Annapolis Sailing Charters
Sail the Chesapeake Bay on your own private yacht. Select a trip from our popular itineraries below, see more sailing trips in the Chesapeake Bay or contact us to customize an itinerary just for you.
Catch the gorgeous Chesapeake Bay sunset aboard a luxury catamaran. Perfect for a romantic evening, cocktails with friends or a way to end a day exploring Annapolis.
“Just sit right back and…” feel the wind in your hair, go for a swim or just enjoy the views. Great for office outings and happy hour hangs.
Birthdays, anniversaries, bachelorette parties and other occasions are more fun on your own private yacht! We’ll tailor a cruise for your special day.
Annapolis Sailing Lessons
ASA certified instructor, Captain Shawn Owen helps students of all skill levels become confident and safe sailors. With decades of experience teaching snowboarding and music, Shawn has a laid back, positive attitude and a passion for sailing and seamanship that will be contagious when you sail with us.
Learn To Sail
Browse Our charter fleet
This catamaran features expansive deck spaces and an innovative open-concept design, creating a seamless flow between the interior and exterior.
Experience the ultimate luxury sailing adventure on the stunning Chesapeake Bay aboard the exquisite 2017 Beneteau Oceanis 45, a true gem in the world of yacht chartering.
Let us plan your customized “escape” on this well appointed catamaran sailing the Chesapeake Bay out of Annapolis, MD
- Janece K
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Life is Just Better on a Boat
sail with us!
Sailing changed my life for the better in nearly every way. It makes me more present, more thoughtful, more focused, healthier, happier, just better as a person in most every way. I would be honored to help share it with you and then watch it become a part of your life.
Keep it chronic.
- Captain Shawn