The 14 Best Cruises And Boat Tours in Hilton Head Island
Hilton Head Island isn’t just about golf courses and beaches—it’s also a prime spot for water-based adventures. Whether you’re into playful pirate escapades, spotting dolphins in their natural habitat, or enjoying a sunset from the deck of a classic yacht, Hilton Head offers something for every boater’s fancy. Some tours, like the Pirate Ship Adventure and Black Dagger Pirate Cruise, turn kids into tiny pirates for a fun, interactive experience. Others, like the Sunset Dolphin Cruise and Dolphin Nature Cruise, focus on wildlife and scenic views, perfect for relaxing afternoons. For those interested in sailing history, the America’s Cup Yacht and Sailing Yacht Cruise provide a taste of competitive and classic sailing.
In this guide, we’ll walk through the top 14 boat tours in Hilton Head, highlighting what makes each one special. From family-friendly adventures to private luxury cruises, we’ll give you the details on what’s included, what to expect, and who it’s best suited for. Planning your water outing can be tricky with so many options, but this will help you find exactly the experience that fits your style and budget.
Quick Overview
This list covers a variety of water adventures—pirate-themed cruises perfect for families, wildlife and dolphin-watching tours, scenic sunset cruises, and luxury private boat charters. Prices range from around $41.99 for a quick pirate adventure to over $549 for a private sunset experience. Durations are typically between 1.5 to 2 hours, with some offering longer evening or private options. Whether you want a lively, interactive experience or a peaceful sail with wildlife sightings, Hilton Head’s boat tours cater to all ages and preferences.
1. Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
Starting with a bang, this pirate adventure aboard the Black Dagger turns kids into pirates while the adults enjoy the scenery. The crew provides pirate costumes and lessons, and everyone joins a treasure hunt around Hilton Head waters. The $41.99 price is quite reasonable for 1 hour 30 minutes of family fun, especially since multiple departures make it flexible for your schedule. Kids love the interactive elements like water cannon battles, face painting, and tattoos, while parents appreciate the lively atmosphere.
This cruise is very well-reviewed, with families noting that everyone—regardless of age—had a blast. One reviewer said, “We all said it was our most fun experience,” emphasizing how inclusive and engaging it is. The crew’s energy and attention to detail make it stand out. Bottom line: Perfect for families with young children looking for a memorable, playful outing.
2. Hilton Head Island: Sunset Dolphin Cruise
For lovers of wildlife and stunning scenery, this $48, 1.5-hour sunset cruise is a highlight. The focus here is on spotting dolphins in the wild, with the captain providing informative narration about local wildlife and the history of Hilton Head. The guaranteed dolphin sightings and the chance to watch the sun dip behind the islands of Daufuskie and Hilton Head make this a peaceful yet exciting experience.
Guests rave about the enthusiasm of the crew, with comments like “Very informative” and “Great crew, amazing experience.” Snacks and drinks are available for purchase, so you can relax and soak in the view. This trip suits nature lovers who appreciate a tranquil evening on the water without too much activity—ideal for couples or anyone looking to unwind.
3. Hilton Head Island: Pirate Cruise on the Black Dagger
Another pirate-themed option, this $42, 1.5-hour cruise focuses on interactive fun and storytelling. You’ll learn pirate talk, get a temporary tattoo, and participate in a water cannon battle against Stinky Pete, the tiny pirate. The highlight is the treasure hunt for stolen sunken treasure, which involves finding a key and winning a game.
Rated 4.9/5, guests describe it as “marvelous and very entertaining,” especially praising the staff and crew’s energy. It’s best suited for families with children who love pirates and games, but adults can join in the fun too. The immersive nature of the cruise adds lots of value for a modest price.
Bottom line: A lively, interactive pirate voyage packed with humor and adventure—great for making lasting memories.
