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Catamaran Sailing Charters  – Charleston, Kiawah Island, Seabrook Island, Edisto, Beaufort

We offer occasional private captained Catamaran Sailing Charters in coastal South Carolina on our Leopard 48 Catamaran.  We are limited to 6 passengers.  If you have more than 6,  we can possibly partner with another boat in the area to reach your number!

Pilar Sailing CatamaranHosted by Master Captain Stephen Bell and First Officer Dawn Bell. Leave from North Edisto Inlet near Seabrook & Kiawah Islands south of Charleston SC.

Dolphin watches, sunset sails, beaching/swimming, paddle-boarding, fishing, open ocean sailing and more.

Choose from :

  • Day sail for up to 6 people – $1400 includes all food and drinks
  • 2 Day Sail  for up to 4 people including overnight stay anchored near beach – $2800 includes all food and drinks
  • Gulf stream trip for fishing with overnight on open ocean – contact us for customized trip quote with your requested dates

Cabins available:  2 private double bed cabins with heads available for 2 to 4 people.

See Yacht Pictures here

Message us for more details or call 704.870.7091.


Watch our videos of catamaran sailing in the area.

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Charter Sailing Videos
Watch our sailing adventures in the North Edisto River inlet - Charleston, Kiawah, Seabrook Island, Edisto


South Carolina Sailboat Charter Trip Options

We will choose from the following routes depending on wind direction.

  1. Sail out Edisto River and out the channel to the gulf stream, where we will sail and fish all day, then continue sailing all night back to Seabrook/Kiawah Island.  We can do this trip in most types of wind. 2 days
  2. Sail to Charleston, explore the city sights near the water, anchor overnight, then sail back to Seabrook/Kiawah the next day.  Can also stay 2 nights in Charleston if desired.  Best wind for this trip is straight east but could also do this on a south wind going to Charleston, and a north wind going back. 2-3 days
  3. Sail to Edisto Island Beach & Beaufort – anchor overnight, then sail back.  Best to have north wind going, and south wind returning. 2 days
  4. Sail to Edisto Island Beach, Hunting Island, Fripp’s, Prichard’s, and finally Hilton Head.    Stop as desired along the way, anchoring overnight where appropriate.  Return the same.  Best to have north wind going, and south wind returning. 1 week
  5. Sail to Georgia – Sail to Tybee Island, and Savannah.  Stop at other SC islands along the way as desired and as time allows.  Return the same way.  Best to have north wind going, and south wind returning. 1 week


Island Activity Possibilities


  • Horseback riding along the beach (reserve in advance)
  • Bike riding around the island (rentals at Seacoast Outfitters)
  • Bike ride to beach for the day
  • Paddleboard rentals
  • Deveaux Bank – private island
  • Take smaller boat through marsh for fishing, birdwatching and visiting Driftwood Beach
  • See Angel Oak Tree – 400 year old, 66.5 ft tall, arms that reach ground.
  • Oysters on the Grill on board Pilar
  • Shopping at Freshfields
  • Dining at Freshfields


Charleston Tea Plantation
6617 Maybank Hwy, Wadmalaw Island, SC 29487
Hours: Open ⋅ Closes 4PM, Phone: (843) 559-0383

Firefly Tea Plantation
6812 Bears Bluff Rd, Wadmalaw Island, SC 29487
Hours: Open ⋅ Closes 5PM, Phone: (843) 557-1405

Deep Water Vineyard
6775 Bears Bluff Rd, Wadmalaw Island, SC 29487
Hours: Open ⋅ Closes 5PM, Phone: (843) 559-6867

Rockville Historic District from the 1800s as a resort town
Wadmalaw Island, SC



  • Meeting Street
  • Crafts Market
  • Shopping
  • Restaurants
  • Battery/Historic Home Oceanside Walk
  • Historic Building walk
  • Horse drawn carriage tour

Plantations – Must see at least one!

  • Boone Hall Plantation has been recognized as the #1 Plantation in the Charleston area according to USA Today’s 10BEST and is a “must see” according to NBC Daytime Television.
  • Magnolia Plantation & Gardens is SC’s “Most Visited Plantation” and the only garden in South Carolina selected as one of “America’s Most Beautiful Gardens.”
  • McLeod Plantation Historic Site was established in 1851. An important Gullah/Geechee heritage site, carefully preserved in recognition of generations of enslaved people & its cultural & historical significance.
  • Drayton Hall is best known for its architectural significance.  American’s oldest unrestored plantation open to the public c. 1738.


  • Charles Towne Landing State Historic Site – where settlers landed in 1670.  664 acre park – 80 acres gardens, zoo and 17th century sailing ship replica.