Sail Selina II — Intimate Sailing Charters in Saint Michaels

Sail Selina II — Saint Michaels Sailing on the Miles River

Sail Selina II is a charter yacht operating from Saint Michaels, Maryland, offering a variety of sailing experiences on the Miles River and Chesapeake Bay. The Selina II lineup includes overnight excursions, sunset champagne cruises, two-hour day sails, wine and beer tasting cruises, moonlight sails, private sailing lessons, half-day private charters, and nautical weddings and elopements.

Why book a Selina II cruise?

• Historic sailing experience: Guests sail aboard the historic Selina II for authentic Chesapeake Bay time on the water.
• Small-group focus: Private charters accommodate up to six guests; wedding ceremonies can host up to 12.
• Local storytelling: The Two Hour Chesapeake Day Sail is hosted by Captain Iris, who shares local history and offers optional crew participation.
• Specialty tastings and celebrations: Wine Tasting Cruises include three reds and three whites; Beer Tasting Cruises feature unlimited samples of Maryland microbrews; the Special 4th of July Fireworks Cruise includes an open bar and chocolate Piroulines.

Signature trips and what to expect

• Overnight Excursion on the Selina II — An overnight adventure with a sunset champagne cruise, picnic-style crab cake dinner, cozy overnight accommodations, and a quiche breakfast on the return sail. Ideal for families or small groups seeking a multi-hour experience on the water.

• Sunset Champagne Cruise — A scenic harbor tour at golden hour with light hors d'oeuvres and champagne, paired with narration about St. Michaels and the Miles River shoreline.

• Two Hour Chesapeake Day Sail — A two-hour sailing trip where passengers can relax, participate as crew, or learn local maritime stories from Captain Iris. Complimentary refreshments are provided.

• Wine & Beer Tasting Cruises — Two-hour curated tasting sails: a wine cruise with three red and three white pours and a beer cruise offering unlimited samples of award-winning Maryland microbrews. Each tasting includes a mini-harbor tour and a favorite glass to finish.

• Moonlight Cruise — Evening sailing under sundown and moonrise with complimentary champagne and chocolate for a quiet, scenic experience.

• Private Sailing Lesson — Two-hour instruction focusing on line handling, sail raising, and steering aboard the historic Selina II for hands-on learning.

• Half Day Private Sail & Nautical Weddings — Private half-day charters include picnic or crab cake options for up to six guests. Nautical Weddings & Elopements provide ceremony options for up to 12 guests with a post-ceremony celebratory sail.

Booking and practical details

Sail Selina II departs from Saint Michaels harbor on the Miles River. Many experiences require advance reservations and are designed for small groups. Guests should review individual trip descriptions for capacity limits, menu features (for example, crab cakes and quiche on overnight sails), and specialty inclusions like open bars or tasting pours. These curated, small-group sails combine Chesapeake Bay sailing tradition with personalized service.

Keywords and local search focus

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Book a Selina II experience for an intimate, hands-on Chesapeake sailing outing that highlights local flavor, historical storytelling, and private-group comfort.