4. America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head
This $52.95 1 hour 30 minutes sail offers a peaceful alternative to high-energy adventures. Board a 39-foot sailboat that once competed in the America’s Cup, and enjoy gliding through calm waters with views of the Harbour Town Lighthouse and Marina. The experience is ideal for those wanting a serene, scenic cruise with the chance to try sailing themselves under the guidance of the crew.
Guests mention the attentive crew and the opportunity to relax with a cold beer or refreshing beverage. It’s suited for sailing enthusiasts or travelers seeking tranquility and scenic beauty. Keep in mind, it’s less action-packed but highly authentic for lovers of classic sailing.
Bottom line: Perfect for a peaceful, scenic sail with a touch of sailing history.
5. Hilton Head Sunset Dolphin Watching Cruise
At $47.65, this 1 hour 30 minutes cruise specializes in dolphin sightings at sunset. The naturalist narration enhances the experience, and the frequent dolphin sightings make it one of the best options for wildlife lovers. As the sun sets, the water turns shimmering and the light creates perfect photo opportunities, including the iconic Haig Point lighthouse.
Reviewers highlight the informative captain and beautiful scenery, though some wished for more dolphin sightings. It’s ideal for romantic couples, small groups, or anyone wanting a blend of wildlife viewing and scenic beauty with a relaxed atmosphere.
Bottom line: A beautiful, relaxed way to combine wildlife watching with a memorable sunset.
6. Hilton Head Island Dolphin Watching Nature Cruise
This $42.35, 1.5-hour cruise emphasizes wildlife encounters and landmarks, sailing through Calibogue Sound and Atlantic Ocean. Your guide provides live narration as you look out for dolphins, egrets, herons, and other creatures. The route covers Bull Island, Haig Point Lighthouse, and other scenic spots.
Rated 4.5/5, guests love seeing dolphins up close and the informative commentary. It’s suitable for nature buffs and families wanting a relaxed, educational experience. The boat is comfortable, and the focus on wildlife makes it a good value for those interested in natural history.
Bottom line: A friendly, educational cruise that combines wildlife with scenic coastal landscapes.
7. Hilton Head Island: America’s Cup Sailing Yacht Cruise
For a blend of racing history and sailing skill, this $53, 1.5-hour trip aboard the Stars & Stripes yacht offers a unique perspective. The crew shares insights into America’s Cup racing as you sail past Hilton Head’s scenic coastline. It’s a hands-on experience, with the chance to learn how to sail and watch for dolphins.
Guests praise the friendly crew and the lovely weather during their trips. It’s best for sailing enthusiasts or those curious about competitive sailing. The focus is on education and fun, making it appealing for adults and teens alike.
Bottom line: A chance to experience what it’s like to race in the America’s Cup, combined with scenic views and hands-on sailing.
8. Private Hilton Head Sunset Boat Cruise (Up to 14 Passengers)
At $596.49 for up to 14 guests, this private sunset cruise offers an exclusive experience. You’ll sail around Skull Creek while enjoying personalized commentary and wildlife watching—possibly dolphins, otters, and turtles. The customized route allows you to tailor your experience, making it perfect for special occasions.
Guests rave about Captain Steve’s hospitality and the spectacular sunset views. It’s suited for families, couples, or groups celebrating an event. Bring your own drinks and snacks to enhance the experience.
Bottom line: An intimate, flexible option for those wanting privacy and personalized service on Hilton Head’s waters.
9. Hilton Head Island: Dolphin Cruise & Nature Tour
This $45, 1.5-hour tour offers a combination of wildlife viewing and scenic cruising. Your naturalist captain guides you through the waters, with guaranteed dolphin sightings and insights into the local ecosystem. The route covers key landmarks like the Harbor Town Lighthouse and Savannah River Bridge.
Guests appreciate the friendly captain and the educational commentary. It’s well-suited for families and anyone interested in nature and marine life.
Bottom line: A balanced cruise of wildlife and scenery, ideal for those wanting entertainment and education.
