THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Experience the beauty of Chesapeake Bay on a private two-hour sail with Captain Iris in St. Michaels, Maryland. Enjoy hands-on sailing, local stories, and complimentary refreshments while cruising the Miles River.
Experience the beauty of Chesapeake Bay on a private two-hour sail with Captain Iris in St. Michaels, Maryland. Enjoy hands-on sailing, local stories, and complimentary refreshments while cruising the Miles River.
Book with Sail Selina II
Verified experiences and guided adventures in the surrounding area.
Operated by Sail Selina II · Saint Michaels, Maryland
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.
easy.
2 hours.
Basic mobility is needed for boarding and moving around the deck; suitable for most fitness levels.
No prior experience is necessary; guests are welcome to participate as much or as little as they like.
Complimentary snacks and local wine are served during the sail to enhance your experience.
Tours are private with a maximum capacity of 6 guests for an intimate experience.
Wear comfortable, layered clothing and non-slip shoes suitable for boating conditions.
Yes, children are welcome but should be supervised closely for safety on deck.
Outside food and drinks are not permitted; however, refreshments are provided onboard.
St. Michaels has a rich maritime history, known for its shipbuilding and role in the War of 1812.
Captain Iris practices sustainable sailing and promotes awareness of local marine ecosystems to protect the Chesapeake Bay.
Sail Selina II is a charter sailing operation based in Saint Michaels, Maryland, offering a curated selection of small-group sails, private lessons, and specialty cruises on the Miles River and adjacent Chesapeake waterways. The business operates the historic Selina II and presents a range of experiences, including two-hour day sails, a two-hour wine tasting (three reds and three whites), beer tasting cruises with unlimited samples of Maryland microbrews, moonlight and sunset champagne cruises, and overnight excursions featuring a sunset champagne cruise, picnic-style crab cake dinner, and a quiche breakfast on the return. The Two Hour Chesapeake Day Sail is hosted by Captain Iris, who shares local stories and offers optional crew participation. Private Sailing Lessons are offered in two-hour sessions covering line handling, sail raising, and steering. Sail Selina II accommodates private charters and specialty events, with private sails hosting up to six guests and Nautical Weddings & Elopements allowing ceremonies and celebration sails for up to 12 guests. The Special 4th of July Fireworks Cruise features an open bar, chocolate Piroulines, and a six-person limit. Many sails include complimentary refreshments, and select cruises serve champagne and chocolate. Operating from Saint Michaels harbor, Sail Selina II focuses on personalized, hands-on sailing experiences, safety aboard a well-maintained historic yacht, and creating memorable outings for families, friends, couples, and small groups.
Book with Sail Selina II