Your Sailing Community

Courageous Sailing is a nonprofit community sailing and youth development organization committed to providing people of all ages and backgrounds with opportunities to learn, sail, and enjoy Boston Harbor.



We are OPEN!!

Members are welcome to make reservations today! 

If you are looking to join us on the water this season, check out our lessons and membership pages. 


Help Support Courageous

Updates on Pier 4 Closure

Pier 4 is partially closed in 2022 for emergency structural repairs, and Courageous operations are moving to Pier 3 and the base of Pier 4.

Read the latest updates

Friday, November 23rd through Monday, November 26th

Black Friday Sales

It is almost Thanksgiving, and you know what that means... Black Friday Sales are on the way! These are our lowest prices of the year. What better time to treat a loved one (or yourself) to a season of sailing in 2019!

Start sailing

Saturdays | Nov - March

Frostbite Racing

It's that time of the year again when we call on our most intrepid racers to join us for our best racing of the year: frostbiting!

Please contact Caitlyn Ridgely if you're interested in racing or volunteering this winter.

Frostbite this winter

Pier 4, Charlestown

Courageous' main office and sailing location is on Pier 4 in the historic Charlestown Navy Yard.

(857) 452-1769

Seasonal Hours: May - October
Monday 12:00 pm - Sunset
Tuesday 12:00 pm - Sunset
Wednesday 12:00 pm - Sunset
Thursday 12:00 pm - Sunset
Friday 12:00 pm - Sunset
Weekends 10:00 am - Sunset

Please note: Dock call falls 30 minutes before sunset each day

Jamaica Pond

Sailing on Jamaica Pond in cooperation with the Boston Department of Parks & Recreation. Click here for more information!

(857) 452-1770

Seasonal Hours: Temporarily Closed to Rentals

Monday 12:00 pm - 7:30 pm
Tuesday 12:00 pm - 7:30 pm
Wednesday 12:00 pm - 7:30 pm
Thursday 12:00 pm - 7:30 pm
Friday 12:00 pm - 7:30 pm
Weekends & Holidays 10:00 pm - 7:30 pm

We sometimes close locations early due to weather. Check this website or social media pages for information, or call ahead for the latest update. No boats are allowed to depart within 60 minutes of sunset.