Be whisked back in time to the Roaring ’20s aboard this beautifully restored 1929 sailing ship. The pinnacle of luxury yachts at the time, the Shearwater is a blue water ocean cruiser which has been around the globe. She’s sailed the Pacific, been through the Panama Canal and won classic yacht races in NY and New Zealand. Like New Yorkers, she’s got character and depth. With a length of 82 feet (larger than the Mayflower) and a width of 16.5 feet, she’s one of largest sailboats built in her era yet her sleek feel provides an intimate experience for up to 37 passengers. Seating is ad-hoc: find a place to sit on a bench, a deck-box or the owner’s favorite spot: directly on the original Rangoon teak deck. A spiral staircase drops you below to check out the exquisite mahogany interior, you’ll be immersed in the Gatsby era and Gilded Age while looking at modern-day New York City skyline.

The original Clipper City was built as a cargo schooner just prior to the Civil War. Rebuilt and refurbished from the original plans which were borrowed from the Smithsonian Institution, at 158 feet, the Clipper City is a unique way to host up to 149 guests on a sailing adventure around New York Harbor. (If your party is smaller than 37, you may wish to consider our smaller sailing ship, the Shearwater.) Parties and events on the 120-foot-tall, historic tall ship are absolutely breathtaking, under the unfurled sails. The sweeping deck and full bar make for welcoming and comfortable gatherings, as you and your guests sail the harbor, out to the Statue of Liberty and beyond, enjoying a wide range of beverages and catering options.