Top Hilton Head Island Cruises & Sailing

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. Roasted Pork Loin - Buttermilk Whipped Potatoes, Peppercorn Sauce, 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*

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.

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.

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.

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.

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!

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.

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.

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.

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.

Your comfortable passenger ferry offers the shortest route from Hilton Head to Daufuskie, with a smooth 30-minute ride dock to dock. No long crossings. No complicated transfers. Just a quick, scenic trip across the water that gets you to the island faster — and gives you more time to explore. Designed with families in mind, our boat features spacious seating, shade, and a stable ride that’s comfortable for all ages. Whether you're traveling with young kids, grandparents, or a group of friends, our crew makes boarding simple and stress-free. Choose the most convenient departure point, the fastest crossing, and a family-friendly experience that makes your day seamless from start to finish.

Experience the magic of a Sip & Sunset - BYOB Adults only Dolphin Cruise on Hilton Head Island, where breathtaking coastal views meet great music for an unforgettable evening on the water. As the sun dips below the horizon, casting vibrant hues across the sky, relax aboard this fun and comfortable cruise while enjoying a curated music list. Glide through the scenic waterways of the Lowcountry, spotting playful dolphins and taking in panoramic views of the island’s pristine coastline. Whether you’re celebrating a special occasion or simply unwinding after a day of exploring, this Hilton Head sunset cruise offers the perfect blend of relaxation, fun & coastal charm.

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 is the best as you get everything all in one! You will see local wildlife, beautiful stately waterfront homes, breathtaking water views and end the evening with a wonderful sunset. The local wildlife you will see are Atlantic bottlenose dolphin and a variety of shorebirds. What better way to spend the evening?

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.

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.

Enjoy a delicious Latin-inspired menu freshly prepared by the award-winning chefs of the Sea Pines Resort, featuring bold flavors and coastal flair. Think zesty, savory, and perfect for pairing with your favorite drink—and speaking of drinks, enjoy happy hour pricing on cocktails, wine, and beer throughout the entire cruise! As we cruise through the beautiful intracoastal waterways, you’ll be treated to stunning Lowcountry views, sightings of playful Atlantic bottlenose dolphins, and a narrated tour highlighting the rich history of Hilton Head and nearby Daufuskie Island—all with a refreshing drink in hand. Whether you’re celebrating a birthday, date night, or just want to unwind, this early evening cruise offers a laid-back vibe with gorgeous daylight views from start to finish.

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.

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.

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.

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.

Glide through the tranquil waters of Hilton Head's Broad Creek Estuary on a captivating kayak tour that brings you face-to-face with playful dolphins and other fascinating wildlife. For 25 years, our expert guides have led adventurers of all ages through this serene environment, sharing entertaining stories and insights about the local ecosystem. As you paddle alongside these intelligent creatures, keep an eye out for manatees, otters, and a variety of beautiful bird species, making every paddle unique. The area we paddle through is the favorite feeding grounds for dolphins in Hilton Head which makes it more likely that you'll be paddling with dolphins than any other kayaking area in Hilton Head. This is the place to be and no other kayak company on the island has direct access to this favorite spot for the dolphins to feed and play! This family-friendly experience promises not only fun but also unforgettable memories in the heart of nature.

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.