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Bay Commodore

Chesapeake Bay Sailing

If you are not receiving invitations, please reach out to the Bay Commodore directly.

Bay Sailing opportunities: Most Fridays, Saturdays and Sundays. Check the bay schedule below. It will be updated throughout the season.

Raft-Ups: Set for Memorial Day and Labor Day, from Friday, to Monday.

If you have additional questions, please check our FAQ. If you need more information, please email me.

Bay Sail Schedule

  • Advanced Coastal Cruising 4-Day Sail, ASA 106

    • 24 Apr 2025
    • 10:00 AM
    • 27 Apr 2025
    • 5:00 PM
    • Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
    • 4
    • 2 registrants
    Register

     

    Coastal Cruising 4-Day Training Sail 

    Boat Name: Adventurer (48' schooner)

    Slip: Dock F, Slip 2, Port Annapolis, 7074 Bembe Beach Road, Annapolis, MD 21403

    Skipper: Duncan Hood

    Purpose/Training: A 4-day long trip on the Chesapeake Bay.  This is a training sail designed for people want to achieve ASA 106 and be able to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.  People who wish to receive the ASA certification must have completed the prerequisite courses and time on the water prior to starting this sail.  There is a significant amount of planning required of students for this event.  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.

    Check back soon for sail plan. Join waitlist if sail sells out. 

    Preference will be given to crew who are obtaining their first ASA 106 certification.

    Certifications:
    ASA 106 certification awarded upon successful completion of this sail and a written test. Pursuance of either certification is not a requirement of participating on this sail.

    Prerequisites for ASA 106: ASA 101, 103, 104, and 105.

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

    End - Port Annapolis, MD

    POC: Bay Commodore at baycommodore@pentagonsailing.org

    A maximum of 2 FVSMs may be used for this sail. If you are using an FVSM(s), select the applicable registration type with FVSM(s) option. Check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.  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.

    Registration cost includes charter fees, ASA 106 exam and certification fee. PSC no longer receives a discount on ASA textbooks.  Purchase one directly online.
    Show details

  • ASA-104 Bareboat Cruising Certification

    • 08 May 2025
    • 9:00 AM
    • 10 May 2025
    • 5:00 PM
    • Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
    • 4
    Register

    ASA 104 Bareboat Cruising Certification (a 3-day, 2-night sail)

    Boat:
    48' Schooner Adventurer

    Skipper:
    Duncan Hood

    This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification. 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 training. This three-day, two-night trip will give you more than enough 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 certification. PSC no longer gets a discount from ASA for the textbook.  Purchase one online.  Food and drinks on board are the crew's responsibility. 

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

    Prerequisites:
    ASA requires 101 and 103 certifications 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 the next day.

    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

    PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM


    Show details

  • Close Quarter Maneuvering (ASA 118)

    • 17 May 2025
    • 9:00 AM - 5:00 PM
    • Waypoints Annapolis, 222 Severn Ave, Annapolis, MD 21403
    • 4
    Register

    BAY TRAINING DAY SAIL - CLOSE QUARTER MANEUVERING (CQM)

    Boat Name: Dufour 430 - 3 cabin - Epiphany - 2022

    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

    Certifications:
    ASA - ASA 118 (Docking Endorsement) certification awarded upon successful completion of CQM Session and a written test.
    PSC Bay Skipper - Two sails required to fulfill all CQM requirements in the D-CS qualification card.

    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.

    PSC no longer gets a discount from ASA for the textbook. Purchase one online.

    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.

    Participants are encouraged to join the Bay Skipper Program

    Show details

  • Close Quarter Maneuvering (ASA 118)

    • 18 May 2025
    • 9:00 AM - 5:00 PM
    • Waypoints Annapolis, 222 Severn Ave, Annapolis, MD 21403
    • 5
    Register

    BAY TRAINING DAY SAIL - CLOSE QUARTER MANEUVERING (CQM)

    Boat Name: Dufour 430 - 3 cabin - Epiphany - 2022

    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

    Certifications:
    ASA - ASA 118 (Docking Endorsement) certification awarded upon successful completion of CQM Session and a written test.
    PSC Bay Skipper - Two sails required to fulfill all CQM requirements in the D-CS qualification card.

    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.

    PSC no longer gets a discount from ASA for the textbook. Purchase one online.

    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.

