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Chesapeake Bay    &  Bahamas

Premium sailing instruction and experiences

Beginner to expert, the only place on the Chesapeake Bay for positive instruction and hands-on skill-building aboard premium yachts

30,000+

Students Trained

125+

Years sailing experience

65+

Years of Liveaboard
Cruising

Sail with the experts

Unplug from your high-pressure lifestyle and find freedom, mastery and escape

Our students typically struggle with:

01

High-pressure careers

03

Inability to relax

02

Work-life balance

04

Too many screens

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Your Adventure Starts Here

Welcome to the  closest sailing school  on the Chesapeake Bay to the  Washington DC Beltway. 

We do things a little differently.
Here's how:

Premium Yachts

We don’t do cheap

We are the only sailing school on the Chesapeake Bay to offer students of all levels hands-on experience aboard our fleet of premium VIKO yachts. 

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Hands-on Learning

We don’t do boring

Our goal is to equip you with the skills and confidence to sail any vessel anywhere in the world. We provide the most personalized, hands-on learning of any school on the Bay.

Patient Instructors

We don’t yell

We only hire patient, seasoned, lifetime mariners who create a positive learning environment that maximizes your skill acquisition and enjoyment.

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We swapped our house for a sailboat and lived aboard for four years with our five children.

This is a family business

Answering the call to adventure, our time on the water gave us the experience, skills and passion to help you take the helm of your life and your sailing dreams.

Become a sailor

Our Courses

01

Sailing
Basics

In just 2 days, those who have minimal experience get to take the helm right away, learn to drive a boat under sail, and trim sails to catch the most wind.

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See all 20+
Courses

Go from beginner to ASA-certified offshore sailor with our full range of courses.

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"We had so much fun! It was so informative and we feel like we have been caught by the sailing bug. The boats we sailed on were gorgeous, and Phineas gave us confidence when we were learning. He was a great teacher!"

 Taylor Hendri

My wife and I have been sailing for 40 years (i.e. before there *were* certifications) and needed the ASA 104 rating to continue chartering. I learned a *lot* throughout this week."

Clint Goss

Simply the best! Drove over 3 hours from home to take the ASA101 and 103 courses based on the reputation The Sailing Academy has built. Both Captain Angie and Captain Phin are such good coaches and teachers. So patient and made it so enjoyable to learn. I will be back!

Surinder Singh

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FAQs

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"I wanted freedom, open air and adventure. I found it on the sea."

- Alain Gerbault

Are we the right fit for you?

At the Sailing Academy, we know you are the kind of person who is all-in with your career but you also need an outlet from it all. You wonder, “where can I learn to sail near the DC area?” or “where can I join a sailing club near me?” because you want to live out your sailing dreams. In order to do that, you need the best sailing school and instructors in the area - that means ASA-certified instructors who treat you with respect and give you a chance to learn through hands-on experience and will not nit-pick or criticize you but actually instill the confidence and skills you need. 

 

The problem is that you don’t have a lot of time and you’re not sure which sailing school to choose. You know the learning process needs to be just as much a part of the adventure and escape for you as the outcome. Wasting time in the classroom or learning things you won’t use would make you feel stuck and stressed. 

We believe that you deserve freedom in how you learn and that your free time needs to be respected. We understand how precious it is to you.

That’s why we get you aboard our premium yachts immediately for learning so that the jump to larger vessels is minimal and all your skills transfer seamlessly. That’s also why we have highly experienced, expert instructors who equip you with the necessary skills using a positive coaching style, letting you try things for yourself and are patient and even-keeled no matter the situation. 


Here’s how it works: you sign up for a course to try sailing or get your basics down. You give it a try and find out that sailing really does make you come alive. Then, you book the next level course to work on your skill mastery. We journey with you from beginner to seasoned mariner. 


So, book your course today, so you can stop being so tightly wound and start taking hold of your freedom, peace and adventure.  

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Ready for your unplugged adventure?

Book a course today!

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