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Sailing 101 in the Charleston Harbor

Charleston, United States

Experience hosted by Jay

2.5 hours
Includes drinks
Up to 6 people
Hosted in English

What you'll do

After a brief safety speech, we will shove off the dock and head into the scenic Charleston Harbor. As we raise the sails and turn the engine off, you'll immediately feel the relaxation set in and discover why the sailboat is named Mental Heeling.
You'll be involved as much (or as little) as you prefer as we navigate the Harbor together. Tacking and gybing our way to the various landmarks including: Fort Sumter, The Battery, USS Yorktown, Castle Pinckney and the iconic Ravenel Bridge.
Guests under the age of 13 will be required to wear a life jacket per the US Coast Guard. I will have adult and child life jackets onboard.
Other things to note
You will receive a Welcome Message via Airbnb messenger upon booking, PLEASE READ!
Booking Tip- book early in your visit in case we need to reschedule due to weather.
You can bring any snacks/drinks that you would like. Adults 21+ may bring alcohol. **Please avoid bringing any glass**
After a brief safety speech, we will shove off the dock and head into the scenic Charleston Harbor. As we raise the sails and turn the engine off, you'll immediately feel the relaxation set in and discover why the sailboat is named Mental Heeling.
You'll be involved as much (or as little) as you prefer as we navigate the Harbor together. Tacking and gybing our way to the various landmarks including: Fort Sumter, The Battery, USS Yorktown…

Jay's commitment to safety

This host committed to Airbnb’s COVID-19-related safety and cleaning guidelines—including adhering to social distancing guidelines, practising good hygiene and ensuring that all participants wear a mask.
Learn more

What's included

  • Drinks
    Of age guests are welcome to bring alcoholic beverages (please avoid glass)...
From $138
/ person
Book for a private group
Sat, 24 Apr
$138 per person
$138 per person
Wed, 5 May
$138 per person
$138 per person
Thu, 6 May
$138 per person
$138 per person

Meet your host, Jay

Host on Airbnb since 2014
  • 359 Reviews
  • Identity verified
Captain Jay
After being laid off from the Financial Industry in 2009 during the "Great Recession" I decided to migrate south and trade spreadsheets for sailing. In 2014, I purchased my 1988 30ft Catalina MKII and named her Mental Heeling as that is what she does best. Come out and see one of the most beautiful cities as it was meant to be seen, from the water.

Instagram: @MentalHeeling

Captain Jennifer
Jen loves sharing the history and ecological wonders that make the Lowcountry the special place that it is.

Captain Trey:
Swim coach to sailing captain
Captain Jay
After being laid off from the Financial Industry in 2009 during the "Great Recession" I decided to migrate south and trade spreadsheets for sailing. In 2014, I purchased my 1988 30ft Catalina MKII and named her Mental Heeling as that is what she does best. Come out and see one of the most beautiful cities as it was meant to be seen, from the water.

Instagram: @MentalHeeling

Captain Jennifer
Jen loves sharing the history and ecological wonders that m…
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Where you'll be

While visiting Charleston, it's a must to see this beautiful city from the water and under sail on Mental Heeling, a 1988 30ft Catalina MKII. Views include Fort Sumter, Castle Pinckney, The Ravenel Bridge, USS Yorktown and Historic Charleston Battery

Rated 4.97 out of 5 from 359 reviews.

Laura
April 2021
We had a wonderful experience sailing with Jay. He was very personable and knowledgeable. We had a 4 and 5 year old with us and he was also very accommodating to them. Would highly recommend for any trip to Charleston!
Kiri
April 2021
Captain Jay has planned an awesome experience for his guests! He and his crew teach sailing basics, cater to guests’ individual experiences, and offer incredible historical and anecdotal knowledge of the area. They also had some great recommendations for dining and entertainment on shore. I can’t recommend this experience enough. It is not to be missed!!
Captain Jay has planned an awesome experience for his guests! He and his crew teach sailing basics, cater to guests’ individual experiences, and offer incredible historical and ane…
Mat
April 2021
Captain Jay and his crew member Allison were fantastic. My wife booked this outing as a relaxing activity for our babymoon, and it did not disappoint! Captain Jay made us feel welcomed and comfortable, and provided us with the most beautiful, relaxing, and fun sunset sail— he even snapped some wonderful candid photos of us that we will cherish for years to come. I HIGHLY recommend anyone visiting Charleston to take advantage of this reasonably priced experience.
Captain Jay and his crew member Allison were fantastic. My wife booked this outing as a relaxing activity for our babymoon, and it did not disappoint! Captain Jay made us feel wel…
Zoë
April 2021
I scheduled this trip months in advance to surprise for my bf - it totally exceeded my expectations. We had such an amazing morning on the water, and met a few others onboard and all had a great time. Jay was a fantastic host, making sure all of our boating questions were answered, teaching us about the city, and giving us all a role to play from setting sail to driving the boat! Even though I was AWFUL at steering, Jay kept us safe (lol) and we stepped onto land feeling like we had the most magical morning!!
I scheduled this trip months in advance to surprise for my bf - it totally exceeded my expectations. We had such an amazing morning on the water, and met a few others onboard and a…
Elizabeth
April 2021
Great sail! So relaxing. Jay was super informative about the basics of sailing and eager to teach. I declined and sat back to enjoy the experience. I highly recommend his trip and will go again when I return to Charleston in a few months.
Ricardo
April 2021
Jay’s meet up instructions were superb. He answered all questions I had about sailing. I recommend this sail experience to relax around the Charleston harbor.

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Activity advisory

Expert industry partners
Every adventure follows industry guidelines. We partnered with the Adventure Travel Trade Association, expert leaders in adventure travel, to define best practices and standards for safety.
Know your comfort level
Please note outdoor activities carry risks, and you may be exposed to dangerous situations as part of this experience. Make sure you can participate safely given your abilities and the conditions (such as location, weather, and equipment).

Things to know

Cancellation policy

Any experience can be cancelled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Government ID

You’ll need to take a picture of yourself that matches the photo on your ID. This is so Airbnb can confirm who’s actually going on the experience. You’ll only have to do this once.

Guest requirements

Up to 6 guests ages 5 and up can attend. Parents may also bring children under 2 years of age.

What to bring

Light jacket

Sunglasses