Charleston Sailing Adventures

Charleston Sailing Adventures Come experience the adventure of sailing! The 27' Prevailing Winds offers private sailing charters for up to 6 passengers. Contact us today to book!

Charleston Sailing Adventures offers small group sailing experiences aboard our catamarans Prevailing Winds and Double Fun. The 40' Double Fun also offers private sailing charters, but for groups up to 24 passengers! Double Fun also hosts our daily public sunset sail (most popular). All trips depart from the Charleston Maritime Center, located in historic downtown Charleston. Passengers often enjo

y up-close sightings of dolphin, birds, sea turtles, and more, all while gliding silently by under sail. All tours are professionally guided by USCG licensed Captains and can include narration on local marine wildlife, environmental ecology, and Charleston's amazing sights and history.

Memorial Day Weekend sail, anyone?? ⛵️If you're spending the long weekend in Charleston, there's no better place to be t...
05/23/2025

Memorial Day Weekend sail, anyone?? ⛵️

If you're spending the long weekend in Charleston, there's no better place to be than out on the water. 🇺🇸

As we set sail, we’re also taking a moment to honor those who gave their lives in service. We’re grateful for the freedom to enjoy days like this.

https://fareharbor.com/embeds/book/charlestonsailingadventures/items/

Snapped a dreamy sail photo? Don’t keep it to yourself. 😉Huge thanks to everyone who’s been tagging us lately—these shot...
05/16/2025

Snapped a dreamy sail photo? Don’t keep it to yourself. 😉

Huge thanks to everyone who’s been tagging us lately—these shots are just a few of our recent favorites.

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Tag us on your next adventure for a chance to be featured—we’re always down to share your masterpieces!

Summer in Charleston means bachelorettes, wedding weekends, grad celebrations, and friends rolling into town just becaus...
05/13/2025

Summer in Charleston means bachelorettes, wedding weekends, grad celebrations, and friends rolling into town just because.

If you’ve got a crew and want to get out on the water, our private charters are the way to go.

Daytime or sunset sails, big or small groups—we’ve got options.

⛵ Prevailing Winds is perfect for up to 6 people.

⛵ Double Fun fits up to 24 and is great for those larger groups.

Trips start at 1.5–2 hours and can be extended if you're really feeling it.

Pro-tip: Planning ahead is smart (especially this time of year).

Click here to check availability and get your group set: https://fareharbor.com/embeds/book/charlestonsailingadventures/items/
Charleston Sailing Adventures
Charleston Bachelorette
Large Group Sailing
Sailing Charters

Give Mom the gift of a few hours on the water this Mother's Day 🌊If Mother’s Day snuck up on you, don’t stress—we’ve got...
05/08/2025

Give Mom the gift of a few hours on the water this Mother's Day 🌊

If Mother’s Day snuck up on you, don’t stress—we’ve got an easy (and thoughtful) gift idea. 👇

A sailing experience is a sweet way to say thank you—quiet water, fresh air, maybe a glass of wine. 🍷

Perfect for moms, mother figures, or anyone who's shown up like one. 💕

Gift cards are available online—no wrapping required and last minute shopping approved: https://bit.ly/4mobuMn

🌎 Happy Earth Day! 🌊The best views of Charleston are out here—and it’s up to all of us to keep them this beautiful. That...
04/22/2025

🌎 Happy Earth Day! 🌊

The best views of Charleston are out here—and it’s up to all of us to keep them this beautiful. That’s why we sail, harnessing the power of the wind instead of relying on a motor. Less fuel, less noise, and a whole lot more magic.

Let's sail sustainably today and every day. 💙

The end of one chapter. The beginning of a new. ☀️For the past 6 years we’ve been fortunate to have at the helm of our ...
04/22/2025

The end of one chapter. The beginning of a new. ☀️

For the past 6 years we’ve been fortunate to have at the helm of our boats as well as keeping Brian and the crew in line.

Jenny has been by Captain Brian’s side even before Charleston Sailing Adventures was founded, and he’s “been even more fortunate over the past 15 years to call her crewmate, climbing buddy, best lady at my wedding, and, mostly, friend.”

While we’re sad to see her leave, we’re excited for her next adventure out on the West coast! Give her a follow to stay up-to-date on her adventures. We send her away with proclamations of our undying love and a friendly reminder to send us postcards whenever she can. 💌

Fair winds, Cap! We’ll be here whenever you’re ready for a visit 💙⛵️

Fur on deck? Absolutely encouraged. 🐾⛵️It’s , so consider this your official reminder that Charleston Sailing Adventure...
04/11/2025

Fur on deck? Absolutely encouraged. 🐾⛵️

It’s , so consider this your official reminder that Charleston Sailing Adventures is VERY pet-friendly. Usually we like your pets more than you. Jk. Kinda. 😏

Treat your furry first mate to a little wind-in-the-ears action on your next sail.

Tired of windy days ruining your sail? Meet our new Wind-Free Sailing Adventure—perfectly still waters, guaranteed! 😎Apr...
04/01/2025

Tired of windy days ruining your sail? Meet our new Wind-Free Sailing Adventure—perfectly still waters, guaranteed! 😎

April Fools! 😜

Book a real sail today—winds included.

Address

10 Wharfside Street
Charleston, SC
29401

Opening Hours

Monday 9am - 7pm
Tuesday 9am - 7pm
Wednesday 9am - 7pm
Thursday 9am - 7pm
Friday 9am - 7pm
Saturday 9am - 7pm
Sunday 9am - 7pm

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Our Story

Independently owned and operated, Charleston Sailing Adventures offers intimate, customized experiences in Charleston Harbor. Prevailing Winds, our 27’ Stiletto Catamaran, is your vessel for adventure. And we’ve just started taking out a new boat too so we can offer even more charters. We host a number of trips for up to six people, and each one is BYOB! Feel the wind whip through your hair as you take in the beautiful views. Your USCG-licensed captain will tell you about Charleston’s history and the local marine wildlife as you enjoy the sunset or keep your eyes out for a pod of dolphins. Whether you’re looking for a fun adventure or a romantic cruise, we’ll make sure your sail is one to remember.