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 $299 (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 and when we return to the dock, excellent restaurants are steps away for dinner (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 around 8:30 am, and checkout is at 9:30 am. Ask about our combo cruises with our special events. 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


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, Concert venue, Gourmet/Fine Dining, Historical interests, Live Music, Movie Theater, Museum, National/State parks, Nature area, 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, Vineyard, Winery, Zoo

Inn Details

Establishment type


On-site amenities

CD player, Conference Rooms, Copier, Fax Machine, Library, 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 rental, Bicycle riding trails, Billiards, Bird watching, Boating, Canoeing, Fishing, Golfing, Kayaking, Restaurant on site, Sailing, Powerboat rentals, Sailing schools, Historic tours, Sailing, Shopping, Sight-seeing, Swimming, Tennis courts, Tennis racket rental, Water sports

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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.



Ken and Ellen Kaye, and Jennifer Kaye

Languages spoken


About the innkeepers

The innkeepers are the boat owners. The couple were public school teachers in Connecticut before pursuing their dream to own and operate this sailing yacht. They taught instrumental music and art. Jennifer, their daughter took a semester at sea in college and urged them to pursue this new venture.

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

Special meal options

Low fat , Vegetarian