The Sailing Academy

Your adventure starts here! The Sailing Academy is the closest sailing school on the Chesapeake Bay to the Washington, D.C., Beltway, blending prime conditions with easy access. Family owned and operated; our teaching method is closer to on-the-water coaching rather than simply taking a class. Our goal is to equip learners with both proficiency and confidence so they can achieve their own sailing dreams—whether that is to cruise the Chesapeake Bay or to eventually cross oceans.

Premium Yachts
We are the only school on the Bay training on premium VIKO yachts- our keelboats are sized 26–35 ft, equipped with wheel steering, inboard engines and more that translate up and bridge classroom skills to real-world cruising.

Full-Time, Patient Instructors
Our instructors are not casual weekend sailors—they’re lifetime mariners with 125+ years of combined experience, many having lived aboard for extended periods. They coach with patience (no yelling!), expert-level calm, and constructive guidance.

Support After Certification
Once certified, you’ll have access to our charter fleet or membership in our Sailboat Club—an affordable way to keep sailing all season long. Returning students have the opportunity for discounted “Skill Builder” sessions in-between certifications.

Accessible Sailing Content
Follow along on our social media for free instructional videos, sailing tips, cruiser hacks and more from our team! @thesailingacademy on Instagram, and TikTok.

Certifications

101

Keelboat Sailing 1

Welcome aboard to ASA 101, the gateway to your sailing adventure! This foundational course sets the stage for mastering the art of sailing

103 Coastal Cruising

Welcome to ASA 103 Coastal Cruising, where you take your sailing skills to the next level!

104 Bareboat Cruising

ASA 104 Bareboat Cruising, where your sailing journey reaches a new level of independence and adventure

105 Coastal Navigation

ASA 105 Coastal Navigation is essential for anyone ready to move beyond day sailing and take command of extended trips along the coast.

106 Advanced Coastal Cruising

Advanced Coastal Cruising is the ultimate course for sailors looking to sharpen their skills and expand their cruising horizons

114 Cruising Catamaran

ASA 114 Cruising Catamaran is the key to unlocking the unique pleasures and challenges of multihull sailing

118 Docking Endorsement

ASA 118 Docking Endorsement is the perfect course for sailors who want to master the art of docking with confidence and precision.

Amenities

ASA 'Challenges'Couples CoursesDay Sail Charters (member-only)Day Sail Charters (public)Private CoursesRacing CoursesSail Trim CoursesSailboat CruisesSpinnaker CoursesSummer Camps for KidsSunset CruisesTeam Building CoursesVacation ChartersWeekday CoursesWeekend CoursesWomen Only CoursesYouth Courses

INITIATIVES

10% Discount

Veterans Program

At American Sailing we recognize the sacrifices made by the brave men and women who have served or are serving in our country’s armed forces. As a token of our appreciation, and our way of saying thank you, we invite veterans and active military personnel to share our passion for sailing by offering a discount on our ASA 101 Keelboat 1 sailing course.

Learn More

Gallery

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David Clark

I just wanted to write and say how wonderful my ASA 103/104 sailing experience in the Bahamas was for me. Captain Phin provided excellent training, and allowed me to have lots of hands on training! The Hudson Force 50 was a great yacht to live aboard too! I would absolutely recommend the sailing academy for training if you wish to obtain ASA certification.

Clint Goss

A *fantastic* week taking ASA 103/104 with Phinehas on a Viko 30 and a Sabre 38 (photo of the Sabre 38 is in the Pirate’s Cove marina that we sailed to). The setting is a country club-style marina with pool, BBQ, showers (clean!). They allowed me to bunk on the air-conditioned Sabre 38 for the week, which was a *big* plus. Phin is a born teacher – relaxed, knowledgeable, experienced, detailed, and fun. The program used all the material provided in the ASA texts, plus The Sailing Academy’s own material. Rather than simply “teaching to the test”, they covered a broad range of topics, issues, and techniques…

JF M

I took the Sailing Basics and ASA101 course at The Sailing Academy and the experience was great in every way. The team is extremely professional, extremely knowledgeable and very welcoming. The quality of the training went far beyond my expectations. I learned a lot in 4 days and feel capable of sailing independently and safely thanks to it. What’s more, the instructors are patient, caring, know how to instill confidence and pay particular attention to safety. The equipment and boats are new and top quality. I’ll be continuing my training with The Sailing Academy and…

Hakan L.

I can highly recommend ASA 106 with The Sailing Academy. Capt Jeff is a superb instructor. I left with a whole new understanding of sail trim, heavy weather sailing, safety at sea and many other topics. Although it is a challenging course, the overall experience was pleasant, fun and very memorable!