Schooner Woodwind

80 Compromise St., 21401 , Annapolis, MD 21403 USA (Show map)


Woodwind's Boat & Breakfast includes a delightful two-hour sunset sail, overnight stay aboard the 74-foot, wooden Schooner Woodwind and a gourmet breakfast while overlooking the Annapolis Harbor. For $309 (for a couple) including all taxes, you can experience a unique, romantic, and unforgettable overnight stay. The way it works: Enjoy our terrific sunset sail, where you can raise a sail, steer the boat, or just sit back and relax with a cold beverage (we have a cash bar filled with local craft beers, wine and bubbly), When we return to the dock, the captain will go through a 15 minute briefing about staying aboard and how things work aboard a boat and the crew will start putting the boat away for the night. This is the time for a wonderful dinner and excellent restaurants are steps away (not included in price). Woodwind will be waiting for you dockside when you're ready to sleep or to socialize with other guests or the captain, and to relax on deck. Breakfast is served outside, on deck around 8:00-8:30 am. Breakfast consists of a delicious crab and asparagus quiche, fresh berries and yogurt to make a "Woodwind" parfait and the most delicious apple cake on the East Coast. Locally roasted coffee is served almost by sunrise. Check out is 9:30 am. Available Saturday nights only from the first Saturday in May through end of September.



Location Type

Historic town, On the water, Waterfront, Downtown, Small town, Waterview


Baltimore, MD (BWI-Baltimore Washington) 22 miles

Directions to property:

Located in historic Annapolis at the Annapolis Marriott Waterfront Hotel Docks at 80 Compromise Street. Look on our website for the best directions.

Area Attractions

Amusement Park, Antique Shopping, Aquarium, Art Galleries, Beach, Casino, Concert venue, Eco-tourism, Gourmet/Fine Dining, Historical interests, Live Music, Movie Theater, Museum, National/State parks, Nature area, Night life, Ocean, Chesapeake Bay, Historic Buildings, United States Naval Academy, Walking Tours, St. John's College, Sailing/boating center, Outlet Stores, Performing Theater, Picnic area, Religious Services, River, Tours, University, Vineyard, Winery, Zoo

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Inn Details

Establishment type


On-site amenities

CD player, Coffee/Tea facilities, Conference Rooms, Fridge, Library, Parking, Telephone, Wedding Facilities, Wet bar , Includes a 2 hour Sunset Sail, Narrated tour, cash bar filled with local microbrews

Room amenities

Air conditioning, Amenities Basket

On-site activities

Bicycle riding trails, Bird watching, Boating, Restaurant on site, Sailing, Powerboat rentals, Sailing schools, Historic tours, Sailing, Shopping, Sight-seeing

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  • Check In:: 6:00pm
  • Check Out:: 9:30am
  • Open All Year Round: No
  • Smoking Allowed: Outside only
  • Drinking Allowed: Yes
  • Alcohol Provided Yes
  • Suitable For Children: No no children overnight under 16, unless you book three cabins
  • Childcare Provided: No
  • Guest Pets Allowed: No
  • Disabled Access No

Terms and Conditions

  • Accepted payments AMEX, VISA, Discover, Mastercard, Travelers checks, Cash
  • Deposit Amount Required: Paid in full on credit card
  • Cancellations: Once you have booked with a credit card, your stay is charged to your card. If you need to cancel your stay, our policy is if we can rebook your stateroom, then we will refund your account minus a $25 cancellation fee. If we cannot re-book your stateroom, then no refunds are given.
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Ken and Ellen Kaye, and Jennifer Kaye

Languages spoken


Resident Pets

About the innkeepers

The innkeepers are the boat's captains. These captains were selected for their enthusiasm of sailing as well as their attention to safety. The captain of the vessel on the sunset sail will be your host/hostess for the night, so if there is any kind of issue that arises, they are prepared to deal with it. We have four different captains that absolutely love working the Boat and Breakfast and they all look forward to sharing their love for the Bay, sailing and the wonderful town of Annapolis.

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  • Time Served: 8:00 - 9:00 am
  • Serving Location: Outdoors overlooking the harbor, Breakfast/dining area

Special meal options

Low fat , Vegetarian

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