20 Best Private Drivers In Hilton Head Island

Private drivers on Hilton Head Island are a practical choice for reliable transportation and guided experiences. Local operators offer well-organized tours, including dolphin watching excursions and sunset cruises aboard comfortable vessels. The best services are family-run operations that maintain their boats meticulously and provide clear communication.

We especially appreciate the pontoon rentals that combine luxury with adventure – perfect for families wanting to explore the island’s waterways at their own pace. The wheelchair-accessible options show thoughtful attention to inclusive travel, a hallmark of quality service.

Check out these outstanding tour options that consistently earn top marks from our travelers.

Key Points

1. Hilton Head Island offers a variety of private boat rental services, including luxury pontoon options that accommodate up to 15 people with wheelchair accessibility.
2. Scenic destinations accessible by boat include popular landmarks like Daufuskie Island Lighthouse, Harbour Town Lighthouse, and Skull Creek Boat House.
3. Unique experiences like private dolphin watching tours, sunset cruises, and tubing trips provide opportunities for wildlife sightings and memorable adventures.
4. Boat rental companies are family-owned, ensuring personalized service and high customer satisfaction, with flexible booking and cancellation policies.
5. Pricing for private boat rentals in Hilton Head Island ranges from $265 to over $1,000, with options to accommodate groups of different sizes.

90-Minute Private Dolphin Tour in Hilton Head Island

A 90-minute private dolphin tour in Hilton Head Island offers an intimate, immersive experience to observe the island’s abundant marine life.

Operated by Cross Island Cruises, the tour boasts 421 reviews with a perfect 5-star rating. For $319, groups of up to 6 can embark on this exclusive excursion led by a licensed captain and naturalist.

Guests can expect frequent dolphin sightings, with the potential to see up to 50 dolphins during the tour. The knowledgeable captain provides insights into the local ecology and wildlife, creating an engaging and memorable family-friendly adventure.

With free cancellation and a convenient meeting point, this private dolphin tour is an exceptional value for those seeking an up-close encounter with Hilton Head’s natural wonders.

Read our full review: 90-Minute Private Dolphin Tour in Hilton Head Island Review
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2 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental

For those seeking a private and luxurious boat experience in Hilton Head Island, the 22-foot Luxury Pontoon Rental offers an exceptional opportunity.

Accommodating up to 12 people, the rental features high-quality craftsmanship, including a full-size captain’s chair, Bluetooth sound system, and power steering.

Explore the island at your own pace, with suggested destinations like the Daufuskie Island Lighthouse and Skull Creek Boat House.

The owners, Jason and Jennifer Wheeler, ensure maximum time on the water, and the rental is wheelchair accessible.

With a 2-hour duration and free cancellation up to 24 hours in advance, this pontoon rental provides a comfortable and convenient way to experience the beauty of Hilton Head Island.

Read our full review: 2 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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2-Hour Private Hilton Head Dolphin Watching Cruise

The 2-Hour Private Hilton Head Dolphin Watching Cruise provides travelers with an immersive opportunity to encounter the island’s captivating marine life.

With a 100% traveler recommendation and a Badge of Excellence, the cruise offers a personalized experience for groups of up to 6 people. Priced at $379 per group, the tour includes the use of the boat and complimentary amenities like a cooler and ice.

While food and drinks are welcome on board, they aren’t included. Customers rave about the knowledgeable and friendly captains, as well as the incredible sightings of dolphins, bald eagles, and scenic landscapes.

Suitable for most travelers, this private cruise is an excellent choice for families and groups seeking a memorable and educational outing on the water.

Read our full review: 2-Hour Private Hilton Head Dolphin Watching Cruise Review
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2 Hour Private 24 Ft. Luxury Pontoon Hilton Head Boat Rental

Travelers seeking a more immersive Hilton Head experience can consider the 2 Hour Private 24 ft. Luxury Pontoon Hilton Head Boat Rental.

