The Downtown Sailing Center upcoming events

Inner Harbor Lunch Daysail (Sunday, April 12, 2026)

Sun, 12 Apr 2026 13:30:00 GMT

Inner Harbor Lunch Daysail

Join us for a fun, casual sail around Inner Harbor - we can go searching for the FSK buoy, poke around the Peninsula, or practice cruising skills out near Dundalk. Then, we will dock at an Inner Harbor restaurant, Pusser’s or Nick’s Fishhouse likely, to grab lunch together before heading back to the DSC.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

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 10 PM on the day before the event.

Sailing Resume Workshop (Monday, April 13, 2026)

Mon, 13 Apr 2026 23:30:00 GMT

Have you ever been asked to supply a sailing resume and weren’t sure how to proceed?

Come by the Liberty Room Monday evening, April 13 at 7:30 pm to get tips, advice and some formatting ideas to put one together.

Fort Carroll Lunch Daysail (Sunday, April 26, 2026)

Sun, 26 Apr 2026 13:30:00 GMT

Fort Carroll Lunch Daysail

We will set sail towards the Francis Scott Key Bridge, and anchor for lunch by Ft Carroll, or Sollers Point just outside the channel. We’ll have lunch on the vessel while anchored and can take in the sights of Fort Carroll and likely those fishing as well. Expect at least a 12 nautical mile round trip, around a 5 hour activity including lunch, sailing, and cleaning of the vessel after returning to the docks.

We will set out by 1000; please arrive dockside at 0930.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

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 10 PM on the day before the event.

Cruising Full Flower Moon Sail (Friday, May 01, 2026)

Fri, 01 May 2026 21:30:00 GMT

Cruising Full Flower Moon Sail

Join us for a casual evening sail to catch the full moon out on the water.

The plan is to head out around sunset, 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.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

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.

Kinetic Sculpture Race Daysail (Saturday, May 02, 2026)

Sat, 02 May 2026 13:00:00 GMT

Kinetic Sculpture Race Daysail

Join us for a lively day cruise around the harbor to catch the Kinetic Sculpture Race, one of Baltimore’s most iconic and beloved events! We’ll sail together to a great viewing spot where you can watch these creative, human-powered sculptures make their way across land and water. Relax onboard, take in the views, and enjoy the festive atmosphere. Pack a lunch or snacks to enjoy during the day, and get ready for a unique and entertaining experience on the water.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

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 10 PM on the day before the event.

Overnight Cruise to Annapolis (Saturday, May 09, 2026)

Sat, 09 May 2026 13:00:00 GMT

Overnight Cruise to Annapolis

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.

Set sail for an unforgettable overnight adventure to Annapolis, MD! We’ll cruise across the Chesapeake Bay, enjoying scenic views and time on the water before arriving in the historic sailing capital of the U.S. Once docked, you’ll have time to explore the charming waterfront, unwind with a happy hour drink, and enjoy dinner at one of Annapolis’ many local restaurants. After a relaxing evening, we’ll spend the night aboard and wake up to a peaceful morning on the water before sailing back. The trip is a perfect blend of adventure, relaxation, and classic Chesapeake sailing.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

Skipper(s) will contact participants via Circle to communicate the actual dock-call time and cruising logistics.

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 10 PM on the day before the event.

Oxford Weekend Sail (Saturday, May 23, 2026)

Sat, 23 May 2026 11:00:00 GMT

Oxford Weekend Sail

Join us for a holiday weekend sail down to Oxford, MD on the Choptank River of the Eastern Shore. We will take-in the waterfront sites of the Tred Avon River while exploring the colonial era charm of this maritime community. We will break up our return trip with a stopover on Harris Creek, before carrying on to either Tilghman Island or the Western Shore’s Western River or Rhode River.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

Skipper(s) will contact participants via Circle to communicate the actual dock-call time and cruising logistics.

Event Start Time

0700

Event End Time

1500 (+2 days)

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 10 PM on the day before the event.

Cruising Full Blue Moon Sail (Sunday, May 31, 2026)

Sun, 31 May 2026 21:30:00 GMT

Cruising Full Blue Moon Sail

Join us for a casual evening sail to catch the full moon out on the water.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

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.

Cruising First Thursday Sail (Thursday, June 04, 2026)

Thu, 04 Jun 2026 21:30:00 GMT

Cruising First Thursday Sail

Join us for an evening sail as we meander to the Canton Waterfront park to take-in WTMD’s First Thursday concert! We may or may not dock in Canton, so plan to bring a snack to hold you over on this evening sail.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

Event Start Time

1730

Event End Time

2030

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.

Worton Creek and Land's Point Winery Overnight Sail (Saturday, June 06, 2026)

Sat, 06 Jun 2026 11:00:00 GMT

Worton Creek and Land's Point Winery Overnight Sail

Sail on Sweet Dreams or Sunrise across the Bay to a quiet anchorage in Worton Creek. Swim from the boat in Worton Creek (the water is so fresh that there’s no jellyfish!). Visit Land’s Point Winery by traveling to their dock via dinghy for a wine tasting. Return to the boat for a grilled dinner on board and watch the sunset while relaxing for the evening.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

Skipper(s) will contact participants via Circle to communicate the actual dock-call time and cruising logistics.

