On a boat
Paddle boats, boat tours, sailing and kayaking on Baltimore's Inner Harbor and beyond: pedal a Chessie dragon boat yourself, buy a seat on a cruise, book a whole sailboat, or catch Pride of Baltimore II on the rare day she sails from home. Twelve ways to get on the water for its own sake, not just across it.
Updated Sep 30, 2026 · each stop says the day its sources were read, and what they left unconfirmed
This is for anyone who has walked the Inner Harbor promenade and wanted to be out on the water rather than beside it. Baltimore grew up around its harbor, and there are more ways onto it than the tour boats at the piers suggest: a Chessie dragon paddle boat you pedal yourself, a kayak club, a community sailing school, a pirate ship, dinner afloat, a Baltimore clipper on the rare day she is home, and a quieter arm of the harbor altogether.
The order runs from doing the work yourself to having it done for you. The first three put you in charge of the boat. The next five sell you a seat, ending with the ship worth rearranging a trip for. Then the water gets quieter and the boats smaller: the Middle Branch, a sailboat for six, a yacht with nobody aboard you did not invite. The last stop never leaves the dock, and does not pretend to.
Before you go
- Most of this is an April to October list. The Chessie boats run on through November, the Watermark sunset sailing stops after September, and the Spirit of Baltimore's dinner cruises and Pusser's indoor room are the two you can count on in winter.
- Book ahead for Urban Pirates, City Cruises, Sea Baltimore and Boat Baltimore. Watermark's 45-minute harbor loop is the one you can walk up to and buy at the kiosk on the pier.
- With small children: nobody under two or under 35 pounds goes on the Chessie boats, and Urban Pirates needs a ticket for every rider, infants included, with a 10 percent city amusement tax and a $6 booking fee on top of its prices.
- Parking is sorted for you in three places: free at Port Covington Marina for Boat Baltimore, free on the Museum of Industry campus by the sailing center, and validated at Harbor Court Garage after a City Cruises sailing. For the Inner Harbor boats it is a Pratt, Lombard or Light Street garage; in Fells Point, a meter or the Caroline Street garage.
- 1
Departs Inner Harbor · On the water · $
Chessie Dragon Paddle Boats and Electric Pirate Ships
Start with the cheapest way onto the water for a group: dragon-shaped pedal boats and little solar-charged electric pirate ships, tied up between the Historic Ships at the Inner Harbor piers. The Living Classrooms Foundation runs them as a youth job-training operation, so your half hour does some good as well as some pedaling. A Chessie takes four for $25 a half hour; an electric boat takes six for $40. Everyone wears a life vest, nobody under two or 35 pounds goes aboard, and it runs daily, weather permitting, until late November.
Sources read Sep 18, 2026
Not confirmed: Daily opening and closing times are not published. Accessibility, parking, whether booking is possible in advance. Harborplace demolition starting in Q4 2026 may affect the pier surroundings.
Hours: Daily, April through November, weather permitting; the foundation does not publish daily opening and closing times · full listing
- 2
Departs Fells Point · On the water · $$
Canton Kayak Club
Want to steer for real? This is how people here paddle without owning a boat. It is a kayak share rather than a rental: join, and you get unlimited use of kayaks, paddles and life jackets from a dozen docks around central Maryland, including Bond Street Wharf in Fells Point and The Cove on the Baltimore Peninsula. Orientation comes with the joining fee, training runs mid-April to mid-September, and the season is May to October. Ignore the name: there is no Canton dock anymore. At Fells Point the gangway can be steep at some tides.
Sources read Sep 18, 2026
Not confirmed: Membership pricing is not published on the home page. Age policy, accessibility, per-dock addresses and posted access hours are all unpublished.
Hours: Docks are member-access during the May to October season; no posted hours · full listing
- 3
Departs Federal Hill · On the water · $$$
The Downtown Sailing Center
The same idea under sail, and the one for anyone who has always meant to learn. A nonprofit community sailing center and school on Key Highway, going since 1994 and built so people can sail without owning a boat. Join early: the early-bird rates are less than half the regular ones, Crew at $210 against $600 and Skipper at $475 against $1,100. Member sails run twice a week, April to October, in four-hour daylight slots booked online, but the usable sea breeze only lasts through most of September. Its adaptive program sails Access Dinghies with weighted daggerboards.
Sources read Sep 18, 2026
Not confirmed: Whether non-members can book a one-off day sail, and what it costs, is not published; the About page mentions day sails and private outings but gives no price. Exact season start and end dates.
