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About Us

Seas the Bay Sailing grew out of the owner’s love of sailing and the Chesapeake Bay. We are a small family-owned business that is dedicated to ensuring that you and your guests delight in the joys of sailing.  The Seas the Bay sailing family is committed to sharing this passion and experience with anyone who dreams of a day on the Bay!  Sailing with Seas the Bay Charters, you won’t just see Annapolis, you will feel Annapolis like a local, and have an authentic, non-tourist experience!

Captain Chris has been sailing for over 40 years, and has sailed offshore for over 25 years. His sailing adventures have taken him from Maine to Key West, Bermuda, Guadalupe, Puerto Rico, and Cuba to name a few. Safety at sea is his number one priority and you will be in excellent hands.

Susan is co-owner and operator of Rosapepe Retreats, a boutique Italian tour company that accompanies visitors to her family hotel in Italy, and provides a unique and authentic experience in southern Italy.

Susan and Chris will make your sailing experience a day to remember, with comfortable accommodations, wonderful food and breathtaking sights.

Meet the Crew

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Captain Chris

Capt. Chris Bell brings an exceptional background and experience to his leadership at Seas the Bay Sailing Charters. Captain Chris has been sailing for over 40 years, and has sailed offshore for over 25 years. His sailing adventures have taken him from Maine to Key West,  Bermuda, Guadalupe, Puerto Rico, and Cuba to name a few.  In addition to being an avid cruiser, Capt Chris spent more than 30 years as crew or skipper on a multitude of racing sailboats from 12 to 55 feet.  On top of spending many seasons racing “around the buoys” in and around Annapolis and the Chesapeake Bay, he has participated in the famed Newport to Bermuda race, the Annapolis to Newport Race and the Miami to Havana Race.  Chris has sailed through every imaginable weather condition. He holds an OUPV / 6-Pack Captains License from the U.S.C.G.

Capt. Chris is known for his good humor, easy manner, and exceptional seamanship.  He maintains his beloved “Southerly” with the same meticulous care and love that a true sailor would lavish on the vessel that carries him safely from adventure to adventure.


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First Mate Susan

Susan’s love of sailing began in 2014 when she met Captain Chris.  Her first experience was, unbeknownst to her, a once-in-a lifetime adventure on a sailor’s bucket list – an offshore sailing race from Miami to Havana.  There is no better way to understand what sailing is all about than experiencing three days and nights of offshore racing.  Susan and Chris married soon after, and have continued their sailing adventures.

Susan lived as an expat in Rome, Italy and Mexico City, Mexico.  She has traveled Europe, Scandinavia, Latin America, Africa, the Middle East, Australia, Cambodia and Thailand and understands intimately the experience of the tourist, and non-tourist alike.

When not running sailing charters on the Chesapeake Bay, Susan operates a tour company specializing in trips to her family hotel in Southern Italy.   She has spent years accompanying friends and arranging travel for acquaintances to Italy. (www.rosapeperetreats.com)

Susan has a passion for sharing her love of adventure and unique experiences with visitors whether in Annapolis or Italy.  Her flair for making sure everyone is happy and well-fed serves to make the adventure that much more special.

Susan feels that everyone needs a day to be a VIP and promises an unforgettable experience when you sail with Seas the Bay.

About the Boat

Our Irwin 54 was designed and personalized for maximum comfort and safety. 

Southerly is engineered to sail with effortless grace and speed. The spacious deck boasts an easy to board walk-in cockpit for entertaining and sail handling.

Some of the features that make our boat so special are the electrically operated sails, and “elevator” like folding swim/dive platform in the transom, as well as comfortable and well-placed stern rail seats for enjoying cocktails and views.

Below deck, the feeling of warmth and generous lay-out makes this vessel welcoming to all who board.  The richly varnished teak, along with color-coordinated décor make this a home away from home.  The salon is elegantly appointed with two handsome L-shaped settees, an elaborate and sophisticated navigation station, liquor lockers, and a serving bar with a swiveling captain's chair. The galley is a gourmet's dream with a generous amount of space for food preparation and storage. The dining salon comfortably accommodates six to eight guests.

Southerly is a sailing vessel like no other and we can’t wait to share it with you!

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Our Location

Annapolis is a walking town rich with history and culture. From quaint restaurants to cute boutiques it has so much to offer to the visitor and local alike.

But nothing compares to experiencing the Sailing Capital of the U.S. from a Sunset Sail on the Bay. When you sail with Seas the Bay you will be awed by the expanse and sheer magnitude of the Bay Bridge from the boat. Above all, taking in the sweeping vistas of the Annapolis skyline from the water with the sun setting behind the historic buildings is truly an experience you will treasure forever.

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