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Host your own sailing Regatta! Large groups up to 32 people can book a racing event with Sail Montauk. No experience necessary. Designate race participants as crew on our 4 Catalina 22's while others cheer and lounge from the party viewing boat. Light instructions will be given and there will be a Sail Montauk captain aboard each boat for your safety. 

Perfect for team building, corporate outings, bachelor/bachlorette parties and other large groups;  we can customize the race day to suit your needs.

Call us at 631-522-5183 or email to plan your team event. 

Subject to availability, these events book fast!



After a dockside briefing, racers will head out on the sailboats while onlookers board the party viewing boat for the first session. A race session will typically have 2-3 short races. Once completed, racers will raft up to the party viewing boat for refreshments and bragging rights.


Depending on group size and preference, the next set of race participants can head out for the second session, or instead choose to make a splash! Swimming and a boat party is always an option.



4 participants max on each race boat. 

(we recommend 2-3 for optimal racing experience)

Our fleet of 4 Catalina 22 sailboats race head to head in a small triangle buoyed course. 2-3 short 10-15min races then participants switch so everyone can share in the experience. The race course is centered around the committee/viewing boat. There is a 4 participant per boat maximum for racing and a Sail Montauk instructor onboard. (12 racers and 4 instructors at any one time) We recommend 2-3 racers per boat for optimal experience.


A 51' committee/viewing boat (32 passenger capacity) will be anchored at the start/finish line where the rest of the group can watch the racing while 8-16 race participants sail. Halfway through we switch, so the rest of the group can sail. All 4 race boats can raft up along the 51' committee boat to swap participants. This is a great time for snacks and refreshments with a little smack talk. In our experience, not everyone will want to participate in racing and will be happy observing from the viewing boat. At the end of the second set of races the sailboats will raft up again to let off participants so the whole group can unite and spend the rest of the time celebrating their sailing experience.


On board experience:

No experience is required. Each boat has a Sail Montauk captain/instructor that will give instructions to the racers.

Each participant will work together to make their boat work fast and efficiently to complete the triangle course before their opponents. Tasks and positions will be assigned to the race participants and they can rotate throughout the race. Instructors will explain how to maneuver the boats by tacking and jibing or heading up and falling off. Participants will have to control the sail trim, keep time and execute tacking and jibing procedures.


*Contact for pricing and booking. 631-522-5183

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