By Michael R. DeLuca
Tod’s Point Sailing School, a local nonprofit organization is open for their fourth season.
According to Bill King, there is a great group of returning US Sailing certified sailing instructors and support staff comprised of local high school and returning college students.

Instructor Matthew Sullivan in front of Tod’s Point Sailing School. June 14, 2025 Photo: Michael R. DeLuca
Mr. King explained that rentals are an important extension for courses since people can take a course and rent and then sail.
“Our Junior classes started June 9 and we have a core curriculum of four sailing classes that teach students everything,” said Matthew Sullivan, an instructor at the sailing school. “From the basics, all the way up to the physics of how sailing works.”
“There’s a good amount of learning involved, but we always try to keep it fun on the water,” said Matthew Sullivan.
Safety, of course, is paramount. Sullivan said the sailing school provides provide PFD’s (Life Jackets) to everyone in the water and people are required to wear them.
To date, the program has served 1,042 Junior Sailors, 382 Adult Sailors, provided 3,286 hours of Boat Rentals and 329 hours of Private Sailing Lessons.

Tod’s Point Sailing School in Old Greenwich. June 2025 Photo: Michael R. DeLuca
Along with private sailing instruction. People can rent sailboats and paddlecraft. The fleet consists of Zests, Quests, Catamarans, Kayaks and Paddleboards. Reservations can be made in advance.
“We’re open for rentals everyday from now until Labor Day. All of the boats on our beach are available to rent with kayaks, paddle boards, and all of the sailboats we have to offer. Boats go out on the water at 9:30am,” Sullivan explained. “The last boat goes out at 5:00pm. You can come in and make a reservation or call ahead to make sure you have a slot!”
There are a variety of classes for Juniors and Adults.
Junior classes are scheduled on weekdays with two-week Core courses and one week Just for Fun courses. There are four progressive levels of Core courses, Sailing One through Sailing Four. Just For Fun courses cover various activities including Paddling, Catamarans, Racing and a Tera Bites course for our youngest sailors ages 8 – 9.
Adult courses are held on weekends although they do offer a few Adult weekday classes in June. Adult core classes run for two consecutive weekends each and are also progressive starting with Basic Sailing designed for first time sailors and then moving up through Intermediate Sailing and Advanced Sailing. Adult Family courses are one weekend courses and include Catamaran Sailing and Paddling.
All course registrations may be made online.

Kayaks, Sails, Boats, and more at Tod’s Point’s Sailing School. June 2025 Photo: Michael R. DeLuca
“Just for Fun” courses include Tera Bites, WaterCats and Paddle Explorers.
Tera Bites is for younger kids, too young or small for the Core Curriculum courses. Tera Bites is a gentle introduction to sailing for 8- and 9-year-olds. They meet daily Monday through Friday for two hours each day.
WaterCats is a catamaran sailing experience designed for those students with no sailing know-how but offers hands-on sailing for any student that would like to explore catamaran sailing.
Paddle Explorers offers non-sailors an opportunity to venture out onto local waters with a supervised experience.
Staff are available to answer any questions about the program by phone 203-637-2022 or by email: info@TodsPointSailingSchool.org.
Rental and Private Lesson reservations can also be made by phone or email.
Weather and Tides are very important for boaters. On the bottom bar of each of the website pages are links to real-time weather conditions at Greenwich Point and to local tides.
More information on the Tod’s Point Sailing School is available online.

Paddle Board lineup Tod’s Point Sailing School. June 2025 Photo: Michael R. DeLuca

Breathtaking view and the Sailing Life at Tod’s Point. June 2025. Photo: Michael R. DeLuca

Tod’s Point Sailing School offers smaller boats to learn in for the youth. June 2025. Photo: Michael R. DeLuca

The RS CAT 14 Sailboat offered at Tod’s Point Sailing School. June 2025. Photo by Michael R. DeLuca

The workings of a sailboat at Tod’s Point Sailing School. June 2025. Photo by Michael R. DeLuca