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Best results for

Sailing in Hilton Head, SC

Showing 25-37 of 37 results
Brunch Sailing Cruise in Hilton Head Island

Brunch Sailing Cruise in Hilton Head Island

Savor brunch and drinks aboard a Lowcountry catamaran

4.9 • 51 reviews
$105/ person
Hilton Head Island Sunset Cruise

Hilton Head Island Sunset Cruise

Sail into sunset with room for your group and your own refreshments

4.9 • 51 reviews
$1,328& up
Shared Afternoon Sailing Tour in Bluffton

Shared Afternoon Sailing Tour in Bluffton

Take the helm or relax on a motor-free public afternoon sail

5.0 • 390 reviews
$127/ person
Private Morning Sailing Charter in Bluffton

Private Morning Sailing Charter in Bluffton

Customize a private sail with offshore cruising or an anchored swim

5.0 • 390 reviews
$1,213& up
4-Hour Sailing Charter in Hilton Head Island

4-Hour Sailing Charter in Hilton Head Island

Shape a private sail around your group’s ideal afternoon

5.0 • 390 reviews
$1,113
Shared Sunset Sail near Bluffton

Shared Sunset Sail near Bluffton

End the day sailing beneath the changing coastal sky

5.0 • 390 reviews
$110/ person
4-Hour Sailing Charter in Hilton Head Island

4-Hour Sailing Charter in Hilton Head Island

Tailor a private sail with time to anchor and swim

5.0 • 390 reviews
$1,113
Sunset Sail in Hilton Head Island

Sunset Sail in Hilton Head Island

An evening sail with sunset views, sails, and the chance to spot wildlife

5.0 • 390 reviews
$138/ person
Sail A Rosé Fireworks Cruise In Hilton Head Island

Sail A Rosé Fireworks Cruise In Hilton Head Island

2-hour rosé fireworks sail from Broad Creek Marina

4.9 • 51 reviews
$99/ person
Private Morning Sail & Dolphin Watch in Bluffton

Private Morning Sail & Dolphin Watch in Bluffton

A calm morning sail for coastal views and wildlife watching

5.0 • 390 reviews
$472& up
Watch Shelter Cove Fireworks on a Hilton Head Sail

Watch Shelter Cove Fireworks on a Hilton Head Sail

Sail at sunset, then anchor to watch Shelter Cove fireworks

4.9 • 118 reviews
$530
Morning Sailing Charter in Hilton Head Island

Morning Sailing Charter in Hilton Head Island

Sail Hilton Head’s morning waters and look for coastal wildlife

5.0 • 390 reviews
$419
Fireworks Sailing Cruise in Hilton Head Island

Fireworks Sailing Cruise in Hilton Head Island

Sail for 2 hours and watch fireworks from the water

4.9 • 51 reviews
$99/ person
12
Hilton Head Things To Do
SailingBoat Tours88Fishing Charters65Bike Rentals64Dolphin Watching51
More
  • Historical Tours34
  • Kayaking Tours32
  • Ghost and Haunted31
  • Yacht Charters28
  • Boat Rentals18
  • Dinner Cruises15
  • Ferries15
Sunrise and Sunset Tours
12
  • Beach Tours11
  • Bike Tours8
  • Horse and Carriage Tours7
  • Museum Tours7
  • Private Fishing Charters7
  • Horseback Riding6
  • Jet Skiing6
  • Stand Up Paddle Boarding6
  • Community and Heritage5
  • Ecotours5
  • Escape Games5
  • Segway Tours5