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Captain
All listings in Charleston

Great sailboat rentals near Charleston, South Carolina.

Page 1 of 18 listings

Luxury BYOB Sailing in the Charleston Harbor
Sailing in Charleston · 6 guests

Luxury BYOB Sailing in the Charleston Harbor

5.0
Superowner
Best of 2023
$220hour
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
$275hour
Private Luxury BYOB Sailing in the Charleston Harbor
Sailing in Charleston · 6 guests

Private Luxury BYOB Sailing in the Charleston Harbor

5.0
Superowner
Best of 2023
$200hour
Sailing Catana 431 Catamaran Yacht in Charleston on Folly Beach, South Carolina
Sailing in Folly Beach · 6 guests

Sailing Catana 431 Catamaran Yacht in Charleston on Folly Beach, South Carolina

5.0
$350hour
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

New
$175person
Well Appointed Beneteau 32, Folly Beach, SC
Sailing in Folly Beach · 6 guests

Well Appointed Beneteau 32, Folly Beach, SC

5.0
$190hour
 CATAMARAN/DOLPHIN SAIL  FOLLY BEACH SC
Sailing in Folly Beach · 6 guests

CATAMARAN/DOLPHIN SAIL FOLLY BEACH SC

New
$190hour
Luxury sailboat charters on Charleston Harbor
Sailing in Mount Pleasant · 6 guests

Luxury sailboat charters on Charleston Harbor

New
$275-$300hour

Sailing Reviews in Charleston

  1. 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!

  2. AG

    Amberlyn

    Luxury BYOB Sailing in the Charleston Harbor

    One of the best adventures I’ve been on with my girlies! Would rate him 100 stars if I could! Thank you so much for making us feel comfortable and so accommodating

  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!