Flip Flop Party on the Pier! 

Welcome to the Flip Flop Party on the Pier! Join us for a fun-filled evening at Courageous Sailing located on Pier 4 in Charlestown (197 8th street for GPS). Get ready to kick off your shoes, put on your favorite pair of flip flops, and dance the day away by the water. We'll have music and drinks to keep the party going. Don't miss out on this awesome event - grab your friends and help us celebrate one of the best events summer has to offer! Our party is for land-lubbers and sailors alike. Sailors interested in joining us on the water before the event begins should <a href="https://courageoussailing.org/events/courageous-events/flip-flop-regatta/">check out our website</a> for details about the regatta. See you there!

Courageous Sailing 

Make-A-Mark

Make-A-Mark is back! Join us under the tent on Pier 4 to celebrate and support Courageous Sailing's free sailing and learning programs for metro Boston kids. There will be Bites and snacks, live music by the Chicken Slacks and an auction and raffle!

Courageous Sailing Open House @ Jamacia Pond

Courageous Sailing Open House @ Jamacia Pond Join us on the water for our open house! 11:00am-2:00pm FREE 20 minute rides on any of our vessels.  Paddleboard Single Kayak Double Kayak Rowboat Sailboat   Sailboat is skippered by one of our instuctors and seats up to 4 guests. Rowboats Seat up to 3 adults.    Please review the available slots through the link and click on the button to sign up. Thank you!

Pond Boathouse

Stand Up Paddleboard Yoga Jamaica Pond

Experience yoga from a brand new perspective! Sign up for our 90 minute, comprehensive introduction to SUP yoga - no prior experience necessary! Each class consists of a brief paddleboarding tutorial, a paddle to our yoga moorings, and an hour of yoga.

Courageous Sailing

Stand Up Paddleboard Yoga Classes

Courageous Sailing at Jamaica Pod

Courageous Sailing Open House: Sunday 4/27 Free Sailing

Join us on Pier 4 in Charlestown (197 8th street) for FREE 20-minute sails for you and your family and friends. Courageous welcomes all prospective sailors to come down to the Charlestown Navy Yard and join us for fun in the sun on Boston Harbor. Light refreshments and discounts on our most popular memberships and lessons will be available all weekend long! Kiddo (all ages) and dog-friendly! <a href="https://www.signupgenius.com/go/5080949A8A928A5FA7-55407533-courageous">Saturday April 26</a> &amp; <a href="https://www.signupgenius.com/go/5080949A8A928A5FA7-55407533-courageous">Sunday April 27</a>: 11am-2pm

Courageous Sailing Pier 4 Charlestown

Courageous Sailing Open House: Saturday 4/26 Free Sailing!

Join us on Pier 4 in Charlestown (197 8th street) for FREE 20-minute sails for you and your family and friends. Courageous welcomes all prospective sailors to come down to the Charlestown Navy Yard and join us for fun in the sun on Boston Harbor. Light refreshments and discounts on our most popular memberships and lessons will be available all weekend long! Kiddo (all ages) and dog-friendly! <a href="https://www.signupgenius.com/go/5080949A8A928A5FA7-55407533-courageous">Saturday April 26</a> &amp; <a href="https://www.signupgenius.com/go/5080949A8A928A5FA7-55407533-courageous">Sunday April 27</a>: 11am-2pm

Courageous Sailing Center- Pier 4 Charlestown

Flip Flop Party on the Pier

Welcome to the&nbsp;Flip Flop Party on the Pier! Join us for a fun-filled evening at&nbsp;Courageous Sailing&nbsp;located on Pier 4 in Charlestown (197 8th Street for GPS). Get ready to kick off your shoes, put on your favorite flip flops, and dance the day away by the water. We'll have music and drinks to keep the party going. Don't miss out on this awesome event - grab your friends and help us celebrate a return to the best event summer has to offer! Our party is for land-lubbers and sailors alike. Sailors interested in joining us on the water before the event begins should check out our website for details about the regatta. See you there!

Courageous Sailing Center- Pier 4

Courageous Sailing Open House: Sunday 4/21 Free Sailing

Join us on Pier 4 in Charlestown (197 8th street) for FREE 20-minute sails for you and your family and friends. Courageous welcomes all prospective sailors to come down to the Charlestown Navy Yard and join us for fun in the sun on Boston Harbor. Light refreshments and discounts on our most popular memberships and lessons will be available all weekend long! Kiddo (all ages) and dog-friendly! <a href="https://www.thebostoncalendar.com/events/courageous-sailing-open-house-saturday-4-20-free-sailing">Saturday April 20</a> &amp; <a href="https://www.thebostoncalendar.com/events/courageous-sailing-open-house-sunday-4-21-free-sailing">Sunday April 21</a>: 11am-2pm

Courageous Sailing Open House: Saturday 4/20 Free Sailing!

