Top Hilton Head Island Tours, Sightseeing & Cruises - page 5

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.

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.

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.

Explore the captivating history of Beaufort on a charming 50-55 minute horse-drawn carriage tour. Discover the elegance of the past as you glide past moss-covered Live Oaks, stunning Antebellum homes, historic churches, and iconic movie sites, all narrated by a knowledgeable guide. This fully narrated experience provides insight into Beaufort's unique charm and rich history, making it an excellent choice for families and history buffs alike. - Duration: 50-55 minutes of narrated history - Family-friendly; children under 3 ride for free - Reservations recommended for this unique journey

Voted Best of Hilton Head year after year, Hilton Head Island Boat Rentals welcomes you to explore Hilton Head by boat! The new 2024 Luxury Group Pontoon is recommended for parties 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 screams 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 cover or see the sites this boat is perfect for your group. The destinations pre-marked includes Daufuskie Island, Harbourtown LightHouse, Sandbar, Skull Creek BoatHouse and Fishing Holes.

Voted Best of Hilton Head year after year, Hilton Head Island Boat Rentals welcomes you to explore Hilton Head by boat! The new 2024 Luxury Group Pontoon is recommended for parties 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 screams 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 cover or see the sites this boat is perfect for your group. The destinations pre-marked includes Daufuskie Island, Harbourtown LightHouse, Sandbar, Skull Creek BoatHouse and Fishing Holes.

Uncover the hidden gems of Beaufort on this immersive 5-6 hour tour led by a native guide. Visit breathtaking sites including Frampton Plantation House, The Sands beach, the historic Old Sheldon Church ruins and more. Enjoy captivating stories about the area's history and wildlife, with opportunities to spot local plants, birds, and even collect shark teeth. This excursion is perfect for families and nature lovers alike, offering a unique glimpse into the Lowcountry's beauty. - 5-6 hour guided excursion exploring Beaufort's natural wonders - Visit iconic locations like Downtown Beaufort’s Historic District and Frampton Plantation House - All admission fees, water, sunscreen, and bug spray included - Optional snacks or lunch available for purchase

Explore Hilton Head in style with the 26” Mid Cross Bar Beach Cruiser, perfect for leisurely rides along the beach and town. This comfortable unisex bicycle is designed for easy mounting and dismounting, accommodating riders from 5’2” to 6’2” and a maximum weight of 250 lbs. Ideal for paved paths, the cruiser features smooth-rolling tires and a comfy saddle for a relaxed ride. Each rental includes a lock for security, and while baskets are not included by default, they can be added for convenience. - Enjoy a stable and easy-to-ride cruiser for all skill levels - Perfect for casual beach and town exploration - Includes a lock for added security with rentals - Optional baskets available for carrying personal items or beach gear

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

This trip is completely customizable and based on your preferences. At Outside Hilton Head, we specialize in unforgettable outdoor adventures in the Lowcountry. Our team of expert guides, including master naturalists and USCG licensed Captains, is dedicated to providing exceptional experiences. From kayaking and paddleboarding to dolphin tours and custom watersport adventures, we offer something for everyone.

Looking for a more personal sailing experience without the cost of a private charter? Our Afternoon Public Sail is the perfect balance. With a maximum of just 6 guests onboard, you’ll enjoy an intimate, relaxed atmosphere. Aboard our newest and largest sailboat. Join us for a 2-hour afternoon sail spotting dolphins, 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. Our 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 an intimate sailing experience with only 6 guests on board - Spot dolphins and wildlife while sailing through Port Royal Sound - Participate in sailing activities or relax as you prefer - Perfect for small groups looking for a unique afternoon adventure

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.

Enhance your beach day with the Backpack Beach Chairs and Umbrella Set from Island Cruisers, a trusted family-owned business since 1985. This convenient rental allows you to relax comfortably while enjoying the sun and surf. With free island-wide pick-up and delivery, you can easily focus on your beach activities without the hassle of transporting equipment. Perfect for families or groups looking to enjoy a day at the beach. - Enjoy a comfortable beach experience with two backpack chairs and an umbrella - Free island-wide pick-up and delivery for your convenience - Ideal for families and friends planning a beach day - Explore additional rentals like coolers and beach games for even more fun

Explore Hilton Head effortlessly with the 26” Electric Beach Cruiser. This electric bike is designed for comfort and convenience, featuring an integrated motor, hand brakes, and a wide cruiser seat for a smooth ride. Riders can choose between pedal assist or throttle operation, reaching speeds up to 20 mph, which makes it perfect for longer distances or cruising against the wind. - Ideal for easy and enjoyable exploration of Hilton Head - Suitable for riders 5’ and taller, up to 250 lbs - Choose between pedal assist and throttle operation - Equipment trailer available for added convenience

Unforgettable 60-minute Private Hilton Head Boat Tours! Suitable for All Ages. Ready to make memories that last a lifetime? Book a Hilton Head boat tour for your friends and family today! Cruising through the Low Country Waters, let us show you stunning scenery and wildlife on our private Hilton Head Island dolphin tours. Hilton Head Island is located in the perfect location for regular sightings of Atlantic Bottlenose Dolphins swimming freely in their natural habitat alongside seabirds and more! You may also see salt marshes, gated communities, historic mansions, and twinkling marina lights, depending on your chosen tour

Voted Best of Hilton Head year after year, we welcomes you to explore Hilton Head by boat! The new 2024 Luxury Group Pontoon is recommended for parties 8 or more. It is without a doubt the best rental boat on Hilton Head Island for large groups. The quality and craftmanship of this Bennington screams 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 cover or see the sites this boat is perfect for your group. The destinations pre-marked includes Daufuskie Island, Harbourtown Light House, Sandbar, Skull Creek Boat House and Fishing Holes.

What sets this experience apart is the way it adapts — not just to you, but to the moment itself. Group sizes are intentionally limited, creating a relaxed, unhurried atmosphere with personalized guidance throughout. Perfect for couples, families, and anyone who wants more than just snapshots Transportation is provided between select spots, allowing you to experience a variety of settings without the guesswork. Rather than following a fixed route, each expedition is shaped in real time based on light, weather, and timing. Conditions on Hilton Head Island can change quickly, and knowing where to go — and when — makes all the difference. You’ll be taken to locations chosen specifically for their photographic potential that day, mostly lesser-known areas most visitors never encounter. It’s not just about seeing the island — it’s about experiencing it with intention, and coming away with something lasting.

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.

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.

This trip is completely customizable and based on your preferences. At Outside Hilton Head, we specialize in unforgettable outdoor adventures in the Lowcountry. Our team of expert guides, including master naturalists and USCG licensed Captains, is dedicated to providing exceptional experiences. From kayaking and paddleboarding to dolphin tours and custom watersport adventures, we offer something for everyone.

This is our most popular boat trip! Hilton Head and surrounding areas boast a large and active population of Atlantic Bottlenose Dolphin, with great viewing opportunities year-round! Join us for a PRIVATE 90-minute Sunset dolphin cruise! We will explore the Broad Creek Wildlife Area, Calibogue Sound and nearby marshes. Your Captain will guide you to points of interest, while explaining the unique connections between history, culture and nature in the Lowcountry. This tour is great for families!

***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!

Rent a 16-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

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