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Cruising skipper registration slots are open immediately and we encourage skippers to sign up as soon as they know they can commit to an event. Cruising crew slots open 6 weeks out from the event start date.
General Overview
Join us for a relaxing late-summer cruise to the picturesque waterfront town of St. Michaels, one of the Chesapeake Bay's most beloved cruising destinations. This weekend offers a wonderful blend of scenic sailing, local food and drink, maritime history, and classic Chesapeake traditions. Whether you're looking to build cruising experience, spend time with fellow club members, or simply enjoy a weekend on the water, this trip has something for everyone.
After sailing across the Bay from Baltimore on Friday, we'll settle into the marina and enjoy an evening exploring St. Michaels. Participants will have the opportunity to visit St. Michaels Winery or Eastern Shore Brewing, both popular local favorites, before gathering for dinner at Foxy's Harbor Grille, a lively waterfront restaurant known for its fresh seafood, tropical atmosphere, and harbor views.
On Saturday, we'll enjoy one of the Chesapeake's most unique events—the Log Canoe Races, featuring historic racing sailboats and skilled crews. Participants will also have the option to visit the renowned Chesapeake Bay Maritime Museum, with its historic vessels and exhibits celebrating the Bay's maritime heritage, or spend the day exploring St. Michaels' charming shops, galleries, waterfront parks, and cafés.
Later that afternoon, we'll depart St. Michaels and cruise to a nearby protected river anchorage for a peaceful evening on the water. We'll gather for a casual potluck-style cookout under the stars before settling in for a relaxing night at anchor. On Sunday morning, we'll enjoy a leisurely breakfast aboard before weighing anchor and sailing back to Baltimore.
Tentative Itinerary
Friday: Sail to St. Michaels, visit St. Michaels Winery or Eastern Shore Brewing, and enjoy dinner at Foxy's Harbor Grille.
Saturday: Watch the Log Canoe Races with the option to visit the Chesapeake Bay Maritime Museum or explore the town before cruising to an anchorage destination for a cookout under the stars.
Sunday: Return sail to Baltimore.
Trip details, marina reservations, dinner reservations, and the final anchorage location will be shared closer to the departure date based on weather, river conditions, and slip availability.
Event Start Time
0730
Event End Time
1700 (+2 days)
Estimated Shared Costs
Slip fees: ~$125/night/boat -> $31/person for the trip; Anchorages available
Boat fuel fund: Suggested contribution $30/person
Learning Objectives: Navigation (electronic and/or paper charts) through Kent Narrows and/or Bloody Point, checking tides and appropriately timing passage through shallow areas, anchoring in a crowded zone, docking and departing a busy marina, rafting up with appropriate offset and use of lines.
Skipper(s) will contact participants via Circle to communicate the actual dock-call time and cruising logistics.
Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.
Weather cancellations will be announced by 10 PM on the day before the event.
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.
If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 8 PM on the day before the event.
Join us for a casual evening sail to catch the full moon out on the water.
The plan is to head out around sunset (please check circle for a message from the skippers about a specific time to meet!), sail through dusk, and be on the water as the moon rises. Depending on conditions, we’ll keep things flexible—maybe a relaxed cruise, maybe a bit more hands-on sailing if people are interested. Everyone is welcome to participate as much or as little as they’d like, whether that’s helping out with the boat or just settling in and taking it all in.
Learning Objectives: practice night navigation, recognizing other vessels lights and using lighted markers, docking at night.
Weather cancellations will be announced by 11 AM on the day of the event.
1730-1900
2130
Shared Costs
No slip or dockage fees expected. Please consider a $5 contribution to the fuel fund!
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!
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.
Experience one of the Chesapeake Bay's favorite fall traditions with an overnight cruise to the charming waterfront town of Rock Hall for its annual Fall Fest. We'll sail across the Bay to Maryland's Eastern Shore, spend the night in one of Rock Hall's welcoming marinas, and enjoy a day exploring a festival that celebrates the town's rich watermen's heritage with fresh oysters, local seafood, live music, and artisan vendors.
For additional information about Fall Fest please refer to https://rockhallfallfest.org/program/ or https://www.facebook.com/rockhallfallfest/. Fall Fest is from 10am - 4pm, so with a four hour cruise to reach Rock Hall, please note we plan to leave the DSC docks early and promptly on Saturday morning.
0700
1500 (+1)
Slip fees: ~$140/boat -> ~$35/person
Boat fuel fund: Suggested contribution $10/person
Optional - individual paid dinners from food vendors at Fall Fest
Learning Objectives: Navigation (electronic and/or paper charts), checking tides and appropriately timing passage through shallow areas, docking and departing a busy marina
1730-1800
The Downtown Sailing Center
1425 Key Highway, Suite 110, Baltimore, MD 21230(410) 727-0722 • info@downtownsailing.org
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