Top Hilton Head Island Cruises & Sailing

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Come aboard the Spirit of Harbour Town for a 3 course dinner cruise prepared by the chefs of Sea Pines Resort *SHARE YOUR MEAL PREFERENCES AT CHECKOUT IN THE SPECIAL REQUIREMENTS SECTION* APPS Heirloom Tomato Panzanella Salad - Greens, Tomatoes, Mozzarella, Cucumbers, Focaccia, Basil, Apple Cider Vinaigrette ENTREE (Select 1) 1. Berbere Spiced Pork Loin - Buttermilk Whipped Potatoes, Mango Chutney, Shaved Fennel Slaw 2. Blackened Mahi Mahi -Buttermilk Whipped Potatoes, Pineapple Salsa, Shaved Fennel Slaw 3. Roasted Chicken Breast - Buttermilk Whipped Potatoes, Chimichurri, Shaved Fennel Slaw 4. Pasta Primavera - Fresh Vegetables, Olive oil, Garlic, White Wine, Herbs DESSERT (Select 1) 1. Sunset Key Lime Pie - Raspberry Coulis, whipped cream 2. Chocolate Torte - Raspberry Coulis, whipped cream KIDS (3-12) 1. Chicken Tenders - Mashed Potatoes and Fresh Vegetables 2. Chicken Alfredo pasta - Parmesan Cream, Roasted chicken *Children's Menu comes with salad & dessert choice*

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.

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.

As you join us in the golden hour, you will get to see a beautiful sunset over the water as well as some great wildlife. We will explore the waters of Broad Creek and the Calibogue Sound in search of dolphins. Our tour guide knows most of our local dolphins by name and will introduce you to them as we come across them. We will teach you how to tell them apart, too! Not only will you get to know the dolphins as individuals, but you will also learn about bottlenose dolphins as a species and how they adapt to our local lowcountry ecosystem. With this tour, you will get 90-120 minutes to relax on the water and take in the natural sites. Our boat holds up to 24 people and sits low to the water for optimal viewing on this dolphin watching cruise.

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

Go sailing at sunset in Hilton Head Island with this private dolphin-watching tour. Climb aboard a sailboat and cruise out into Port Royal Sound during this tour. Keep an eye out for wildlife including dolphins, manatees, sting rays, and more. Learn about sailing if you choose or just sit back and enjoy the ride, complete with sunset views.

See Hilton Head Island from a fresh perspective with this private sunset dolphin tour. Meet your boat captain at Palmetto Bay Marina for a private tour that can accommodate up to six people. Keep an eye out for Atlantic bottlenose dolphins as you learn about their feeding patterns, social behavior, and more. Admire sunset views from the deck of the boat.

Explore beyond Hilton Head with a half-day excursion to Daufuskie Island. Climb aboard a ferry for a scenic ride with this round-trip ticket. Learn about local wildlife from a naturalist boat captain during the trip. On Daufuskie Island, choose between a relaxed lunch, a golf cart rental, or a scenic stroll. After a few hours, board the ferry again for the return journey.

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 forget to bring your camera for photos of the most incredible view of the lowcountry sunset. This tour is one-of-a-kind and memorable for all ages!

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.

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.

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.

Set sail on a thrilling 2-hour journey with an exclusive private charter boat, designed for up to 14 passengers. Discover the enchanting waterways of Hilton Head in style. Onboard your customized 25-foot (7.6-meter) boat, an expert captain will skillfully navigate and unveil the wonders hidden along the shores. Sit back, relax, and relish in the unparalleled beauty that surrounds you. Your perfect aquatic adventure in Hilton Head awaits.