Hours: Member sails twice a week, April to October; reservations in four-hour daylight slots through the online portal. No walk-up hours published. · full listing
- 4
Departs Fells Point · On the water · $$
Urban Pirates
From here someone else does the sailing. This is the one to take children on, and the only boat here with a costume: a real ship, the Relentless, out of the Ann Street Pier in Fells Point on hour-and-a-half family adventure cruises. Book ahead, buy a ticket for every rider down to infants, and check in on time, because the boat leaves 30 minutes later. It sails in the rain unless the captain calls it off. Thursday and Friday family sailings only run mid-June to September. Without the children, the bring-your-own-grog sailings go as late as 10pm on Saturdays.
Sources read Sep 28, 2026
Not confirmed: Urban Pirates does not state its season start and end dates anywhere on its own site; April to October comes from the Maryland and Visit Baltimore tourism listings, not from the operator. Prices exclude the 10 percent Baltimore City amusement tax and a $6 booking fee. The access answer covers the ship, not the pier approach.
Hours: Family cruises Thu-Sun 10am, 11:30am, 2pm and 3:30pm (afternoons Sat-Sun only; Thu-Fri mid-June to September). Adult B.Y.O.G. Fri-Sat 5:30pm, 7pm, 8:30pm and 10pm (10pm Saturday only). · full listing
- 5
Departs Inner Harbor · On the water · $$
Watermark Baltimore Sightseeing Cruise
The one to do on impulse. Walk up to the kiosk at the Finger Piers on Light Street, and 45 minutes later you have seen how the whole city sits around its water: narrated, with a full bar, past Federal Hill, Locust Point, Canton, Fells Point and Harbor East, and out toward Fort McHenry and the Domino Sugars sign. At $25, or $12 for a child, it is the quickest way to make sense of the neighborhoods. Departures run hourly through the afternoon, and Watermark says most of its boats are wheelchair accessible.
Sources read Sep 18, 2026
Not confirmed: Watermark publishes times per date in its booking calendar rather than as a fixed daily schedule, so the 1pm to 5pm pattern is one sampled date and not a guarantee. Same-day slots close for online sales before departure. Age policy is not published.
Hours: Hourly afternoon departures, 1pm to 5pm on the date sampled; each date's times are published in the booking calendar · full listing
- 6
Departs Inner Harbor · On the water · $$
Watermark Baltimore Sunset Cruise
The same piers and the same operator, at the hour that counts. The Saturday sailing leaves at 6:30pm as the harbor goes gold and comes back at 7:30 with the city switching its lights on while you are still out in it. There is a playlist and a bar for drinks and snacks, and at $36, or $18 for a child, it is the cheapest sunset on this list and the only one sold by the seat. Saturdays only, April through September, and this is the one Watermark cruise that asks you to leave the dog at home.
Sources read Sep 18, 2026
Not confirmed: Watermark publishes each sailing date in its booking calendar rather than committing to every Saturday, so a given week can be unavailable. The Visit Baltimore listing quotes $35 for adults against the $36 on the operator's own page. Age policy is not published.
Hours: Sat 6:30pm to 7:30pm · full listing
- 7
Departs Inner Harbor · On the water · $$$
City Cruises Baltimore and the Spirit of Baltimore
When an hour is not enough, the big boat a few doors along at 561 Light Street makes a whole evening of it. The Spirit of Baltimore's Signature Dinner Cruise boards at 6:30 for 7pm on Friday and Saturday, an hour earlier other nights, and stays out two and a half hours, with a buffet and a live DJ. The decks are enclosed, so it sails year round: this is the winter answer. The lighter option is the harbor tour, an hour past the Constellation, Fells Point, the National Aquarium and the Liberty Ship John W. Brown, March to October. Dinner starts from $123, the tour from $27.
Sources read Sep 28, 2026
Not confirmed: Fares move with the date and only settle in the booking calendar; the pages print a starting price, from $123 for the dinner cruise and from $27 for the harbor tour. Which of the Baltimore boats and decks are accessible is not published. Reservations are effectively required.
