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    • 23 Apr 2026
    • 6:00 PM
    • 03 May 2026
    • 4:30 PM
    • Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
    • 0


    ASA 101/103 Combined Beginner Sailing Course #1 [April]

    Never sailed before, or has it been a while? This is the course that will get you started!

    Upon completing this combined course, you can skipper a sloop-rigged keelboat of approximately 20 to 30 feet in length by day in light to moderate winds (up to 20 knots) and sea conditions.   Full details at https://pentagonsailing.org/Beginner-Sailing-Course.

    Classroom: Phillips School - Contemporary Education, Activity Room, 7010 Braddock Rd., Annandale, VA  22003

    • 101 Classroom Apr. 23 (6:00 PM to 8:30 PM)
    • 103 Classroom Apr. 30 (6:00 PM to 8:30 PM)

    On-the-Water Location: Capital Cove Marina @ Joint Base Anacostia-Bolling (JBAB)

    • 101 OTW - Apr. 25 & 26 (8:30 AM to 4:30 PM)
    • 103 OTW - May 2 & 3 (8:30 AM to 4:30 PM)

    If you have questions - please get in touch with the Training Commodore at trainingcommodore@pentagonsailing.org.

    P.S. You must be a Pentagon Sailing Member to register for this course. If you are not a member, please head over to https://www.pentagonsailing.org/newmember to start your membership.  Additionally, students must obtain an American Sailing ID (ASID), ASA textbooks, and ASA International Log Book prior to earning ASA certifications.   Please see https://americansailing.com/learn-to-sail/certifications/ for details.

    • 03 May 2026
    • 12:00 PM - 4:00 PM
    • JBAB - Capitol Cove Marina
    • 2
    Register

    ASA 101/103 Challenge (By Invitation Only)

    Invitation-only event for ASA 101/103 OTW and Exam Challenges.


    • 05 May 2026
    • 9:00 AM - 5:00 PM
    • Sail Solomon Sail Solomon, Spring Cove Marina, 455 Lore Road, Solomons MD 20688
    • 0

    Bay Training Sail

    Boat Name: SV Second Site2023 Seawind 1260 Catamaran.

    Skipper: Duncan Hood

    Training/Purpose: The ASA 214 IQC certifies a candidate for teaching ASA 114, Cruising Catamaran course. Certification requires the Instructor Candidate to pass written examinations and on-the-water skill evaluation. 

    Prerequisites ASA 204

    Certifications:
    ASA - ASA 214 certification awarded upon successful completion of this sail and a written test.

    POC: Bay Commodore

    • 16 May 2026
    • 9:00 AM - 5:00 PM
    • Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
    • 0
    Join waitlist

    BAY TRAINING DAY SAIL - CLOSE QUARTER MANEUVERING (CQM)

    Boat Name: Beneteau 323 Allora

    Skipper: Jonah Brewer

    Purpose/Training: This class focuses on teaching students how to safely maneuver a sailboat under power in close quarters in various wind and sea conditions including docking/un-docking, line handling, use of spring lines, backing, turning and holding position in restricted water.  

    You can find the syllabus here.

    Prerequisites: ASA 101/103

    Location:  Sail Solomons

    Certifications:
    ASA - ASA 118 (Docking Endorsement) certification awarded upon successful completion of CQM Session and a written test.

    POC: baycommodore@pentagonsailing.org

    One FVSM may be used for this sail. If you are using an FVSM, select the Bay Training Day Sail with FVSM payment option. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options. 

    Purchase your ASA-118 textbook through the ASA website.

    The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this but will not be responsible for finding a replacement.

    • 17 May 2026
    • 9:00 AM - 5:00 PM
    • Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
    • 0
    Join waitlist

    BAY TRAINING DAY SAIL - CLOSE QUARTER MANEUVERING (CQM)

    Boat Name: Beneteau 323 Allora

    Skipper: Jonah Brewer

    Purpose/Training: This class focuses on instructing students how to safely maneuver a sailboat under power in close quarters in various wind and sea conditions including docking/un-docking, line handling, use of spring lines, backing, turning and holding position in restricted water.  

    You can find the syllabus here.

    Prerequisites: ASA 104

    Certifications:
    ASA - ASA 118 (Docking) certification awarded upon successful completion of CQM Session and a written test.

    Location: Sail Solomons

    POC: baycommodore@pentagonsailing.org

    One FVSM may be used for this sail. If you are using an FVSM, select the Bay Training Day Sail with FVSM payment option. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.

