Best Match Racing inBoston, MA

Join us for a Match Race aboard the Adirondack Schooners.  This is the perfect team building event for an adventure in Boston Harbor aboard these stunning yachts. Match racing in Boston Harbor aboard the Adirondack Schooners with Classic Harbor Line Boston offers an exciting combination of sailing competition and classic maritime charm. This unique sailing experience pits two elegant, 80-foot schooners—styled after late 19th-century yachts—against each other in a head-to-head race through the iconic waters of Boston Harbor. Guests aboard each sailboat become part of the action, cheering on their crew and taking in spectacular views of the city skyline, historic landmarks, and the vibrant waterfront. This is truly an unforgettable nautical adventure.

Our skilled captains and crew bring both professionalism and a deep love of sailing to every race. Whether you’re an avid sailor or simply looking for a unique way to enjoy the harbor, the match race combines sport, storytelling, and sightseeing into an epic event. With limited seating to maintain an intimate and interactive atmosphere, each trip feels personal. It’s an ideal activity for team-building, special occasions, or just an exciting day out on the water in a beautiful classic schooner.