Hours: Signature Dinner Cruise: Friday and Saturday board 6:30pm, cruise 7 to 9:30pm; Sunday to Thursday board 5:30pm, cruise 6 to 8:30pm, on the dates in the booking calendar. Harbor Tour: one hour, Friday to Sunday and select dates, March to October. Lunch, brunch, happy hour and after-dark dance cruises run on published dates. · full listing
- 8
Departs Inner Harbor · On the water · $$
Pride of Baltimore II
The one worth rearranging a trip for. Pride of Baltimore II is a reproduction Baltimore clipper and the state's sailing ambassador, and she is rarely home: most of her season goes to grant-funded Chesapeake sailing and multi-week port calls in places like Havre de Grace, Cambridge and Chestertown. When she is here she sells public day sails from Constellation Pier 1, at $55, or $25 for twelve and under, and any date we hold is in the list of what is on soon at the foot of this guide. If one lands while you are in town, take it.
Sources read Sep 18, 2026
Not confirmed: Whether more Baltimore dates will be added. The operator states dates, times and locations are subject to change. Accessibility and age minimums.
Hours: By published sail date only; the October 10, 2026 Baltimore day sail runs 4-6pm · full listing
- 9
Departs Middle Branch Park · On the water · $
Canoe and kayak programs at Middle Branch Park
The Middle Branch is the quieter arm of the harbor below the Hanover Street bridge, a different piece of water from the Inner Harbor entirely, and the one place on this list where you see the city from underneath rather than from the promenade. The city runs canoe and kayak programs and guided tours from Middle Branch Park, or you can put your own boat in. The limit is the calendar: the city publishes no days, times or prices, only that paddling here is a warm-weather thing. Bring your own kayak and the park is open daily.
Sources read Sep 20, 2026
Not confirmed: Days, times, prices and how to register. The city's page says the programmes exist and the Rowing and Water Resource Center runs them, and publishes none of the detail, so ring before traveling. Times quoted elsewhere online do not appear on any city page.
Hours: By the programme rather than by posted hours; the park itself is open daily · full listing
- 10
Departs Fells Point · On the water · $$$
Sea Baltimore Sunset Sail
For a proper sail without learning to sail, go back to Fells Point: two and a half hours on a 46 foot Hunter that takes six guests, picking up at Broadway Pier, with local craft beer and wine aboard. Six is small enough that the trip bends to whoever is on it rather than running to a script, and two and a half hours is long enough to get well out of the harbor and back. This is the one to book first and build the day around, because dates and prices only show in the operator's booking calendar.
Sources read Sep 18, 2026
Not confirmed: Sea Baltimore keeps prices and departure times inside its booking widget and publishes neither on the page, so the $$$ band is an estimate. Season, days of the week and accessibility are not published, and the pickup is given as Broadway Pier with no street address or dock number.
Hours: Published per date in the operator's booking calendar; no fixed weekly times · full listing
- 11
Departs Port Covington · On the water · $$$
Boat Baltimore Private Sunset Cruise
The whole boat rather than a seat on it, and the one for a birthday or an anniversary. Two hours on a 45 foot sailing yacht out of Port Covington Marina, capped at six, with a captain and crew doing the work. It starts at $299 for two, then $69 for each extra adult and $35 for a child under 12, so a full boat splits to about the price of a nice dinner. Sparkling wine is included, you bring the rest with no corkage and you pick the music. There is a restroom aboard and the parking is free.
Sources read Sep 18, 2026
Not confirmed: Boat Baltimore's home page gives 2121 Aliceanna St as its address while the cruise page and the Visit Baltimore listing both put departures at Port Covington Marina, 321 E Cromwell St. The home page's 'departing from Baltimore Peninsula' matches Port Covington, which is the same place under its newer name. The home page also advertises that kids sail free, which the $35 child rate on this cruise contradicts. Season dates come from the Visit Baltimore listing for the 2025 season rather than from the operator, and departure times are not published anywhere.
Hours: Booked by time slot through the operator, which advertises four departures a day; times are not published · full listing
- 12
Departs Canton · On the water · $$
Pusser's Landing
End on the water without going anywhere, which after a day out is sometimes the point. Canton had no working waterfront restaurant for two years after Bo Brooks closed in 2023, until Pusser's moved up from Annapolis into the space at Lighthouse Point Marina in July 2025, with a 104-seat floating dock bar attached. If you came by boat, pull up and tie off: patrons get two hours of free docking. It opens at noon Wednesday to Sunday and stays to 11pm on Friday and Saturday. The building is open year round; the dock bar keeps no published season.
Sources read Sep 18, 2026
Not confirmed: Whether the floating dock bar closes for winter. Age policy, accessibility, reservations policy.
Hours: Mon-Tue 3-10pm; Wed-Thu 12-10pm; Fri-Sat 12-11pm; Sun 12-10pm · full listing
