Sailing Adventures with Sail Selina II in Saint Michaels
Difficulty
easy
Duration
2 hours to overnight
Fitness Level
Appropriate for most fitness levels; minimal physical exertion needed unless choosing a sailing lesson.
Overview
Set sail on the iconic Chesapeake Bay aboard Sail Selina II in Saint Michaels, Maryland. Discover a mix of historic waters, expert captains, and personalized cruises that elevate your maritime adventure.
Details
Saint Michaels, Maryland, sits on the Chesapeake Bay’s Eastern Shore, a historic maritime town where water defines the rhythm of life. Here, Sail Selina II offers an immersive way to experience these iconic waters aboard the eponymous Selina II, a beautifully maintained sailboat steeped in local legacy. Whether you’re drawn by the sun dipping below the horizon or the call of gentle ocean breezes on a moonlit voyage, this isn’t just a boat trip—it’s a chance to connect deeply with Chesapeake Bay’s natural and cultural heartbeat.
Sail Selina II’s offerings go beyond standard charters. From casual two-hour day sails to full-day private excursions, passengers glide past grand waterfront estates and historic harbors that whisper stories of Captain Iris’s family heritage and the area’s maritime past. The captain’s deep knowledge adds layers to every cruise, whether you’re savoring wine or beer, celebrating a special moment like a proposal or wedding, or simply floating under stars on a moonlight sail.
Distinctive trips like a Fourth of July fireworks cruise or overnight excursions on the Selina II open up unique perspectives on Chesapeake’s vast waterways. The boat’s classic lines and comfortable layout make for a refined yet accessible experience, blending hands-on sailing lessons with the luxury of private time on the water. Guests frequently highlight the captain’s expertise in not only sailing but also local history, wildlife spotting, and safe seamanship, the latter validated by a notable rescue on the bay.
St. Michaels offers more than just a backdrop. This region’s mix of tidal creeks, salt marshes, and open bay create a dynamic ecosystem punctuated by waterfowl, ospreys, and seasonal migrations. The Selina II’s cruises invite you to witness this shifting landscape from a privileged vantage point. Ideal for adventurers craving a thoughtful blend of relaxation, education, and nautical thrills, Sail Selina II represents one of the Chesapeake Bay’s most genuine and memorable maritime experiences.
Adventure Tips
Book Early for Special Event Cruises
Popular specialty sails like sunset champagne or fireworks cruises fill quickly, so reserve ahead to secure your preferred date.
Dress in Layers and Bring a Windbreaker
Even in summer, bay breezes can be cool on the water—layered clothing keeps you comfortable throughout your trip.
Arrive 15 Minutes Early
Give yourself time to check in and get acquainted with the boat before departure, maximizing your time on the water.
Communicate Dietary Needs in Advance
For wine or beer tasting cruises, notify the crew ahead if you have allergies or preferences to ensure availability and safety.
Local Insights
Hidden Gems
- Niffy’s Island Wildlife Sanctuary nearby for birdwatching
- Tilghman Island’s oyster farms for fresh Chesapeake Bay shellfish
Wildlife
- Ospreys hunting overhead
- Blue herons wading in marshes
History
St. Michaels has been a Chesapeake Bay shipbuilding and seafood hub since the 18th century, with rich maritime heritage reflected along the shorelines.
Conservation
Local sailing operators including Sail Selina II actively support clean water initiatives and responsible wildlife viewing to protect bay ecosystems.
Frequently Asked Questions
Photography Tips
Best Times
Best Viewpoints
- Alongside the historic waterfront homes
- Approaching Eastern Neck National Wildlife Refuge
- From the bow during fireworks cruises
What to Photograph
Recommended Gear
Windbreaker Jacket
Protects against cool spring breezes and unpredictable weather on the water.
spring specific
Non-slip Deck Shoes
Critical for safe footing aboard the Selina II’s polished deck.
Sunscreen
Prevents sunburn during exposed daytime sails on the Chesapeake Bay.
summer specific
Binoculars
Enhances wildlife and landmark viewing during clear fall sails.
fall specific