Adult Program

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.

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

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.

Thank you for your purchase!


Adult Program memberships and courses at Courageous are a crucial part of funding scholarships in our entirely need-blind youth programs, while supporting our adult program's mission of affordable, accessible, high-quality sailing.  Thank you for being part of the Courageous community!

If you have purchased a membership or course as a gift for someone else, please let us know who the gift is intended for so that we can serve them as best we can!  If you have purchased a family membership, please let us know who the other skippers are under the membership.

We look forward to seeing you on the water in 2012!  If you have any questions about courses or memberships in the meantime, don't hesitate to contact Dave or Cha by email or by giving us a call in the office at 617-242-3821.


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.

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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!


We see that you have cancelled your purchase...

If you have any questions about courses or memberships, feel free to contact Dave or Cha by email or by giving them a call in the office at 617-242-3821.

Adult Program memberships and courses at Courageous are a crucial part of funding our youth program, while supporting our adult program's mission of affordable, accessible sailing.  At Courageous, supporting a good cause does not come at the expense of quality: we offer some of the best courses, best instructors, and best value in sailing on Boston Harbor, hands down.

We are eager to have you join the Courageous community, so please let us know if there is anything we can do to change your mind!