OYSTER BAY HISTORY TOUR FIELD GUIDE
A Summer Sail with Teddy: CHRISTEEN’s Rough Riders Reunion in Oyster Bay
A guided cruise aboard the historic oyster sloop CHRISTEEN that pairs scenic sailing in Oyster Bay with Theodore Roosevelt reenactors and a ceremonial celebration—this guide explains what to expect and how to plan.
A Summer Sail with Teddy: CHRISTEEN’s Rough Riders Reunion in Oyster Bay.
Step aboard the historic oyster sloop CHRISTEEN and glide across the waters of Oyster Bay for a living‑history celebration. Operated in collaboration with The WaterFront Center, Friends of Sagamore Hill, and the Town of Oyster Bay, the Rough Riders Reunion pairs gentle coastal sailing with a special ceremony featuring Theodore Roosevelt reenactors who bring TR to life on deck.
Highlights
Outing Highlights
Sail aboard the historic sloop CHRISTEEN
The centerpiece of the outing is the oyster sloop CHRISTEEN—an authentic, historic vessel that hosts this themed cruise along Oyster Bay’s sheltered waters.
Theodore Roosevelt reenactors and a ceremonial moment
Actors portraying Theodore Roosevelt and his Rough Riders lead a special ceremony onboard, turning the cruise into a staged reunion that celebrates Roosevelt’s connection to Oyster Bay.
Scenic sailing in waters Roosevelt once navigated
The route follows the scenic reaches of Oyster Bay—waters associated with Roosevelt—offering views of the harbor and a maritime context for the historical commemoration.
What the day feels like
What the cruise feels like
The outing is a calm, ceremonial sail: passengers board the CHRISTEEN, cruise the sheltered harbor of Oyster Bay, and gather for a staged ceremony led by Theodore Roosevelt reenactors—an intimate blend of maritime atmosphere and historical pageantry.
Suitability
Who it's for
Who this cruise suits—and who should look elsewhere.
Practical planner
Details to review before reserving
$85 per person; operators note a limit of eight spots per customer.
No children under three years old; all children must be accompanied by an adult over the age of 18. No animals are allowed aboard.
The official trip information does not list specific gear requirements for passengers.
The cruise is presented by The WaterFront Center in partnership with Friends of Sagamore Hill and the Town of Oyster Bay.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How much does the CHRISTEEN Theme Cruise cost?
$85 per person.
Are children allowed on the cruise?
Children are permitted but no children under three years old may board; all children must be accompanied by an adult over the age of 18.
Can I bring my pet?
No animals are allowed aboard.
Is there a limit to how many spots one person can buy?
Yes—there is a limit of eight spots per customer.
Who is presenting the Rough Riders Reunion cruise?
The event is presented by The WaterFront Center in collaboration with Friends of Sagamore Hill and the Town of Oyster Bay.