sailing courses with focused on-the-water instruction

Sailing School

ASA Sailing Courses in Chesapeake Bay, MD

We offer a full range of ASA sailing courses with focused on-the-water instruction. Whether you’re a novice learning the basics and pursuing ASA certification or an experienced sailor hoping to fine-tune your skills with a private sailing lesson, we have a course for you. Sail with us on the Chesapeake and Caribbean, and take your sailing to the next level!

Sail Solomons has been recognized by the American Sailing Association as an “ASA Outstanding School” each year from 2008 through 2012. Our instructors have been awarded “ASA Outstanding Instructor” from 2007 through 2012, making us the most-awarded sailing school on the Chesapeake Bay!

Sailing since 1988

ASA Courses

Our scheduled sailing courses range from novice to advanced, beginning with basic introductory courses and extending through the ASA continuum to advanced cruising. Our small class size (2-4 students) allows a hands-on focus with maximum on-the-water training. Most courses are conducted on weekends, to accommodate your busy lifestyle.

Cruising courses are taught in a live-aboard environment to fully immerse you in the cruising experience. Mid-week combination courses are also available to get you on the fast track to cruising!

ASA is the leading authority on sailing instruction in the USA. As an ASA school, Sail Solomons offers a full range of ASA certification courses that are recognized internationally, so you can begin to charter the globe!  ASA course prices include instruction, ASA texts, and certification materials. All Sail Solomons instructors are ASA-certified and licensed by the US Coast Guard.

Specialized Courses

Whether you are a novice looking for private sailing instruction or an experienced sailor hoping to fine-tune your skills, we have a course for you. Our full complement of tailored and private instruction includes “On Your Own Boat”, electronic navigation, marine systems and a program for “Couples cruising in harmony”. Let us tailor a course for you!

Caribbean Courses

Experience the learning vacation of a lifetime – Sail Solomons in the Caribbean! Join one of our fabulous monohull or catamaran flotillas for a full week of glorious tradewind sailing. Immerse yourself in island life – warm, crystal-clear waters, sunshine, swimming and snorkeling on tropical reefs, and basking in island hospitality. Pursue ASA certification in our intermediate and advanced courses, or simply hone your sailing skills without certification. Our Caribbean courses are conducted onboard luxury yachts from select charter companies. Courses include ASA 104 Bareboat Charter and ASA 114 Cruising Catamaran.

Instructor Training

A very special group of sailors feel the need to share their knowledge and passion for sailing with others by becoming sailing instructors. If you are in that select group, Sail Solomons’ resident ASA Instructor Evaluator can help you achieve your goal with instructor training and ASA Instructor Qualification Clinics. These demanding clinics test your sailing skills, professional knowledge and presentation techniques to the national standard set forth by the American Sailing Association. Once qualified, you will have a ticket to teach for ASA schools, and get paid to do what you love best!

Course Schedule

2024 On Water CoursesMayJuneJulyAug
Introduction to SailingOn RequestOn RequestOn RequestOn Request
ASA 101 Keelboat 1 (Part A) (2 day course)
A&B required for certification
4-5, 18-191-2,15-16, 29-3013-14, 27-2810-11, 24-25
ASA 101 Keelboat 1, (Part B) (2 day course)
A&B required for certification
11-12,25-268-9, 22-236-7, 20-213-4, 17-18
ASA 101 Keelboat 1 
3 day private for two students
25-27, On RequestOn RequestOn RequestOn Request
ASA 102 Basic Keelboat 2
ASA 103 (Basic Coastal Cruising)17-1914-1626-289-11
ASA 104 (Bareboat Cruising)21 May – June 214-1612-1423-25
ASA 104/114 Combo
(4 day live aboard)
ASA 106 (Advanced Coastal Cruising)April 3-10
Key West to Solomons
ASA 114 (Catamaran)29-3013-143-4
ASA 116 Dinghy Endorsement
New for 2024!
One Day class
8th & 9th
One day course, offered each date
6th & 7th
One day course, offered each date
ASA 118 (Docking Endorsement)7th, 8th, 9th, 10th
One day course, offered each date
5th, 6th, 7th
One day course, offered each date
16, 17, 18 (3 One day classes)
Instructor Qual Clinics
IQC 202 – Keelboat 2
202: 18th
Classroom Courses 2023DatesLength
ASA 119 (Marine Weather)February 10-11 & 17-184 day WEBINAR, two consecutive weekends 
ASA 105 (Coastal Navigation)March 2-3 & 16-174 day course, two weekends, in person
Caribbean Courses- Tentative Marinique/St. LuciaJanuary 2025
ASA 104 (Bareboat) / ASA 114 (Catamaran)Jan 18-25 (Tentative
ASA 104 (Bareboat) / ASA 114 (Catamaran)Jan 25- Feb 1 (Tentative)
Sailing Club

Our ever-popular Sailing Club gives members access to the daysailer or cruising fleet for low cost and stress-free sailing. Members enjoy social events, crew networking, discounts on courses, Caribbean flotillas and much more!

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