After being laid off from the Financial Industry in 2009, I decided to migrate south and trade spreadsheets for sailing. In 2014, I purchased my 1988 30ft Catalina MKII and named her Mental Heeling. Come out and see Charleston from the water. @SailMentalHeeling
To help protect your payment, always use Airbnb to send money and communicate with hosts.
4.98, · 881 reviews
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, · 2 days ago
Jay and crew were great hosts! Due to storms in the area, we needed to reschedule our trip. Jay was in contact during the entire time and easily set a new date. Everything went smoothly and was so relaxing. He offered to let us be as involved as we would like, even offering to let us steer the boat! I cannot say enough good things about our evening. It is so worth it! Enjoy!
Alice
United States
, · 2 weeks ago
Great host. Fun ship. Good way to see the city.
Jessica
Austin, TX
, · 3 weeks ago
This was the highlight of our vacation! Jay and Christian were incredibly personable. Christian shared so much oyster and marine life knowledge — they both did a fantastic job reading the room and tailoring the experience to the group. They also gave a ton of recommendations for food and drink in the area. This was a fun, informative, and memorable experience!
Mallory Kaitlyn
Connecticut, United States
, · 3 weeks ago
Beautiful experience. We had pretty much perfect sailing weather and the sunset views of the harbor were to die for- especially at the very front of the boat!
Emma
Dansville, NY
, · May 2025
What can beat wrapping up a day with a beautiful sunset sailing!!! Amazing experience with lovely people!! Jay and his assistant took good care of us!! HIGHLY RECOMMEND 🧡
Jun
Phoenix, AZ
, · May 2025
Jay and Bella did a great job on our sail, we had GREAT conversations and Jay did very well on providing some history while sailing. This will always be a trip when I am in Charleston.
The weather was great for the sail, and we meet great new people who provide a lot of good information for our stay in Charleston.
Thank you so much for the forever memories.
Bernadette
Midland, NC
Things to know
Guest requirements
Guests ages 6 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 and see Charleston Harbor
4.98 · 881 reviews
From $149 / guest
From $149 per guest
Free cancellation
What you’ll do
Enjoy views
See landmarks based on wind, current, tide conditions.
Raise sails
Participate as much or as little as you prefer.
Explore landmarks
Views of Fort Sumter, The Battery, USS Yorktown, Castle Pinckney, Ravenel Bridge.
Shove off dock
You'll feel relaxation set in as we sail.
Safety speech
I'll cover essential safety information.
Hosted in English
Where we’ll meet
The Harborage At Ashley River Marina
Charleston, South Carolina, 29401
About me
Sailor and storyteller
After being laid off from the Financial Industry in 2009, I decided to migrate south and trade spreadsheets for sailing. In 2014, I purchased my 1988 30ft Catalina MKII and named her Mental Heeling. Come out and see Charleston from the water. @SailMentalHeeling
To help protect your payment, always use Airbnb to send money and communicate with hosts.
Sail and see Charleston Harbor
Raise sails, turn off the engine, and relax in scenic Charleston Harbor.
Jay and crew were great hosts! Due to storms in the area, we needed to reschedule our trip. Jay was in contact during the entire time and easily set a new date. Everything went smoothly and was so relaxing. He offered to let us be as involved as we would like, even offering to let us steer the boat! I cannot say enough good things about our evening. It is so worth it! Enjoy!
Alice
United States
, · 2 weeks ago
Great host. Fun ship. Good way to see the city.
Jessica
Austin, TX
, · 3 weeks ago
This was the highlight of our vacation! Jay and Christian were incredibly personable. Christian shared so much oyster and marine life knowledge — they both did a fantastic job reading the room and tailoring the experience to the group. They also gave a ton of recommendations for food and drink in the area. This was a fun, informative, and memorable experience!
Mallory Kaitlyn
Connecticut, United States
, · 3 weeks ago
Beautiful experience. We had pretty much perfect sailing weather and the sunset views of the harbor were to die for- especially at the very front of the boat!
Emma
Dansville, NY
, · May 2025
What can beat wrapping up a day with a beautiful sunset sailing!!! Amazing experience with lovely people!! Jay and his assistant took good care of us!! HIGHLY RECOMMEND 🧡
Jun
Phoenix, AZ
, · May 2025
Jay and Bella did a great job on our sail, we had GREAT conversations and Jay did very well on providing some history while sailing. This will always be a trip when I am in Charleston.
The weather was great for the sail, and we meet great new people who provide a lot of good information for our stay in Charleston.
Thank you so much for the forever memories.
Bernadette
Midland, NC
Things to know
Guest requirements
Guests ages 6 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.