This family-owned and operated service offers a luxury pontoon perfect for groups of up to 15. With features like Bluetooth, power steering, and a large Garmin GPS, guests can comfortably explore Hilton Head’s coves and destinations like the Daufuskie Island Light House.

The rental includes a dock team to assist with launching and returning, and customers enjoy five-star service.

With free cancellation up to 24 hours in advance, it’s an excellent option for those wanting to discover the area by water.

Read our full review: 2 Hour Private 24 Ft. Luxury Pontoon Hilton Head Boat Rental Review
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2-Hour Private Hilton Head Sunset Cruise

Frequently, travelers to Hilton Head Island can enjoy a 2-Hour Private Hilton Head Sunset Cruise, a highly-rated and personalized experience on the Calibogue Sound.

This private vessel cruise boasts 238 reviews and a 100% recommendation from travelers, earning a Badge of Excellence. Guests can expect to see wildlife like Atlantic bottlenose dolphins and may even receive shark teeth from the knowledgeable captain.

The cruise provides stunning views of Harbour Town and allows guests to bring their own food, drinks, and coolers. Priced from $399 for up to 6 people, this sunset cruise offers a relaxing and memorable way to experience the natural beauty of Hilton Head Island.

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3 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental

Although Hilton Head Island is renowned for its picturesque beaches and world-class golf courses, the 3-Hour Luxury Pontoon Private Boat Rental offers an unparalleled opportunity to explore the island’s stunning waterways.

Priced at $508.25 for up to 12 people, this family-owned and operated service has been voted “Best of Hilton Head” year after year.

The 2024 luxury pontoon boat features a full-size captain’s chair, Bluetooth, power steering, and a large touch screen Garmin GPS/Pathfinder, allowing passengers to effortlessly navigate to destinations like the Daufuskie Island Lighthouse and Skull Creek Boat House.

With flexible pickup options and ample public parking, this boat rental provides a hassle-free and memorable experience on the water.

Read our full review: 3 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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3 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental

The 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental offers a unique and unforgettable experience for parties of 8 or more. Priced at $561.75 per group, the 3-hour rental features a 2024 Bennington pontoon boat equipped with modern amenities, including a full-size captain’s chair, Bluetooth, and a large touchscreen Garmin GPS/Pathfinder.

The vessel can accommodate up to 15 passengers and provides a retractable full-size sunshade and a swim ladder for added convenience. Guests can choose their preferred dock location and explore destinations such as the Daufuskie Island Lighthouse, Sandbar, and Skull Creek Boat House.

With free cancellation up to 24 hours in advance and a reserve now, pay later option, this rental offers flexibility and convenience for a memorable boating adventure.

Read our full review: 3 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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4 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental

Nestled along the picturesque shores of Hilton Head Island, the 22 Ft. Luxury Pontoon Private Boat Rental offers a delightful way to explore the waterways.

This 22-foot pontoon boat can accommodate up to 12 people, making it ideal for group outings. At $668.75 per rental, guests can enjoy a 4-hour excursion equipped with a Garmin GPS, Bluetooth sound system, and other amenities.

The rental includes a flexible pickup location and a relaxed cancellation policy. Adventurers can discover local landmarks, anchor in secluded coves, or simply bask in the sun while cruising.

With ample seating, a retractable sunshade, and wheelchair accessibility, this pontoon boat rental provides a comfortable and convenient way to experience the beauty of Hilton Head Island.

Read our full review: 4 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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4 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental

Hilton Head Island’s 24 Ft. Luxury Pontoon Private Boat Rental offers an exceptional on-the-water experience. Priced from $675 for up to 15 guests, the 4-hour rental provides access to Daufuskie Island, Harbour Town Lighthouse, and other scenic spots.

The new 2024 Bennington pontoon features captain’s chairs, Bluetooth, power steering, and a large touchscreen Garmin GPS. While gas isn’t included, the average cost is $10 per hour.

With free cancellation up to 24 hours in advance, this luxury rental is perfect for parties looking to explore Hilton Head by water. Dock team assistance and the boat’s comfort, style, and functionality ensure an enjoyable outing year after year.

