Come to Courageous Sailing! You can go sailing on your own or let one of our expert skippers take the helm and discover Boston from the water. Whether your ideal outing is a family trip, a Corporate Sailing Event or the thrill of competing in a regatta, we have the best option for you!
We are just a few minutes away from Downtown Boston.
Regular Price: $30 for nonmembers, $25 for members
Click Book Now to buy AND schedule your course! Click Buy Now to purchase, but schedule at a later date. Click Redeem to schedule a course you previously purchased.
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.
Private lessons are perfect if you prefer to learn one-on-one, need more scheduling flexibility than our group classes offer, want to troubleshoot specific skills to earn a rating, or would like to bring a group of mixed ages or experience levels. We also offer private lessons for children and teens, individually or in groups of up to 4. Let us know what you’re looking for, and we’ll do our best to make it happen! Both Rhodes 19s and J/22s fit up to 3 or 4 students, along with the instructor. Minimum of 2 hours per lesson; price includes up to 4 students.
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 Seafarer 30, Erickson 28, 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 are 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.
Advanced Keelboat covers:
Black Friday-Cyber Monday: 20% OFF!
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.
Upon passing the exam at the end of the course, your US SAILING Bareboat Cruising certification will signify 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.
Black Friday-Cyber Monday: 20% OFF!
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, 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. Twenty-four hours is not enough to prepare students for every challenge a cruising boat can present, but it is enough to develop comfort around big boat basics, so that 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. The additional experience will also typically help boost the Courageous skipper rating of students with solid Rhodes boathandling skills, enabling access to the outer harbor and Harbor Islands.
Regular Price: $550
Black Friday-Cyber Monday: 20% OFF!
Optional US SAILING Certification Fee: $75
Included text: US Sailing Basic Keelboat
Click Book Now to buy AND schedule your course. Click Buy Now to purchase, but schedule at a later date. Click Redeem to schedule a course you previously purchased.
When your goal is to become a competent, confident sailor with a solid understanding of the basics, this is the course to take. At the end of the two-weekend class, most students are ready or almost ready to skipper one of our Rhodes 19 keelboats on their own. Your instructor, who will always be in the boat with you and up to two fellow students, will guide you through the sailing fundamentals, combining short chalk talks and extensive on-the-water coaching to help you develop and reinforce new skills. You’ll learn all you need to know to rig and unrig your boat, leave and return to the dock safely, adjust your sails and rudder to make the boat go where you want it to go, and tie some important knots (always a good way to impress your non-sailing friends!).
It’s a lot of work, but by the completion of the course, most students are ready for a Red or Yellow Flag skipper rating , which means they can safely skipper a small keelboat in light to moderate conditions without an instructor. Students who earn a Yellow Flag rating can also take a written test to obtain their US Sailing Basic Keelboat certification, a standard recognized throughout the U.S. and in many other parts of the world.
Basic Keelboat Complete courses take place over two consecutive weekends, Saturday/Sunday/Saturday/Sunday from 10-4:30 each day, with a half hour hour lunch break. A new course starts almost every Saturday.
Basic Keelboat Part 1
The Regatta celebrates the life and vision of Boston's Richard B. Ross, a Dorchester native who believed in the transformative power of education. Before Richard tragically lost his life in the attacks of September 11th, 2001, he was a passionate sailor who took great pleasure in passing on his love of sailing to others. One of the ways his family continues to honor him is by providing generous support to Courageous in his name.
On a day when a slow moving low weather front left New England regattas becalmed and fogbound, Boston Harbor served up enough good breeze to keep 17 collegiate teams moving in Rhodes 19's for five great races. Afterward, teams gathered on Pier 4 for a barbecue. Our heartfelt thanks and appreciation goes out to the Ross family for their generous support of the regatta and Courageous Sailing. Thanks, too, to all sailors for participating; Ken Legler for being a great booster of this event, and Russ Bolt for taking so many great pictures! And congratulations to teams from Williams, Roger Williams and Northeastern for taking the top spots!
1st place/11pts, Williams College - Joshua Revkin & Isaac Loh
2nd/11pts, Roger Williams - Tucker Blagden & Andrew Vachon
3rd/15pts, Northeastern - Mike O'Brien & Carolyn Mason
The names of the participants on the winning boat will have their names inscribed onto the Richard B. Ross Memorial Trophy, which hangs in the Courageous Sailing Boathouse for perpetuity.
All funds raised by the College Bowl go directly to benefit Courageous's FREE youth programs.