Adult Program

Courageous memberships make it very easy to get started and to step up to the next level when the time comes.  We offer a flexible range of options for our core 19’ to 24’ keelboat fleets to suit your sailing plans, your schedule and your budget.

All memberships include barbeques, racing, fireworks-watching parties, moonlight sails, Harbor Island camping trips, and discounts on courses.  As a Courageous member, you’ll be a part of an enthusiastic, inclusive community of sailors...and you’ll be helping Courageous provide free and low-cost sailing opportunities for Boston kids.

Rhodes 19 - The backbone of our fleet, Courageous Sailing fields a remarkable 27 Rhodes 19s. They are easy to handle and offer a fun, comfortable sailing experience for sailors of all calibers from novice to seasoned one-design racer.

J/22 –There comes a time when you want to sail in a higher gear. The J/22 is a fast and highly responsive keelboat, built for speed and performance. It features a symmetric spinnaker and more refined sail controls.

J/24*.  With a more diverse sail plan, a larger cabin and an engine, our J24s will equip you to set your sights further and explore more of Boston Harbor and the Islands.

Check outs: Please note that all members must pass an on the water check out and obtain a “Flag Rating” [link to] for each boat they will be sailing.  Typically, as the boat size increases, so do our expectation around seamanship and skill-level.

Flexible access: All Rhodes 19 and J22 memberships are available in variety of options to fit every schedule.  Our basic, full membership enables 7 day/week access all season long.  We also offer weekend, weekday, one-month and even one-day options.  We also offer a family membership, which is a shared membership for families with more than one skipper who might use the membership at different times.  *Due to limited availability we only offer the full membership for our J/24s.

2016 prices have stayed level, but upgrades are now included!  We have done away with the optional $50 guest pass and $50 damage waiver and built them into the price of all memberships.  Simply put, invite as many guests as you like.  And, if something breaks due to normal wear and tear, you’re covered.  We’ve taken these $100 of upgrades and included them into the price of all memberships through an increase of just $50 – passing along a small savings for all members who used to purchase both.

Adult Program Frequently Asked Questions

Where should I park? What’s the easiest way to get there?

Most of the Charlestown parking near Courageous is metered or resident parking, so your best bet is is to park at the Nautica Parking Garage (88 Constitution Road, 02129). Remember to ask the Courageous Front Desk to validate your ticket; rates are typically $7-$11 with validation. Make sure to allow an extra 15 minutes to stroll through the Navy Yard to Pier 4, and take a look at the map so you know where to walk. From the Nautica, leave the water and piers on your right and walk into the Navy Yard. Pass the Constitution Museum on your right, then Pier 3 (where the MBTA ferry leaves from). Turn right at the next pier, walking along the U-shaped inlet of water on your right and a park on your left. Walk past the round brick building and onto Pier 4--you’ll see the masts of our boats on the left of the pier. Go to the left side of our boathouse, which is a little white building with a flag on top.

You may also park at the Flagship Wharf Garage (197 8th Street, 02129), which is closer but more expensive. Street parking is an option if you’ve got extra time to look for it. There are 2-hour metered spots on 1st Street (free and unlimited on Sundays), free Sunday parking in residential spots on the far side of Chelsea Street, and very rare free spots on Terry Ring. No guarantees on this information--make sure to check the signs!! Do not park on any of the piers, including Pier 4.

Public transportation is also available (Green Line, Orange Line, 93 bus, or the MBTA ferry from Long Wharf to Pier 3), and biking is the perfect way to get to Courageous. Please check our website for more information and a map.

When should I plan to arrive?

Please arrive at Courageous about 10 minutes early, and check in at the Front Desk. Make sure to allow extra time for parking and the walk over. If you’re running late, please give us a call and let us know. If you arrive late for a 2-hour sail, we may not be able to give you the full two hours. 

What should I bring? What should I wear? What about food?

