Two Hour Chesapeake Day Sail in St. Michaels, MD

Set sail on the Selina II for a captivating two-hour Chesapeake Bay adventure departing from historic St. Michaels, Maryland. Led by Captain Iris, whose family connection to the area adds a personal touch, this tour offers a blend of engaging maritime history and hands-on sailing experience. Whether you're eager to help hoist the sails and navigate the waters or prefer to lounge on deck taking in the scenic Miles River views, this outing has something for every guest. As you glide past charming waterfront homes and marshland landscapes, enjoy refreshing complimentary snacks and beverages, including local wine. The day sail is perfect for couples, families, and small groups seeking an intimate, immersive experience that combines boating, storytelling, and the unique culture of St. Michaels. Beyond the relaxing breeze and Chesapeake charm, the sail offers a rare glimpse of the area's rich nautical heritage conveyed through stories about Captain Iris’ grandfather's boat, connecting history with the present.