    Participants are encouraged to join the Bay Skipper Program

    Show details

  • 2025 PSC Memorial Day Raft-Up: Club-Chartered Catamaran

    • 24 May 2025
    • 9:00 AM
    • 26 May 2025
    • 5:00 PM
    • Waypoints Annapolis, 222 Severn Avenue, Bldg. 15 MD 21403 Annapolis, Maryland
    • 6
    Register


    2024 PSC Memorial Day Raft-Up: Club-Chartered 47' Catamaran

    • Location: Waypoints Annapolis, 222 Severn Ave, Annapolis, MD 21403 Google maps
      • Parking space may be limited. Try to carpool.

    REGISTRATION

    • 2025 PSC Memorial Day Raft-Up: Club-Chartered Boat (3-Day Bay Sail) – shared cabin, OR salon

    Miscellaneous costs (fuel, pump-out, dock fees, meals) not included.

    Boat: 47' Catamaran Fountaine Pajot Saona 47 Maestro - 3 + 1 cab. - Dark Star - 2019

    Skipper:  Jonah Brewer email vicecommodore@pentagonsailing.org 

    This is a multi-day social sail over the Memorial Day weekend. We depart the marina on Saturday and meet other boats on the bay, raft-up, and spend the day on the water. See flyer attached below.

    Theme: TBD

    Location: TBD

    This is a great multi-day experience, where you get to experience the liveaboard style, plus you get to raft-up with other boats. The sail is a great time to practice any skills you may need for a certification, or just to make sure you keep them sharp. If all you want is relax, there will be multiple fore-decks where you can do so.

    Monday we return to our home ports.

    We look forward to seeing you. Please pass the information about the Raft Up to anyone who wants to attend and let the skipper know if you have any questions.

    Registration price only covers charter costs. Additional costs such as food, pump-out, fuel, and slip fees will be shared by the crew.

    The charter boat is a catamaran with three 2-person cabins and three singles in salon (sleeping nine). You can check it out here.

    The 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.

    POC: Bay Commodore Sumeet C.

    PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

    Show details

  • ASA-104 Bareboat Cruising Certification

    • 30 May 2025
    • 9:00 AM
    • 01 Jun 2025
    • 5:00 PM
    • Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
    • 2
    Register

    ASA 104 Bareboat Cruising Certification (a 3-day, 2-night sail)

    Boat:
    48' Schooner Adventurer

    Skipper:
    Duncan Hood

    This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification. 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 training. This three-day, two-night trip will give you more than enough 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 certification. PSC no longer gets a discount from ASA for the textbook.  Purchase one online.  Food and drinks on board are the crew's responsibility. 

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

    Prerequisites:
    ASA requires 101 and 103 certifications 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 the next day.

    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

    PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM


    Show details

  • Advanced Coastal Cruising 4-Day Sail, ASA 106

    • 05 Jun 2025
    • 10:00 AM
    • 08 Jun 2025
    • 5:00 PM
    • Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
    • 5
    • 1 registrant
    Register

     

    Coastal Cruising 4-Day Training Sail 

    Boat Name: Adventurer (48' schooner)

    Slip: Dock F, Slip 2, Port Annapolis, 7074 Bembe Beach Road, Annapolis, MD 21403

    Skipper: Duncan Hood

    Purpose/Training: A 4-day long trip on the Chesapeake Bay.  This is a training sail designed for people want to achieve ASA 106 and be able to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.  People who wish to receive the ASA certification must have completed the prerequisite courses and time on the water prior to starting this sail.  There is a significant amount of planning required of students for this event.  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.

    Check back soon for sail plan. Join waitlist if sail sells out. 

    Preference will be given to crew who are obtaining their first ASA 106 certification.

    Certifications:
    ASA 106 certification awarded upon successful completion of this sail and a written test. Pursuance of either certification is not a requirement of participating on this sail.

    Prerequisites for ASA 106: ASA 101, 103, 104, and 105.

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

    End - Port Annapolis, MD

    POC: Bay Commodore at baycommodore@pentagonsailing.org

    A maximum of 2 FVSMs may be used for this sail. If you are using an FVSM(s), select the applicable registration type with FVSM(s) option. Check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.  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.

    Registration cost includes charter fees, ASA 106 exam and certification fee. PSC no longer receives a discount on ASA textbooks.  Purchase one directly online.
    Show details

  • Bay Day Sail #1

    • 07 Jun 2025
    • 9:00 AM - 5:00 PM
    • Waypoints Annapolis 222 Severn Avenue, Bldg. 15 MD 21403 Annapolis, Maryland
    • 5
    Register

    Bay Day Sail

    Boat Name: Jeanneau 51 - Recovery Room 2018

    Skipper: Pablo Destefanis

    Purpose/Training: Bay day sails are predominantly recreational. Day sails are designed to build experience and provide an enjoyable on-the-water experience. There is not a specific list of training objectives for this sail.

