St. Michaels Sailing
Day Sail
2 Hour sail for up to six passengers from St Michaels Harbour Inn Marina, Maryland. (Six passengers is a legal limit.)
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
Sunset Cruise
2 Hour sail for up to six passengers from St Michaels Harbour Inn Marina, Maryland. (Six passengers is a legal limit.)
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.
Moonlight Cruise
2 Hour sail for up to six passengers from St Michaels Harbour Inn Marina, Maryland. (Six passengers is a legal limit.)
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.
41’ CATBOAT
WORKING BATHROOM
SPEAKERS FOR MUSIC
SIX PASSENGER MAXIMUM
PET FRIENDLY
$25 BYOB CORK FEE
ONE DRINK INCLUDED
CABIN AREA
WATER AVAILABLE
SELINA II
Designed after the classic New England Crosby Cat Boats, the Selina II was built in 1926 at Sweets Shipyard in Greenport, NY as a family yacht for the Samuel Hirds of Dering Harbor on Shelter Island, NY. At 41 feet 6 inches overall length, she is the largest of the surviving vintage catboats. Her 16-foot beam makes her incredibly roomy and stable, the ultimate in sail boat ride comfort.
She is gaff-rigged, with a 48-foot mast and a 35-foot boom. On a normal sailing day, she carries about 1000 square feet of canvas, and our guests are treated to an authentic, old-fashioned sailing experience. Passengers can opt to participate and help raise the sail, or simply sit back, relax, and enjoy the ride.
REVIEWS
1100+ Reviews 5.0/5.0 AVG
Wonderful sailing experience with Captain Iris on the Selina II! We enjoyed an amazing wine tasting (really delicious selections from round the world), saw a pod of playful dolphins, and beautiful sunset… 3 cruises, all unique and amazing!
★★★★★ Dirk K
If you are looking for a fun, educational and highly enjoyable adventure I would recommend sailing with Captain Iris on Selina II. The boat only carries 6 passengers so you feel like it is a private tour! Captain Iris provided the perfect mix of historical information, interactive sailing instructions and a wonderful time enjoying a peaceful sail. Just a wealth of knowledge and friendly interactions. Our only regret was not booking a full days adventure.
★★★★★ C J
Captain Iris and Gavin made today’s voyage a great experience. Booked for our wedding anniversary. Couldn’t have picked a better sailboat. We loved the small group atmosphere . We got to sit right with the Captain while she ran the boat and gave us some great history of sailboats, St. Michael’s, wine, beers, local restaurants and so many other great conversations, you do not get on large group trips. We will definitely do again when we are back in town. Highly recommend Captain Iris and Sail Selina II.
★★★★★ Larry C
We took a moonlight sail on Selina II. The winds were mild but Captain Iris kept us entertained with her vast knowledge of yachting and the stars while crew Colin hoisted the sail and kept supplied us with beverages. It was a wonderful evening that we will treasure.
★★★★★ Jean N
EXPERIENCE DESCRIPTION
Ready to embark on an unforgettable adventure? Step aboard and become a valued member of our crew on this 2-hour Chesapeake boat cruise, where you’ll experience the thrill of sailing firsthand.
Or if you’re seeking tranquility and awe-inspiring vistas, settle into your seat, breathe in the salty sea air, and lose yourself in the captivating beauty of the Eastern Shore during this fantastic 2-hour Maryland sailboat cruise.
Unique, upscale, and exclusive, the luxury sailing yacht Selina II limits her passengers to just 6 guests for an intimate taste of the history of sailing.
Indulge in the sensory feast of freshly varnished mahogany and brightly polished brass aboard the premier charter boat in St. Michaels, MD. As you journey through maritime history, your captain will reveal the secret behind why yachts opt for varnish instead of paint, all the while treating you to exclusive behind-the-scenes insights into the operation of classic sailing vessel. Allow yourself to be transported to another era, where timeless elegance and maritime splendor await your discovery.
LOCATION
Best Boat Tours
Our platform was inspired by a love for sailing and a desire to simplify the search for diverse maritime adventures.
At SailXP we're dedicated to connecting enthusiasts with unforgettable moments on the water, ensuring every sail leaves you with cherished memories.
Top Rated Boat Rides
Our curation process guarantees that every listed adventure meets the highest standards of quality and customer satisfaction.
With SailXP you can trust that you're accessing a collection of the finest sailing journeys, all conveniently available through our intuitive booking site.
