Our Magnificent Sag Harbor Charter Fleet is Available for Every Size Group and Every Occasion
The SailHamptons fleet is one of the most diverse, encompassing, and wonderful fleets on the East End. Meticulously kept and based in Sag Harbor, our boats have something for everyone. Our yachts providing Sag Harbor Charters together have a combined Coast Guard Certified Capacity of 91 guests. They are all lovely and intimate, however, for smaller groups.
LUNA
Private Luxury for up to 41 Guests from Sag Harbor, Shelter Island, or Greenport
Luna is our flagship. She has the largest deck and passenger capacity space of any sailing charter on the Hamptons. She is extensively equipped with all types of serving ware, cutlery, glassware, silverware and service. She has additional capacity for different types of food service and experiences. Luna’s shallow draft allows her to pick up from many spots and even provide service to many local dining destinations. Learn more about Luna.
COSMOS
At the intersection of trimaran performance and luxury sailing, meet the Classic Mahogany Trimaran: “Cosmos.”
Cosmos is our Classic Mahogany Trimaran. She is Coast Guard Certified for 26 guests. While we will book larger groups, we prefer to limit group size to 15 guests. This number is comfortable with our spacious and luxurious deck appointments. Cosmos blends the wonderful performance and stability of a trimaran with the luxury of the SailHamptons experience. She is available for Sag Harbor Charters and points throughout the East End. Learn More about Cosmos
Blue Sky
Coming Soon: A Lobster Yacht like no other. Blue Sky joins the SailHamptons fleet Summer 2026. Blue Sky is a proper Maine Downeaster built by John Williams Boat Company.