Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake Bay aboard the Annapolis Sailing Cruise’s Schooner Woodwind classic yachts.

Annapolis Sailing Cruises: Schooner Woodwind

Step aboard the schooners Woodwind or Woodwind II for a two-hour sailing adventure on the Chesapeake Bay. Departing from Annapolis, these classic 74-foot wooden vessels invite you to help raise the sails, take the helm, or simply relax while soaking in stunning views of the Bay Bridge, Thomas Point Shoal Lighthouse, and the marine life and wildlife of the Bay. This Chesapeake Gateways Network Experience, managed by Annapolis Sailing Cruises: Schooner Woodwind, offers an immersive connection to the Bay’s culture, history, and environment through an unforgettable sailing experience.

Each public sail is shaped by the wind, weather, and guest curiosity. Watch ospreys dive for fish, watermen haul in their catch, or clouds hint at changing conditions. As you sail, the crew shares stories about the Chesapeake’s maritime heritage and wildlife.

For visitors of all ages, this is more than a boat ride: it’s a chance to see the Bay from a new perspective. Special themed cruises, like the Monday night History Sail, explore topics from regional geology to historic landmarks. Youth groups and school trips are welcomed with hands-on programs that connect sailing to lessons in ecology, teamwork, and navigation.

As a Chesapeake Gateways Network Experience, Annapolis Sailing Cruises: Schooner Woodwind fosters discovery, stewardship, and a lasting appreciation for the Bay. Visit their website to learn more and plan your trip.

Details

Duration

120 Minutes

Activity

Boat Tour

Annapolis Sailing Cruises: Schooner Woodwind offers multiple cruises with up to four trips daily. Visit their website for more information.

Pets Allowed

No

Activity Fee

Yes

Visit their website for more information on fees for each cruise.

Location

80 Compromise St, Annapolis, MD 21401

Reservations

Yes

Tickets are on sale now. Visit their website for more information.

Season

Spring, Summer, Fall

For the 2026 Season, Annapolis Sailing Cruises: Schooner Woodwind is open from April 11- October 31.

Time of Day

Day, Dawn, Dusk

Accessibility Information

I have a mobility issue, or I am traveling with someone who has a mobility issue, is this cruise suitable?

• The Woodwind boarding ramp is approx 22″ wide with rope handlines on one side (crew members will offer their arms and hands to help guests board). The current tide determines the angle of the ramp (higher tides mean a steeper slope to the ramp). At the end of the ramp, guests must step down (approx -11″) onto the deck.

• The cockpit area provides bench seating with a non-cushioned backrest and an area where guests can brace their legs. This is the most suitable place for guests with mobility and/or stability issues to sit and feel the most secure. In order to access this area, guests must step (or swing legs) over and down approx 13.5″ to the bench and then down to the cockpit floor (approx 16″ down).

• As Schooner Woodwind is a sailboat, she may at times, sail heeled over at an angle of 5-20 degrees from one side to the other. Guests with mobility issues will likely find it difficult to move around the boat and/or keep themselves seated comfortably when the boat is heeling.

• The restrooms (heads) are located below deck – accessed by means of a companionway ladder (about six steps).

Can I bring my mobility aid aboard?

• Most wheelchairs and walkers do not fit aboard the Woodwind without compromising the safety of the boat and/or other passengers aboard. Mobility aids can be left at our Dock Office and retrieved following the cruise. The captain has the authority to determine if it is safe for the other passengers aboard to allow mobility aids aboard.

Are you ADA compliant?

• The vessel configuration does not violate the law. There are no vessel configuration regulations now in place with which to comply.

Please consider all of these factors before deciding to purchase a ticket for a cruise on the Schooner Woodwind. The captain has the right to determine if a specific person with limited mobility will be a danger to other guests aboard due to the current conditions. In such cases that a person is not able to sail, a refund will be provided to this person and one caregiver that stays behind.