Private Sails


  • 2 Hours of instruction
  • Flexible schedule
  • Private Lessons or Harbor Cruises available
  • Available for all skill levels on our R19 of J80 fleet


The easiest way to get out on the water – no experience required! Whether you’re looking for a relaxing, affordable way to give sailing a try or to check out Courageous, or you’re a seasoned sailor hoping to dust the rust off with some one-on-one instruction, our Private sails are for you!

Private Lesson

You’ll be amazed by how much you can learn in just a few hours! Private sailing lessons are a one-on-one experience with a qualified instructor. Nervous about docking? Need some extra help heaving-to or completing a man overboard drill? Our instructors are here to help! Fully customizable based on what skills you are looking to strengthen. Private sailing lessons are a good choice if you’re working towards a particular rating here at Courageous, prefer one-on-one coaching, or you need more scheduling flexibility. In order to get the most out of every lesson, there is a two-hour minimum.

Private lessons are also a great fit for:

  • Those looking to make-up a missed class day
  • Individuals looking to gain more insight into which of our courses suits their skillset
  • New members looking for a deeper dive into skills necessary for flag ratings at Courageous

Harbor Cruise

Our two-hour Harbor sail is an opportunity for up to 4 (6 in a J80) 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 experienced instructor will be there every step of the way, and we are happy to customize the experience for you. If you’d like a small introduction to sailing, no problem–you’ll be amazed by how much you can learn in just two hours. If a leisurely sailboat 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.

Harbor Cruises are perfect for:

  • Date night – book a later slot to enjoy the sunset over Boston Harbor
  • Fun family activity (all ages are welcome, even our tiny captains are welcome)
  • Weekend or weeknight outing with friends visiting the city

Please Email for Availability

Phone: 857-452-1769


Additional Courses

Looking for a complete Learn to Sail experience? Check out the complete introductory course which can take you from knowing nothing about boats or sailing to a capable skipper in just two weekends.

For more advanced sailors, check out Mid-fleet Performance 1, a two-day course focused on sail trim, and boat handling in our mid-sized keelboats, or Basic Cruising, for those who want to learn about systems and sailing onboard a larger sailboat.

Valid for the 2024 season; please schedule your Private Sail any time between May 1-October 31 2024.  For information on our refund policy, click here.