Know somebody who’s ready to take their sailing skills up a notch, or who is looking for a way to get out on the water without the hassle and expense of boat ownership? Courageous has a variety of courses, ranging from a 12-hour beginner course to Advanced Keelboat to Bareboat Cruising, to challenge sailors of any level. Our different memberships offer access to the boats in our fleet, so that old salts and graduates of our courses can sail Boston Harbor in style.
In just 2 weekends, our Basic Keelboat Complete course will give a total sailing novice the opportunity to learn all they need to sail on their own, for just $440. This hands-on 24-hour US Sailing course is taught by one of our expert instructors in a 19 foot keelboat with up to 3 students. Combine the course with a 30% off Full or Family membership so that the newly minted skipper will be able to sail at Courageous all season long.
If you know someone who would love to give sailing a try, this is a gift they’ll love! This two-hour sail is an opportunity for up to 3 or 4 people to experience the views from Boston Harbor, learn some sailing skills, or just sit back and enjoy the ride on a comfortable Rhodes 19 keelboat. An expert instructor will be there every step of the way, and will be happy to customize the lesson or cruise.
A private charter is a fun opportunity for a group of up to 3-5 people to get out on Boston Harbor in a sailboat, with no need to worry about planning a thing! Experience the fantastic views of the city from the water, learn some sailing skills or take the helm if you’d like, check out some Boston landmarks, or just sit back and enjoy the ride. An expert instructor will be there every step of the way, and will be happy to customize the lesson or cruise for you. We have a variety of boats available for charter, including Rhodes 19s (comfortable 19-foot keelboats), J/22s (faster, more responsive keelboats), and our cruising boats, which can fit 4-5 and are suitable for longer trips around the Harbor Islands. 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 book your charter, please email firstname.lastname@example.org, or call us at 617 242 3821.
Courageous can also accommodate private groups requiring 2 or more boats. See our Corporate Functions page for more information.
Our Basic Keelboat Part 1 course covers the fundamentals of sailing. We’ll teach you how to rig and unrig the boat, leave and return to the dock safely with a bit of guidance, and adjust your sails and rudder to make the boat go where you want it to go. This is the first half of the complete course, and perfect if you just want to try out sailing without committing to a 24-hour course, you prefer a more relaxed pace, or your schedule can’t accommodate two consecutive weekends. Basic Keelboat Part 1 tends to follow a consecutive Saturday/Saturday or Sunday/Sunday schedule, from 10-4:30 each day, with a half hour hour lunch break, but can also be taken in one weekend (Saturday and Sunday) or in 3-hour intervals on weekday evenings.
In twelve hours, you’ll learn enough to get you off to a good start, and you’ll probably find that you can sail with confidence with just a little bit of help from an instructor. Please refer to the Basic Keelboat Complete description for more information.
This course picks up where Part 1 left off. It is the next step for those who already know some of the basics, or for Part 1 graduates who are ready for more. In Part 2, we review the basics like tacking and jibing, and continue with the rest of the Basic Keelboat Complete curriculum, including docking under sail, crew overboard recovery techniques, and refining your boat handling skills. Basic Keelboat Part 2 tends to follow a consecutive Saturday/Saturday or Sunday/Sunday schedule, from 10-4:30 each day, with a half hour hour lunch break, but can also be taken in one weekend (Saturday and Sunday) or in 3-hour intervals on weekday evenings.
By the end of the twelve hours, you arrive at the same place as those who take the 24-hour complete course, eligible for a Courageous skipper rating (which means you can sail without an instructor!) and US Sailing Basic Keelboat certification. Please refer to the Basic Keelboat Complete description for more information.
We offer great discounts on Basic Keelboat Part 2 combined with a membership; check out Membership and Lesson Combos for more information.
Price: $30, $25 for members
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On alternating Saturday and Sunday mornings, join other members and students looking for extra practice, coached one of our senior instructors. This is a great way to build from Red Flag to Yellow Flag, earn your Red Flag (if your instructor has given you specific skills to work on), gain more confidence, or to get back into it if you haven't been sailing in a while. The class starts with an on-shore chalk talk on topics requested by participants, so come prepared with questions. Students will be paired up to sail together in Rhodes 19s (unless you really want to practice single-handing with some supervision!), while the instructor coaches from a motorboat. The class might focus on particular skills, like docking or crew-overboard recovery techniques, or on drills to improve general boat handling--let the instructor know what you’d like to work on. Maximum of 12 participants.