Join us on Pier 4 in Charlestown (197 8th street) for FREE 20-minute sails for you and your family and friends. Courageous welcomes all prospective sailors to come down to the Charlestown Navy Yard and join us for fun in the sun on Boston Harbor. Light refreshments and discounts on our most popular memberships and lessons will be available all weekend long! Kiddo (all ages) and dog-friendly! <a href="https://www.thebostoncalendar.com/events/courageous-sailing-open-house-saturday-4-20-free-sailing">Saturday April 20</a> &amp; <a href="https://www.thebostoncalendar.com/events/courageous-sailing-open-house-sunday-4-21-free-sailing">Sunday April 21</a>: 11am-2pm

Courageous Sailing Open House

Join us on Saturday April 22 or Sunday April 23 from 11-2 for our annual Open House Event. Want to learn how to sail? Thinking about joining Courageous? We invite prospective new sailing students and members to come down to the Charlestown Navy Yard and go for a free sail on Boston Harbor with one of our experienced skippers. Enjoy light refreshments ashore and fabulous views of the city from the end of the pier or aboard a Rhodes 19 during your half hour sail! Reservations are strongly encouraged. Sailboat voyages last 20 minutes and are first come, first served. Last sail departs at 1:40pm. <a href="https://www.signupgenius.com/go/5080949a8a928a5fa7-courageous3?fbclid=IwAR16cEGSfyKIiThbasT_58MhdtFDUZmENDx2pHN0VPJeaT_894MP5fOy_Ww#/">Reservations are strongly encouraged.</a> Please <a href="https://courageoussailing.my.site.com/csguest/s/courageous-sailing-waiver">sign a waiver</a> prior to arrival and arrive 10 minutes early. For families looking to bring more than 4, our boats can accommodate 4 adults or 2 adults and 3 small children. FAQ How is the event structured? Guests are welcome to come and go as they please but are only guaranteed a sail if they sign-up before arrival. For walk-ins, we will get take down the name of your group when you arrive and get you out on the water as soon as possible. For reservations, we will work hard to stick to your scheduled time but ask for grace as sailing times vary based on conditions. There will be light food and beverages available along with a few activities for the kiddos to keep them engaged while they wait. Our staff is on land and available to answer any questions you may have about our Youth and Adult programs, please look for our smiling faces and staff T-shirts. Do I need any experience on the water or with sailboats? No! This event is open to anyone who is interested in sailing, but no prior knowledge is required. Can I bring my kids? Yes, please bring the whole family! Sailing is a sport for all ages. The boats for Open House can accommodate up to 4 adults comfortably (or 2 adults, 3 kids), so if you have a larger group we will need to split between multiple boats. We have lifejackets for people of all sizes (infant-XXL) Do I need to reserve a spot? Yes, <a href="https://www.signupgenius.com/go/5080949a8a928a5fa7-courageous3#/">reservations are strongly encouraged. </a>

Courageous Sailing Center

S22: conversations

Wondering what to do in Boston? Places to eat? Free activities? Good for a group? Date night spot? Girls night out? The best things to do? Ask Joyraft!

Best places to go in Boston? Things to do? Places to eat?

Questions & answers about things to do in Boston

Recs 💬

Community recs 💬

S4: top picks

The most fun, cool and unique things to do in Boston. Can’t miss events, shows and experiences. Concerts, restaurants, bars, free things in Boston and beyond.

The most fun and cool events happening around Boston

Hot and new things to do in Boston

Hot & new

Hot & new 🔥

S11: happening this weekend

What to do in Boston this weekend? From festivals, concerts, performances, free events, screenings and more, Joyraft has the best things to do in Boston.

25+ things to do in Boston/Cambridge/Somerville this weekend

Things to do in Boston this weekend

This wknd

This weekend for you

S21: roundups

Our top picks: outdoor dining, free events, spring festivals, best bars, upcoming concerts, museum parties - the latest in and around Boston.  Slug: joyraft-top-picks-best-things-to-do-boston-ma

Top picks of the best things to do in and around Boston

Joyraft picks: Boston’s best things to do

Roundups ⭐️

Curated by Joyraft ⭐️

S28: calendar experiences

This week in Boston

This week in Boston 📆

This week 📆

S20: c+d experiences

Discover new, unique events and experiences happening in and around Boston. Perfect for date night, good for a group or with a friend. Be the first to know.

The newest events happening in and around Boston

The newest events on Joyraft

Just added

Just added to Joyraft

S16: editor picks

The most unique and can’t miss things coming up in Boston / Cambridge / Somerville and beyond. Festivals, food, drinks, fairs, concerts, art and free activities.

Unique and Can’t Miss Things to Do in Boston

Can’t-miss things to do in Boston 🚨

Can't-miss things to do 🚨

S2 (A): top experiences

The most popular things to do on Joyraft. Concerts, restaurants, bars, events, parties, openings, kid friendly, date ideas, free things in Boston and beyond.

Top 20 things to do in Boston

Top 20: Joyraft’s most popular

Top 20

Top 20 on Joyraft

S3 (A): trending experiences

Discover can’t miss events and things to do in Boston. The most fun, unique and cool events coming to the Boston area this spring and summer.

The hottest events happening in Boston

Trending events on Joyraft

Trending 📈

S17: interest based

Your guide to everything free in and around Boston. From events, to fairs, to festivals, to outdoors. Joyraft has all the free events happening near you.

100+ free things to do in Boston and beyond

Free things to do in Boston

Free things to do

S19: interest based

Kid-friendly events in Boston

S18: interest based

Where to eat and drink in Boston? Joyraft has Boston’s newest bars, restaurants and specials. Drinks and pre fixe dinner menus. Cambridge & Somerville too.

Where

sailcourageous1987

Experiences