Sunset Sail in the Charleston Harbor

Charleston, South Carolina, United States

Experience hosted by Jay

  1. 2.5 hours
  2. Hosted in English
Fun for couples
Something to try together.

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…

What's included

  • Drinks
    Water
    Of age guests are welcome to bring alcoholic beverages (please a...

Meet your Host, Jay

Host on Airbnb since 2014
  • 518 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…
To protect your payment, never transfer money or communicate outside of the Airbnb website or app. Learn more

From $99/ person

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 4.98 out of 5 from 518 reviews.

Libby
November 2021
Jay’s sunset sail was a highlight of our trip to Charleston! He and his staff could not have been more welcoming, friendly and prepared. We felt like we were in great hands.
Uyen
October 2021
Great experience! Captain Jay and Mike were so sweet and knowledgeable. My husband and I had a beautiful sail. Would definitely recommend to anyone wanting a relaxing evening.
Lesley
October 2021
The highlight of our Charleston vacation! A relaxing sail, beautiful sunset and even dolphins! Easy Uber ride from downtown - book, you’ll love it!
Brittany
October 2021
Despite not having the best weather- getting rained on/having to cut the trip short, we had a great time! It was our first time on a sailboat and we can’t wait to do it again. Definitely recommend booking with Jay!
Kaylee
October 2021
Sailing the Charleston Harbor with Jay was the highlight of our trip. Jay and Allison are an awesome crew to make everyone feel comfortable and are incredibly knowledgeable about the Charleston area. We would absolutely recommend this experience! Thank you so much for such an awesome night, Jay!
Chloe
October 2021
Just book it! It was one of the BEST parts of our trip (I got engaged the next day after this experience, haha!) It was so worth it! Jay and Allison were awesome and super knowledgeable. They gave really great recommendations/stories/background in Charleston which was really cool. We cannot wait to book another excursion soon! (We did the sunset sail - it was BEAUTIFUL!)

Choose from available dates

    Things to know

    Guest requirements

    You’ll need a photo that matches the one on your ID to confirm who’s actually going on this experience.
    Guests ages 3 and up can attend, up to 6 guests total.
    All participants must wear a protective face covering and practice social distancing.
    The activity level for this experience is light.

    What to bring

    Light Jacket
    Sunglasses
    Hat
    Sunblock

    Cancellation policy

    Cancel up to 7 days before the Experience start time for a full refund, or within 24 hours of booking as long as the booking is made more than 48 hours before the start time.