Sail Selina II offers tailored sailing experiences on Chesapeake Bay from Saint Michaels, MD. From day sails to romantic cruises, discover how this classic yacht transforms the coastal adventure scene.
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Difficulty
easy
Duration
2 hours to overnight
Fitness Level
Suitable for all fitness levels; most passengers remain seated or assist minimally during sails.
Wildlife
History
Saint Michaels was a key shipbuilding center in the 18th and 19th centuries, and the area’s maritime heritage is still alive in local vessels like the Selina II.
Conservation
Efforts to protect the Chesapeake Bay's delicate ecosystem include sustainable boating practices and education about local water quality, reflected in the responsible operation of Sail Selina II.
Sail Selina II
Sail Selina II offers tailored sailing experiences on Chesapeake Bay from Saint Michaels, MD. From day sails to romantic cruises, discover how this classic yacht transforms the coastal adventure scene.
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.
Location
Saint Michaels, MD
Harbor-based on the Miles River
Tours Offered
10
Two-hour sails to overnight excursions
Private Capacity
Up to 6
Private charters for six guests
Wedding Capacity
Up to 12
Elopements and nautical ceremonies
Book private charters, wine and beer tastings, sunset cruises, or an overnight excursion from Saint Michaels — small groups, hands-on sailing, unforgettable views.
Book Early for Peak Dates
Popular cruises, especially sunset and holiday-themed sails, fill quickly—reserve ahead to secure your preferred time.
Arrive Prepared for Variable Weather
Chesapeake Bay conditions can shift quickly; bring layered clothing and wind protection to stay comfortable.
Notify Special Occasions in Advance
Celebrations like proposals or weddings benefit from early coordination to customize the onboard experience.
Motion Sensitivity Considerations
If prone to seasickness, take preventative measures before boarding, as the bay can be choppy on windy days.
Windbreaker Jacket
Protects against the brisk bay breeze, especially during sunset and overnight sails.
spring|fall|summer|winter
Non-Slip Footwear
Ensures safe footing on the wet deck of the Selina II.
Sunglasses with UV Protection
Reduces glare off the water and enhances visibility on bright days.
spring|summer|fall
Reusable Water Bottle
Keeps you hydrated during warmer day sails and tasting cruises.
summer