If you’d like a private lesson (beginner or more advanced), no problem--you’ll be amazed by how much you can learn in just two hours, even if it’s your first time on the water. Private lessons are a good choice if you're working towards a particular rating here at Courageous, would like one-on-one coaching for specific skills, need more scheduling flexibility than our group courses offer, or want to bring a group of mixed ages or experience levels.
If a leisurely cruise or harbor tour is more your style, great! Or combine a little bit of both for a fun, unique experience. Just let your instructor know what you’re looking for, and we’ll do our best to make it happen!
Life jackets are provided. Both Rhodes 19s and J22s fit up to 3 or 4, in addition to the instructor; choose the J22 option if you’d prefer a slightly larger, faster boat or would like a more advanced lesson. Please contact us directly if you'd like to book a private course, a sail on one of our cruising boats, or a lesson or sail lasting more than two hours.
Want some coaching on how a cruising boat handles? If you’d like the chance to get comfortable with one of our cruising boats before taking out the boat on your own or get some pointers in preparation for a charter of your own, take a private lesson with one of our most experienced instructors. Lessons can be taught on our Erickson 28, CS 30, Pearson 34, Tartan 27, O'Day 240, or J/24, all of which fit from 4 to 5 students.
Whether your goal is to sail fast around a race course or to achieve the perfect spinnaker run home from The Graves, Advanced Keelboat is the course for you. This course is taught in a J/22, a performance boat designed for speed and grace, by our top instructors. If you are working on a Green Flag rating, preparing for a J/22 checkout, or interested in getting into racing, Advanced Keelboat can help you work toward your goals--just let your instructor know what you'd like to focus on. Our 3:1 student to instructor ratio ensures that we'll be able to tailor the course to the interests of you and your fellow students.
Advanced Keelboat covers:
Once you start sailing the bigger boats, it’s hard to stop! And there’s always more to learn. Our Bareboat Cruising course is the next step. It picks up where Basic Cruising leaves off and covers topics such as navigation, anchoring, and heavy weather sailing in much greater detail. You’ll learn the things you need to know when chartering a sailboat: the various techniques used around the world for mooring and anchoring (e.g. stern and bow, fork, Mediterranean, Bahamian); controlling the boat under power with confidence; big boat docking techniques; provisioning; visiting the fuel and pump-out dock; VHF communication; and more. We will also take you through a tour of all the important boat systems, peering behind seat covers and into the bilge until you know exactly where everything is, what it does, and what to do (or who to call!) when it doesn’t work. This course typically includes 3 days of sailing, two overnights at anchor or moored, and additional prep and debrief time. Maximum of 4 students.
Many course participants choose to test for their US SAILING Bareboat Cruising certification, which signifies that you have sufficient skills and knowledge to safely and confidently skipper an auxiliary powered cruising sailboat between 30’ and 45’ in length, in winds above 15 knots, within sight of land during daylight hours. This certification is widely respected and accepted by many sailboat charter companies in the US and other parts of the world. Most Bareboat graduates are also qualified for a Courageous cruising membership.
Are you planning on purchasing your own cruising sailboat (or simply sailing ours!) or chartering in the Caribbean someday? Our US Sailing Basic Cruising certification course is the first step for those who dream of going beyond Boston Harbor. In this course, we apply the fundamentals to bigger boats (up to 30’ in length) with outboard gasoline or inboard diesel engines, cover the basics of navigation, and introduce the tools needed to sail longer distances. While big boats sail just like small boats, there are more systems to learn and techniques to master. Although 24 hours isn't enough to prepare you for every challenge a cruising boat can present, you'll have plenty of time to get to know the outer harbor and develop comfort around big boat basics so you can crew competently or take the helm under the supervision of a more experienced captain. Basic Cruising takes place over two consecutive weekends, Saturday/Sunday/Saturday/Sunday from 10-4:30 each day, with a half hour hour lunch break. Maximum of 4 students.
Graduates may test for their US Sailing Basic Cruising certification. This course will also cover what you need to know to pass the theoretical portion of the Green Flag test, which (along with an on-the-water checkout) enables access to the outer harbor.
Here's a brief overview of what you'll learn in Basic Cruising: