2024 Sailing Season is coming! See you April 13, 2024!

Parking and Directions

There are no designated parking spots for sailing on the Woodwind.  Annapolis can be very challenging when finding parking, so the following info should be helpful. We have done our best to check rates, but these rates are not guaranteed and should be considered a guideline.

PRIVATE PARKING LOTS, CITY GARAGES, AND EASTPORT STREET PARKING are the only ways to park without a 2-Hour Limit.

All Woodwind cruises are 2-hours or longer.

Street Parking & Metered Parking: All have a limit of two hours. These spots do not allow you to extend the time, you must change the zone that your car is parked in and pay for another spot.

Pay for parking ahead of time and know you have a spot! Spot Hero Annapolis

  Closest Parking Lots:

All less than a half-mile away, and in order of proximity

BLUE PINS (1 – 5) on the Custom Google Map Below.

  1. Annapolis Waterfront Hotel (onsite)- Usually parking at the Hotel is for Hotel Guests only. On weekdays they may have parking available for $16 for four hours, and $30 for the whole day.  Very limited advanced purchases for parking may be available at Spot Hero Annapolis. 
  2. Yacht Basin Parking Lot- The lot on the right-hand side of the Annapolis Waterfront Hotel charges by the day. Space is very limited and prices vary from $20-30 a day.

  3. Green Street Parking Lot (not always available)- If you take a left onto Compromise Street (at the foot of St. Mary’s), on the left before Main Street is the Green Street Parking Lot. A private company runs this lot. Rates vary with demand.
  4. Noah Hillman Garage New Garage Now Open!
  5. Carroll’s Creek/Annapolis City Marina Parking Lot – 410 Severn Ave, Annapolis, MD 21403. Less than a half-mile scenic walk, this lot offers spaces at $4 for the 1st hour, $3 for additional hours with a $24 max for the whole day. You could also walk down to the fuel dock at the Marina and take a Water Taxi for $4 a person to the Annapolis Waterfront Dock.

CUSTOM GOOGLE MAP: We made this up to give you up-to-date info on parking garage rates and info on advanced reservations for parking. Clicking on each PIN will give you info and a link if they have advance reserve parking.  You can also get directions to any of the PINS by clicking them and then going to the arrow on the upper right side of the box. This includes getting directions to the boat from whichever garage you choose, or wherever you are at the time.  There are many other Annapolis City Garages, designated by GREEN PINS, that are more than a half-mile away but accessed by a FREE MAGENTA BUS.

Magenta shuttle busThe Free Magenta Bus is a bus that quickly and efficiently moves individuals from the City’s parking garages around the Central Business District and Westgate Circle to Memorial Circle.

Click here for more detailed info on City Parking Garage Rates.

Reserve Parking at a Garage in Advance

The map above shows the Parking Lots with the FREE MAGENTA BUS ROUTE route (the magenta line) that moves the public from the City’s garages around town. And the ride is FREE! (Whether you park there or not!)

Free parking: In Eastport (the other side of the bridge leading from Compromise Street) there are no residential parking limits. If you see a space on the street, you can take it. No parking on red or yellow curbs. And on Fourth street, there might be signs of how long you can park there. From Eastport, you can walk a short couple of blocks or take a water taxi from Carrol’s Creek Cafe’s Marina Dock or the Chart House Restaurant.

Directions to the Schooner Woodwind


Schooner Woodwinds are docked at the Annapolis Waterfront Hotel.
Address: 80 Compromise Street, Annapolis, MD 21401

Printable Bus Driver Directions
Printable Directions to Schooner Woodwind

Pittsburgh: Route 76E (PA Turnpike) to Route 70S to Route 270S to Route 495E to Route 50E to Rowe Blvd. (Exit 24). (242 Miles)

New York: New Jersey Turnpike to Route 95S to 895S (Harbor Tunnel) to Route 97S to Route 50E to Rowe Blvd. (Exit 24). (220 Miles)

Philadelphia: Route 95S to 895S (Harbor Tunnel) to Route 97S to Route 50E to Rowe Blvd. (Exit 24). (120 Miles)

Baltimore: Route 97S to Route 50E to Rowe Blvd. (Exit 24). (20 Miles)

Richmond: Route 95N to Route 50E to Rowe Blvd. (Exit 24). (136 Miles)

Washington D.C.: Route 50E to Rowe Blvd. (Exit 24). (30 Miles)

From Rowe Blvd:

  • Go to Annapolis towards the Capital
  • Take right onto Northwest St. and around Church Circle.
  • Follow around Church Circle (stay in right lanes)
  • Veer right off Church Circle at Duke of Gloucester St.
  • Follow Duke of Gloucester St., take left onto St. Mary’s St.
  • At the base of this street is Compromise Street and the Annapolis Waterfront Hotel
Annapolis Waterfront Hotel from the water
Water view of the Hotel

Woodwind and “the Waterfront” does not validate or reimburse for parking or parking tickets.

Schooner Woodwind