Bring a water bottle, sunscreen, and a few extra layers, including a waterproof jacket. Sunglasses and a hat are good ideas, too. Cameras/phones are welcome--we love to be tagged in photos. If you’ve bought an online deal, make sure to bring your voucher code if you haven’t provided it already.

Feel free to bring snacks or lunch. Coffee, snacks, and sandwiches are available at several locations near Courageous. Our full-day weekend courses incorporate a half hour lunch break. You may leave to purchase lunch, or bring your own; our refrigerator is available for the use of members and students. You’re also welcome to use our grills and bring beer or other drinks to enjoy after sailing (no alcohol before or during sailing). We often host cookouts for members, students, and racers on weekday evenings (Saturdays in the fall)--feel free to join in.

Dress comfortably--jeans and sneakers are just fine. Wear a few layers, since the weather is often hotter or chillier than you expect, and bring an extra layer or two. We recommend wearing closed-toed shoes with good traction and non-marking soles, such as sneakers or boat shoes--no flip flops or heels. Life jackets are provided.

What if there’s bad weather or strong wind?

Well, that depends on what you mean by bad weather. Sailing is fun even when the weather isn’t perfect, and we can’t guarantee sunny days for everyone. So if it’s overcast or raining a bit, we will sail (we have raingear you can borrow, if necessary). We monitor the radar and wind speed closely, so that we can predict when heavy rain or unsafe conditions are likely to pass through.

2-hour sails and private lessons: In Courageous decides to cancel due to likely thunderstorms, heavy rain, dangerously strong winds, or any other reason, we will reschedule your 2-hour sail or lesson free of charge. If the weather is looking bad, give us a call before heading to Charlestown if we haven’t contacted you already.

Courses: We almost never cancel a full day of our courses, as the curriculum includes plenty of onshore material that can be covered when the conditions aren’t safe to sail.

How will I know if my course is canceled or there are restrictions on member sailing?

If your course is canceled, we’ll send out email notifications to students by approximately 8:30 AM, as well as posting an alert on our homepage. If you’re concerned about the weather and need notification before 8:30, please let us know a day in advance. 

It’s always a good idea to check the Courageous homepage for weather alerts and restrictions before heading over to Pier 4, especially if you’re a Red or Yellow Flag skipper--sometimes it’s windier than you realize! ;Alerts are usually posted half an hour before we open, and may change throughout the day. If you’re a member who’s not sure if you’ll be allowed to sail (or if you WANT to sail!), give us a call and we’ll give you the latest scoop on the wind and radar. 

What if I need to reschedule?

2-hour sails and private lessons: As long as you give us a week’s notice or more, rescheduling is no problem at all, and you can even change online bookings yourself. If you need to reschedule less than a week before your scheduled appointment, please give us a call. We will charge a $30 fee for rescheduling within 3 days of your scheduled appointment. Vouchers and private lesson charges are subject to forfeiture for cancellations within 24 hours or no-shows. We cannot guarantee availability for rescheduled appointments.

Courses: Students must attend all dates of their selected course. Make-up time for missed sessions costs an additional $30/hr. Students may reschedule freely up to 1 week before the start of their course; after that a rescheduling fee of $100 will be charged. If Courageous cancels all or part of your course due to weather or any other reason, we will reschedule for a convenient time.

What kind of boat will I be sailing? Could we capsize? Will I get wet?

For our 2-hour sails and most of our courses, you’ll be sailing a Rhodes 19. Rhodes 19s are keelboats, which means that there is a big heavy metal fin on the bottom that prevents the boat from capsizing. On windy days, you may get a bit wet from the spray, but there is a compartment where you can stow items and keep them dry. 

What should I do with my belongings and valuables?

Your cellphone will fall out of your back pocket! Make sure it is zipped into a safe place. If you’d like to store your valuables on land, we can hold them for you behind the Front Desk. The boats are usually dry enough to bring your bag, etc. along with you--just stow your things in one of the side bins. If you’d prefer to leave your things ashore, bring a lock and use one of the lockers in the hall on the way to the bathrooms. Please don’t leave your belongings out in the boathouse or in an unlocked locker, or leave anything overnight. 

