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History of Sail Selina II Tours & Boat Charters, St Michaels Maryland

Sail Selina II Sailing Charters History on the Eastern Shore of Chesapeake Bay

Hop Aboard Sail Selina II Charters for your personalized boat tour

Ahoy, Capt Iris here. Offering you the best personalized experience on a boat tour on the Eastern Shore of the Chesapeake Bay is our #1 goal. When I decided to offer folks sail boat rides in St Michaels, MD on my grandfather’s 1926 historic luxury yacht the Selina II back in 2002, I set a goal for Sail Selina II to be the:

Best in Luxury, Best in Boat Tours, Best in Service.

To be St Michaels, MD #1 attraction. Why do we do that? Because people like you, our passengers, look for sailboat trips that are unique, upscale, and exclusive. Our goal is to have you highly recommend us to all your friends.

Experience the luxury of sailing aboard Sail Selina II, where we limit our passengers to just 6 guests, ensuring an intimate and personalized journey through the rich history of sailing. Say goodbye to crowded boats with over 20 passengers where you feel like just another number. During your 2-hour cruise, you and our fellow guests receive dedicated, tailored service, guaranteeing an unforgettable experience tailored to your personal preferences.”

Public boat tour or private charter, your St Michaels Maryland sailing charter includes a one-on-one personalized tour with our knowledgeable  first class captains and friendly crew on all our relaxing boating trips. Plus it is super easy to book your boat cruise online.

Sail Selina II starts your St Michaels boat tour by taking you through the harbor past the Chesapeake Bay Maritime Museum and the historic landmark, the Hoopers Straight Light House, and then we pass the Inn at Perry Cabin to see where the movie Wedding Crashers was filmed.  On our way into the Miles River we might get to see some wildlife too like osprey & bald eagles and then watch local watermen harvest the blue crabs Chesapeake Bay is so famous for. Once out on the Miles River you get an opportunity to participate raising sails, or simply sit back and relax and watch as a 1000 sq ft gaff rigged sail springs to life as the wind fills the canvass.

I have been very lucky to have had a great team to help me get the business going. Capt Jim Shellum and Gazebo Jon in the early years kept me on track, and Frank Devlin crewed for me for years.  Boy can he pour you a beautiful flute of champagne!

Today I am proud of the high caliber of amazing captains and crew who continue to help Sail Selina II St Michaels, MD offer you first class sailing tours.

At first we just had relaxing 2-hour sailing trips, including our romantic sunset champagne cruise and our super popular day sails. Then people started asking for specialty outings like sailing lessons, wine tasting cruises, beer tasting cruises, romantic boat rides, marriage proposals and nautical weddings aboard the authentic meticulously restored historic 1926 catboat Sail Selina II.

We started our 1st season in Cambridge, MD, from Snappers Restaurant, and the 2nd year we sailed from the Bridge Restaurant on Knapps Narrows on Tilghman Island. It wasn’t until 2004 that a berth opened up at the Harbour Inn in quaint little St Michaels, MD where we have been ever since.

Are you planning a sunset cruise, sailing day trip or a weekend getaway? Minutes away…worlds apart…here in the heart of the historic Chesapeake Bay town of St Michaels, Maryland – makes us the ideal destination for your sailing vacation or sailing getaway and is yet another reason people like you choose to get out on the water for sunset sails and sailing cruises with Sail Selina II.

Once you are here, you’re just steps away from pubs, world-class St Michaels restaurants, shopping, two wineries, the St Michaels Eastern Shore Brewery, Lyons Distillery, yacht tours, the Chesapeake Bay Maritime Museum, our historic waterfront AND boating, kayaking, golfing and biking and a host of other fun activities including the St Michaels, MD water taxi.

And for your best weekend getaway from Washington, DC simply book a room at a St Michaels bed & breakfast or stay on the waterfront at the lovely St Michaels Harbour Inn, Marina & Spa.

Plus St Michaels MD special events are another reason to visit including Chocolate Fest, Wine Fest, Beer Fest, Seaglass Fest, Small Craft Fest, Oyster Fest, and Watermans Day where you can watch the boat docking contest.

Sometimes people ask “When is the best time to sail Chesapeake Bay?” That’s a tough question because it depends on what kind of experience you want. The wind tends to be a bit lighter in the morning and the evenings with the most breeze in the middle of the day. Bad Weather Forecast? Our captains make the weather decision at the time of departure.  If it too unsafe or too unpleasant to go out you have your choice of trying to reschedule, getting a gift card to use in the future, or we offer you a full refund.

