Adirondack Day Sail

Experience the timeless charm of Boston Harbor aboard our classic 2-hour or 1.5-hour afternoon day sails. Step aboard our schooners Adirondack III & IV for an unforgettable journey through the scenic beauty of the harbor.

Our sailing vessels, both 80-foot pilot schooners, boast elegant designs with sleek lines that harken back to a bygone era of maritime elegance. While you're aboard one of our schooners, you'll revel in the smooth, gentle sailing experience, complemented by a touch of speediness for added excitement.

Perfect for families and adventurers alike, our day sails offer a relaxing and immersive way to explore Boston Harbor's iconic landmarks. From the moment you set sail, the distractions of life on land will fade away, replaced by the tranquil joy of gliding across the water on a leisurely cruise.

Don't miss your chance to create lasting memories with loved ones aboard the most elegant sailing excursion in Boston Harbor. Book your adventure today and embark on a voyage of discovery and relaxation unlike any other!

Notable Sites

• One of the first sites you’ll see on our day sail is the Boston Seaport District. There's much to be seen here as the area features many newly constructed buildings, as well as the classic structures that originally comprised Boston’s waterfront community.
• We will point out The Moakley Federal Courthouse at Fan Pier, the World Trade Center, as well as Harpoon Brewery
• As our trip extends, we will sail through the Inner Harbor Islands, getting as close as we can to some of our historical islands including: Castle Island featuring Fort Independence and the Donald McKay Monument, Spectacle Island, and Long Island with the Long Island Head Light House.

Your knowledgeable captain and crew are always ready to answer questions about the sights and history of Boston Harbor and its surrounding areas. From interesting facts to old-time legends, the maritime world of Boston has many great stories to offer. Ask them anything you'd like to know!

About our schooners

Our schooners, the Adirondack III and Adirondack IV, pay homage to the pilot schooners of the 1890s. At 80 feet and 88 feet in length, they feature teak decks, mahogany trimmings, and two bathrooms, offering comfort and convenience. Crafted by Scarano Boat Building of Albany, NY, they are designed for spectacular sightseeing adventures with ample deck space and seating for up to 41 or 70 passengers.

Sailing on these vessels is a delight, as they move through the water efficiently and beautifully. Operated by Coast Guard-certified captains and a friendly, talented crew, our vessels are known for their hospitality and safety. Feel free to ask our crew about the boat or any of the Boston sites as you enjoy your journey through the historic harbor.