Chesapeake Sailing Adventures with Sail Selina II in Saint Michaels
Difficulty
easy
Duration
2 hours to overnight
Fitness Level
Suitable for all fitness levels; most passengers remain seated or assist minimally during sails.
Overview
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.
Details
Saint Michaels, Maryland, a charming harbor town on the Chesapeake Bay, invites adventurers to trade the shoreline bustle for serene sailing aboard Sail Selina II. This historic town is defined by its glassy waterfront views, historic marinas, and the steady lapping of bay waters, making it an ideal launching point for a wide range of memorable nautical experiences. Sail Selina II offers a remarkable spectrum of private and group excursions on the water, from half-day sails that slip past elegant waterfront homes to overnight voyages that stretch into the calm night.
The Selina II herself is more than a boat; she’s a family legacy captained by Iris, whose intimate knowledge of these waters shines in every trip. Her storytelling interweaves local maritime history and lighthouses with firsthand sailing expertise, while her crew ensures an atmosphere that’s both welcoming and informative.
The array of sail options lets guests customize their waterborne adventure: join a lively Beer Tasting Cruise sampling regional brews, raise a glass on the Sunset Champagne Cruise, or learn the ropes during a Private Sailing Lesson. Special occasions find a perfect platform here too, from romantic Marriage Proposal Engagement Cruises to unique Nautical Weddings and Elopements on the bay’s peaceful tides.
What sets this offering apart is its blend of relaxed luxury and authentic sailing culture—the Selina II retains the grace of a classic yacht, yet every voyage feels personal and approachable. The Chesapeake Bay’s legendary sunsets and estuarine ecosystem unfold as natural backdrops while guests float past osprey nests, colonial homes, and hidden coves.
For locals and travelers alike, a cruise on the Selina II is an opportunity to connect with a maritime heritage still alive in these waters. Whether it’s a casual afternoon sail or an intimate overnight adventure, Sail Selina II enriches the Saint Michaels experience with waterside memories few other activities can match.
Adventure Tips
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.
Local Insights
Hidden Gems
- Mallets Bay Cove – quiet bay area perfect for spotting flighty osprey
- Historic waterfront homes lining Talbot Street – rich in Chesapeake Bay architecture
Wildlife
- Osprey – often visible soaring over the bay or perched near nesting sites
- Striped Bass – a prized fish species inhabiting these estuarine waters
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.
Frequently Asked Questions
Photography Tips
Best Times
Best Viewpoints
- Aboard the Selina II deck facing eastern shorelines
- Harbor entrance capturing historic lighthouses
- Near the anchorage with the town skyline backdrop
What to Photograph
Recommended Gear
Windbreaker Jacket
Protects against the brisk bay breeze, especially during sunset and overnight sails.
spring|fall|summer|winter specific
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 specific
Reusable Water Bottle
Keeps you hydrated during warmer day sails and tasting cruises.
summer specific