Experience Sail250® from the Water with Watermark
Sail250® Maryland Cruises with Watermark set June 25-28, 2026
Join Watermark as Baltimore hosts one of the largest maritime celebrations in the nation. Sail250® Maryland and Airshow Baltimore is a gathering of international tall ships, military ships, and aircraft celebrating the 250th anniversary of the founding of the United States.
20+ Historic Ships
Baltimore welcomes a fleet of international and U.S. tall ships, historic vessels, and modern military ships to commemorate America’s 250th anniversary. Joining the celebrations will be airshows and flyovers with the Blue Angels, the U.S. Air Force’s F16 Viper demo team, Great Britain’s Red Arrows aerobatics team, The Patrouille de France, and more. Click here to see the lineup of visiting vessels.
Baltimore Sightseeing Cruise
Step aboard for a 45-minute narrated cruise of Baltimore’s Inner Harbor. Discover Charm City’s rich maritime history. Sights include Fort McHenry, the famous Domino Sugar sign, Under Armour headquarters, and more. And keep a lookout overhead for flyovers from any number of flight teams here as part of Sail250 Maryland and Airshow Baltimore.
Sail250 Flyover and Airshows
Sit back and relax on this 90-minute cruise around Baltimore’s and get a water-view of the 20-plus tall ships and military vessels docked here for Sail250 Maryland. Your live narrator will regale you with tales of Baltimore’s maritime history, its shipping industry, and of course the many vessels here commemorating America’s 250. Plus there will be impromptu flyovers throughout the Sail250 Maryland celebration.
Countdown to the 250th Celebration:
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Don’t Miss Your Chance to Cruise Sail250®
Thursday, June 25th 2026
Sail250 Port and Fleet Cruise
- Date: Thursday, June 25
- Time: 10:30 am
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
Sail250 Port and Fleet Cruise
- Date: Thursday, June 25
- Time: 5:00 pm
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
Friday, June 26th 2026
Sail250 Port and Fleet Cruise
- Date: Friday, June 26
- Time: 10:30 am
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
SAIL250 Aerial Show
- Date: Friday, June 26
- Time: 11:45 am
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
Sail250 Aerial Show
- Date: Friday, June 26
- Time: 2:15 pm
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
Sail250 Port and Fleet Cruise
- Date: Friday, June 26
- Time: 4:45 pm
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
Saturday, June 27th 2026
Sail250 Port and Fleet Cruise
- Date: Saturday, June 27
- Time: 10:30 am
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
SAIL250 Aerial Show
- Date: Saturday, June 27
- Time: 11:45 am
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
SAIL250 Aerial Show
- Date: Saturday, June 27
- Time: 2:15 pm
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
Sail250 Port and Fleet Cruise
- Date: Saturday, June 27
- Time: 4:45 pm
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
Naptown Brass Band Cruise
- Date: Saturday, June 27
- Time: 7:00 pm
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
Sunday, June 28th 2026
SAIL250 Port and Fleet Cruise
- Date: Sunday, June 28
- Time: 10:30 am
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
SAIL250 Aerial Show
- Date: Sunday, June 28
- Time: 11:45 am
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
Sail250 Aerial Show
- Date: Sunday, June 28
- Time: 2:15 pm
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
Sail250 Port and Fleet Cruise
- Date: Sunday, June 28
- Time: 4:45 pm
- Location: Baltimore Finger Piers
Order Today. Limited Tickets.
About Sail250® Event & More
Maryland and Baltimore are part of a five-city national event which also includes the ports of New Orleans, Norfolk, New York and Boston. The event offers ship crews, cadets and midshipmen, aviators and, of course, visitors from all over the world to join in an unforgettable experience and a world-class celebration of all things maritime and aviation in commemoration of our Nation’s semiquincentennial.
The Maryland event will feature the return of the U.S. Navy Blue Angels Flight Demonstration Squadron and other aviation performers for an airshow over Baltimore Harbor, flyovers at Baltimore Inner Harbor, and the Open House at Martin State Airport. SAIL250® Maryland Fleet, Flight, and Festival activities will take place at Baltimore’s Inner Harbor, Fells Point, North Locust Point, Baltimore Peninsula, and Martin State Airport.
SAIL250® Maryland & Air Show Baltimore is produced by Living Classrooms’ Historic Ships in Baltimore in partnership with the United States Navy, Maryland Department of Commerce Office of Tourism, City of Baltimore and Baltimore County as well as Sail Baltimore, Air Support, Martin State Airport, United States Coast Guard, and other agencies and organizations.
Sail250® FAQs & Resources
What if we are traveling with a large group?
Watermark welcomes groups of all sizes. While we aren’t offering group discounts for Sail250 Maryland & Air Show Baltimore, groups of 20 or more can save the per-person booking fee by making their reservations with Watermark Group Manager Becky Stokes at 410-268-7601 ext. 200.
Is there a waitlist if an event has already sold out?
If events sell out, we will have a waitlist in the event of cancellations.
Are pets allowed on Watermark cruises?
We love well-behaved, leashed dogs, and they ride free on our regularly scheduled cruises. We ask that owners on our boats clean up after their pets in the event that “nature calls.”
Pets are NOT allowed on our special event cruises including:
- Extended cruises
- Bay Lighthouses Cruise
- Chesapeake Bay Trio Cruise
- Day on the Bay to St. Michaels
- Cruises to festivals in St. Michaels
- Live music cruises
- Baltimore Sunset Cruise with Live Music
- Annapolis Sunset Cruise with Live Music
- TGIF Live Music Cruise
- Any other live music cruise
- Baltimore Sunset Cruise
- Fireworks cruises
- Blue Angels and any air show cruise
- Brunch and dinner cruises
Will the cruise be cancelled for weather or if the aerial show is cancelled?
We will cruise rain or shine; tickets are non-refundable. The Sail250 Maryland & Air Show Baltimore cruises will take place rain or shine. In the event that the aerial shows are cancelled for weather or other reasons, Watermark will still cruise. Tickets are non-refundable.
Are food and drink allowed on board?
All vessels have full-service bars on board. No outside food or beverages are allowed. Please note that Watermark’s vessels are cashless and accept credit card, debit card, and contactless payments.
Where can I park?
Be sure to allow yourself time to find parking and arrive at the dock before for your scheduled departure. Discounted parking is available, space allowing, at the Harbor Court / Royal Sonesta Garage, 30 East Lee Street. Ask the Watermark ticket agent or a Watermark crew member for the discount QR code.