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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

  • ASA-104 Bareboat Cruising Certification

    • 15 Aug 2025
    • 9:00 AM
    • 17 Aug 2025
    • 5:00 PM
    • Herrington Harbour North Marina 389 Deale Rd, Tracys Landing, MD 20779
    • 0
    Join waitlist

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

    Boat:
    36' Catalina The 7 OCs

    Skipper:
    John O'Connor

    This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification. Experienced instructor, John O'Connor, will teach this class on his 36' Catalina 1985 MK1 sloop The 7 OCs.  John 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. There are preparation requirements in advance of this sail including reading the ASA textbook, chart work and provisioning planning.

    Your fee covers ASA certification. Students should purchase the textbook on their own. Food and drinks on board are the crew's responsibility.  There is $50 refundable fee for those who complete the sail and in accordance with PSC’s Bay Cancellation Policy.

    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 - Herrington Harbour North Marina 389 Deale Rd, Tracys Landing, MD 20779

    End - Herrington Harbour North Marina 389 Deale Rd, Tracys Landing, MD 20779

    Notes:
    The only costs for students are: related ASA cost of 104 including book, chart, chart plotting gear (if you don't already have it) and exam/certification; share of cost of food prepared on board; and, one dinner at a restaurant ashore. 

    Questions:
    Email Bay Commodore

    PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM


    Show details

  • Bay Night Sail #4

    • 15 Aug 2025
    • 6:00 PM
    • 16 Aug 2025
    • 7:00 AM
    • Herrington Harbour North (HHN) 389 Deale Road, Tracey’s Landing, MD 20779, Dock R9
    • 0
    Join waitlist

    Bay Night Sail

    • Location

    Herrington Harbour North (HHN) 389 Deale Road, Tracey’s Landing, MD 20779, Dock R9

    • Spaces left

    4

    REGISTRATION

    • Bay Night Sail – $25 refundable deposit. The deposit will be refunded to those who complete the sail or cancel in accordance with the PSC Bay Cancellation Policy

    Bay Night Sail

    Boat Name: Family Knot, Gemini 105MC 35’ Catamaran

    Skipper: David Kunselman

    Purpose/Training: This night sail on a member-owned sailboat is being offered to PSC members trying to gain night sailing experience required for the PSC Bay Skipper program.  We will get underway before sunset, sail all night, and return to slip after sunrise.  Training objectives include night navigation including interpretation of aids to navigation (ATONS). There is no charge for this training, but participants are asked to contribute for fuel expenses and to bring your own food and beverages.  Prerequisites: Completion of ASA 101 and 103. 

    POC: Bay Commodore at baycommodore@pentagonsailing.org

    Please consider joining 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
    • 3
    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
    • 4
    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:  Ross R. 

    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:

    FLOATING FOOD NATIONS
    Each boat = 1 country. Represent it with décor, food, drinks, and spirit!
    You don’t have to be authentic — just fun and flavorful.


    We have provided a list of 15 nations for your convenience - choose one for your boat!


    Choose one nation for your boat!

    Raft Up Location: Shaw Bay (float plan will be provided to skippers)

    Marina and Dinner: on Sunday, August 31, at Pirates Cove Marina in Galesville, MD at 1800. Each boat must make its own reservations. Please contact Harbourmaster Pat at 3019286605 and be sure to mention that you are part of the PSC flotilla.

    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: Communications Commodore

    PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

    Show details

  • 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
    • 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

  • 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
    • 1
    • 5 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

  • Bay Night Sail #5

    • 12 Sep 2025
    • 6:00 PM
    • 13 Sep 2025
    • 7:00 AM
    • Herrington Harbour North (HHN) 389 Deale Road, Tracey’s Landing, MD 20779, Dock R9
    • 0
    Join waitlist

    Bay Night Sail

    • Location

    Herrington Harbour North (HHN) 389 Deale Road, Tracey’s Landing, MD 20779, Dock R9

    • Spaces left

    4

    REGISTRATION

    • Bay Night Sail – $25 refundable deposit. The deposit will be refunded to those who complete the sail or cancel in accordance with the PSC Bay Cancellation Policy

    Bay Night Sail

    Boat Name: Family Knot, Gemini 105MC 35’ Catamaran

    Skipper: David Kunselman

    Purpose/Training: This night sail on a member-owned sailboat is being offered to PSC members trying to gain night sailing experience required for the PSC Bay Skipper program.  We will get underway before sunset, sail all night, and return to slip after sunrise.  Training objectives include night navigation including interpretation of aids to navigation (ATONS). There is no charge for this training, but participants are asked to contribute for fuel expenses and to bring your own food and beverages.  Prerequisites: Completion of ASA 101 and 103. 

    POC: Bay Commodore at baycommodore@pentagonsailing.org

    Please consider joining the Bay Skipper Program

    Show details

  • ASA 204 - IQC Instructor Training for Bareboat Cruising

    • 19 Sep 2025
    • 9:00 AM
    • 21 Sep 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 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
    • 3
    • 3 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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