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Annapolis Waterfront Activities: Enjoy the Best of the Bay

Annapolis Waterfront

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Welcome to the Annapolis Waterfront Activities guide! Annapolis, the sailing capital of the United States, offers a myriad of activities by the water. Whether you’re an adventure seeker or looking for a relaxing day by the bay, this guide covers everything you need to know about enjoying the Annapolis waterfront

Why Annapolis Waterfront is a Must-Visit

Annapolis, Maryland, boasts a stunning waterfront along the Chesapeake Bay, blending historical charm with modern attractions. The waterfront is the heart of the city, bustling with maritime activities, scenic views, and vibrant local culture. Let’s dive into the top activities you can enjoy at the Annapolis waterfront.

Sailing in Annapolis: The Sailing Capital

Annapolis Sailing Cruises: Annapolis Sailing Cruises has been operating since 1959 and offers daily trips, including sunset sails and private charters. The knowledgeable crew and stunning views make it an unforgettable experience.

Kayaking and Paddleboarding: Up Close with Nature

Kayak Annapolis

Explore the scenic waterways of Annapolis with Kayak Annapolis. Guided tours take you through the city’s creeks and coves, offering a unique perspective on the local wildlife and historic sites.

annapolis canoe and kayak

Stand Up Paddle Annapolis: Paddleboarding is a popular activity at the Annapolis waterfront. Stand Up Paddle Annapolis provides rentals and lessons, making it easy for beginners to get started. Paddle along the peaceful waters and enjoy a fun workout.

stand up paddle annapolis

Fishing: A Relaxing Day by the Water

Fishing Charters: Annapolis offers numerous fishing charter services, such as Fish-Finders Charters and Chesapeake Bay Sport Fishing. These charters provide all the necessary gear and guidance for a successful day on the water.

Public Fishing Piers: For a more laid-back experience, try fishing from one of Annapolis’s public fishing piers. The Annapolis Maritime Museum pier is a popular spot, offering easy access and beautiful views. Jonas and Anne Catherine Green Park has some of the splendid views and offerings for peaceful personal quality time.

Chesapeake Bay Fishing Reports: Before heading out, check the Chesapeake Bay fishing reports for the latest information on fish activity and best spots. This ensures you have the best chance of making a great catch.

Dining by the Water: A Culinary Delight

Chart House: Located at the end of Second Street, Chart House offers stunning waterfront views and a menu featuring fresh seafood and prime steaks. It’s the perfect spot for a romantic dinner or a special occasion.

Pusser’s Caribbean Grille: Enjoy Caribbean-inspired cuisine and tropical drinks at Pusser’s. The outdoor deck provides a relaxed atmosphere with beautiful views of the harbor.

Iron Rooster: For a delicious brunch with a view, head to Iron Rooster. Known for its all-day breakfast and creative dishes, it’s a favorite among locals and visitors alike.

Historic Tours and Museums: A Glimpse into the Past

Annapolis Maritime Museum: Discover the maritime history of Annapolis at this interactive museum. Exhibits focus on the Chesapeake Bay’s ecology and the city’s rich nautical heritage.

Historic Annapolis Harbor Tours: Take a guided tour of the Annapolis Harbor and learn about the city’s history and landmarks. These tours are both educational and scenic, providing a comprehensive view of the area.

Thomas Point Shoal Lighthouse Tour: Visit one of the most iconic lighthouses on the Chesapeake Bay. The tour includes a boat ride to the lighthouse and a guided tour of its interior, offering a fascinating look at maritime history.

Boat Rentals and Cruises: Explore at Your Own Pace

Annapolis Electric Boat Rentals: Rent an electric boat and explore the waters at your leisure. These boats are easy to operate and provide a quiet, eco-friendly way to enjoy the bay.

Watermark Cruises: Offering a variety of cruises, Watermark provides everything from historical tours to cocktail cruises. Their fleet of well-maintained vessels ensures a comfortable and enjoyable experience on the water.

City Dock Boat Rentals: For a more traditional boating experience, City Dock offers a range of boat rentals, including powerboats and sailboats. Spend a day on the water and take in the sights at your own pace.

Sunset Cruises: A Magical End to the Day

Schooner Woodwind: Experience the beauty of the Chesapeake Bay at sunset aboard the Schooner Woodwind. This two-hour cruise includes stunning views, a relaxing atmosphere, and the chance to help hoist the sails.


What are the best Annapolis waterfront activities?

Sailing, kayaking, paddleboarding, fishing, and dining by the water are among the top activities.

Can beginners enjoy sailing in Annapolis?

Yes, there are various programs and cruises available for all skill levels, including the US Naval Academy Sailing Programs.

Where can I rent boats in Annapolis?

Annapolis Electric Boat Rentals, Watermark Cruises, and City Dock Boat Rentals offer a range of options.

Are there guided tours available on the Annapolis waterfront?

Yes, historic harbor tours and lighthouse tours are popular options for learning about the area’s history and landmarks.

What dining options are available by the waterfront?

Chart House, Pusser’s Caribbean Grille, and Iron Rooster are some of the top waterfront dining spots.

Is fishing popular in Annapolis?

Yes, fishing charters and public fishing piers offer great opportunities for anglers of all levels.


The Annapolis waterfront is a vibrant hub of activity, offering something for everyone. Whether you’re an avid sailor, or simply looking to relax and enjoy the scenery, you’ll find plenty of ways to enjoy your time by the water. Use this Annapolis Waterfront Activities guide to plan your visit and make the most of what this charming city has to offer.


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