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.
Annapolis Sunset Cruise
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.
Celebrate Your Special Event
Birthdays, anniversaries, bachelorette parties and other occasions are more fun on your own private yacht! We’ll tailor a cruise for your special day.
Chesapeake Overnight Sail
Get away for a night or two (or 5) and enjoy adventures on the water, excursions into nearby towns, sunset cocktails and sleeping under the stars.
Annapolis Dinner Cruise
A romantic getaway or a casual evening with friends and family. We’ll serve dinner from a downtown restaurant or have your meal catered on-board.
A floating concert series on back creek in Annapolis
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.
If you’ve never sailed before and are interested in trying it out to see what all the fuss is about, this class may be the perfect way to give it a shot.
Interested in one on one training? Or maybe you want to get you and your crew up to speed before an upcoming charter? We can customize private instruction for up to 4 people for an extremely competitive rate.
New boat owner needing insurance checkout or just looking to brush up skills on your own boat? We offer instruction and certifications aboard your boat to maximize benefit and personal knowledge of your vessel.
The American Sailing Association is a national and global leader in sailing education and bareboat chartering certifications. We offer ASA Courses 101-106, as well as the 114 catamaran certification. If bareboat chartering is something you see in your future, then this could be your best avenue to achieve the necessary skills and qualifications required to handle your own charter vessel.
Learn To Sail
Browse Our charter fleet
Sea Dancer
With sleek lines and a stable, confident ride, Sea Dancer’s an ideal platform for everything from a relaxed day on the Bay to a celebratory cruise with your favorite people.
Sea to Sky
Offering exceptional comfort, space, and performance with a luxurious private owner’s suite, generous guest cabins, and signature Lagoon stability. This catamaran delivers a smooth, stylish sailing experience for couples, families, or small groups.
SIA
Bright, open, and inviting – the perfect size for small groups who want plenty of space to relax, laugh, and celebrate out on the Chesapeake.
Slowdown
This modern marvel stands out with sleek lines and a spacious deck layout, ideal for leisurely cruises or adventurous voyages.
- 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
