Annapolis Naval Sailing Association upcoming events

Skipper Intro / Check Out (Sunday, August 30, 2026)

Sun, 30 Aug 2026 17:00:00 GMT

Become a skipper for ANSA!

As ANSA continues to grow, we are looking to expand our pool of skippers to support member sails, training, and to fully utilize our growing fleet.

We know there are capable sailors within our membership who may be interested in stepping into a skipper role — and we’d like to gauge that interest.

If you’ve ever thought about skippering an ANSA boat, this is a great opportunity to raise your hand and start the conversation.

What We’re Looking For
At a minimum, prospective skippers should:

Hold ASA 103 (Basic Coastal Cruising) or higher
Be comfortable taking responsibility for a vessel and crew
Have solid boat handling skills, including docking and close-quarters maneuvering
Demonstrate sound judgment and a safety-first mindset

What to Expect
Becoming an ANSA skipper is a structured process designed to set you up for success. This includes:

On-the-water assessments
Mentorship with current ANSA skippers
Demonstration of boat handling, safety procedures, and leadership

This is not a pass/fail test; it’s a development path to ensure consistency, safety, and confidence across our skipper ranks.

Skippers may also use ANSA vessels for personal sails!

Interested?
If you’d like to be considered, please join us for this intro and meetup to get familiar with our fleet, meet current skippers, and discuss path forward.

ASA 101 Basic Keelboat (Saturday, September 05, 2026)

Sat, 05 Sep 2026 13:00:00 GMT

Keelboat 1 - Basic Keelboat Sailing

ASA 101 is an introductory sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

Class Fee: $495

Veteran/Active Duty: $445

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 101 Basic Keelboat (Sunday, September 06, 2026)

Sun, 06 Sep 2026 13:00:00 GMT

Keelboat 1 - Basic Keelboat Sailing

ASA 101 is an introductory sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

Class Fee: $495

Veteran/Active Duty: $445

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 101 Basic Keelboat (Monday, September 07, 2026)

Mon, 07 Sep 2026 13:00:00 GMT

Keelboat 1 - Basic Keelboat Sailing

ASA 101 is an introductory sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

Class Fee: $495

Veteran/Active Duty: $445

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 103 Coastal Cruising (Friday, September 11, 2026)

Fri, 11 Sep 2026 14:00:00 GMT

Basic Coastal Cruising

ASA 103 is an intermediate sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

ASA 101 is a prerequisite as well as at least 24 hours additional sailing time.

Class Fee: $475

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 104 Bareboat Coastal Cruising (Friday, September 11, 2026)

Fri, 11 Sep 2026 14:00:00 GMT

Bareboat Coastal Cruising

This course helps prepare you with first-hand, on board experiences useful for chartering a large, 30-45’, monohull sailing vessel. The schedule will be three consecutive days with 2 nights, one at anchor and one at a destination port, weather and circumstances permitting.

The goal is for you to be able to skipper a sloop-rigged, auxiliary powered keelboat of approximately 30 to 45 feet in length during a multi-day cruise upon inland or coastal waters in moderate to heavy winds (up to 30 knots) and sea conditions. The course discusses knowledge of provisioning, galley operations, boat systems, auxiliary engine operation, routine maintenance procedures, advanced sail trim, coastal navigation including basic chart plotting and GPS operation, multiple-anchor mooring, docking, health & safety, emergency operations, and weather interpretation. The course is taught on board and you will rotate between the duties and responsibilities of skipper, lookout, navigator, and crew.

Students will coordinate to provision for the sail.

We will sail on a Dufour 430 with 3 private full-size cabins and 1 bunk bed cabin for instructors.

Private full size Cabin, 1 sailor: $1,395

Private full size Cabin, 2 sailors: $1,695

You must be a member of ANSA to sail with us. /ansa.org/join-us/

Please refer to the full class description here to view prerequisites and requirements.

ASA 103 Coastal Cruising (Saturday, September 12, 2026)

Sat, 12 Sep 2026 13:00:00 GMT

Basic Coastal Cruising

ASA 103 is an intermediate sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

ASA 101 is a prerequisite as well as at least 24 hours additional sailing time.

Class Fee: $475

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 103 Coastal Cruising (Sunday, September 13, 2026)

Sun, 13 Sep 2026 13:00:00 GMT

Basic Coastal Cruising

ASA 103 is an intermediate sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

ASA 101 is a prerequisite as well as at least 24 hours additional sailing time.

Class Fee: $475

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 104 Bareboat Coastal Cruising (Monday, September 14, 2026)

Mon, 14 Sep 2026 14:00:00 GMT

Bareboat Coastal Cruising

Students will coordinate to provision for the sail.

