Hilton Head Island Cruises & Sailing Tours tours

Hilton Head Island Cruises & Sailing Tours - Page 2

32 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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4.55

Hilton Head Island Dolphin Watching Cruise at Sunset

From $45

1 provider live

Watch the sunset shimmer over Broad Creek

Boat cruise

4.55

Hilton Head Dinner Cruise

From $148

1 provider live

Savor a chef-curated Southern feast

Bottled water

4.52

Hilton Head Dolphin Watching Sail

From $485

1 provider live

Sail through Port Royal Sound

Soda/Pop

4.51

Hilton Head Island Catamaran Cruise at Sunset 2 hr

From $80

1 provider live

Enjoy refreshing drinks as you relax

2-hour catamaran sail

4.5

Hilton Head Sunset Sail

From $93

1 provider live

Set sail into the sunset

Official English Guide

4.49

Hilton Head Crabbing Expedition Boat Cruise

$50-$55

2 providers combined

Experience crabbing in Hilton Head's waters

Possible dolphin sightings

4.48

Hilton Head Pirate Cruise for Families 90 Min

From $42

2 providers combined

Step aboard the Black Sparrow for a pirate adventure

90 Minute Pirate Experience

4.48

Hilton Head Sunset Kayak and Cruise

$53-$550

3 providers combined

Sail into the horizon on a sunset cruise

All gear & tour guide

4.47

Hilton Head Brunch Under Sail Catamaran Cruise

From $95

2 providers combined

Savor complimentary mimosas and brunch

Alcoholic Beverages

4.47

Hilton Head Private Dolphin Catamaran Sail

From $359

1 provider live

Watch dolphins and birds in their natural habitat

Private catamaran tour

4.4

Hilton Head Scenic Cruise with Buffet

$74-$83

4 providers combined

Savor a Southern-inspired brunch buffet

Southern-inspired brunch buffet

4.3

Hilton Head Dolphin Cruise at Sunset 90 min

From $55

2 providers combined

Relax and unwind during a stunning Lowcountry sunset

Bottled water