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 http://www.courageoussailing.org/adult/flag-ratings] 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.