Deer Isle Yacht Club

Sylvester Cove, Sunset, Maine

Sailing Lessons


DIYC offers sailing lessons to members and the general public (all ages and skill levels) annually from late June to early August. General information on our programs appears below but please ask any questions (or just say hi) to the Instruction Committee any time at lessons@deerisleyachtclub.com or to the Rear Commodore (club officer responsible for instruction and racing) at rear.commodore@deerisleyachtclub.com.

Core program. Targets kids ~8-12. These young sailors are taught both on land at the Club, in the Cove, and occasionally beyond in the Bay in our fleet of six Optimist (“Opti”) sailing dinghies. 2-hour lessons are offered most weekdays from late June to early August at 10 AM and 1 PM rain or shine. Though consistent participation will produce the most learning and enjoyment, we are happy to welcome students for just one or two lessons. Beginners will learn safety and basic seamanship, more experienced sailors are introduced to racing both in Optis and in Bull’s Eyes. Interested sailors may pursue US Sailing “Small boat beginner sailor” certification. Lessons are not offered every day and they do fill up - please confirm lessons will be available before showing up by writing to lessons@deerisleyachtclub.com. Passing a swim test is required.

Older kids / adults / families. Sailors over 12 years old (or over ~115 lbs.) will likely find the Optis too small for their taste/comfort and will likely want to explore waters beyond the Cove. We offer individual and small group lessons in the Bull’s Eye, a ~16’ boat that can comfortably accommodate as many as four adult students in addition to the instructor. Learn to rig, sail, and even race or just get out on the water for a skippered small-boat cruise. By appointment (usually weekdays at 3:30 PM), write to lessons@deerisleyachtclub.com.

Lessons on your boat. We are happy to provide lessons on almost any type of small sailboat whether or not the boat is moored in our Cove. By appointment, write to lessons@deerisleyachtclub.com.

Rowing lessons. Hour-long rowing lessons for kids as young as five introduce younger children to safety, seamanship, and the management of small boats. Great way to get future Opti students ready to sail. By appointment (usually weekdays at 9 AM) write to lessons@deerisleyachtclub.com.

Motorboat lessons. Learn to safely and responsibly operate and care for a small motorboat in your choice of a Boston Whaler 130 Sport, a Boston Whaler 170 Montauk, or your own small motorboat. Offered to ages 12+. By appointment (usually weekdays at 3:30 PM), write to lessons@deerisleyachtclub.com.

Useful links

About our instructors (and how to become one)

What to bring to your lesson

Additional information for DIYC members (login required).

Program contacts

Spencer Dickinson III, Rear Commodore (responsible for club programs including lessons and racing)

Sarah Dickinson, Instruction Committee Chair

Upcoming Club Events

  • August 08, 2025 5:00 PM Edgewood Farm