Top South Carolina Sailing Trips

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South Carolina Adventures

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Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
Likely to Sell Out
Likely to Sell Out
Hilton Head Island, USA
4.9 (688)

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (688)
$47.99
$46.99
Private Luxury Yacht Charters, BYOB & Dolphins
Special Offer
Special Offer
Charleston, USA
5.0 (422)

Private Luxury Yacht Charters, BYOB & Dolphins

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the...

2 hours 30 minutes
2 hours 30 minutes
2 hours 30 minutes
5.0 (422)
$525
$524
Private Hilton Head Sunset Sailing Tour with Dolphin Watching
Likely to Sell Out
Likely to Sell Out
Hilton Head Island, USA
5.0 (123)

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island -...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (123)
$525
$524
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail
Special Offer
Special Offer
Hilton Head Island, USA
5.0 (119)

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (119)
$485
$484
Private Morning Sail, Dolphin and History Tour on Mystique
Special Offer
Special Offer
Charleston, USA
5.0 (85)

Private Morning Sail, Dolphin and History Tour on Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (85)
$525
$524
Private Sailing Charter with Captain, BYOB
Likely to Sell Out
Likely to Sell Out
Charleston, USA
5.0 (83)

Private Sailing Charter with Captain, BYOB

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (83)
$500
$499
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
Likely to Sell Out
Likely to Sell Out
Mount Pleasant, USA
4.9 (74)

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (74)
$64
$63
Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB
Special Offer
Special Offer
Charleston, USA
4.9 (63)

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also...

2 to 4 hours • Free Cancellation
2 to 4 hours • Free Cancellation
2 to 4 hours • Free Cancellation
4.9 (63)
$760
$759
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique
Special Offer
Special Offer
Charleston, USA
5.0 (54)

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Top10Adventures® for over...

2 to 4 hours • Free Cancellation
2 to 4 hours • Free Cancellation
2 to 4 hours • Free Cancellation
5.0 (54)
$599
$598
Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate
Special Offer
Special Offer
Charleston, USA
5.0 (50)

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also...

2 to 4 hours • Free Cancellation
2 to 4 hours • Free Cancellation
2 to 4 hours • Free Cancellation
5.0 (50)
$599
$598
Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering
Special Offer
Special Offer
Charleston, USA
5.0 (40)

Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also...

2 to 4 hours • Free Cancellation
2 to 4 hours • Free Cancellation
2 to 4 hours • Free Cancellation
5.0 (40)
$599
$598
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
Special Offer
Special Offer
Charleston, USA
5.0 (35)

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Top10Adventures® since 2012,...

2 to 4 hours • Free Cancellation
2 to 4 hours • Free Cancellation
2 to 4 hours • Free Cancellation
5.0 (35)
$575
$574
2 - Hour Private Hilton Head Morning Dolphin Watching / Sail
Special Offer
Special Offer
Hilton Head Island, USA
5.0 (33)

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (33)
$465
$464
Private Afternoon Harbor Cruise on Kismet for parties up to 20
Special Offer
Special Offer
Charleston, USA
5.0 (29)

Private Afternoon Harbor Cruise on Kismet for parties up to 20

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (29)
$1,549
$1,548
Private Charleston Harbor Catamaran Sail
Special Offer
Special Offer
Mount Pleasant, USA
5.0 (28)

Private Charleston Harbor Catamaran Sail

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (28)
$950
$949
Luxury Sunset Sail on Serendipity Catamaran in Charleston
Special Offer
Special Offer
Charleston, USA
5.0 (9)

Luxury Sunset Sail on Serendipity Catamaran in Charleston

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (9)
$150
$149
Wednesday Happy Hour Sunset Sail - Drinks Included
Special Offer
Special Offer
Mount Pleasant, USA
5.0 (7)

Wednesday Happy Hour Sunset Sail - Drinks Included

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (7)
$76
$75
Sunday Mimosa Brunch Charleston Harbor Sail - Food Included
Special Offer
Special Offer
Mount Pleasant, USA
5.0 (7)

Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran,...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (7)
$75
$74
Public Sunset Sail with only 6 people
Special Offer
Special Offer
Hilton Head Island, USA
5.0 (2)

Public Sunset Sail with only 6 people

Enjoy an intimate sunset sailing experience aboard a cozy vessel with only six guests. Glide through the picturesque waters of Port Royal Sound as the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (2)
$141.03
$140.03
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor
Likely to Sell Out
Likely to Sell Out
Charleston, USA
4.6 (770)

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.6 (770)
$56
$55

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