Two Hour Chesapeake Day Sail in St. Michaels, MD
Difficulty
easy
Duration
2 hours
Fitness Level
Basic mobility is needed for boarding and moving around the deck; suitable for most fitness levels.
Overview
Experience the beauty of Chesapeake Bay on a private two-hour sail with Captain Iris in St. Michaels, Maryland. Enjoy hands-on sailing, local stories, and complimentary refreshments while cruising the Miles River.
Two Hour Chesapeake Day Sail
$85 Per Passenger or $495 Private Charter | Max 6 People | Add On Beer/Wine Tasting!
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Adventure Photos
About This Adventure
Embark on a two-hour sailing adventure aboard the Selina II, where Captain Iris shares captivating stories of St. Michaels and her grandfather's boat. Experience the thrill of sailing on the Miles River, participate as crew, or simply relax. Enjoy complimentary refreshments and stunning waterfront views on this memorable journey.
Two-Hour Day Sails on the Selina II Sailing Yacht
Rates & Duration
2 Hour Sail
Passenger: $85 Private Charter: $495 All ages welcome!
Beer/Wine Tasting Add On an additional $20 per person (21 and older).
Max 6 people. Please note: if you are not booking a private charter, this sail requires 2+ people to book in order to go out. Amusement tax and crew gratuity added on.
About
We depart from the dock at the Harbour Inn and Marina in St Michaels and Capt. Iris (or her relief captain) gives a brief harbor tour. She talks about what you are seeing along the picturesque waterfront, the history of St Michaels and about the story of her grandfather’s boat, Selina II. Then we depart the harbor and go out into the Miles River, put up sails, and follow the wind. You are welcome to participate as a working crew member, or simply sit back and relax, we’re here to help you complete your historic yacht experience. Guests often ask what they should bring, we recommend comfortable shoes, sunscreen, cameras, and a light jacket in spring and fall.
Tour Inclusion
- Bottled Water
- Soda, Beer, Wine & Champagne available for sale
- Binoculars, Sunscreens, Sunglasses, Wind-gear and more!
- Free parking, 7 days a week
- Rain Jackets, hats, blankets
- souvenir Baseball Caps available for sale
Adventure Tips
Dress in layers
Weather on the water can change quickly, so bring layers to stay comfortable throughout your sail.
Use non-slip shoes
Wear closed-toe, non-slip shoes to safely move on deck during the sail.
Bring sunscreen
Protect exposed skin from sun reflection off the water with a high SPF sunscreen.
Stay hydrated
Although refreshments are provided, bringing a personal water bottle is a good idea to stay hydrated.
Local Insights
Wildlife
- Ospreys soaring above the river
- Blue herons stalking the shallows
History
St. Michaels has a rich maritime history, known for its shipbuilding and role in the War of 1812.
Conservation
Captain Iris practices sustainable sailing and promotes awareness of local marine ecosystems to protect the Chesapeake Bay.
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Adventure Hotspots in Baltimore
Frequently Asked Questions
Recommended Gear
Light jacket or windbreaker
Keeps you warm against cool breezes during spring sails.
spring specific
Non-slip deck shoes
Provides traction and safety while moving on the boat’s deck.
Polarized sunglasses
Reduces glare off the water for better visibility and eye protection.
Wide-brim hat
Protects your face and neck from direct sun exposure.
summer specific