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All listings in Charleston

Great sailboat rentals near Charleston, South Carolina.

Page 1 of 112 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
$220/hour
Instant Book
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
 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
🎉🐬⛵️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
$250/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
Sailing The Edge of America - Folly Beach
Sailing in Folly Beach · 6 guests

Sailing The Edge of America - Folly Beach

New
$200/hour
Shared Bachelor/Bachelorette Catamaran Cruise Charleston - Bar Onboard
Sailing in Mount Pleasant · 100 guests

Shared Bachelor/Bachelorette Catamaran Cruise Charleston - Bar Onboard

New
$370/hour
Charleston Luxury Shared Sunset Sail - 50ft Catamaran Enjoy the Bar
Sailing in Mount Pleasant · 100 guests

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

New
$225/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 Reviews in Charleston

  1. KM

    Kayla

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

    We had the best day with Ryan! He was so friendly & kind, the catamaran was amazing, and his cute pup was an added bonus! We would love to do another charter with Ryan next time we're visiting Folly Beach!

  2. CAIT

    CAIT

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

    We have gone sailing numerous times now with Sail Folly! Every time the experience is amazing. They are incredible and you always see amazing wildlife.

  3. 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!

  4. 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!

  5. 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.

  6. 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!