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All listings in Charleston

Great sailboat rentals near Charleston, South Carolina.

Page 1 of 113 listings

FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr
Sailing in Folly Beach · 6 guests

FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

5.0
Best of 2025
$200/hour
Luxury BYOB Sailing in the Charleston Harbor
Sailing in Charleston · 6 guests

Luxury BYOB Sailing in the Charleston Harbor

5.0
Superowner
$220/hour
Instant Book
Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB
Sailing in Charleston · 6 guests

Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB

5.0
Superowner
$200+/hour
Instant Book
 CATAMARAN/DOLPHIN SAIL  FOLLY BEACH SC
Sailing in Folly Beach · 6 guests

CATAMARAN/DOLPHIN SAIL FOLLY BEACH SC

5.0
Best of 2025
$190/hour
40 ft Luxury Catamaran Sailing Yacht in Charleston
Sailing in Mount Pleasant · 6 guests

40 ft Luxury Catamaran Sailing Yacht in Charleston

5.0
Superowner
$300/hour
🎉🐬⛵️HUGE Sailing Catamaran Yacht in Charleston on Folly Beach, South Carolina
Sailing in Folly Beach · 6 guests

🎉🐬⛵️HUGE Sailing Catamaran Yacht in Charleston on Folly Beach, South Carolina

5.0
$225/hour
Well Appointed Beneteau 32, Folly Beach, SC
Sailing in Folly Beach · 6 guests

Well Appointed Beneteau 32, Folly Beach, SC

5.0
Best of 2025
$190/hour
Sunday Funday Mimosa Bar Shared Sail– Ultimate Brunch on the Water! Catamaran
Sailing in Mount Pleasant · 100 guests

Sunday Funday Mimosa Bar Shared Sail– Ultimate Brunch on the Water! Catamaran

New
$135/hour
Charleston Luxury Sunset Sail Tickets - 50ft Catamaran Enjoy the Bar
Sailing in Mount Pleasant · 100 guests

Charleston Luxury Sunset Sail Tickets - 50ft Catamaran Enjoy the Bar

New
$32/hour
Mermaid Monday Sunset Shared Sunset – Ladies' Night Discounts & Bar Specials
Sailing in Mount Pleasant · 1,000 guests

Mermaid Monday Sunset Shared Sunset – Ladies' Night Discounts & Bar Specials

New
$32/hour
Private Events Charleston's Luxury 50ft Catamaran w/Bar Party Sail
Sailing in Mount Pleasant · 100 guests

Private Events Charleston's Luxury 50ft Catamaran w/Bar Party Sail

New
$1,600+/hour
Sailing The Edge of America - Folly Beach
Sailing in Folly Beach · 6 guests

Sailing The Edge of America - Folly Beach

New
$200/hour
Instant Book
Charleston Afternoon Harbor Sail Tickets – Unwind Before Happy Hour Catamaran
Sailing in Mount Pleasant · 100 guests

Charleston Afternoon Harbor Sail Tickets – Unwind Before Happy Hour Catamaran

New
$370/hour

Sailing Reviews in Charleston

  1. RW

    Ronnie

    FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

    Johnny, thanks so much for the trip. Although we have been in the waters around Folly many times over the years, we had never been on a catamaran. It was awesome! We saw so much in just 2 hours! Baby stingray swimming by about 2 feet away, countless dolphins playing and splashing in the water,me stepping on a huge blue crab (that scared me to death! lol!) to my first EVER sighting of a live logger head turtle right by the boat… it was absolutely incredible. Oh, forgot to mention the sea shell my wife found (as big as my hand). Thank you for a great trip!

  2. CV

    Carlee

    Luxury BYOB Sailing in the Charleston Harbor

    We had a blast sailing! Our captain was very friendly and made sure to answer all of our questions about the area. There was plenty of room to spread out on the boat and they made sure to make us feel welcome and serve us our refreshments we brought on board :) Would book again!

  3. BA

    Blake

    Luxury BYOB Sailing in the Charleston Harbor

    This was the highlight of our trip to Charleston. The time flew by because of the great company provided by the captain and his first mate. They are at your service whether you want to sit in the ultra comfy been bags on the bow or ask tons of questions about sailing and Charleston history, while being waited on for you drink or food needs. Highly recommend scheduling a trip while in town.

  4. KM

    Kristen

    Luxury BYOB Sailing in the Charleston Harbor

    Wit and Crystal were great! We enjoyed our sail very much! As soon as we got on board, Crystal had all our food and drinks put away in the fridge to stay cold! we got a brief intro to the boat and we were off! Wit seemed to genuinely enjoy chartering guests around on his boat and Crystal was so attentive to our needs. We never had an empty hand! We really enjoyed the trip! We saw many sights and even a dolphin! I can’t wait to bring back some friends next time!

  5. LC

    Leslie

    Luxury BYOB Sailing in the Charleston Harbor

    This was quite the adventure!! Wit's boat is beautiful! We've sailed multiple times and this is one of the nicest we've been on. Only 3 people so it was more than spacious enough. First boat ever to have the bean bag chairs and I'm still sad I didn't get a chance to sit in one!! We got caught in a pop up storm and Wit handled it unbelievably well. It definitely added to the experience!! After that we were pretty chill just cruising the harbor. Loved hearing his stories! Next time we'd love to have his whole family along! Thank you for a wonderful afternoon on the water!

  6. LS

    LORI

    Luxury BYOB Sailing in the Charleston Harbor

    We had a wonderful time sailing around the harbor. It felt so good to relax and enjoy the sunshine and ocean breezes. Our captain and first mate Holly were informative, friendly and knowledgeable. The sailboat is beautiful with plenty of space. Overall, it was a perfect evening! Thank you!