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Set sail on a private full-day adventure in Saint Michaels, Maryland. Enjoy sailing, wine tasting, and gourmet food while exploring the stunning Chesapeake Bay.
Set sail on a private full-day adventure in Saint Michaels, Maryland. Enjoy sailing, wine tasting, and gourmet food while exploring the stunning Chesapeake Bay.
Book with Sail Selina II
Verified experiences and guided adventures in the surrounding area.
Operated by Sail Selina II · Saint Michaels, Maryland
Experience an unforgettable full day private sail with Sail Selina II in Saint Michaels, Maryland. This unique boat tour combines the joy of sailing with the delight of a food and wine tour, offering a personalized and luxurious adventure on the Chesapeake Bay. Whether you're a sailing enthusiast or a first-timer, this private sailing trip delivers a peaceful escape from daily life with breathtaking views of the bay’s serene waters and historic waterfront. The experience includes carefully curated wine selections and gourmet snacks to complement the scenic journey. Perfect for couples, small groups, or celebrations, the trip highlights include exploring quiet coves, spotting local wildlife, and learning about the bay’s maritime heritage. The crew at Sail Selina II provides expert guidance while ensuring comfort and safety throughout the day. Whether you want to relax and soak in the sun or actively participate in sailing, the trip is tailored to your preferences. Saint Michaels provides a charming backdrop with its quaint harbor town vibe and rich history. This private sailing adventure is ideal for those seeking a blend of relaxation, adventure, and local flavors in an intimate setting.
easy.
6–8 hours.
Suitable for all fitness levels; minimal physical exertion is required but being comfortable on a boat is recommended.
No experience is required; the crew will handle sailing, but guests can choose to participate if they wish.
Guests enjoy gourmet snacks and a curated selection of wines sourced locally to enhance the experience.
The boat comfortably accommodates small groups of up to 6 guests for a private experience.
In case of unsuitable weather, trips can be rescheduled or canceled with a full refund.
Yes, children are welcome but must be supervised and wear life jackets at all times.
All trips depart from the harbor in Saint Michaels, Maryland.
Saint Michaels played a strategic role during the War of 1812 and is known for its preserved maritime heritage.
Efforts to protect Chesapeake Bay include sustainable fishing practices and habitat restoration programs supported locally.
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