Menu
Log in

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

    • 20 Sep 2025
    • 11:00 AM - 5:00 PM
    • Herrington Harbour North (HHN) 389 Deale Road, Tracey’s Landing, MD 20779
    • 0
    Registration is closed

    Bay Day Sail

    • Location

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

    REGISTRATION INFORMATION

    • Bay Day 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 Day Sail - Monohull 

    Boat Name: The 7OCs

    Skipper: John O'Connor

    Purpose/Social: This day sail on a member-owned 1985 Catalina 36 MK1 monohull sloop is being offered to PSC members as a social sail.  There is no charge for this sail.  Participants bring their own food and beverages. The refundable deposit noted in Registration Information applies.  Prerequisites: None. 

    POC: Bay Commodore at baycommodore@pentagonsailing.org

    Please consider joining the Bay Skipper Program

    • 21 Sep 2025
    • 11:00 AM - 5:00 PM
    • Herrington Harbour North (HHN) 389 Deale Road, Tracey’s Landing, MD 20779
    • 0
    Registration is closed

    Bay Day Sail

    • Location

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

    REGISTRATION INFORMATION

    • Bay Day 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 Day Sail - Monohull 

    Boat Name: The 7OCs

    Skipper: John O'Connor

    Purpose/Social: This day sail on a member-owned 1985 Catalina 36 MK1 monohull sloop is being offered to PSC members as a social sail and to mark the last full day of Summer 2025. There is no charge for this sail.  Participants bring their own food and beverages. The refundable deposit noted in Registration Information applies.  Prerequisites: None. 

    POC: Bay Commodore at baycommodore@pentagonsailing.org

    Please consider joining the Bay Skipper Program

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


    • 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
    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!


© Pentagon Sailing Club
Powered by Wild Apricot Membership Software