    POC: Bay Commodore

    One FVSM may be used for this sail. If you are using an FVSM, select the Bay 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.

    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.

    Please consider joining the Bay Skipper Program

    Show details

  • Bay Day Sail #2

    • 08 Jun 2025
    • 9:00 AM - 5:00 PM
    • Waypoints Annapolis 222 Severn Avenue, Bldg. 15 MD 21403 Annapolis, Maryland
    • 8
    Register

    Bay Day Sail

    Boat Name: Jeanneau 51 - Recovery Room 2018

    Skipper: Pablo Destefanis

    Purpose/Training: Bay day sails are predominantly recreational. Day sails are designed to build experience and provide an enjoyable on-the-water experience. There is not a specific list of training objectives for this sail.

    POC: Bay Commodore

    One FVSM may be used for this sail. If you are using an FVSM, select the Bay 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.

    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.

    Please consider joining the Bay Skipper Program

    Show details

  • ASA 114 Cruising Catamaran

    • 14 Jun 2025
    • 9:00 AM - 5:00 PM
    • Waypoints Yacht Charters, 222 Severn Avenue, Bldg. 15, Annapolis MD 21403 Annapolis, Maryland
    • 9
    Register

    Bay Training Sail

    Boat Name: Fountaine Pajot Saona 47 Maestro - 3 + 1 cab. - Dark Star - 2019

    Skipper: Dave Kunselman

    Training/Purpose: This sail is open to all club members. It is not necessary to be pursuing the ASA 114 certification. However, many aspects of this sail are designed around the ASA 114 Cruising Catamaran curriculum. Day sailing only included. ASA 114 is an advanced cruising standard for individuals with cruising experience. The standard includes those skills unique to a 30-50 foot multihull.
    *Note: Club training will take priority. If a member pursuing ASA 114 joins the waitlist, they will be given the spot of someone on the sail socially, but no later than three weeks before the sail.

    Prerequisites for ASA 114: ASA 101, 103, and 104.

    Certifications:
    ASA - ASA 114 certification awarded upon successful completion of this sail and a written test.

    POC: Bay Commodore

    A maximum of 2 FVSMs may be used for this sail. If you are using an FVSM(s), select the applicable Overnight Sail with FVSM(s) payment option. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.

    Show details

  • ASA 114 Cruising Catamaran

    • 15 Jun 2025
    • 9:00 AM - 5:00 PM
    • Waypoints Yacht Charters, 222 Severn Avenue, Bldg. 15, Annapolis MD 21403 Annapolis, Maryland
    • 11
    Register

    Bay Training Sail

    Boat Name: Fountaine Pajot Saona 47 Maestro - 3 + 1 cab. - Dark Star - 2019

    Skipper: Dave Kunselman

    Training/Purpose: This sail is open to all club members. It is not necessary to be pursuing the ASA 114 certification. However, many aspects of this sail are designed around the ASA 114 Cruising Catamaran curriculum. Day sailing only included. ASA 114 is an advanced cruising standard for individuals with cruising experience. The standard includes those skills unique to a 30-50 foot multihull.
    *Note: Club training will take priority. If a member pursuing ASA 114 joins the waitlist, they will be given the spot of someone on the sail socially, but no later than three weeks before the sail.

    Prerequisites for ASA 114: ASA 101, 103, and 104.

    Certifications:
    ASA - ASA 114 certification awarded upon successful completion of this sail and a written test.

    POC: Bay Commodore

    A maximum of 2 FVSMs may be used for this sail. If you are using an FVSM(s), select the applicable Overnight Sail with FVSM(s) payment option. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.

    Show details

  • ASA-104 Bareboat Cruising Certification

    • 20 Jun 2025
    • 9:00 AM
    • 22 Jun 2025
    • 5:00 PM
    • Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
    • 6
    Register

    ASA 104 Bareboat Cruising Certification (a 3-day, 2-night sail)

    Boat:
    48' Schooner Adventurer

    Skipper:
    Duncan Hood

    This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification. 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 training. This three-day, two-night trip will give you more than enough 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 certification. PSC no longer gets a discount from ASA for the textbook.  Purchase one online.  Food and drinks on board are the crew's responsibility. 