When is the best time to sail on Boston Harbor?

Some of the best sailing of the year is in May, June, and September...and don’t be afraid to book a course or 2-hour sail in October! We love fall sailing because the harbor tends to be less crowded, the wind is often excellent, and a warm jacket is all you need if it’s chilly. The hotter months in July and August are great too, but prone to lighter winds and the occasional thunderstorm. 

How can I buy sailing gear or Courageous merchandise?

Courageous offers 20% off Gill sailing gear; just ask at the Front Desk for a catalogue. Gear can be embroidered with Courageous’s logo. Sailing gloves, charts, drybags, and Courageous T-shirts, hats, jackets, floatable keychains, water bottles, and more are also for sale at the Front Desk, subject to availability. If you have any questions about buying gear locally or online, our staff will be happy to give you advice.

Can I bring children?

Of course! Courageous is a great place to sail with kids. We have a variety of life jackets for children and babies. There must be one responsible adult per child under the age of 12 (in addition to the instructor), unless you’ve discussed it with us in advance. 

Can pets sail at Courageous?

Chill pets are welcome, but you must bring a (pet-specific) life jacket for them. Please keep your dog on a leash, and be aware that there are often other dogs here. If you and/or your pet are fairly new to sailing, a 2-hour sail probably isn’t the best time to bring your pet on the boat.

I loved my 2-hour sail! How can I keep sailing?

Great! Courageous makes it easy. If you are new to Courageous and decide to sign up for a course or membership after your sail (whether purchased through us or through an online deal), we’ll be happy to give you a 15% discount off of one item. Check out our courses and membership options. Please contact us directly within one week of your two-hour sail to take advantage of this offer.

12 Quick Tips and Reminders For Courageous Members
  1. All new members must go through an orientation and checkout sail before using the fleet.  Returning members can skip the orientation this year, but must review and sign an orientation review sheet at the front desk.

  2. Check-in with a checkout. Returning members can go on a checkout, even if they already have a skipper rating. Checkouts are a good way to connect with our instructor staff, get some feedback on your skills and receive recommendations on taking your sailing to the next level.

  3. Stay connected and be social.  Our Facebook page is a great place to keep up with our day to day activities.  We post racing results, pictures, updates on media and events, and much more on our page.  We also post weather/wind updates, early closures, and restrictions (i.e. No red flags today, reefing for everyone else due to 15 knot winds gusting to 18) on our Facebook page. Meet your fellow members at weekly barbecues, parties, harbor trips, our new group practice classes, thursday night racing, and online through our members-only website.

  4. Meet Dave DiLorenzo, Director of Adult Programs, and Cha-Ling OConnell, Assistant Director of Adult Programs. Feel free to contact them with any questions regarding Adult Program membership or courses!

  5. Bookmark and check our calendar for the most detailed view of what's happening at Courageous.

  6. Bookmark and get in the habit of using "Boat Bookings", our online boat reservation system.  While boats are usually available, our fundraising events and youth program can sometimes stretch the fleet to capacity on nice days at peak hours.  Members can make up to two reservations at a time. Note that if we run out of Rhodes 19s entirely during events, we will upgrade qualified skippers to J/22s and other boats as available.

  7. Be Reachable! For safety, members must be reachable at all times while on the water, either via VHF radio or cell phone. If we cannot reach a member via VHF radio of cell phone, we will assume the worst and send a safety boat out to find the member, and the member may be subject to a $50 fee to cover search expenses.  Be sure that radios or cell phones are on, charged, and the ringer/volume set to high!  We have a collection of radios that we can loan to members, and highly encourage sailors to invest in their own if they will be sailing outside the inner harbor.