    Purchase your ASA-118 textbook via the ASA website.

    The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this but will not be responsible for finding a replacement.

    • 21 May 2026
    • 6:00 PM
    • 31 May 2026
    • 4:30 PM
    • Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
    • 0
    Join waitlist

    ASA 101/103 Combined Beginner Sailing Course #2 [May]

    Never sailed before, or has it been a while? This is the course that will get you started!

    Upon completing this combined course, you can skipper a sloop-rigged keelboat of approximately 20 to 30 feet in length by day in light to moderate winds (up to 20 knots) and sea conditions.   Full details at https://pentagonsailing.org/Beginner-Sailing-Course.

    Classroom: Phillips School - Contemporary Education, Activity Room, 7010 Braddock Rd., Annandale, VA  22003

    • 101 Classroom May 21 (6:00 PM to 8:30 PM)
    • 103 Classroom May 28 (6:00 PM to 8:30 PM)

    On-the-Water Location: Capital Cove Marina @ Joint Base Anacostia-Bolling (JBAB)

    • 101 OTW - May 23 & 24 (8:30 AM to 4:30 PM)
    • 103 OTW - May 30 & 31 (8:30 AM to 4:30 PM)

    PSC Members may use up to 2 FVSMs for this class. FVSMs are worth $25.00 each for this class. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing either of these pricing options.

    If you have questions - please get in touch with the Training Commodore at trainingcommodore@pentagonsailing.org.

    P.S. You must be a Pentagon Sailing Member to register for this course. If you are not a member, please head over to https://www.pentagonsailing.org/newmember to start your membership. Additionally, students must obtain an American Sailing ID (ASID), ASA textbooks, and ASA International Log Book prior to earning ASA certifications. Please see https://americansailing.com/learn-to-sail/certifications/ for details.

    • 05 Jun 2026
    • 9:00 AM
    • 07 Jun 2026
    • 5:00 PM
    • Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
    • 0
    Join waitlist

    ASA 104 Bareboat Cruising or 204 Instructor Training for Bareboat Cruising

    Boat:48' Schooner Adventurer

    Skipper:
    Duncan Hood

    This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification or ASA 204 Instructor Qualification. Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey. Duncan has offered to host club members on his boat during this sail and provide ASA 104 or 204 training. This two-day, one-night trip will give you more than enough experience to demonstrate confidently all the required skills and knowledge covered by the ASA 104/204 course so that you can charter a boat.

    Your fee covers ASA exam and certification. Food and drinks on board are the crew's responsibility. 

    Additional information on ASA 104:ASA 104, Bareboat Cruising Certification

    Prerequisites:
    For 204 ASA requires 104 certification before taking the course and recommends a minimum of 80 on-the-water sailing hours.

    Locations:
    Start - Dock F, Slip 2 Port Annapolis, MD

    End - Port Annapolis, MD

    Itinerary: 
    Sail from Port Annapolis and return to the same location.

    Notes:
    A maximum of 1 FVSM may be used for this sail. If you use an FVSM, select the applicable ASA 104/204 with the FVSM payment option. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing this pricing option. The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

    Questions:
    Email Bay Commodore

    PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM


    • 13 Jun 2026
    • 9:00 AM
    • 14 Jun 2026
    • 5:00 PM
    • Sail Solomon Sail Solomon, Spring Cove Marina, 455 Lore Road, Solomons MD 20688
    • 5
    Register

    Bay Training Sail

    Boat Name: SV Second Site2023 Seawind 1260 Catamaran.

    Skipper: Joanne and John Spahn

    Training/Purpose: The ASA 114 certifies a candidate for Cruising Catamaran.

    You’ll learn about the distinct components of catamarans, including hull design, rigging, and onboard systems. The course emphasizes safety, from the proper use of jacklines to understanding capsizing risks and recovery. You’ll practice essential sailing maneuvers under both sail and power, including handling twin engines, navigating tight spaces, and performing man-overboard recoveries.

    Learn more about ASA 114 and order your text book through the ASA Website.

    Prerequisites ASA 101, 103, 104.

    POC: Bay Commodore

    • 18 Jun 2026
    • 6:00 PM
    • 28 Jun 2026
    • 4:30 PM
    • Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
    • 3
    Register

    ASA 101/103 Combined Beginner Sailing Course #3 [June]

    Never sailed before, or has it been a while? This is the course that will get you started!

