Build team racing skills and strategy on Long Island Sound
4 hours
4 people
Practice structured, high-level team racing with individual sailors and club teams. Build skills, strategy, and community on the water.
Cancel more than 5 days before for a refund (processing fee not refunded). Within 5 days you may reschedule but no refund. Within 72 hours no refund or reschedule. If the operator cancels due to dangerous weather, you may choose a refund (processing fee not refunded) or reschedule. No-shows get no refund.
Arrive 15 minutes before your scheduled start time.
Wear layers appropriate for the forecast. Bring a hat, apply sunblock before you leave land and reapply as needed on the water, and consider bringing a bottle of water.
If the operator cancels due to imminent and potentially dangerous weather, you can choose to reschedule or get a refund (processing fee not refunded). If the operator delays your start by 30 minutes or more, you can choose to reschedule or get a refund (processing fee not refunded). Delays under 30 minutes are reschedule-only.
The WaterFront Center
The sailing experiences here get rave reviews, particularly aboard the historic Christeen. Guests consistently praise the knowledgeable captains and crew who share fascinating stories while navigating Oyster Bay's waters. The sunset sails seem especially popular, and many appreciate the hands-on experience of helping raise the sails on a vessel with such remarkable history. Beyond sailing, the kayak rentals and wildlife tours are winners too, with naturalists like Lauren earning special mentions for their expertise in spotting ospreys and other local wildlife. There's a concerning pattern worth noting though. Multiple groups report last-minute cancellations, sometimes just an hour before scheduled departures, with birthday celebrations being particularly affected. Several reviewers describe frustrating interactions with staff during these situations and mention inconsistent explanations. That said, the majority of visitors have smooth, memorable experiences with friendly, helpful staff both on the water and at the front desk. The kayaking, sailing lessons, and scenic tours consistently deliver when things go as planned, making this a solid choice if you stay flexible with your schedule.
We booked a special birthday sail on the Christeen for 20 people. Everyone had an amazing time! Our captain and crew were so fun and knowledgeable-sharing fascinating information as we sailed around beautiful Oyster Bay. The front desk staff is also very welcoming and helpful! We plan to book another sail next summer in the evening. Highly recommend!
Mari D'Alessandro
October 6, 2025
We booked a special birthday sail on the Christeen for 20 people. Everyone had an amazing time! Our captain and crew were so fun and knowledgeable-sharing fascinating information as we sailed around beautiful Oyster Bay. The front desk staff is also very welcoming and helpful! We plan to book another sail next summer in the evening. Highly recommend!
Mari D'Alessandro
October 6, 2025