Hilton Head Island Cruises & Sailing Tours

17 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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4.67

Hilton Head Dolphin Watching Cruise 2 hr

From $299

Experience dolphins up close

Use of the boat and all amenities

4.58

Hilton Head Private Dolphin Tour

$297-$599

Experience dolphin sightings

Rental of a 24 ft. luxury pontoon boat

4.56

Hilton Head Crabbing Expedition Boat Cruise

$50-$55

Explore Hilton Head's picturesque low country

Possible dolphin sightings

4.55

Hilton Head Happy Hour Cruise with Live Music

$70-$83

Savor Baja-style tacos on board

90-minute scenic cruise aboard the Spirit of Harbour Town

4.55

Hilton Head Island Pirates and Pizza Boat Tour

From $55

Sail on a pirate ship

Pirate ship tour

4.54

Hilton Head Brunch Under Sail Catamaran Cruise

From $95

Savor complimentary mimosas and brunch bites

Alcoholic Beverages

4.51

Hilton Head Sunset Kayak and Cruise

$53-$550

Sail into the horizon on a sunset cruise

All gear & tour guide

4.49

Hilton Head Private Sunset Cruise

$53-$549

Watch the sun set over Hilton Head's coast

Private cruise

4.48

Hilton Head Dolphin Cruise at Sunset

From $50

Savor a 1.5-hour sunset cruise

1.5 Hour Sunset Cruise

4.43

Hilton Head Pirate Cruise Adventure

From $42

Step aboard the Black Sparrow for a pirate adventure

90 Minute Pirate Experience

4.4

Hilton Head Lunch and Dinner Cruise

$74-$83

Savor a Lowcountry lunch buffet

Lowcountry Lunch Buffet

4.34

Hilton Head Island Lowcountry Boil Dinner Cruise

$118-$128

Savor a traditional Lowcountry Boil dinner

Dinner with local shrimp, smoked sausage, corn, and potatoes