Hilton Head Island Cruises & Sailing Tours

16 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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4.69

Hilton Head Dolphin Watching Cruise

$269-$299

Create unforgettable family memories

Use of the boat and all amenities

4.67

Hilton Head Private Dolphin Tour

$323-$399

Experience guaranteed dolphin sightings

Rental of a 24-foot luxury Bennington Pontoon boat

4.55

Hilton Head Pirate Cruise for Kids 1.5 hr

From $42

Step aboard the Black Sparrow for a pirate adventure

Pirate-themed cruise

4.55

Hilton Head Dinner Cruise with Live Music

$70-$83

Savor a Latin-inspired menu

Outdoor dining on shaded upper deck

4.55

Hilton Head Island Pirates and Pizza Boat Tour

From $55

Sail on a pirate ship

Pirate ship tour

4.55

Hilton Head Brunch Under Sail Catamaran Cruise

From $95

Savor complimentary mimosas while sailing

All Fees and Taxes

4.53

Hilton Head Sunset Kayak Tour

$53-$550

Sail into the horizon on a sunset cruise

All gear & tour guide

4.5

Hilton Head Crabbing and Sailing Adventure

$48-$53

Sail on a real America's Cup yacht

Possible dolphin sightings

4.45

Hilton Head Island Dinner Cruise

$74-$83

Savor a Latin-inspired 3-course meal

Private table with steward service

4.39

Hilton Head Private Sunset Cruise

$53-$549

Watch the sun set over Hilton Head

Private boat

4.39

Hilton Head Dolphin Tour with Sunset & Fireworks

$60-$475

Witness dolphins in their natural habitat

Narrated by an experienced naturalist/guide

4.36

Hilton Head Lowcountry Boil Dinner Cruise

$118-$128

Savor a traditional Lowcountry Boil

Bottled water