We will sail on a Dufour 430 with 3 private full-size cabins and 1 bunk bed cabin for instructors.

Private full size Cabin, 1 sailor: $1,395

Private full size Cabin, 2 sailors: $1,695

You must be a member of ANSA to sail with us. /ansa.org/join-us/

Please refer to the full class description here to view prerequisites and requirements.

ASA 101 Basic Keelboat (Friday, September 18, 2026)

Fri, 18 Sep 2026 14:00:00 GMT

Keelboat 1 - Basic Keelboat Sailing

ASA 101 is an introductory sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

Class Fee: $495

Veteran/Active Duty: $445

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 106 Advanced Coastal Cruising (Friday, September 18, 2026)

Fri, 18 Sep 2026 14:00:00 GMT

Advanced Coastal Cruising

Sail with ANSA for 4 days, 3 nights, including 2 overnights down and up the Chesapeake Bay. We will go where the wind takes us but include sailing through the night at least one night or more depending on conditions. Sailors will provision, plan, navigate, stand watches and focus on safety and advanced sailing techniques. We will sail on a Dufour 430 sloop with 4 cabins.

The goal of ASA 106 is to enable sailors to safely act as skipper and crew of a sailing vessel from 30 to 50 feet in length in inland and near coastal waters (within 200 miles of shore) in any weather conditions on a liveaboard coastal passage of at least 48 hours underway, including a continuous underway period of at least 24 hours. We will remain within the Chesapeake Bay and tributaries for this class.

Class fee: $1,595

Prerequisites for this class include ASA 101, 103, 104 and 105, Coastal Navigation.

Purchase your text book in advance, view prerequisites and class knowledge and skills outline here:

https://americansailing.com/learn-to-sail/certifications/asa-106-advanced-coastal-cruising/

There will be an advance Zoom session to meet up and do some planning and prep.

ASA 101 Basic Keelboat (Saturday, September 19, 2026)

Sat, 19 Sep 2026 13:00:00 GMT

Keelboat 1 - Basic Keelboat Sailing

ASA 101 is an introductory sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

Class Fee: $495

Veteran/Active Duty: $445

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 101 Basic Keelboat (Sunday, September 20, 2026)

Sun, 20 Sep 2026 13:00:00 GMT

Keelboat 1 - Basic Keelboat Sailing

ASA 101 is an introductory sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

Class Fee: $495

Veteran/Active Duty: $445

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 118 Docking (Saturday, September 26, 2026)

Sat, 26 Sep 2026 13:00:00 GMT

Close Quarters Maneuvering (Docking)

Learn to dock a wheel helm 30' vessel with prop wash and prop walk (no bowthruster) in a variety of conditions and locations.

This is a two day class. Class fee is $315.

You should have the equivalent training and experience of ASA 103, Basic Coastal Cruising, as a prerequisite. Additional class details and requirements HERE.

Please purchase the textbook for this class in advance and read the book to get the most out of the class time.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 118 Docking (Sunday, September 27, 2026)

Sun, 27 Sep 2026 13:00:00 GMT

Close Quarters Maneuvering (Docking)

Learn to dock a wheel helm 30' vessel with prop wash and prop walk (no bowthruster) in a variety of conditions and locations.

This is a two day class. Class fee is $315.

You should have the equivalent training and experience of ASA 103, Basic Coastal Cruising, as a prerequisite. Additional class details and requirements HERE.

Please purchase the textbook for this class in advance and read the book to get the most out of the class time.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 101 Basic Keelboat (Friday, October 16, 2026)

Fri, 16 Oct 2026 14:00:00 GMT

Keelboat 1 - Basic Keelboat Sailing

ASA 101 is an introductory sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

Class Fee: $495

Veteran/Active Duty: $445

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 101 Basic Keelboat (Saturday, October 17, 2026)

Sat, 17 Oct 2026 13:00:00 GMT

Keelboat 1 - Basic Keelboat Sailing

ASA 101 is an introductory sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

Class Fee: $495

Veteran/Active Duty: $445

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.

ASA 101 Basic Keelboat (Sunday, October 18, 2026)

Sun, 18 Oct 2026 13:00:00 GMT

Keelboat 1 - Basic Keelboat Sailing

ASA 101 is an introductory sailing course provided over 3 days on a 30' keelboat with a wheel helm. We sail in the West River and Chesapeake Bay.

Class Fee: $495

Veteran/Active Duty: $445

Please purchase the textbook in advance of the class so that you can begin studying and doing the exercises.

Refer to the full class description here and policies and procedures to view prerequisites and requirements.

You must be a member of ANSA to take a class. Membership fees range from $55 to $75 depending on selected level. Please join ANSA after your successful registration for this class.