About our St Michaels Maryland charter boat | Sail Selina II (original) (raw)

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!