D I N I N G

Waterfront scene in Annapolis, Maryland with sailboats docked and historic buildings in the background.
People participate in an outdoor tug-of-war event near a waterfront, with orange and white barricades separating the teams. The setting includes trees with autumn foliage and an American flag in the background.
Aerial view of a waterfront town with houses, docks, and boats on a river. The scene includes lush trees and a clear sky, suggesting a coastal setting. In the background, more boats are visible on the open water.
Boats docked in a harbor with a sunset sky, historic buildings, and calm water.
Aerial view of Annapolis, Maryland, featuring the Maryland State House with a dome, surrounded by historic buildings and trees. The Chesapeake Bay with boats and shoreline are visible in the background under a blue sky.
A busy street parade featuring American and Maryland flags, with a crowd of people on both sides. In the background, there are boats and water visible, suggesting a coastal location.
Street view with the Maryland State House dome in the background, American flag, brick buildings, and a sign for "Mary Land Inn."
Maryland State House dome and façade, Annapolis
Lighthouse on a pier during sunset over a calm Chesapeake Bay
Boats on a busy waterfront with a crowd along the shore, surrounded by buildings and greenery.

  • Annapolis Canoe and Kayak (GREAT FOR THE FAMILY!)
    Only a 12-minute walk. Enjoy some time out on the water renting canoes and kayaks for an hour or the whole week. | 410-263-2303

    Capital SUP
    Offers stand up paddle board (SUP) lessons and guided tours throughout Annapolis. | 410-919-9402

    Naptown Tiki Club
    The first and only tiki boat bar in Annapolis. Fitting up to 16 passengers, this BYOB private floating tiki bar is the best way for friends, families, and colleagues to safely sip, cruise, and celebrate out on the water.

    Pirate Adventures (GREAT FOR THE KIDS!)
    A chance for families to get caught up in a real-life pirate adventure. Be amazed as the crew taps into the wonder of a child’s imagination. Watch your children live life as a pirate as they search for sunken treasure and fire the water cannons. | 410-263-0002

    Schooner Woodwind
    Annapolis Sailing Cruises: Two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, offer a variety of public sailing cruises. Woodwind II was famously seen and used in the movie, “Wedding Crashers”. | 410- 263-7837

    Z Flight Watersports
    Z Flight Watersports brings parasailing to Annapolis!15-minute walk | 305-240-4482

  • Annapolis Walking Tours by Watermark(Downtown Annapolis)
    Period dressed Colonial guides keep U.S. and Annapolis history alive and have been sharing their passion for history and folklore to adults, students, and groups of all types for decades. Enjoy one of their tours whether it be learning about Annapolis’ history, finding spooky ghosts around the town, or admiring the rich architecture that gives Annapolis its charm. | 410-268-7601

    Historic Downtown Annapolis/City Dock
    Filled with many restaurants and shops. A 17-min. walk to the heart of downtown. It is a great place to watch boats of all kinds come in and turn around in ego alley. 

    United States Naval Academy
    Guided walking tours of the USNA are available through the visitor center. 

  • Annapolis Harbour Center
    Retail complex with a small-town feel offering specialty shops, Nordstrom Rack, Harbor Cinema movie theater & an Amish market.

    Annapolis Town Center
    Annapolis Town Center is an entertainment-focused, mixed-use destination where retail and dining happily coexist. Target, Anthropologie, Pottery Barn, Warby Parker, and much more.

A T T R A C T I O N S  &  A C T I V I T I E S

T R A N S P O R T A T I O N

Private Car Service | Driven | 410.562.1070 | drivenmembers.com

Uber and Lyft | Both service Annapolis

Water Taxi | 410.263.0033 or VHF 68