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Cruising Calendar

Upcoming events

  • Cruising Full Moon Sail

    • 12 Apr 2025
    • 4:30 PM - 9:30 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 3
    Register

    Cruising Full Moon Sail

    Spend some time on the water under the full moon! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Season Start Intro Sail

    • 03 May 2025
    • 12:00 PM - 5:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 6
    Register

    Welcome to Cruising sail

    Let's get out on the water and start the season off strong with a sail on our Cruisers!

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Women's Raft-Up

    • 10 May 2025
    • 8:00 AM - 6:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 10
    Register
    Show details

  • Cruising Full Moon Sail

    • 12 May 2025
    • 4:30 PM - 9:30 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 6
    Register

    Cruising Full Moon Sail

    Spend some time on the water under the full moon! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Annapolis Overnight

    • 17 May 2025
    • 8:00 AM
    • 18 May 2025
    • 5:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 0
    Join waitlist

    Annapolis Overnight

    First overnight trip of the season! Destination: Annapolis. Details for the trip will be determined by the Skipper and the Crew that register!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Chestertown Overnight

    • 24 May 2025
    • 8:00 AM
    • 26 May 2025
    • 5:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 3
    Register

    Chestertown Overnight

    Second overnight trip of the season! Destination: Chestertown Tea Party Festival. Details for the trip will be determined by the Skipper and the Crew that register!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising First Thursday Concert Sail

    • 05 Jun 2025
    • 3:30 PM - 8:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    First Thursday Concert Sail

    Take out a cruiser and anchor / tie up in Canton to enjoy WTMD's First Thursday Concert series in style!

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Full Moon Sail

    • 11 Jun 2025
    • 4:30 PM - 9:30 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 7
    Register

    Cruising Full Moon Sail

    Spend some time on the water under the full moon! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Whitehall Bay Overnight

    • 14 Jun 2025
    • 8:00 AM
    • 15 Jun 2025
    • 5:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 4
    Register

    Whitehall Bay Overnight

    Destination: Whitehall Bay. Details for the trip will be determined by the Skippers and the Crew that register!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Solstice Sail

    • 20 Jun 2025
    • 4:30 PM - 9:30 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 7
    Register

    Cruising Solstice Sail

    Spend some time on the water on the solstice! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Bodkin Day Sail

    • 21 Jun 2025
    • 7:00 AM - 5:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 7
    Register

    Cruising Bodkin Day Sail

    Head past the bridge on a day trip out to Bodkin Bay! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising First Thursday Concert Sail

    • 03 Jul 2025
    • 3:30 PM - 8:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    First Thursday Concert Sail

    Take out a cruiser and anchor / tie up in Canton to enjoy WTMD's First Thursday Concert series in style!

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Full Moon Sail

    • 10 Jul 2025
    • 4:30 PM - 9:30 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 7
    Register

    Cruising Full Moon Sail

    Spend some time on the water under the full moon! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Bodkin Day Sail

    • 13 Jul 2025
    • 7:00 AM - 5:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    Cruising Bodkin Day Sail

    Head past the bridge on a day trip out to Bodkin Bay! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Havre De Grace Overnight

    • 18 Jul 2025
    • 8:00 AM
    • 20 Jul 2025
    • 5:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 7
    Register
    Show details

  • Cruising First Thursday Concert Sail

    • 07 Aug 2025
    • 3:30 PM - 8:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    First Thursday Concert Sail

    Take out a cruiser and anchor / tie up in Canton to enjoy WTMD's First Thursday Concert series in style!

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Full Moon Sail

    • 09 Aug 2025
    • 4:30 PM - 9:30 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    Cruising Full Moon Sail

    Spend some time on the water under the full moon! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Fairlee Creek Overnight

    • 15 Aug 2025
    • 8:00 AM
    • 17 Aug 2025
    • 5:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    Fairlee Creek Overnight

    Destination: Fairlee Creek. Details for the trip will be determined by the Skippers and the Crew that register!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Bodkin Day Sail

    • 24 Aug 2025
    • 7:00 AM - 5:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    Cruising Bodkin Day Sail

    Head past the bridge on a day trip out to Bodkin Bay! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Choptank / Oxford Overnight

    • 30 Aug 2025
    • 8:00 AM
    • 01 Sep 2025
    • 5:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    Choptank / Oxford Overnight

    Destination: Choptank / Oxford. Details for the trip will be determined by the Skippers and the Crew that register!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising First Thursday Concert Sail

    • 04 Sep 2025
    • 3:30 PM - 8:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    First Thursday Concert Sail

    Take out a cruiser and anchor / tie up in Canton to enjoy WTMD's First Thursday Concert series in style!

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Full Moon Sail

    • 07 Sep 2025
    • 4:30 PM - 9:30 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 7
    Register

    Cruising Full Moon Sail

    Spend some time on the water under the full moon! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Full Moon Sail

    • 06 Oct 2025
    • 4:30 PM - 9:30 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    Cruising Full Moon Sail

    Spend some time on the water under the full moon! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Rock Hall Overnight

    • 11 Oct 2025
    • 8:00 AM
    • 13 Oct 2025
    • 5:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    Annapolis Overnight

    Destination: Rock Hall FallFest. Details for the trip will be determined by the Skipper and the Crew that register!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Halloween Sail

    • 31 Oct 2025
    • 12:00 PM - 4:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 7
    Register

    Cruising Halloween Sail

    Celebrate spooky vibes out on the Inner Harbor! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details

  • Cruising Full Moon Sail

    • 05 Nov 2025
    • 4:30 PM - 9:30 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 8
    Register

    Cruising Full Moon Sail

    Spend some time on the water under the full moon! This event has priority registration for Cruising Members.

    If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!

    Waivers Required

    If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

    Have Questions?

    If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.


    Show details