Supporter Corner

Wednesday Night Fleet Racing with Sagamore

As a supporter, you can sign up to sail one of Oakcliff’s Match 40s and Shields at Sagamore’s Wednesday Night Fleet Racing! Through our system, you can either sign up as a complete team or sign up as an individual and have us place you on a team. Sign up on our Calendar. Sailors should report to Oakcliff at 5:30 for a prebrief and team assignments. Please bring a water bottle, PFD if you have one (if not, we can lend one), sunscreen, and gloves (also available for purchase at Oakcliff base). This is a great way to polish your fleet racing skills and learn all the positions on our Match 40s and Shileds. Debriefs will happen on the dock after mooring the boats at Sunset. Before you come, please review our How to Rig a Match 40 video and documents. Please be prepared to do all positions on the boat if you are signing up alone – it will be a great learning experience! 

All sailors must be 2024 Oakcliff supporters. We also encourage supporters to create teams and sign up for a three-week series to optimize their learning and coaching. 

Supporter Open Sails

Supporter open sails are select Fridays, from May to September. Reserve a boat and bring your family or team to sail the Match 40s. You can also reserve Lasers, Sunfish, and a paddleboard. See below for rigging instructions. On Fridays, a Classics Race will take place at 4:30pm.  We are also bringing back the BBQ!  We are going back to our roots and asking it to be pot-luck. Sign up or cancel no later than 10am the day of. Sign up on our Calendar. Through our calendar system, you can choose to join us for two separate time slots – 2-4pm or 4-6pm. You can also choose to do both. All sailors must be 2024 Oakcliff supporters. 

For those sailing Lasers, the Sunfish or paddleboard: Report to Oakcliff’s High Performance Beach, 1 Bayview Ave, to get rigged and launch. If you park by the beach, parking is only allowed on the same side of the street as our beach. Parking is not allowed on the opposite side of the street. You can also park at Oakcliff and walk. See our rigging guides down below. 

For Match 40s or classics: Report to Oakcliff base, 4 South Street, 15 minutes before your scheduled time and let us know you’re here and pick up your radio. An Oakcliff staff member will take you to Oyster Bay Marine Center and ferry you to the mooring field. Oakcliff staff will not always be available to rig your boat, so please read the rigging instructions for your boat. If you need assistance of any kind, please radio Oakcliff Base on VHF 69. After sailing and deriging, washdown the boat on the mooring with salt water, rinse with fresh water from your blue jug, and then radio Oakcliff base on VHF 69 for pickup. We are very busy here at Oakcliff, so please bear with us as we accommodate you as our supporters. 

All sailors: Remember your  PFD, VHF Radio, sunscreen, hat, water, and sailing gloves


For Supporters interested in Offshore, we have a pathway to evaluate your skill and ease you into the distance racing experience. First you must sail in the Spring or Fall American Yacht Club Race Series with the Oakcliff team on the Farr 40s. We would also encourage supporters to do deliveries of our boats with us when available - make sure to watch your email for those opportunities. Then you do one of the three overnight races: Around Block Island, Ida Lewis, or the Vineyard Race. After that, based on your skill level, you will be eligible for one of the three ocean races: Newport to Bermuda, Annapolis to Newport, or Marblehead to Halifax. You can also join our Offshore Acorn Program. Email for more information. 


Match Racing with Oakcliff

Match racing is a great way to test your sailing skills! If you are new to match racing, we suggest you start by familiarizing yourself with our Match 40 sailboats at Wednesday Night Racing. Once you’ve done that, gather your team and sign up for our Thursday Supporter Sails in the Match 40, where we run match racing drills for those interested.  Drills are the best way to learn the ins-and-outs of match racing. When you and your team feel confident with the match racing basics, put in an application for one of our Grade 5 events, the entry-level match racing regattas. Each Grade 5 is a one-day event held on Sunday, with optional skills & drills on Saturday. 

Frequently Asked Questions

Can I bring friends for supporter sails? 

Have a friend who is considering becoming a supporter and want to take them out? We allow non-supporters to come to supporter open sails or Wednesday night fleet racing once before they must become supporters. Supporter donations are what make us able to run these fun programs – so please become a supporter if you can. 

Can I bring my kids? 

Sure! Just make sure you have a life jacket or tell us ahead of time so we can accommodate you – in New York, children under the age of 16 MUST wear a life jacket when on the water. 

Can I eat or drink on the boats?

Picnic lunches or bagged lunches are totally fine, provided you bring all your trash back with you and make sure the boat is clean. We do not allow glass or alcohol on the boats. 

Can I take a boat out by myself?

If you would like to sail the boats on your own time, or with your own crew,  you can look into a charter with us. 

Does Oakcliff provide learn to sail courses or close on the water coaching?

We do NOT provide learn to sail coaching. We are a “learn to race” program for those who are looking to advance their sailing ability. If you are local to the Long Island area, you can check out the Waterfront Center for learn to sail courses. Once you complete that, feel free to come back to us to continue on to your next step in sailboat racing. As for coaching, during Open Sails and Wednesday Night, we are very hands off on coaching – we are very busy around Oakcliff and cannot take the time to coach every supporter one-on-one. If you have a question on the water, please radio Oakcliff base on VHF 69. We thank you for respecting our time and bearing with us!