Hilton Head Island Cruises & Sailing Tours

10 experiences to discover

Day & Sunset Cruises Dinner Cruises Sailing Trips

Explore the best cruises & sailing tours tours and activities in Hilton Head Island. Our unbiased ratings help you find the perfect experiences for your trip.

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4.6

Hilton Head Private Sunset Cruise

$323-$385

Relax on a private sunset cruise

Cooler with ice

4.59

Hilton Head Private Sunset Cruise

$486-$529

Watch the sun fade on the Hilton Head horizon

Parking Fees

4.59

Hilton Head Sunset Dolphin Cruise

From $55

Relax during a stunning Lowcountry sunset

Vessel & Captain

4.58

Hilton Head Pontoon Boat and Sunset Cruise

$486-$550

Sail into the horizon on a private cruise

Pontoon boat rental

4.57

Hilton Head Pirate Cruise for Kids

$37-$42

Step aboard the Black Sparrow

Pirate-themed cruise

4.47

Hilton Head Island Sailing Yacht Cruise

$47-$48

Sail on a 12-meter racing yacht

Cruise

4.35

Hilton Head Dolphin Watching Dinner Cruise

$70-$74

Admire wild dolphins in their natural habitat

Captain

4.33

Hilton Head Dolphin Watching Cruise with Sunset & Fireworks

$62-$69

Delight in up-close dolphin sightings

Dolphin-watching boat tour

4.23

Hilton Head Island Hibachi Dinner Cruise at Sunset

From $128

Savor hibachi-style cuisine prepared onboard

2-hour dinner cruise

3.21

Hilton Head Island Sunset Dinner Cruise

From $106

Savor a freshly prepared 3-course dinner

Fuel surcharge