Read our full review: 4 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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5 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental

An exceptional 5-hour luxury pontoon boat rental on Hilton Head Island, this 22-foot Bennington offers a delightful on-the-water experience for parties of up to 12 guests.

Family-owned and voted Best of Hilton Head year after year, this rental boasts 100s of five-star reviews over a decade.

Amenities include a full-size captain’s chair, Bluetooth, power steering, retractable sunshade, swim ladder, anchor, and a large touch screen Garmin GPS/Pathfinder.

Guests can explore Hilton Head’s waterways, including the Daufuskie Island Lighthouse, sandbar, and Skull Creek Boat House.

With flexible booking and free cancellation, this rental provides an effortless way to enjoy the island’s natural beauty.

Read our full review: 5 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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5 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental

This 24-foot luxury pontoon boat rental on Hilton Head Island provides guests with a delightful 5-hour on-the-water experience for parties of up to 15 people.

Priced at $829.25 per group, the boat features a full-size captain’s chair, Bluetooth, power steering, retractable sunshade, and a large touch screen Garmin GPS/Pathfinder.

Explore the island’s scenic destinations, including the Daufuskie Island Lighthouse and Skull Creek Boat House, with the option to be picked up at the dock of your choice.

The rental includes free cancellation up to 24 hours in advance and a reserve now, pay later option.

Read our full review: 5 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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6 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental

Why not embark on a 6-hour private boat rental adventure aboard a luxurious 22-foot Bennington pontoon on Hilton Head Island?

This family-owned service, voted best in Hilton Head year after year, offers a premium experience. With a capacity of up to 12 people, the boat features comfort amenities like a full-size captain’s chair, Bluetooth connectivity, and a large touchscreen Garmin GPS/Pathfinder.

Explore the island’s waterways, anchor in quiet coves, or visit popular destinations like the Daufuskie Island Lighthouse. At $856 per group, this rental provides exceptional value, with a dock of your choice and a free pickup service.

With hundreds of five-star reviews and a flexible cancellation policy, this boat rental is an ideal way to enjoy Hilton Head’s scenic beauty.

Read our full review: 6 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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6 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental

Setting out on a 6-hour private boat rental adventure aboard a luxurious 24-foot Bennington pontoon on Hilton Head Island offers an unparalleled experience.

Priced at ₹77,006 per group of up to 8 people, this family-owned and operated rental comes highly recommended, with hundreds of five-star reviews.

The pontoon features a full-size captain’s chair, Bluetooth, power steering, and a large touch screen Garmin GPS/Pathfinder, allowing you to explore destinations like the Daufuskie Island Lighthouse and Skull Creek Boat House in comfort and style.

With a wheelchair-accessible design and a dock team to assist with launching, this private rental ensures a seamless and enjoyable outing on the waters of Hilton Head.

Read our full review: 6 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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7 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental

A 7-hour private rental of a 22-foot luxury Bennington pontoon boat allows visitors to explore Hilton Head Island from the water.

Priced at $909.50 for up to 12 people, the rental features a full-size captain’s chair, Bluetooth power steering, a retractable sunshade, and a large touchscreen Garmin GPS/Pathfinder.

After launching from Hilton Head Island, guests can cruise around the island, including Daufuskie Island, anchor in quiet coves, or visit marked destinations.

The rental includes assistance from the dock team, though gas isn’t included (average cost is $10 per hour).

This private group experience is wheelchair accessible, with itineraries subject to change.

Read our full review: 7 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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8 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental

Visitors exploring Hilton Head Island can enjoy a unique 8-hour private boat rental experience.

The family-owned company, led by Jason and Jennifer Wheeler, offers a 22-foot luxury pontoon boat for up to 12 people at €911.19 per group.

The new 2024 Bennington pontoon features top-of-the-line amenities, including a full-size captain’s chair, Bluetooth power steering, and a large touchscreen Garmin GPS.

Renters can explore destinations like the Daufuskie Island Lighthouse, the sandbar, and Skull Creek Boat House.