Event Start Time

0700

Event End Time

1500 (+1 day)

Approximately 25.0 NM from the DSC

5 hours of sailing time to destination

5 Gallons of Fuel (one-way) = 10 Gallons Total

Shared Costs

No slip fees

BOAT FUEL FUND: Suggested contribution $30/person

Shared cost for Dinner on board: roughly $100/boat = about $25/person

Cruise Plan

Option 1:

Sail from DSC to Worton Creek (25 nm, 5 hours)
Anchor in Worton Creek
Swim from the boat
Optional Dinghy to Land’s Point Winery (reserve group wine tasting ahead of time)
Cookout dinner on board
BYO Breakfast on board

Option 2:

Sail from DSC to Worton Creek Marina (25 nm, 5 hours)
- Marina fees: ? (split)
Optional Dinghy to Land’s Point Winery (reserve group wine tasting ahead of time)
Cookout dinner on board
BYO Breakfast on board

Return: Sail back to DSC from Worton Creek anchorage, or Worton Creek Marina. Arrive back at the DSC around 3 pm, depending upon departure time and wind.

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 10 PM on the day before the event.

Georgetown and Fairlee Creek Weekend Sail (Friday, June 19, 2026)

Fri, 19 Jun 2026 11:00:00 GMT

Georgetown and Fairlee Creek Weekend Sail

Sail up to Georgetown, MD on the Sassafras River the first day to the Georgetown Yacht Harbor. Stay overnight on mooring buoys in the Marina. Go out to dinner at local restaurant on Friday evening. On Saturday morning we will do breakfast at local restaurant and then sail back down the Sassafras river and south down the bay to Fairlee Creek. Anchor upon arriving and swim that afternoon and also visit Oak Landing and Jellyfish Joel’s beach bar. Grill dinner aboard and watch sunset and relax. On Sunday morning have breakfast aboard and then sail back to DSC arriving mid to late afternoon.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

Skipper(s) will contact participants via Circle to communicate the actual dock-call time and cruising logistics.

*Skipper note: The channel in/out of Fairlee Creek is shallow and has a strong current. Recommend shallowest draft boats for this trip, and read up on the approach ahead of time.

Event Start Time

0700

Event End Time

1500 (+2 days)

Shared Costs

Friday’s sail to Georgetown is 40.9 nm, approx 8 hours sailing time, from DSC. Saturday’s sail from Georgetown to Fairlee Creek is 21 nm, approx 4 hours sailing time. Sunday’s sail from Fairlee Creek to DSC is 23.1 nm, approx 4.5 hours.

Slip Fee ($0.85/feet/night) for Georgetown Yacht Harbor

BOAT FUEL FUND: Suggested contribution $30/person

Shared cost for Saturday dinner on board: roughly $100/boat = about $25/person

Cruise Plan

Option1:

Sail from DSC to Georgetown Yacht Harbor (40.9 nm, 8 hours)
Moor in the harbor
Dinner and Breakfast in town
Sail from Georgetown Yacht Harbor to Fairlee Creek (21 nm, 4 hours)
Spend evening anchored, swim and BBQ dinner, Sunday breakfast BYO
Sail from Fairlee Creek to DSC (23.1 nm, 4 hours)

Option 2

Return: Sail back to DSC from Fairlee Creek anchorage. Arrive back at the DSC around 3 pm, depending upon departure time and wind.

Provisions

In the interest of everyone’s time to prep for this cruise, Albert will purchase the food (Sweet Dreams) for the cockpit cookout dinner. Then crew will split the cost of this meal and any add'l common supplies (via Cash, Cash App, Venmo, Zelle)

BYO:

(1) dinner ashore. Bring (3) lunches, (2) breakfasts, preferred beverage(s). Snacks: (with some to share) fruit , vegs , cheese , crackers , chips , pretzels , cookies , baked goods , etc.

Coffee☕️ prepared by the Ship’s Barista (JamesBr. or Alt. Vol.)

Ice & Water: Block ice, cube ice, and drinking water will be provided. Bring refillable insulated water bottle.

Suggested Gear(recommended):

Pack light - for the weather. Bring PFD, foulies, mid-layer, hat(s), sunscreen, insect repellant, swimsuit, towel, float toys, toiletries, medications(AN), change of clothes, change of deck shoes, light sleeping covers (pillow opt.), personal flashlight or headlamp, cell phone, USBa cord or battery pack, personal fan (battery-powered, USBa, or 12v auto plugs available).

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 10 PM on the day before the event.

Sail 250 Blue Angels Airshow and Grill Picnic Daysail (Sunday, June 28, 2026)

Sun, 28 Jun 2026 14:00:00 GMT

Sail 250 Blue Angels Airshow and Grill Picnic Daysail

Sail through the Baltimore Harbor to see the spectacular SAIL 250 ships from the water. Anchor at the Canton Waterfront to watch the Blue Angels Airshow from a unique vantage point on board. Enjoy a grilled picnic dinner and social time with your crewmates. Potluck: bring drinks and a side dish or dessert to share.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

*Skipper Note: Stay up to date on Sail 250 restrictions and guidance and adjust plans as necessary.

Event Start Time

10:00

Event End Time

17:00

1.5 nm to Canton Waterfront Basin

20 minutes of sailing time to destination

0.6 gallons of fuel (round trip)

Shared Costs

BOAT FUEL FUND: Suggested contribution $5 per person

Shared cost for Grilling and supplies on board: roughly $50 per boat = $10 - $12 per person

Cruise Plan

Option 1:

Sail from DSC through Baltimore Harbor, observe Sail 250 boats
Anchor in Canton Waterfront Basin
Grill to prepare cookout lunch/ Potluck: Bring side dish or dessert and drinks to share
Watch Blue Angels Airshow between Noon and 4 p.m. (exact time of show TBD)

Return: Sail back to DSC; arrive at approximately 4:30 pm

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 10 PM on the day before the event.

Cruising Full Strawberry Moon Sail (Monday, June 29, 2026)

Mon, 29 Jun 2026 21:30:00 GMT

Cruising Full Strawberry Moon Sail

Join us for a casual evening sail to catch the full moon out on the water.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

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.