St. Michaels Sailing

Two Hour Chesapeake Day Sail

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.

Sunset Champagne Cruise

Included in these outings are a brief harbor tour. Capt Iris (or her relief captain) talks about what you are seeing along the picturesque waterfront, the history of St. Michaels and about the history of her grandfather’s boat. Then we depart the harbor and go out into the Miles River, put up sails, and follow the wind.

Immediately following the raising of the sails, we raise our glasses and toast the wind. You are welcome to a choice of a really easy to drink Champagne, an un-oaked Chardonnay, Pinot Grigio, Shiraz, a selection of handcrafted beers from all over Maryland, sodas and water, all accompanied by a light tray of hors-d'oeuvres: carrots, sesame rounds, and black olive tapenade hummus.

Guests often ask what they should wear. We recommend you come ready to go to dinner, wear comfortable shoes, and don’t forget your camera. We suggest a light jacket in spring and fall. And ladies: no heels please!

Moonlight Cruise

We sail every evening May-August from 7:30-9:30 and call it our moonlight cruise. On some of those evenings that’s when the sun is setting, and on some evenings the moon is also visible. Once a month the full moon rises as the sun sets, making being on the water the most magical experience known to any sailor. We depart the dock and go out into the Miles River, put up the sails, and follow the soft evening wind. Champagne and chocolate are complimentary. $95 per person, + tax and tip.

Wine Tasting Cruise

Available with prior reservations, our 2-hour wine tasting cruises include an introduction to the basics of wine tasting, sampling 3 reds and 3 whites, and scorecards for keeping track of your notes. We finish by enjoying a full glass of your favorite wine. We serve wines from around the world with a constantly changing selection based on the most recent of Capt Iris' favorites. Fun! $95 per person, minimum 2 guests, or by private charter up to 6 guests $545 plus there is a 10% amusement tax in St. Michaels harbor, and a-20% gratuity for the crew. Wine Cruises are available Sun-Sat 12:30-2:30pm and 3:00-5:00pm.

Beer Tasting Cruise

Available anytime with prior reservations, these cruises include unlimited samplings of Maryland Microbrewery’s finest cold beer with a flight of six to eight different award winning brews. Fun!
$95 per person, minimum 2 guests, or by private charter up to 6 guests $545. Plus there is a 10% amusement tax in St. Michaels harbor, and a 20% gratuity for the crew. Beer tasting Cruises are available Sun-Sat 12:30-2:30pm and 3:00-5:00pm.

Half Day Private Sail

Join us on the Selina II for a private half day sail that is bound to have everyone smiling ear to ear. We depart the dock and do a mini harbor tour (St Michaels is very pretty to see from the waterfront) and then we go out into the Miles River, put up sails and follow the wind. On our 1/2 day sail we can cater a simple picnic lunch or an Eastern Shore favorite, crab cakes lunch. Wonderful!

Private Sailing Lesson

Congratulations on your interest in learning to sail! Or for the experienced sailor, to learn the art of the gaff rig. Because Selina II is a historic vessel, we offer a very different approach to learning to sail. In the two hours, we spend together you can expect to learn the basics: line handling, how to raise the sail, steering the boat, reading the wind, and the physics behind what makes the boat go towards the wind. We’ll cover simple boat handling, parts of a boat, a few basic knots, touch on weather, talk about rules of the road, simple four points of sail, determining proper sail set and practice tacking. You’ll come away realizing you’ve only scratched the surface! $365 for two hours, can be anywhere from one up to six guests. Plus there is a 10% amusement tax in St. Michaels harbor, and it is customary to tip the ship’s mate like a restaurant, 15%-20%.

Full Day Private Sail

Join us on the Selina II for a private full day sail that is bound to have everyone smiling ear to ear. We depart the dock and do a mini harbor tour (St Michaels is very pretty to see from the waterfront) and then we go out into the Miles River, put up sails and follow the wind. On our full day sail we can cater a simple picnic lunch or an Eastern Shore favorite, crab cakes lunch. Wonderful!