A curated fleet of historic yachts — not replicas.
ABOUT US
A curated collection of historic yachts, each with a story.
Caine & James offers private charters in Sag Harbor —
defined by character, heritage, a narrative steeped in history and luxury that whispers.
No crowds. No templates. Just time on the water, done properly.
THE FLEET
Each vessel is privately chartered. No shared cruises
MIAMI
Private Charters | Up to 6 Guests
Built in 1916 by William Hand and the Lawley yard, Miami is a rare surviving example of early American yachting design.
Once commissioned by Carl Fisher, she carries a legacy tied to the origins of Miami Beach and Montauk.
Today, she offers intimate, beautifully paced charters for those who appreciate something truly original.
NORTH STAR
Private Charters | Up to 12 Guests
North Star is a 42-foot yacht built in 1958 by Stephens Brothers in Stockton, California—a classic of West Coast craftsmanship.
She later became a staple of the Seattle yachting scene, cruising Puget Sound and the San Juan and Gulf Islands.
Now based in Sag Harbor, she brings that legacy east, offering a timeless experience on the water.
Gallery
Request Your Charter
Tell us a bit about your ideal day on the water.
We’ll respond with availability and options.
Most charters are custom — pricing depends on vessel and duration.
Response time: typically within 1–2 hours during the season.