Step aboard the historic CHRISTEEN for the Rough Riders Reunion cruise on Oyster Bay, where maritime tradition meets vivid Theodore Roosevelt reenactments. Discover a summer adventure that sails through local history and stunning coastal scenery.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels; no physical exertion required beyond boarding the vessel.
Wildlife
History
Oyster Bay was a strategic naval site during Theodore Roosevelt’s presidency and remains central to Long Island’s maritime heritage.
Conservation
The CHRISTEEN’s operators promote sustainable boating practices to minimize environmental impact on Oyster Bay’s delicate marine ecosystem.
The WaterFront Center
The WaterFront Center in Oyster Bay, New York, operates hands-on maritime programs and rentals focused on sailing, paddling, and coastal ecology. Founded to make the harbor accessible to families, learners, and community groups, the center offers guided Ecology & Wildlife Cruises aboard the historic CHRISTEEN with Naturalists, private charters on the IDA MAY, Discover Sailing lessons, and public sails.
Programs include two-hour Ecology & Wildlife Cruises on CHRISTEEN with touch tanks and sail-handling; private IDA MAY charters for up to 44 guests; and CHRISTEEN private charters for up to 24 guests. Discover Sailing provides intimate two-hour instruction with a certified instructor for up to four guests. Sailing rental season passes permit regular access to the center’s Sonar fleet after a check-out exam. Returning sailors can confirm qualification through a 30-minute Returner’s Recertification Test featuring a 20-question assessment to rent Sonar, Hobie Getaway, or Hobie Wave boats.
Paddle programming includes single and double kayak rentals, stand-up paddleboard (SUP) rentals, Paddle Group Tours, a Monthly Paddle Pass, and a Paddle Rental Season Pass. Specialty offerings feature SUP Yoga and the Puppy Paddle, led by instructor Deanna from Salty Soul Yoga, where dogs wear lifejackets. The WaterFront Center also runs sunset cruises, harbor tours, fishing charters on the IDA MAY, community open sails, and themed events. As a visible Oyster Bay resource, the center combines certified instruction, community-focused programming, and a mix of private and public water experiences. Booking information, schedules, and safety policies are available through the center's official program listings online.
Location
Oyster Bay, NY
Harbor-based programs and rentals
Group Capacity
IDA MAY 44 • CHRISTEEN 24
Private and public sail options
Pass Options
Monthly & Seasonal
Sailing and paddle passes available
Certified Instruction
Certified Instructors
Discover Sailing and SUP Yoga leaders
Reserve ecology cruises, private charters, Discover Sailing lessons, or paddle and season passes for Oyster Bay adventures.
Arrive Early for Boarding
To secure a good spot on the CHRISTEEN, arrive at least 30 minutes before departure time.
Bring a Light Jacket
Breezes on the water can be cool even on warm days; a light jacket will keep you comfortable.
Use Sun Protection
Wear sunscreen and a hat, as much of the cruise is exposed to direct sunlight.
Motion Sickness Precautions
If you're prone to seasickness, consider taking medication before boarding for a more enjoyable trip.
Water Bottle
Stay hydrated while out on the water during sunny summer days.
summer
Light Jacket or Windbreaker
spring
Camera or Smartphone
Capture stunning views of Oyster Bay and the reenactment ceremony.
Sunscreen
Protect your skin from prolonged sun exposure on the open water.
summer