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Waypoints Annapolis

Annapolis, Maryland, United States

About

Waypoints Annapolis is located at 222 Severn Avenue, in Building 15 Suite 36. Nestled in the charming city of Annapolis, Maryland, the school offers a relaxed and welcoming environment for sailors of all levels. Whether you're just starting out or looking to hone your skills, the friendly atmosphere makes learning to sail an enjoyable experience.

Courses (3)

ASA Certified

Bareboat Cruising

104All Levels
3 days1-2 per berth

Contact for pricing

Coastal Cruising

103All Levels
3 days1-2 per berth

Contact for pricing

Basic Keelboat Sailing

101All Levels
3 days1-2 per berth

Contact for pricing

The Area

Waypoints Annapolis is conveniently located in the heart of Maryland’s sailing community, offering easy access to the Chesapeake Bay and its surrounding waters. Our facility provides a comfortable and professional environment for sailors of all levels, from beginners to experienced mariners. Whether you're looking to learn the basics or refine your skills, our location allows for hands-on instruction in a variety of sailing conditions, ensuring a comprehensive learning experience.

Getting There

From Baltimore/Washington International Thurgood Marshall Airport (BWI), you can easily reach Annapolis by rental car, ride-hailing service, or shuttle. The drive takes approximately 30-40 minutes via I-97 North. If you prefer public transportation, you can take a MARC train from BWI Rail Station directly to the Annapolis station; from there, a short taxi or ride-hailing ride will bring you to 222 Severn Avenue. For travelers arriving at Washington Dulles International Airport or Ronald Reagan Washington National Airport, rental cars or ride-hailing services are the most convenient options, with Dulles about an hour’s drive and Reagan about 45 minutes. Once in Annapolis, head to Severn Avenue, where our school is located at Building 15 Suite 36; parking is available nearby.

Best Time to Go

The best time to sail in Annapolis is during late spring through early fall, when the weather is warm and the winds are generally steady. Summer months, especially July and August, offer the most consistent sailing conditions, making it ideal for both beginners and experienced sailors to enjoy the Chesapeake Bay.

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Frequently Asked Questions

Waypoints Annapolis offers the following courses: Bareboat Cruising, Coastal Cruising, Basic Keelboat Sailing. Please review the listings above for details and pricing.

The primary training location is in Annapolis, Maryland, United States. You can view the exact meeting point and map in the location section on this page.

Yes, Waypoints Annapolis is an internationally recognized ASA school offering official certifications.

You can contact Waypoints Annapolis directly using the contact buttons (email, phone, or WhatsApp) provided on this page to check availability and book your spot.

See something wrong or have a question? Message us at hello@sailingtree.com

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