true Lowcountry evening—served hot and on the water.

Increase your odds of seeing dolphins in the wild on this dolphin watching cruise from Hilton Head. Sail out from easy-to-find Palmetto Bay Marina at your selected departure time: admire views of the shore, look for wildlife, and learn about the local ecosystem. Plus, take a quick stop to look for shells, starfish, and sand dollars at “Disappearing Island,” a strip of land only accessible at low tide.

Hilton Head Island is known as one of North America’s best spots for watching dolphins in the wild. Get out on the water and take in amazing views of these intelligent, playful creatures during this private boat tour. With a Lowcountry Master Naturalist as your captain and guide, you’ll learn all about the ecology of Hilton Head while watching the dolphins along with other wildlife including rays, sharks, and sea turtles. Just your group (up to six passengers) cruising the waters, watching dolphins eating, playing, and socializing.

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.

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 birds that call the tidal marsh home. Once on Page Island, you'll be launched in our comfortable kayaks and led on a scenic paddle through the Daufuskie Island nature web. Learn all about the local ecosystem and the critters that live there.

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.

If you’re keen to spend some time exploring Daufuskie Island independently, then this is an easy and stress-free option. A great alternative to sightseeing tours, this transport package gives you the freedom to plan your own itinerary. Simply travel on a ferry from Hilton Head to Daufuskie Island, then choose how you spend your day. Possibilities include golf cart rental, or visiting the favorite foodie hotspot of Daufuskie Crab Company.

Cruise along the coastal waterways of Hilton Head Island aboard a private boat during this sunset cruise. Board your vessel and see as the sky changes from blue to shades of orange and pink as the sun begins to set. While you sail, keep your eyes peeled for local wildlife like dolphins, turtles, and even otters.

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.

Explore the waters around Hilton Head, South Carolina aboard your own vessel during this morning excursion. Meet your dedicated captain and sail to Port Royal Sound to begin your tour. Take in the views of Hilton Head, Pickney Island, Paris Island, and many other landmarks while you keep your eyes peeled for playful dolphins that play in the wake of the boat.

Search for crabs alongside marine science students on this Lowcountry crabbing tour from Hilton Head. As you sail out on the Lowcountry’s famous salt marshes, your knowledgeable guides share tons of information about the rich local ecosystem and the wildlife that calls it home—see some of it for yourself, including whatever you pull up in your crabbing pots. Take home some of your catch if you get any.

Embark on the extraordinary Mini Boat Disappearing Island Tour on Hilton Head Island, SC, and unlock a hidden paradise that only reveals itself at low tide. This one-of-a-kind adventure takes you on a thrilling boat ride to a secluded island that vanishes beneath the waves as the tide rises. Explore pristine beaches, observe unique wildlife, and enjoy unparalleled views of the Lowcountry coastline. Perfect for nature lovers, adventure seekers, and those looking to experience the magic of the ocean in an entirely new way, this tour offers a rare opportunity to witness one of Hilton Head’s most fascinating natural wonders.

Discover the waterways of Hilton Head with this private pontoon boat rental. Bring a group of up to 10 people for a scenic cruise along Skull Creek and out to the mouth of the Atlantic Ocean. Keep an eye out for Atlantic bottlenose dolphins as you explore Cooper River, May River, and Daufuskie Island. Customize the itinerary according to your interests.

Set out on a private adventure on Hilton Head Island’s waterways with this pontoon boat rental. Receive professional orientation on navigating and then choose an itinerary that matches your interests. Keep an eye out for dolphins as you cruise along Skull Creek and travel to the mouth of the Atlantic Ocean. Pontoons can comfortably fit up to 10 people.

See Hilton Head from a fresh perspective with this half-day private pontoon boat rental. Set out on the scenic waters of Skull Creek and keep an eye out for Atlantic bottlenose dolphins. Personalize the itinerary according to your interests and check out Cooper River, Daufuskie Island, or Palmetto Bluff. Pontoon boats can accommodate up to 10 people in your private party.