Kayaking & Paddleboarding

Annapolis Sailing School

The Annapolis Sailing School now has Stand-up paddle boarding and Kayaking off Bembe Beach for our Keel Boat Club members. This is one of the only shallow water entries for SUP and kayaking in Annapol...

Boating

Annapolis Sailing School

America's oldest and Annapolis' largest sailing school. Learn to sail the "Annapolis Way" with classes for kids and adults of all skills levels. KidShip Sailing is a weekly sailing camp that offers a...

Events & Festivals

Annapolis Spring Sailboat Show

For three days in April, the Chesapeake Bay's thriving marine industry will relocate to City Dock. From sailboats to sails, from St. Michael's to Main Street, the region's favorite retailers exhibit a...

Performing Arts

Annapolis Summer Garden Theatre, Inc.

An outdoor community theatre led by volunteers, ASGT produces musical theatre (featuring live music) each summer at "one of the most unique venues in the area" [BroadwayWorld.com]. Fun, casual, and ne...

Tours

Annapolis Tours by Watermark

Journey into history, culture, and fun year round; enjoy an unforgettable walking tour through historic Annapolis with period dressed guides. Tour the Maryland State House, the grounds of the United S...

Shopping Districts & Malls

Annapolis Towne Centre at Parole

Stroll, shop, savor and mile at the “Centre of it All!” Fabulous stores and a world of fine dining can be found in one spectacular destination, created with your perfect day in mind. Your trip jus...

Shuttle

Annapolis Trolley / Towne Transport

For more than 50 years we have offered mini-coach buses, wheelchair-accessible vans, a modern fleet of air conditioned school buses, air conditioned trolley's, and transportation for any occasion, fro...

Hotels

Annapolis Waterfront Hotel

The Annapolis Waterfront Hotel, located in the heart of downtown, is the city's only waterfront hotel. City Dock, historic sites, dining and nightlife, shopping and the United States Naval Academy ar...

Whole House Rentals

Annapolis-Eastport Vacation Rentals

Long and Foster Annapolis-Eastport offers short term vacation rentals.  Hosts in our program offer families the hospitality of their private homes to guests.  When guests arrive they find a welcomin...

Specialty Shops

Annebeth's

Entertaining gifts. Stop in for a selection of wines under $9.00. Products from Mary Phillips Designs, Tea Forte, Pacifica Candles, Dolfin chocolate, Japanese sushi-ware, Envirosax....

Italian

Arturo's Trattoria

With the opening of Arturo’s Trattoria, chef/owner Arturo Ottaviano brings to Northern Anne Arundel County the same exquisite Italian coastal cuisine that established his flagship restaurant, Osteri...

Events & Festivals

Artwalk

ArtWalk is a community public art project bringing grand scale art to the walls of exterior buildings, using the city of Annapolis itself as an open air gallery. The purpose of ArtWalk, a 501-3c non-...