    Upon completing this combined course, you can skipper a sloop-rigged keelboat of approximately 20 to 30 feet in length by day in light to moderate winds (up to 20 knots) and sea conditions.  Full details at https://pentagonsailing.org/Beginner-Sailing-Course.

    Classroom: Phillips School - Contemporary Education, Activity Room, 7010 Braddock Rd., Annandale, VA  22003

    • 101 Classroom June 18 (6:00 PM to 8:30 PM)
    • 103 Classroom June 25 (6:00 PM to 8:30 PM)

    On-the-Water Location: Capital Cove Marina @ Joint Base Anacostia-Bolling (JBAB)

    • 101 OTW - June 20 & 21 (8:30 AM to 4:30 PM)
    • 103 OTW - June 27 & 28 (8:30 AM to 4:30 PM)

    PSC Members may use up to 2 FVSMs for this class. FVSMs are worth $25.00 each for this class. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing either of these pricing options.

    If you have questions - please get in touch with the Training Commodore at trainingcommodore@pentagonsailing.org.

    P.S. You must be a Pentagon Sailing Member to register for this course. If you are not a member, please head over to https://www.pentagonsailing.org/newmember to start your membership.  Additionally, students must obtain an American Sailing ID (ASID), ASA textbooks, and ASA International Log Book prior to earning ASA certifications. Please see https://americansailing.com/learn-to-sail/certifications/ for details.

    • 27 Jun 2026
    • 9:00 AM
    • 30 Jun 2026
    • 5:00 PM
    • Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
    • 2
    Register

    ASA 106 Offshore Cruising or 206 Instructor Training for Bareboat Cruising

    Boat:48' Schooner Adventurer

    Skipper:
    Duncan Hood

    This a unique opportunity to gain real sailing experience while earning ASA's 106 Offshore Cruising certification or ASA 206 Instructor Qualification. Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey. Duncan has offered to host club members on his boat during this sail and provide ASA 106 or 206 training. This four-day, three-night trip will give you more than enough experience to demonstrate confidently all the required skills and knowledge covered by the ASA 106/206 course so that you can charter a boat.

    Your fee covers ASA exam and certification. Food and drinks on board are the crew's responsibility. 

    Additional information on ASA 106:ASA 106, Offshore Cruising Certification

    Prerequisites:
    For 206 ASA requires 106 certification before taking the course and recommends a minimum of 80 on-the-water sailing hours.

    Locations:
    Start - Dock F, Slip 2 Port Annapolis, MD

    End - Port Annapolis, MD

    Itinerary: 
    Sail from Port Annapolis and return to the same location.

    Notes:
    A maximum of 1 FVSM may be used for this sail. If you use an FVSM, select the applicable ASA 106/206 with the FVSM payment option. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing this pricing option. The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

    Questions:
    Email Bay Commodore

    PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM


    • 10 Jul 2026
    • 9:00 AM
    • 12 Jul 2026
    • 5:00 PM
    • Sail Solomons, Spring Cove Marina, 455 Lore Road, Solomons MD 20688
    • 5
    Register

    ASA 104 Bareboat Cruising Training

    Boat: Moxie2007 Jeanneau 39i

    Skipper: Bill Diehl

    This an opportunity to gain real sailing experience on the Bay while earning ASA's 104 Bareboat Cruising certification. This two-day, one-night trip will give you experience to demonstrate confidently all the required skills and knowledge covered by the ASA 104 course so that you can charter a boat.

    Your fee covers ASA exam and certification. Food and drinks on board are the crew's responsibility. 

    For additional information and to purchase your textbook go to the ASA 104 website: ASA 104 Bareboat Cruising Certification

    Prerequisites: ASA 101 and ASA 103

    Location:
    Sail Solomons 
    Spring Cove Marina, 455 Lore Road, Solomons MD

    Itinerary: 
    Sail from Sail Solomons and return to the same location.

    Notes:
    A maximum of 1 FVSM may be used for this sail. If you use an FVSM, select the applicable ASA 104 with the FVSM payment option. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing this pricing option. The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

    Questions:
    Email Bay Commodore

    • 16 Aug 2026
    • 9:00 AM
    • 18 Aug 2026
    • 5:00 PM
    • Sail Solomons, Spring Cove Marina, 455 Lore Road, Solomons MD 20688
    • 6
    Register

    ASA 104 Bareboat Cruising Training

    Boat: Moxie2007 Jeanneau 39i

    Skipper: Matt Tobias

    This an opportunity to gain real sailing experience on the Bay while earning ASA's 104 Bareboat Cruising certification. This two-day, one-night trip will give you experience to demonstrate confidently all the required skills and knowledge covered by the ASA 104 course so that you can charter a boat.