  8. Be aware of wind conditions, tidal currents, and sunset!  We post this information each day on the whiteboard in the boathouse.  Members are responsible for anticipating the time required to return to Courageous, including the impact of wind speed variations - members are responsible for paying the fee for being towed back to Courageous unless the tow is due to equipment failure not caused by the member.  As we do not have running light on our J/22s or R-19s, any member still out on the harbor by sunset must be towed in for safety reasons, and will be subject to a towing fee.  Towing fees are $50 for inner harbor, $100 for outer harbor. 

  9. Volunteer!  It takes a whole lot of community effort to keep costs down and provide funding for our youth programs.  There are tons of ways to help, from lending a hand on the dock, to replacing telltales, to taking prospective new members out sailing during our open house.  Interested and available?  Send us an email or give a call to Dave or Cha.

  10. We have great deals for our members on sailing gear, so check out our online store or take a look at the catalogue at the boathouse! 

  11. Our picnic tables and grills are available to use anytime that we are open - perfect for a post sail barbecue on a summers night!  While we have a strict no-alcohol-before-or-during-sailing policy, feel free to enjoy a post-sail personal beverage responsibly.

  12. Last but not least, when you're unsure, just ask! All of our staff are here to help - whether you're unsure how to depart the dock under certain wind conditions, or wondering how to get involved in certain programs, or thinking of taking a class. Ask staff at the front desk, on the dock or feel free to call or email Dave or Cha.

img home 2hour

The easiest way to get out on the water.

No experience required!

Regular Price: $190

Black Friday-Cyber Monday: 50% OFF!

If you're looking for an relaxing, affordable way to give sailing a try or check out Courageous, this is it! The two-hour sail is an opportunity for up to 3-4 people to experience the fantastic views from Boston Harbor, learn some sailing skills, or just sit back and enjoy the ride on a comfortable, stable nineteen foot keelboat. An expert instructor will be there every step of the way, and will be happy to customize the experience for you. If you'd like a private lesson (beginner or advanced), no problem--you'll be amazed by how much you can learn in just two hours. If a leisurely cruise or harbor tour is more your style, great! Or combine the two for a fun, unique experience. Feel free to bring a picnic or snacks for the sail (note that alcohol isn't permitted before or during sailing). Life jackets are provided.

To schedule a sail on a J/22 or one of our larger cruising boats, or a sail lasting longer than two hours, please contact us directly.

If you enjoy your sail as much as we believe you will, Courageous makes it easy to keep sailing with discounts for anyone who is introduced to us through a 2-hour sail! Sign up within a week of your sail, and get a $45 discount on a 12-hour course, or a $95 discount on either a Basic Keelboat Complete course or a Full or Family membership. Please contact us directly to take advantage of this offer.

Purchase + Schedule




Looking for information about reedeming a 2 hour sail purchased online from Amazon Local or Living Social? Click here.

We want to make sure that each and every one of our customers has the best experience possible sailing with us, whether as a passenger on a leisurely cruise set against the breathtaking Boston skyline, taking a private lesson to try sailing out, or enrolling in one of our highly acclaimed keelboat courses. The details of each option are outlined below so that you can learn precisely what we're offering, and how and when you can redeem!

Weekends and evenings will book up quickly and all time slots are first come, first served.

How to book

  •  You will use the online schedule to reserve your spot. Have your code ready.

  • Enter your unique voucher code at the top of the page, by clicking on the Promotion code button.


  • You should see a number 1 on the left if the code is accepted. 


  • Click the Book button for the deal you are redeeming. 


  • Follow the instructions to schedule your course. If you selected the same course that your voucher is valid for, you will not be asked for any additional payment. 

To reserve your course now and get on the water, follow the button for your course below!


2-hour Private Lesson or Harbor Cruise for up to 4 people

This deal gets you one of our Rhodes-19 sailboats with an instructor for 2 hours. The R-19 can fit 3 adult passengers easily, or 4 if you don't mind a squeeze. Our instructor can teach you and your friends some sailing skills if you want a lesson, or she can simply skipper the boat while you enjoy the ride for the harbor cruise option - it's up to you!

