Charleston Harbor Sailing

04/25/2026

Many know Captain Will from Charleston Harbor Sailing , but one of his passions is racing! Will and his crew finished Charleston Race Week in first place in the inshore handicap fleet for the second year in a row.🥇The handicap fleet was 9 boats strong, consisting of a variety of boats ranging from 23 to 38 feet.

Charleston Race Week was the first event aboard Will’s new boat, Stella, a 1984 Impulse 26. Charleston Race Week is the biggest keelboat regatta in the western hemisphere. 👏👏👏

04/23/2026

Unlock the secret to life✨

Link in bio to book your private sail today!

03/02/2026

Before we set sail, let’s get you ship-shape with the details... Book in our 🔗 or contact us below:

Call/Text 843-256-6225
Info@charlestonharborsailing.com
Downtown Charleston | 33 Lockwood Dr

02/26/2026

These are the moments we love to experience in the Lowcountry ⛵️

02/14/2026

Come experience “Joy” in its purest form…💗⛵️

04/15/2025

We couldn’t be more proud!! 🥇 Our very own Captain Will led his dad and 3 brothers to a first-place finish in the Inshore Handicap division at this year’s Charleston Race Week aboard his boat, Stella.

⛵️Charleston Race Week is the largest keelboat regatta in the western hemisphere, drawing hundreds of teams from across the country and around the world.

Stella won four out of nine races, and never finished worse than third, finishing the event with a low total of 12 points. Challenging conditions favored patience and tactical skill, allowing Stella remain at the front of the pact despite being the one of smallest boats in the fleet.

Charleston Race Week is the first event of the summer racing season, and this win comes on the heels of an extremely successful winter season, with a division win in the Nassau Cup Ocean Race and first place in the ORC 3 Division of the SORC Islands in the Stream series, as well as a second place finishes in the Ft. Lauderdale to Key West Race and the Wirth Munroe Ocean Race.

03/05/2025

We love hosting dreamy photoshoots on our sailboat. You can book a private charter and bring a photographer any day of the week. Just give us a heads up so we can plan the best sailing course to ensure the best photos 😍📸

06/18/2024

Meet our Captain!! ⛵️ Captain Will Monts is a lifelong sailor. His maritime journey began at the age of 6 in Bluffton, SC, where he honed his sailing skills in Optimist dinghies. This early passion evolved into competitive racing and numerous seafaring tales. With a wealth of sailing experiences nationally and globally, Will has accumulated a treasure trove of maritime adventures, fishing achievements, and two prestigious international championships.

With over a decade of professional sailing instruction under his belt, Will boasts a repertoire of certifications, including a 50 Gross Ton Master License, US Sailing Certified Instructor, STCW with PDSD, and First Aid/CPR credentials. Having navigated thousands of nautical miles and actively participated in local, regional, and national regattas,

Will’s commitment to safety and exceptional service shines through in every charter, ensuring each guest experience is an unforgettable voyage.

05/13/2024

Our small business was featured on Live 5 News for the Palmetto Life series. We are so grateful to share the JOY of being on the Charleston Harbor with you! Thank you for your support!

04/30/2024

Sit back, relax, and immerse yourself in the breathtaking views during this once-in-a-lifetime escapade. Don't miss out on this truly remarkable experience! Book your adventure today.

Discover Charleston Harbor's Beauty On Board Esprit De Joy Experience the beauty of Charleston Harbor from the vast ocean on an unforgettable journey on board Esprit de Joy. Sit back, relax, and immerse yourself in the breathtaking views during this once-in-a-lifetime escapade. Don't miss out on thi...

12/21/2023

Sailing through the holidays with Santa’s elves on a magical “sleigh” ride! ⛵️🎅🏼✨