With a flexible dock pickup and free cancellation up to 24 hours in advance, this pontoon rental provides an unforgettable way to discover Hilton Head’s waterways.

Read our full review: 8 Hour 22 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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7 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental

For those seeking a memorable Hilton Head boat adventure, the 7 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental is an excellent choice.

Accommodating up to 15 people, this luxury 2024 Bennington Pontoon is the largest rental boat on the island. Guests can enjoy a 7-hour cruise to destinations like the Daufuskie Island Light House and Skull Creek Boat House, with ample amenities such as Bluetooth, power steering, and a large touch screen Garmin GPS.

Backed by a family-owned company with top-rated customer service and reviews, this boat rental provides an unforgettable experience on the waters of Hilton Head Island.

Read our full review: 7 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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8 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental

Renting the 8 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat is an excellent choice for groups of up to 15 people.

At $1,016.50 per group, this family-owned and operated business has earned numerous accolades, including being voted Best of Hilton Head year after year.

With a wheelchair-accessible 2024 luxury pontoon, guests can enjoy features like a full-size captain’s chair, Bluetooth, power steering, a retractable sunshade, and a large touch screen Garmin GPS/Pathfinder.

The 8-hour rental allows ample time to explore Hilton Head’s destinations, such as the Daufuskie Island Lighthouse and Skull Creek Boat House, while the dock team assists with launching and returning the boat.

Read our full review: 8 Hour 24 Ft. Luxury Pontoon Private Hilton Head Boat Rental Review
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Hilton Head Island: Private Dolphin Watching Boat Tour

Nestled along the captivating shores of Hilton Head Island, the Private Dolphin Watching Boat Tour offers a unique opportunity to witness the majestic marine life up close.

This 1.5-hour private tour accommodates up to 6 people, led by a licensed captain who’ll provide a fully narrated experience. Guests can expect to see dolphins in their natural habitat, while also enjoying scenic views of Harbour Town Lighthouse and Daufuskie Island.

The tour includes snacks, bottled water, and soft drinks, as well as complimentary photos. With a 5/5 rating based on customer feedback, this tour promises an unforgettable encounter with Hilton Head’s wildlife.

Read our full review: Hilton Head Island: Private Dolphin Watching Boat Tour Review
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Hilton Head: Private 2-hour Sunset Cruise

Atop the captivating shores of Hilton Head Island, the Private 2-hour Sunset Cruise offers visitors a mesmerizing opportunity to witness the island’s vibrant hues as the sun dips below the horizon.

Priced at $529 for up to 14 participants, this private cruise showcases the scenic waterfront and marine life, led by a knowledgeable English-speaking guide.

With complimentary cancellation up to 24 hours in advance, guests can relax and savor the experience, which is ideal for various occasions, from romantic evenings to family gatherings.

The cruise has earned a stellar 4.9/5 rating from previous guests, who praised the comfortable boat and the chance to spot dolphins.

Read our full review: Hilton Head: Private 2-hour Sunset Cruise Review
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Hilton Head Island: Private Tubing Trip

For an exhilarating adventure on Hilton Head Island, visitors can embark on a private tubing trip that offers a thrilling way to experience the island’s scenic waterways.

The 1-hour excursion, priced from $265 for up to 6 participants, allows guests to glide at full speed on inflatable tubes towed by a motorboat, taking in breathtaking views of the beach and coastal scenery.

The trip includes a live tour guide, free cancellation, and all necessary equipment. However, it’s not suitable for non-swimmers, wheelchair users, or those with mobility issues.

Customer reviews praise the activity as an unforgettable experience for couples, groups, and families.

Read our full review: Hilton Head Island: Private Tubing Trip Review
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Sum Up

Hilton Head Island offers a variety of private boat tours and rentals for visitors to enjoy the area’s natural beauty. From dolphin watching to sunset cruises, these private experiences provide a personalized and exclusive way to explore the island’s waterways. Whether you’re seeking a short tour or an all-day rental, there’s an option to suit your preferences and make your Hilton Head trip even more memorable.