Sailing Charters, Lessons & Captain Services in Annapolis, MD & Abroad

We Have a Chronic Sailing Condition

sail with us and you will too!

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

3 hours // 2 - 13 people

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

3 - 8 hours // 2 - 13 people

Birthdays, anniversaries, bachelorette parties and other occasions are more fun on your own private yacht! We’ll tailor a cruise for your special day.

Mid-Week “3 Hour Tour”

3 hours // 2 - 13 people

“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.

Chesapeake Overnight Sail

1 - 7 days // 2 - 8 people

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.

Plan Your Charter

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.

Introduction to Sailng

Private Sailing Instruction

Learn On Your Boat

ASA Certification Courses

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.

ASA Courses

Learn To Sail

Browse Our charter fleet

Sweet & Salty

4 Cabins // 4 Heads

This sleek and spacious vessel features an open-plan living area including a fully equipped galley, a spacious saloon, and a large dining area.

American Honey

3 Cabins // 3 Heads

This state-of-the-art catamaran seamlessly combines performance, comfort, and elegance to provide an unforgettable chartering adventure.

Starz

3 Cabins // 3 Heads

This sleek and modern vessel feature 3 cabins, each equipped with its own private en-suite bathroom. Expansive deck with plenty of seating and lounging areas.

Lani

4 Cabins // 3 Heads

A magnificent vessel that seamlessly blends luxury, performance, and comfort on the open seas.

Dos Milagros

3 Cabins // 3 Heads

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.

Slowdown

4 Cabins // 2 Heads

This modern marvel stands out with sleek lines and a spacious deck layout, ideal for leisurely cruises or adventurous voyages.

JEHM of the Sea

3 Cabins // 2 Heads

A versatile and comfortable sailboat designed for cruising, well-suited for exploring the waters of the Chesapeake Bay.

Browse Our fleet

"Captain Shawn is patient and brilliant. He helped us become confident and responsible sailors while having a great time! I highly recommend him!"

- Janece K

Stay in the Loop

I want to know about new classes, specials, events and offers from Chronic Sailing.

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