10. Hilton Head Morning Dolphins & Donuts Cruise
Starting bright and early, this $55 morning cruise combines wildlife spotting with breakfast treats. You’ll cruise past landmarks like the Harbourtown lighthouse while trying to catch dolphins and other animals in action. The small group ensures personal attention, and the snacks included make it a relaxed start to your day.
Guests love the friendly captain Bev and the opportunity to see dolphins, often within minutes. It’s ideal for early risers who want an active, engaging morning outing.
Bottom line: A lively morning cruise combining wildlife, scenic views, and a tasty breakfast—great for early risers.
11. Hilton Head Island: Dolphin Nature Cruise
This $42, 1.5-hour trip guarantees dolphin sightings with live narration from your naturalist captain. The cruise explores the headwaters of the Atlantic, with plenty of wildlife in view, including jellyfish and herons. The boat provides a spacious, comfortable ride.
Reviewers mention good value and educational content, making it a solid pick for families or wildlife enthusiasts. The focus on natural habitat makes it more laid-back than active.
Bottom line: A reliable, fun wildlife cruise with guaranteed dolphin encounters.
12. Hilton Head Sunset Dinner Cruise
Enjoy a 3-course dinner on this $106, 2-hour cruise that combines delicious food with scenic views of the sunset. The menu is crafted by award-winning chefs, and you can choose outdoor or indoor seating. As the boat glides through Intracoastal waters, keep an eye out for dolphins and the sunset over Harbour Town.
Guests praise the delicious meal and the calm atmosphere, though parking can be tricky, so arrive early. It’s suited for romantic couples or those celebrating a special occasion.
Bottom line: A relaxing way to enjoy dinner, sunset views, and possibly dolphins in a refined setting.
13. Hilton Head Sunset Dinner Cruise
This $106, 2-hour cruise on the Spirit of Harbour Town presents a classic dinner experience. The three-course meal features local ingredients like blackened mahi mahi or roasted pork, with stunning sunset views over the calico waters. Live music adds to the ambiance, and the cruise offers a relaxed, elegant atmosphere.
Guests note the delicious food and beautiful scenery, but recommend arriving early for parking. It’s perfect for foodies and romantic evenings.
Bottom line: A refined dinner cruise that combines local cuisine with memorable sunset scenery.
14. Hilton Head: Private Sunset Cruise
Finally, for a truly personalized experience, this private sunset cruise costs $549 for your group of up to 14. Captain Bill or Sean will craft your route, and you can bring your own drinks and snacks. Watch the sun dip below the horizon, enjoying intimate views and wildlife sightings.
Guests rave about the personalized service and spectacular sunset views. One reviewer said, “Captain Sean was amazing,” emphasizing the tailored experience.
Bottom line: Best for couples or groups celebrating special events who want exclusivity and total control over their cruise.
How to Choose Your Perfect Hilton Head Boat Tour
When selecting among these options, consider your budget, group size, and interests. If your family loves pirates, the Black Dagger adventures are a must. For wildlife enthusiasts, multiple dolphin cruises—like the Sunset Dolphin Cruise or Dolphin Nature Cruise—offer guaranteed sightings and educational narration. For romantic evenings, the Sunset Dinner Cruises provide scenic beauty and fine dining, while the private sunset cruise caters to those seeking intimacy.
Booking in advance is wise, especially during peak season, and check the departure times to match your schedule. Some tours, like the private cruise, fill quickly, so plan ahead.
Final Thoughts
Hilton Head Island offers a diverse palette of boat trips, from lively pirate adventures to tranquil wildlife sightings and elegant dinner cruises. For families, the Pirate Ship Adventure and Pirate Cruise are perfect for young explorers, while couples seeking serenity might prefer the Sunset Dolphin Cruise or Luxury Private Sunset Cruise. History buffs and sailing enthusiasts will appreciate the America’s Cup Yacht and Sailing Yacht experiences.
No matter your interests, these tours promise a memorable way to see Hilton Head from the water. Early booking is recommended—these experiences fill fast, especially in summer. Pack your camera, bring your curiosity, and get ready for a water-filled adventure.