Top Hilton Head Island Cruises & Sailing - page 2

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.

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.

***Booking 1 person, is booking 1 boat for up to 6 people *** Experience a breathtaking private sunset dolphin tour on Hilton Head Island! Watch dolphins, stunning sunsets, and magical fireworks while cruising the scenic waterways. Perfect for unforgettable memories! Embark on an unforgettable adventure with our Private Sunset & Fireworks Dolphin Tour on Hilton Head Island, SC! This exclusive experience offers front-row seats to breathtaking sunsets and a spectacular fireworks show, all while encountering playful dolphins in their natural habitat. Cruise through scenic waterways as the evening sky transforms into a canvas of colors. Ideal for romantic getaways, family outings, or celebrations, this private tour guarantees magical moments on the water. Witness Hilton Head's natural beauty like never before!

Enjoy an intimate sunset sailing experience aboard a cozy vessel with only six guests. Glide through the picturesque waters of Port Royal Sound as the sun dips below the horizon, painting the sky with brilliant colors. Keep an eye out for dolphins and coastal birds while feeling the gentle evening breeze fill the sails. Whether you prefer to take the helm and learn the basics of sailing or simply unwind with a drink, this serene sail is perfect for friends and couples alike, offering a unique way to experience Hilton Head Island's beauty. - 2-hour sunset sail with a maximum of six guests - Watch the sunset over Port Royal Sound - Spot dolphins and coastal wildlife - Hands-on sailing or relax on deck - Ideal for all skill levels and special occasions

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.

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.

Looking for a more personal sailing experience without booking an entire private charter? The Afternoon Public Sail is the perfect balance. With a maximum of just six guests onboard, you’ll enjoy an intimate, relaxed atmosphere. It’s a shared experience that still feels special, and it keeps the price lower than a private sail. Join us for a 2-hour afternoon sail spotting dolphins, coastal birds, and other local wildlife. Once the sails are raised, feel the power and excitement as the wind fills the sails and the boat heels—this is authentic, hands-on sailing at its best. The experienced captain encourages guests to be as involved or relaxed as they’d like. Discover why sailing is the best way to enjoy the coast—small group, smooth sailing, and unforgettable views. *Enjoy a 2-hour afternoon sail with a maximum of six guests *Spot dolphins and coastal wildlife while sailing *Hands-on sailing experience or relax on deck *Perfect for all skill levels in a tranquil, intimate setting

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.

Go sailing in Hilton Head Island with this private dolphin-watching tour. Motor out to Port Royal Sound and then put up the sails for a true sailing adventure. Keep an eye out for a variety of wildlife including birds, dolphins, manatees, and sting rays during this boat tour. Maximize time with a private tour and learn about sailing from your guide.

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.

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.

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.

Looking for an intimate sunset sailing experience without booking an entire private charter? Your 2-Hour Sunset Public Sail offers the perfect balance. With a maximum of just six guests onboard, you’ll enjoy a peaceful, uncrowded atmosphere that feels private and special—without the cost of a private sail. Set sail through the stunning waters of Port Royal Sound as the day winds down. Watch the sky transform with vibrant sunset colors while keeping an eye out for dolphins, coastal birds, and other local wildlife. Once the sails are raised, feel the evening breeze fill the sails as the boat gently heels—true sailing at its most serene and memorable. Your experienced captain welcomes guests to be as hands-on or as relaxed as they choose. Help trim the sails, learn the basics of sailing, or simply sit back with a drink and take in the breathtaking Lowcountry sunset. This sunset sail is perfect for couples, friends, family and anyone looking to experience Hilton Head Island from the water.

Set sail on a private charter boat for up to 14 passengers to discover Hilton Head's waterways in style. Your captain skillfully navigates and unveils the wonders along the shores so you can relax and enjoy the surrounding beauty. This private tour offers a personalized experience tailored to your group.

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.

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.

Rent a 17-passenger boat for an unforgettable adventure on the Lowcountry waters. With your own captain, enjoy personalized activities tailored to your group's interests. Our USCG licensed captains are also interpretive naturalists, sharing fun facts and stories about the area's unique ecology. Perfect for bachelor/bachelorette parties, family reunions, or any group looking to celebrate in style. - Enjoy a private boat experience with your own captain - Tailor activities to your group's preferences for a custom adventure - Learn about the Lowcountry from our knowledgeable captains - Ideal for celebrations, family gatherings, or group outings

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.

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.

This is an exclusive private trip where your group of up to 24 passengers (including all infants and children) will get to enjoy our Dolphin & Nature Tour. Your boat is a comfortable pontoon boat with cushioned seats, a full top for shade and a restroom on board. Your boats are all certified by the Coast Guard to meet the highest safety ratings. During the tour you will get to enjoy beautiful views of Broad Creek only seen from our local waters. You will also water Atlantic bottlenose dolphin in their natural habitat as well as a variety of marine life and shore birds.

Join us for a magical journey on this Private Disappearing Island Tour, where you’ll enjoy one of our renowned dolphin encounters. Get up close and personal with these incredible creatures, learning their names, unique behaviors, and playful habits. Our expert captains and guides will keep you entertained with fascinating stories, lively music, and plenty of laughter. And for the little ones? Expect a day full of surprises and delights! But the adventure doesn’t stop there. Our boat will gently glide right on the sands of the Disappearing Island, giving you the chance to step off and explore its natural wonders. Wander through a treasure trove of shells, including delicate sand dollars and vibrant starfish. Don’t worry, you’ll have the chance to learn about every fascinating discovery along the way. Staying true to our eco friendly values, we always leave living creatures undisturbed in their natural habitat.

Voted Best of Hilton Head year after year, we welcome you to explore Hilton Head by boat! The new Luxury Group Pontoon is recommended for parties of 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 scream 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 area or see the sites, this boat is perfect for your group. The destinations pre-marked include Daufuskie Island, Harbourtown Lighthouse, Sandbar, Skull Creek Boathouse, and Fishing Holes.

Discover the ultimate Hilton Head Island experience with our Sunset Mini Boat Dolphin Tour! Glide across the sparkling waters on a thrilling mini boat, perfect for an up-close and personal dolphin encounter. As the sun dips below the horizon, witness the breathtaking hues of orange, pink, and purple painting the sky, while playful dolphins leap and swim alongside you. Our expert guides provide fascinating insights about the local ecosystem, making it both educational and enchanting. Ideal for families, couples, and photographers, this tour offers small-group intimacy, ensuring every guest enjoys spectacular views.

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.