Private Sailing Lessons & Professional Services

Private Sailing Lessons

Whether you're looking to fast-track your sailing skills, get personalized instruction aboard our fleet, or need expert guidance on your own vessel — First Reef Sailing offers private lessons tailored to your goals. Our USCG-licensed, ASA-certified captains provide one-on-one attention in a relaxed, professional setting right here on Boston Harbor.

Private Lessons on the Colgate 26

Our Colgate 26 fleet is the perfect platform for learning the fundamentals or sharpening your skills. These nimble, responsive keelboats offer an ideal environment for hands-on instruction.

• $150 per hour

• 3-hour minimum

• Bring up to 3 guests at no additional charge

• Perfect for ASA 101-level skills, sail trim, docking practice, and more

Private Lessons on the Beneteau 36.7

Step up to our Beneteau 36.7 for a bigger-boat experience. This cruising sailboat is ideal for students looking to build confidence on a larger vessel — whether you're working toward your ASA 103/104 or just want more time at the helm of a capable cruiser.

• $200 per hour

• 3-hour minimum

• Bring up to 3 guests at no additional charge

• Great for coastal cruising skills, navigation, anchoring, and heavy-weather techniques

Private Lessons on Your Vessel

Already own a boat? We'll come to you. Our captains will meet you at your marina and provide expert instruction aboard your own vessel — the best way to build confidence on the boat you actually sail.

• $150 per hour plus travel expenses

• Instruction tailored to your specific boat and rigging

• Learn the systems, handling, and quirks of your own vessel

Additional Services

Beyond traditional sailing lessons, our experienced captains specialize in a range of professional services:

• Boat Deliveries — Need your vessel moved up or down the coast? We handle coastal and offshore deliveries with care and professionalism.

• Shakedown Sails — Just bought a new boat or finished a refit? We'll put her through her paces and make sure everything is shipshape.

• Docking Instruction — Docking can be the most stressful part of sailing. We'll build your confidence with hands-on practice in real-world conditions.

• Systems Familiarization — Learn your boat's mechanical, electrical, and safety systems inside and out.

• Passage Planning & Preparation — Get expert help planning your next coastal cruise or offshore adventure.

Ready to Get Started?

Contact us to schedule your private lesson or discuss your specific needs. Whether it's your first time on the water or you're preparing for an offshore passage, we'll build a lesson plan around you.

Email: info@firstreefsailing.com | Phone: (617) 466-3317