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

    Prerequisites:
    ASA requires 101 and 103 certifications 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 the next day.

    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

    PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM


    Show details

  • ASA 204 - IQC Instructor Training for Bareboat Cruising

    • 27 Jun 2025
    • 9:00 AM
    • 29 Jun 2025
    • 5:00 PM
    • Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
    • 5
    Register

    ASA 204 - IQC 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 204 Bareboat Cruising certification. 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 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 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:
    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 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


    Show details

  • ASA 204 - IQC Instructor Training for Bareboat Cruising

    • 27 Jun 2025
    • 9:00 AM
    • 29 Jun 2025
    • 5:00 PM
    • Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
    • 6
    Register

    ASA 204 - IQC 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 204 Bareboat Cruising certification. 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 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 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:
    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 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


    Show details

  • ASA-104 Bareboat Cruising Certification

    • 22 Aug 2025
    • 9:00 AM
    • 24 Aug 2025
    • 5:00 PM
    • Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
    • 6
    Register

    ASA 104 Bareboat Cruising Certification (a 3-day, 2-night sail)

    Boat:
    48' Schooner Adventurer

    Skipper:
    Duncan Hood

    This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification. 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 training. This three-day, two-night trip will give you more than enough 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 certification. PSC no longer gets a discount from ASA for the textbook.  Purchase one online.  Food and drinks on board are the crew's responsibility. 

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

    Prerequisites:
    ASA requires 101 and 103 certifications 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 the next day.

    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

    PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM


    Show details

  • 2025 PSC Labor Day Raft-Up: Club-Chartered Catamaran

    • 30 Aug 2025
    • 9:00 AM
    • 01 Sep 2025
    • 5:00 PM
    • Waypoints Annapolis, 222 Severn Avenue, Bldg. 15 MD 21403 Annapolis, Maryland
    • 8
    Register


    2024 PSC Labor Day Raft-Up: Club-Chartered 47' Catamaran

    • Location: Waypoints Annapolis, 222 Severn Ave, Annapolis, MD 21403 Google maps
      • Parking space may be limited. Try to carpool.

    REGISTRATION

    • 2025 PSC Labor Day Raft-Up: Club-Chartered Boat (3-Day Bay Sail) – shared cabin, OR salon

    Miscellaneous costs (fuel, pump-out, dock fees, meals) not included.

    Boat: 47' Catamaran Fountaine Pajot Saona 47 Maestro - 3 + 1 cab. - Dark Star - 2019

    Skipper:  TBD 

    This is a multi-day social sail over the Labor Day weekend. We depart the marina on Saturday and meet other boats on the bay, raft-up, and spend the day on the water. 

    Theme: TBD

    Location: TBD

    This is a great multi-day experience, where you get to experience the liveaboard style, plus you get to raft-up with other boats. The sail is a great time to practice any skills you may need for a certification, or just to make sure you keep them sharp. If all you want is relax, there will be multiple fore-decks where you can do so.

    Monday we return to our home ports.

    We look forward to seeing you. Please pass the information about the Raft Up to anyone who wants to attend and let the skipper know if you have any questions.

    Registration price only covers charter costs. Additional costs such as food, pump-out, fuel, and slip fees will be shared by the crew.

    The charter boat is a catamaran with three 2-person cabins and three singles in salon (sleeping nine). You can check it out here.

    The 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.

    POC: Bay Commodore Sumeet C.

    PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

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  • ASA-104 Bareboat Cruising Certification

    • 05 Sep 2025
    • 9:00 AM
    • 07 Sep 2025
    • 5:00 PM
    • Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
    • 6
    Register

    ASA 104 Bareboat Cruising Certification (a 3-day, 2-night sail)

    Boat:
    48' Schooner Adventurer

    Skipper:
    Duncan Hood

    This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification. 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 training. This three-day, two-night trip will give you more than enough 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 certification. PSC no longer gets a discount from ASA for the textbook.  Purchase one online.  Food and drinks on board are the crew's responsibility. 

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

    Prerequisites:
    ASA requires 101 and 103 certifications 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 the next day.

    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

    PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM


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  • Advanced Coastal Cruising 4-Day Sail, ASA 106

    • 11 Sep 2025
    • 10:00 AM
    • 14 Sep 2025
    • 5:00 PM
    • Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
    • 4
    • 2 registrants
    Register

     

    Coastal Cruising 4-Day Training Sail 

    Boat Name: Adventurer (48' schooner)

    Slip: Dock F, Slip 2, Port Annapolis, 7074 Bembe Beach Road, Annapolis, MD 21403

    Skipper: Duncan Hood

    Purpose/Training: A 4-day long trip on the Chesapeake Bay.  This is a training sail designed for people want to achieve ASA 106 and be able to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.  People who wish to receive the ASA certification must have completed the prerequisite courses and time on the water prior to starting this sail.  There is a significant amount of planning required of students for this event.  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.