    Your fee covers ASA exam and certification. Food and drinks on board are the crew's responsibility. 

    For additional information and to purchase your textbook go to the ASA 104 website: ASA 104 Bareboat Cruising Certification

    Prerequisites: ASA 101 and ASA 103

    Location:
    Sail Solomons 
    Spring Cove Marina, 455 Lore Road, Solomons MD

    Itinerary: 
    Sail from Sail Solomons and return to the same location.

    Notes:
    A maximum of 1 FVSM may be used for this sail. If you use an FVSM, select the applicable ASA 104 with the FVSM payment option. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing this pricing option. The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

    Questions:
    Email Bay Commodore

    • 10 Sep 2026
    • 6:00 PM
    • 20 Sep 2026
    • 4:30 PM
    • Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
    • 10
    Register

    ASA 101/103 Combined Beginner Sailing Course #4 [September]

    Never sailed before, or has it been a while? This is the course that will get you started!

    Upon completing this combined course, you can skipper a sloop-rigged keelboat of approximately 20 to 30 feet in length by day in light to moderate winds (up to 20 knots) and sea conditions.   Full details at https://pentagonsailing.org/Beginner-Sailing-Course.

    Classroom: Phillips School - Contemporary Education, Activity Room, 7010 Braddock Rd., Annandale, VA  22003

    • 101 Classroom Sep. 10 (6:00 PM to 8:30 PM)
    • 103 Classroom Sep. 17 (6:00 PM to 8:30 PM)

    On-the-Water Location: Capital Cove Marina @ Joint Base Anacostia-Bolling (JBAB)

    • 101 OTW - Sep. 12 & 13 (8:30 AM to 4:30 PM)
    • 103 OTW - Sep. 19 & 20 (8:30 AM to 4:30 PM)

    PSC Members may use up to 2 FVSMs for this class. FVSMs are worth $25.00 each for this class. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing either of these pricing options.

    If you have questions - please get in touch with the Training Commodore at trainingcommodore@pentagonsailing.org.

    P.S. You must be a Pentagon Sailing Member to register for this course. If you are not a member, please head over to https://www.pentagonsailing.org/newmember to start your membership. Additionally, students must obtain an American Sailing ID (ASID), ASA textbooks, and ASA International Log Book prior to earning ASA certifications. Please see https://americansailing.com/learn-to-sail/certifications/ for details.

    • 01 Oct 2026
    • 6:00 PM
    • 18 Oct 2026
    • 4:30 PM
    • Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
    • 12
    Register

    ASA 101/103 Combined Beginner Sailing Course #5 [October]

    Never sailed before, or has it been a while? This is the course that will get you started!

    Upon completing this combined course, you can skipper a sloop-rigged keelboat of approximately 20 to 30 feet in length by day in light to moderate winds (up to 20 knots) and sea conditions.   Full details at https://pentagonsailing.org/Beginner-Sailing-Course.

    Classroom: Phillips School - Contemporary Education, Activity Room, 7010 Braddock Rd., Annandale, VA  22003

    • 101 Classroom Oct. 1 (6:00 PM to 8:30 PM)
    • 103 Classroom Oct. 15 (6:00 PM to 8:30 PM)

    On-the-Water Location: Capital Cove Marina @ Joint Base Anacostia-Bolling

    • 101 OTW - Oct. 3 & 4 (8:30 AM to 4:30 PM)
    • 103 OTW - Oct. 17 & 18 (8:30 AM to 4:30 PM)

    PSC Members may use up to 2 FVSMs for this class. FVSMs are worth $25.00 each for this class. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing either of these pricing options.

    If you have questions - please get in touch with the Training Commodore at trainingcommodore@pentagonsailing.org.

    P.S. You must be a Pentagon Sailing Member to register for this course. If you are not a member, please head over to https://www.pentagonsailing.org/newmember to start your membership.  Additionally, students must obtain an American Sailing ID (ASID), ASA textbooks, and ASA International Log Book prior to earning ASA certifications. Please see https://americansailing.com/learn-to-sail/certifications/ for details.

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