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Set sail on the serene waters of Maryland's Miles River with a private half-day charter aboard the Selina II. Enjoy scenic views, delicious local food, and exclusive access for up to six guests.
Set sail on the serene waters of Maryland's Miles River with a private half-day charter aboard the Selina II. Enjoy scenic views, delicious local food, and exclusive access for up to six guests.
Book with Sail Selina II
Verified experiences and guided adventures in the surrounding area.
Operated by Sail Selina II · Saint Michaels, Maryland
Embark on a relaxing and memorable half-day private sail aboard the Selina II, a beautiful sailing yacht in Saint Michaels, Maryland. This private charter accommodates up to six guests, making it perfect for families, friends, or small groups seeking a personalized experience on the water. Sail through the scenic Miles River and explore the calm, sparkling waters of the Chesapeake Bay. Along the way, enjoy a leisurely harbor tour that offers stunning views of historic waterfront homes and charming marinas. As you glide across the water, indulge in a delicious picnic featuring local specialties such as crab cakes or a fresh selection of seasonal treats paired with fine Maryland wines. This trip blends adventure with comfort, providing plenty of opportunities to relax, snap beautiful photos, and create lasting memories. The knowledgeable crew will ensure your journey is smooth, enjoyable, and personalized to your preferences. Whether you’re new to sailing or have some experience, this half-day charter provides an easygoing yet exciting outdoor adventure that highlights the natural beauty and local flavors of Saint Michaels.
easy.
3–4 hours.
Suitable for most fitness levels as the trip involves mostly sitting and light activity like boarding or moving around the deck.
No prior sailing experience is needed; the crew takes care of all sailing tasks while you relax.
Guests can enjoy locally made crab cakes or a picnic with fresh, seasonal items and complimentary Maryland wines.
The yacht is available for private charters up to six guests to ensure a personalized experience.
Yes, the trip is family-friendly, and children are welcome onboard with parental supervision.
If weather conditions are unsafe, the company will reschedule your trip or offer a full refund.
Pets are not permitted aboard to ensure safety and comfort for all guests.
Saint Michaels was once a busy shipbuilding town during the War of 1812 and retains much of its maritime heritage today.
Efforts in the Chesapeake Bay area focus on protecting water quality and restoring oyster populations to support ecosystem health.
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