Located at the Harbor Inn’s dock at 101 N Harbor Road in St Michaels, MD, we hope you choose to book with us when your search for ‘sailing near me’ and ‘sailboat sunset cruise’ brings up Sail Selina II.

I almost forgot to mention, we are 🐕Pet Friendly, too.

Oh! And after your excursion we will ask you for feedback.  Your input is so important to making Sail Selina II the best St Michaels, MD boat ride to choose!

Seize this incredible opportunity today! For more details about our cruises, simply give us a call at 410-726-9400. Ready to set sail? Purchase your cruise tickets right here and embark on your unforgettable journey!

Book your sail today!


Selina II on Chesapeake Bay

Discover the captivating history of the esteemed yacht Selina II:

If you’re wondering about things to do in St. Michaels MD or seeking top attractions in St. Michaels Maryland, look no further than the iconic 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. Her current sail was built in 2017 by Nathanial Wilson’s sail loft in Boothbay Harbor, ME.

In the early 1960s she passed to the Hird’s daughter Esther who, with her husband Bridg’s help, took care of Selina II at Tuthills Boat Yard on Shelter Island NY until 2001 when she passed on to their daughter Capt Iris, the current owner who brought her to Chesapeake Bay. Pretty neat that she has been in the same family for 3 generations.

In 1976, Selina II was among 90 U.S. ships invited to participate in the Parade of Operation Sail in New York Harbor on the July 4 Bicentennial celebration. Since then, she has been in the New York Harbor Festival in 1977; Boston’s 350th anniversary in 1980; the Norfolk, VA, Portfest in 1983; the Parade of Ships in celebration of the Constitution’s 200th anniversary in 1986; Albany’s Portfest in 1989; Columbus’s famous voyage parades in 1992; and OP Sail 2000 in New York and Boston.

In the fall of 1980, an extensive restoration effort was begun to keep the Selina II in sailing condition. Fifty-five new white oak ribs had to be fashioned, bent, and installed. Additional flooring timbers were required, and then a replacement of the cockpit and cabin interior, which had been removed to reveal the ribs. Except for some changes in the galley and storage areas, as well as accommodations for navigational and safety aids, the Selina II has been kept as true to her original design as possible, including a full 6-foot 2-inch headroom in the open saloon.

In 2001 she passed to the third generation. Capt Iris Robertson who became her steward and undertook a second restoration in preparation for making Selina II available as the premiere sailing charter boat in St Michaels MD. Offering guests an authentic historic yacht experience, join us for one of our many sailboat rides.

In 2001-2002, another round of restoration took place in James Richardson’s boatyard in Lloyds, MD, under the direction of shipwright Tom Howell. An additional 15 ribs were replaced, 20 planks, her stem, sternpost, transom, half of her keelson and keel bolts, catwalks/deck, and a complete mast step fitting. Chain plates and dorade boxes were added, and the forepeak reconfigured to allow the addition of a forward hatch. A chain locker was added to the fo’c’sle, creating a berth for additional sleeping quarters.

Her ship’s complement has included children, grandchildren, and great-grandchildren of her original owners. Raised on and around the Selina II, her current Coast Guard Licensed Captain, Iris Robertson, is a granddaughter of her original owners.

After 75 years of plying the waters of Long Island, the Selina II came to her new home on the Eastern Shore of the Chesapeake Bay in 2001. She sails in and around the Miles River area of the Eastern Shore from her berth in St. Michaels, Maryland, offering Chesapeake Bay charters like day sails, romantic sunset champagne cruises, and specialties like engagements, nautical elopements and sail boat weddings.

Wondering what to do in St Michaels MD? Experience the tranquility of the Chesapeake Bay and unwind in style with Maryland Yacht Charters. Opt for a private boat ride or private sailboat charter and sail away in style. Your Maryland Yacht Charters will have you help you relax, unwind, rejuvenate. Boat rides in Maryland are the best when you are sailing Chesapeake Bay.

Want more info? Call 410-726-9400 or Book your sail today!



Selina II has a dry, uncovered, open, comfortable, and roomy cockpit seating with four captain’s chairs and two cushioned settees.


Soda, Cold Craft Beer, Wine, and Champagne are available for sale during all trips. BYOB fee of $25. Bottled water is complimentary.


There is a marine head onboard; however, it is limited, so we recommend that guests take advantage of the shore-side facilities inside the Harbour Inn before embarking.