Oakcliff Sailing

06/02/2026

Our Graduates are shining a golden future on the sport of sailing and beyond. This newsletter is almost exclusively dedicated to their stories.

We also have some immediate opportunities for you to join in on the learning and the fun. You can dip your toes into offshore sailing with deliveries.

Match Racing is full steam ahead as well. The Grade 3 this weekend is full, but there are more opportunities to race, officiate, or just volunteer and join in the parties throughout the season.And of course our regularly scheduled weekly racing has begun. Click through to read all

Our Graduates are shining a golden future on the sport of sailing and beyond.  This newsletter is almost exclusively dedicated to their stories. 

05/29/2026

Caught up with Captain Glenn at the Annapolis Boat Shows last fall with Oakcliff's We'll be back this Fall https://racingcalendar.org/event-detail/5c2d29e0-a4d6-4233-8869-8229d36dbfa9

05/29/2026

Sailors from our Oyster Bay High School Sailing Team got to experience foiling with SailGP and Brian Reilly at Seawanhaka Corinthian Yacht Club

Teen sailors from Oyster Bay and New York City participated in Sail Grand Prix's Inspire Wing Foiling Clinic.

05/27/2026

Read all of the news and some fun stories. Also thanks to BlockIsland Steve who we inadvertantly forgot to give photo credit to in the newseltter.

Oakcliff grabbed 1st and 2nd in class and best elapsed time and in both ORC and PHRF, in a very wet and cold Storm Trysail Block Island Race last weekend. The practice for Blue at American Spring Series absolutely helped put the crew and boat through the paces. New sails funded by the Schoonmaker Fo...

05/18/2026

Linder here at Oakcliff making Sunday Dinner Paella for the team. Much needed fuel getting OC86, JV66 Temptation and 2 Farr 40s ready for the Around Block Island Race and Newport Bermuda Race ~!

05/14/2026

In search Of: two Sunfish preferably donated - or borrowed - last week of June through 1st week of August

05/10/2026

🚨 new camp dates 🚨

The High Performance Foiling Bootcamp will now run July 18-22 still in Oyster Bay.

This is your chance to get 5 days of comprehensive foiling instruction taking you from never having foiled before to flying around like a pro 😎.

No equipment or experience foiling necessary! Just show up and be ready to go fast 🏎️💨

Registration and information can be found at oakcliffsailing.org 🔗

05/09/2026

More learning: This weekend Sue Reilly leads Basic Race Management and it is great to see so many new faces, getting ready to lead our sport. Signal, Signal, Signal : Thank You!

05/05/2026

Back to Back! A busy few weeks for Oakcliff Sailing and it's just getting started. This season is full throttle!