Specific times and availability may vary. You may reschedule freely up to one week before your scheduled appointment. We will charge a $30 fee for rescheduling within one week of the scheduled appointment. Voucher is subject to forfeiture for cancellations within 24 hours or no-shows.

Redeem + Schedule



12-hour Keelboat Course

Our Basic Keelboat courses are the best way to learn to sail on Boston Harbor! We recommend purchasing two of the LivingSocial vouchers for the full experience of our 24-hour Basic Keelboat Complete course, bundled with two months of membership.

One voucher will allow one adult(aged 18+) to take our introductory 12-hour Basic Keelboat Part 1 course OR our 12-hour Basic Keelboat Part 2 course, and is bundled with one month of membership.

Reedeem + Schedule




More answers to more questions

When is the best time to sail on Boston Harbor?

Some of the best sailing of the year is in May, June, and September. The hotter months in July and August are great, too, but are more prone to light wind and thunderstorms.

What if there's bad weather?

Well, that depends on what you mean by bad weather.  Sailing is fun even when the weather isn't perfect, and we cannot guarantee sunny days for everyone.  So if it's overcast or just a raining a little, we will sail.   In the event of unsafe weather conditions, heavy rain, or heavy winds, we will reschedule the two-hour sails free of charge.  We very rarely cancel our Keelboat courses, as there are plenty of onshore materials in the curriculum, and we can often use the nicer parts of a day for on-the-water activities and then have lunch or shore-school while a storm passes through.  If the weather is looking bad, it's best to give us a call before heading to Charlestown if we haven't already contacted you.

What if I need to reschedule my reservation?

As long as you give us a week's notice, it is no problem at all.  Please refer to the deal descriptions above.  We cannot guarantee availability for rescheduled appointments.

What should I bring with me? How should I dress?

Make sure the bring a printout of you voucher!
Cameras are welcome - we love to see photos from sailors posted to our facebook page!
Depending on the deal you purchased, you'll be outside for 2 to 6 hours.  Prepare accordingly, and check the weather!  We recommend a water bottle, sunblock, sunglasses, clothing suitable to any regular outdoor activity, and a hat.  If it looks like rain, pack a rainjacket.  Sneakers or athletic shoes are fine, but no flip flops or dress shoes.   If you're taking Basic Keelboat, you can either bring a lunch or visit a nearby sandwich shop.  You will be able to bring a bag on-board with you and stash it under the deck, where it will remain dry. 

Can I bring children? 

You may bring children on the 2 hour lesson or cruise.  There must be one responsible adult per child under the age of 12 who can oversee their movement on the boat (and the instructor doesn't count!).  Please let us know in advance if there will be children on board.  If bringing a child under 50 lbs, the customer is responsible for providing a U.S. Coast Guard approved personal flotation device for the child.

When should I arrive at Courageous Sailing?

Please arrive at Courageous 10-15 minutes early so that you can get your full two hours on the water.  If you are running late, please call ahead to let us know!  If you arrive late for your appointment, we will not be able to give you the full two hours.

Where is Courageous Sailing? How do I get there?

Courageous Sailing is located on Pier 4 of the Charlestown Navy Yard.  Various GPS and map services have a hard time finding us, so please us our Parking and Directions page so you don't get lost!  

What kind of boat will I sail on? Do they capsize? Will I get wet?

You'll be sailing in one of our Rhodes 19s.  R-19s are keelboats, which means there is a big heavy metal fin and bulb on the bottom that prevents the boat from capsizing.  On windy days, you may get a bit wet from spray as water breaks over the bow or sides of the boat, but there is a compartment where you can stow items and keep them dry.

I loved my two hour sail! How do I keep sailing ?

Courageous makes it easy.  If, after your sail, you decide to sign up for a course, you'll receive a $45 discount off one of our 12-hour courses or $95 off of one our 24-hour courses.  Check out our great lesson and membership options!