    Check back soon for sail plan. Join waitlist if sail sells out. 

    Preference will be given to crew who are obtaining their first ASA 106 certification.

    Certifications:
    ASA 106 certification awarded upon successful completion of this sail and a written test. Pursuance of either certification is not a requirement of participating on this sail.

    Prerequisites for ASA 106: ASA 101, 103, 104, and 105.

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

    End - Port Annapolis, MD

    POC: Bay Commodore at baycommodore@pentagonsailing.org

    A maximum of 2 FVSMs may be used for this sail. If you are using an FVSM(s), select the applicable registration type with FVSM(s) option. Check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.  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.

    Registration cost includes charter fees, ASA 106 exam and certification fee. PSC no longer receives a discount on ASA textbooks.  Purchase one directly online.
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  • ASA 206 - Advanced Coastal Cruising Instructor

    • 02 Oct 2025
    • 05 Oct 2025
    • Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
    • 4
    • 2 registrants
    Register

    PSC offers ASA 106/206, Advanced Coastal Cruising course on Adventurer with Duncan Hood


    PSC will be offering an ASA 206 class on Duncan Hood's 48' Cherubini schooner, “Adventurer.” This will be a 4 day live-aboard class which, among other exercises, will include the following:


    •        Night time navigation without electronics

    •        Anchoring

    •        Live MOB rescue, swimmer and non-swimmer assisted

    •        Adverse weather preparation

    •        Menu planning & Meal preparation

    •        Docking in different marinas & configurations

    •        Piloting & plotting

    •        Electronic navigation with chartplotter, radar and autopilot

    •        Spinnaker (weather permitting)


    The purpose behind ASA 206 certification is to train students and give them experience sailing a vessel between 30 and 50 feet in length on coastal and inland waters in varied conditions. This is meant to include mechanical problems that may come up, adverse weather conditions, emergency situations, and a single night sail. In this instructor training course (206) we will attempt to address these four areas.

    All exercises are based on ASA 206 requirements as stated in the ASA logbook for that level.

    Attending ASA 206 instructors are expected to have completed ASA 204/205 (Bareboat chartering/Coastal navigation), hold valid USGC Captain's licenses (if receiving consideration/compensation for teaching), and to have held these ratings for one year or more.

    1 FVSM may be used for this course.  Please verify you have available FVSM before registering at this rate.

    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.

    This is always a fun and challenging class. Join us!


    Show details

  • ASA 206 - Advanced Coastal Cruising Instructor

    • 23 Oct 2025
    • 9:00 AM
    • 26 Oct 2025
    • 5:00 PM
    • Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
    • 5
    • 1 registrant
    Register

    PSC offers ASA 106/206, Advanced Coastal Cruising course on Adventurer with Duncan Hood


    PSC will be offering an ASA 206 class on Duncan Hood's 48' Cherubini schooner, “Adventurer.” This will be a 4 day live-aboard class which, among other exercises, will include the following:


    •        Night time navigation without electronics

    •        Anchoring

    •        Live MOB rescue, swimmer and non-swimmer assisted

    •        Adverse weather preparation

    •        Menu planning & Meal preparation

    •        Docking in different marinas & configurations

    •        Piloting & plotting

    •        Electronic navigation with chartplotter, radar and autopilot

    •        Spinnaker (weather permitting)


    The purpose behind ASA 206 certification is to train students and give them experience sailing a vessel between 30 and 50 feet in length on coastal and inland waters in varied conditions. This is meant to include mechanical problems that may come up, adverse weather conditions, emergency situations, and a single night sail. In this instructor training course (206) we will attempt to address these four areas.

    All exercises are based on ASA 206 requirements as stated in the ASA logbook for that level.

    Attending ASA 206 instructors are expected to have completed ASA 204/205 (Bareboat chartering/Coastal navigation), hold valid USGC Captain's licenses (if receiving consideration/compensation for teaching), and to have held these ratings for one year or more.

    1 FVSM may be used for this course.  Please verify you have available FVSM before registering at this rate.

    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.

    This is always a fun and challenging class. Join us!


    Show details

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