Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in Charleston

Great sailboat rentals near Charleston, South Carolina.

Page 1 of 114 listings

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

Luxury BYOB Sailing in the Charleston Harbor

5.0
Superowner
$220/hour
Luxury 42ft Catamaran Sailing Charter in Charleston Harbor
Sailing in Mount Pleasant · 6 guests

Luxury 42ft Catamaran Sailing Charter in Charleston Harbor

5.0
Superowner
$225+/hour
 CATAMARAN/DOLPHIN SAIL  FOLLY BEACH SC
Sailing in Folly Beach · 6 guests

CATAMARAN/DOLPHIN SAIL FOLLY BEACH SC

5.0
$190/hour
Limited Availability
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
$200/hour
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
🎉🐬⛵️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
Superowner
$300/hour
High Demand
Charleston's Largest Private Luxury Sailing Yacht 50ft Windchaser Custom Cruises
Sailing in Mount Pleasant · 12 guests

Charleston's Largest Private Luxury Sailing Yacht 50ft Windchaser Custom Cruises

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
$190/hour
Sailing The Edge of America - Folly Beach
Sailing in Folly Beach · 6 guests

Sailing The Edge of America - Folly Beach

5.0
$200/hour
Limited Availability
Shared Party Boat Sail w/Bar: Charleston Harbor - Perfect for Bach or Birthday
Sailing in Mount Pleasant · 100 guests

Shared Party Boat Sail w/Bar: Charleston Harbor - Perfect for Bach or Birthday

5.0
$375/hour
Tiki Bar, Hoppin, Sandbars, Down Island Vibes with Barrier island views
Powerboats in Folly Beach · 6 guests

Tiki Bar, Hoppin, Sandbars, Down Island Vibes with Barrier island views

New
Superowner
$150/hour
Sunday Mimosa Brunch Sail: Shared Sail with Brunch Bites Included
Sailing in Mount Pleasant · 100 guests

Sunday Mimosa Brunch Sail: Shared Sail with Brunch Bites Included

New
$375/hour
Shared Charleston Harbor Sunset Sail - 50ft Catamaran with Bar Onboard
Sailing in Mount Pleasant · 100 guests

Shared Charleston Harbor Sunset Sail - 50ft Catamaran with Bar Onboard

New
$375/hour
Private Charter Charleston Harbor Sail - 55ft Catamaran with Bar Onboard
Sailing in Mount Pleasant · 100 guests

Private Charter Charleston Harbor Sail - 55ft Catamaran with Bar Onboard

New
$1,625+/hour

Sailing Reviews in Charleston

  1. PM

    Pooja

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

    Went out on a sunset sail with my family for my dad’s 60th birthday. Johnny had everything we needed to have the best time. Would easily choose to sail with Johnny any time we’re back in the area. Everyone had a blast!

  2. JW

    Jamie

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

    This was definitely the highlight of my bachelorette trip to Charleston!! Captain Ryan was amazing, super accommodating and went above & beyond - he even surprised us with a karaoke machine. The boat was awesome & came with anything you could need - pillows & tons of seats, a cooler with ice, a kitchen with cups, a bathroom, etc. Thank you for such a great trip Captain Ryan - we will definitely book again our next trip!

  3. SB

    Shelby

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

    My first sailboat ride was absolutely incredible. The entire experience was so relaxing, and I felt comfortable from the moment we stepped on board. The crew was incredibly accommodating with photos and made sure we had the best spots to capture the views. The scenery was truly stunning, and everything about the trip felt calm and effortless. I couldn’t have asked for a better first sailing experience.

  4. DJ

    Duane

    Charleston's Largest Private Luxury Sailing Yacht 50ft Windchaser Custom Cruises

    We had a great time and even experienced sailing too. Went above and beyond and made sure we had a great time.

  5. AM

    Ann

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

    We had such a lovely, charming ride into a misty and foggy sky! The dolphins came so close to the boat, the air was so fresh, and the sandbar was so beautiful that we got off and explored! Johnny made the experience so memorable for our family adventure!

  6. HS

    Hillary

    Charleston's Largest Private Luxury Sailing Yacht 50ft Windchaser Custom Cruises

    Captain Jen was the most gracious host! The sailboat was immaculate and such a fun experience!