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 guests to just 6, ensuring an intimate and personalized journey through the rich history of sailing. Say goodbye to crowded boats with over 20 passengers, where you often feel like just another face in the crowd. During your 2-hour cruise, you and our fellow guests enjoy dedicated, attentive service, ensuring every detail is tailored to your personal preferences and creating an unforgettable experience.
Whether you’re joining a public boat tour or booking a private charter, each St. Michaels, Maryland sailing charter includes a one-on-one, personalized tour with our knowledgeable, first-class captains and friendly crew. We make it easy for you to book your boat cruise online, so you can start your adventure with just a few clicks.
Your journey aboard Sail Selina II begins by gliding through the harbor past the Chesapeake Bay Maritime Museum and the iconic Hoopers Strait Lighthouse. We’ll even cruise by the Inn at Perry Cabin, where scenes from the movie Wedding Crashers were filmed. As we make our way into the Miles River, keep an eye out for wildlife—majestic osprey, bald eagles, and local watermen harvesting the blue crabs that Chesapeake Bay is famous for. Once out on the Miles River, you’ll have the option to participate in raising the sails or simply relax and watch as the 1,000 sq ft gaff-rigged sail comes to life with the wind filling the canvas.
I’ve been fortunate to have had a wonderful team to help get this business off the ground. Capt. Jim Shellum and Gazebo Jon in the early years kept me on track, and Frank Devlin crewed for me for years—he sure knows how to pour a perfect glass of champagne!
Today, I’m proud of the incredible captains and crew who continue to make Sail Selina II in St. Michaels, MD, a place that offers top-tier sailing tours and unforgettable experiences.
We started with simple, relaxing 2-hour sailing trips, including our romantic sunset champagne cruises and popular day sails. Soon, guests began requesting specialty outings like sailing lessons, wine tasting cruises, beer tasting cruises, romantic boat rides, marriage proposals, and even nautical weddings aboard the meticulously restored, authentic 1926 catboat, Sail Selina II.
We began our first season in Cambridge, MD, at Snappers Restaurant, moved to the Bridge Restaurant on Tilghman Island’s Knapps Narrows the following year, and in 2004, we found a home at the Harbour Inn in quaint St. Michaels, MD, where we’ve been ever since.
Planning a sunset cruise, sailing day trip, or a weekend getaway? Just minutes away but worlds apart, St. Michaels, MD, is the ideal destination for your sailing vacation or getaway, offering a peaceful escape that’s just a short drive from Washington, DC. It’s also the perfect spot for sunset sails and scenic cruises with Sail Selina II.
Once you’re here, you’re steps away from charming pubs, world-class restaurants, shopping, two wineries, the St. Michaels Eastern Shore Brewery, Lyons Distillery, yacht tours, the Chesapeake Bay Maritime Museum, our historic waterfront, and a variety of other activities including kayaking, golfing, biking, and the St. Michaels water taxi.
For the best weekend getaway, book a room at one of St. Michaels’ lovely bed & breakfasts or stay on the water at the St. Michaels Harbour Inn, Marina & Spa. St. Michaels is also home to many exciting events throughout the year, like Chocolate Fest, Wine Fest, Beer Fest, Seaglass Fest, Small Craft Fest, Oyster Fest, and Waterman’s Day, where you can watch the thrilling boat docking contest.
When’s the best time to sail Chesapeake Bay? It’s a tough question since it depends on the experience you’re looking for. Winds are lighter in the morning and evening, with the strongest breezes around midday. If the weather takes a turn, our captains make the call at the time of departure. Should it be unsafe or unpleasant, you have the choice of rescheduling, receiving a gift card for a future cruise, or getting a full refund.
Sail Selina II is conveniently located at the Harbour Inn’s dock at 101 N Harbor Road in St. Michaels, MD. We hope to be the first name that comes up when you search for “sailing near me” or “sailboat sunset cruise.”
And yes, we are pet-friendly! Bring your furry friend along for the adventure.
After your excursion, we’ll ask for your feedback—your input helps us continue to provide the best boat ride in St. Michaels, MD.
Don’t miss out on this incredible opportunity! For more details about our cruises, give us a call at 410-726-9400. Ready to set sail? Purchase your cruise tickets right here and embark on an unforgettable journey!
Book your sail today!
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!
Seating
Selina II has a dry, uncovered, open, comfortable, and roomy cockpit seating with four captain’s chairs and two cushioned settees.
Refreshments
Soda, Cold Craft Beer, Wine, and Champagne are available for sale during all trips. BYOB fee of $25. Bottled water is complimentary.
Toilet
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.