I was laid off from the financial industry in 2009 and decided to migrate south. In 2014, I purchased my 1988 thirty-foot Catalina MKII and named her Mental Heeling. I look forward to sharing the beauty of Charleston from the water with you.
To help protect your payment, always use Airbnb to send money and communicate with hosts.
4.98, · 527 reviews
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, · April 2025
Had a blast with Jay. Great experience, learned quite a bit and just enjoyed being out there.
Tully
Austin, TX
, · October 2024
This sail was the highlight of our trip. Jay is a great captain- very knowledgeable about the area and lets you be as involved in the sailing experience as you wish. He is easy going and fun to talk with. The boat is very comfortable and stable and well appointed. I highly recommend this experience as a guest and as a fellow sailing enthusiast .
Linda
Eufaula, OK
, · September 2024
Captain Jay and Laurah were terrific! We had a beautiful sail on a lovely comfortable well cared for boat. The journey out into the harbor and back was smooth and very enjoyable. The two captains were fun to talk to and perfect hosts. We were celebrating our anniversary and the sail made it all the more special. Highly recommend and have the benefit of learning more about beautiful Charleston from the water.
Marshall
New York, NY
, · August 2024
We loved our time sailing around Charleston with Captain Jay and Christian. They were extremely knowledgeable, kind, and attentive. We had a blast for our 15th wedding anniversary. They even let my wife steer the boat and I helped raise the sails.
Larry
United States
, · July 2024
Mississippi loved our sailing adventure. Jay and Franci were very knowledgeable about sailing and Charleston history.
David
McComb, MS
, · June 2023
If you’re looking for an amazing boat experience in Charleston, you can stop right here. We had Kathleen as our captain and Emmy as first mate. They are so knowledgeable about Charleston history and sailing. My husband and i learned so much. They made sure this experience was personalized to us and truly felt like we were boating around the harbor with two friends. I would highly recommend.
Marguerite
San Antonio, TX
Things to know
Guest requirements
Guests ages 5 and up can attend, up to 6 guests total.
Activity level
The activity level for this experience is light and the skill level is beginner.
Cancel at least 1 day before the start time for a full refund.
Outdoor experiences are vetted for quality
Outdoor experiences are led by explorers, hikers, and other experts, and showcase what makes the city unique. Learn more
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From $149 / guest
From $149 per guest
Free cancellation
Sail Charleston Harbor
4.98 · 527 reviews
From $149 / guest
From $149 per guest
Free cancellation
What you’ll do
Welcome message
Read all instructions carefully.
Safety talk
Understand safety protocols on board.
Shove off dock
Head into the scenic Charleston Harbor.
Raise the sails
Feel relaxation set in as we sail.
Explore landmarks
Enjoy the view of a variety of local landmarks
Hosted in English
Where we’ll meet
The Harborage At Ashley River Marina
Charleston, South Carolina, 29401
About me
Sailing Captain
I was laid off from the financial industry in 2009 and decided to migrate south. In 2014, I purchased my 1988 thirty-foot Catalina MKII and named her Mental Heeling. I look forward to sharing the beauty of Charleston from the water with you.
To help protect your payment, always use Airbnb to send money and communicate with hosts.
Sail Charleston Harbor
Experience the beauty of Charleston from the water.
Had a blast with Jay. Great experience, learned quite a bit and just enjoyed being out there.
Tully
Austin, TX
, · October 2024
This sail was the highlight of our trip. Jay is a great captain- very knowledgeable about the area and lets you be as involved in the sailing experience as you wish. He is easy going and fun to talk with. The boat is very comfortable and stable and well appointed. I highly recommend this experience as a guest and as a fellow sailing enthusiast .
Linda
Eufaula, OK
, · September 2024
Captain Jay and Laurah were terrific! We had a beautiful sail on a lovely comfortable well cared for boat. The journey out into the harbor and back was smooth and very enjoyable. The two captains were fun to talk to and perfect hosts. We were celebrating our anniversary and the sail made it all the more special. Highly recommend and have the benefit of learning more about beautiful Charleston from the water.
Marshall
New York, NY
, · August 2024
We loved our time sailing around Charleston with Captain Jay and Christian. They were extremely knowledgeable, kind, and attentive. We had a blast for our 15th wedding anniversary. They even let my wife steer the boat and I helped raise the sails.
Larry
United States
, · July 2024
Mississippi loved our sailing adventure. Jay and Franci were very knowledgeable about sailing and Charleston history.
David
McComb, MS
, · June 2023
If you’re looking for an amazing boat experience in Charleston, you can stop right here. We had Kathleen as our captain and Emmy as first mate. They are so knowledgeable about Charleston history and sailing. My husband and i learned so much. They made sure this experience was personalized to us and truly felt like we were boating around the harbor with two friends. I would highly recommend.
Marguerite
San Antonio, TX
Things to know
Guest requirements
Guests ages 5 and up can attend, up to 6 guests total.
Activity level
The activity level for this experience is light and the skill level is beginner.