By Jenna Dolch

Nothing says summer in Maryland quite like pulling up to a dock, stepping off the boat and settling in for fresh seafood and waterfront views. Whether you’re arriving by water or simply looking for a memorable meal overlooking the Chesapeake Bay, Maryland’s waterfront restaurants deliver unbeatable scenery, local seafood and plenty of maritime charm. Add in a sailing excursion, harbor cruise or waterfront museum, and you’ve got the perfect Chesapeake Bay day trip. 

Key takeaways

• The bigger picture: Maryland is home to some of the East Coast’s best dock-and-dine destinations. 
• The details: Many waterfront restaurants offer transient slips and marina access for boaters. Visitors can pair waterfront dining with sailing trips, harbor cruises and maritime attractions. 
• The more you know: From Annapolis to the Eastern Shore, waterfront restaurants showcase the best of Chesapeake Bay living. 

Skipper’s Pier Restaurant & Dock Bar 

Located on Rockhold Creek in Deale, Skipper’s Pier has long been a favorite among Chesapeake Bay boaters. The restaurant combines marina views, dock access and a menu packed with Maryland seafood favorites, including crab cakes, oysters and fresh fish. Its spacious outdoor deck provides front-row views of boats cruising through the creek, making it one of the region’s classic dock-and-dine destinations. 

• Address: 6158 Drum Point Road, Deale 
• Hours: Noon-9 p.m. Tuesday-Thursday; 11 a.m.-9 p.m. Friday-Saturday; 11 a.m.-8 p.m. Sunday; 3-9 p.m. Monday  
• Phone: (410) 867-7110 

Chesapeake Inn Restaurant & Marina 

Overlooking the historic C&D Canal in Chesapeake City, Chesapeake Inn offers one of Maryland’s most unique waterfront dining experiences. The restaurant features marina access, outdoor decks and panoramic views of both recreational boat traffic and massive commercial ships traveling through the canal. The lively atmosphere, waterfront setting and varied menu make it a popular stop for both boaters and road-trippers. 

• Address: 605 2nd St., Chesapeake City 
• Hours: 11 a.m.-9 p.m. Monday-Thursday; 11 a.m.-11 p.m. Friday-Saturday; 10 a.m.-9 p.m. Sunday  
• Phone: (410) 885-2040 

Libbey’s Coastal Kitchen & Cocktails 

Situated within Bay Bridge Marina on Kent Island, Libbey’s pairs upscale coastal dining with spectacular Chesapeake Bay views. Boaters can dock just steps from the restaurant, while land-based visitors enjoy panoramic views of the Bay Bridge and passing vessels. The spacious waterfront patio makes it one of the Eastern Shore’s most popular spots for sunset dining. 

• Address: 357 Pier One Road, Stevensville 
• Hours: 11 a.m.-9 p.m. daily 
• Phone: (410) 604-0999 

The Choptank 

Located directly on Annapolis Harbor’s famed Ego Alley, The Choptank offers one of the best waterfront dining locations in Maryland. Guests can watch sailboats, yachts and water taxis glide through the harbor while enjoying seafood, cocktails and harbor views. Its lively atmosphere and prime downtown location make it a favorite stop before exploring Annapolis on foot. 

• Address: 110 Compromise St., Annapolis 
• Hours: 7 a.m.-11 p.m. Sunday-Thursday; 7 a.m.-2 a.m. Friday-Saturday  
• Phone: (443) 808-1992 

Foxy’s Harbor Grille 

A longtime St. Michaels favorite, Foxy’s Harbor Grille delivers a laid-back Eastern Shore atmosphere complete with dock access, tropical drinks and waterfront views of the Miles River. Visitors often arrive by boat before spending the afternoon exploring downtown St. Michaels. The colorful waterfront setting captures everything people love about Maryland’s boating culture. 

• Address: 125 Mulberry St., St. Michaels 
• Hours: 11 a.m.-8 p.m. Sunday-Thursday; 11 a.m.-9 p.m. Friday-Saturday 
• Phone: (410) 745-4340 

The Jetty Restaurant & Dock Bar 

Located in Kent Narrows, The Jetty combines fresh seafood, steamed crabs, live music and direct waterfront access. Its location along one of Maryland’s busiest boating corridors makes it a favorite stop for both locals and visiting boaters. Outdoor seating overlooks the water and provides plenty of opportunities to watch boats pass throughout the day. 

• Address: 201 Wells Cove Road, Grasonville 
• Hours: 11 a.m.-midnight Monday-Wednesday; 11 a.m.-1:30 a.m. Thursday-Friday; 8 a.m.-1:30 a.m. Saturday; 8 a.m.-12:30 a.m. Sunday  
• Phone: (410) 827-4959 

Dock of the Bay 

Tucked away in Sparrows Point, Dock of the Bay is one of the Baltimore area’s hidden waterfront gems. The restaurant sits directly on the water and welcomes visitors arriving by either car or boat. With expansive Chesapeake Bay views, a relaxed atmosphere and regular live entertainment, it’s easy to spend an entire afternoon enjoying the scenery. 

• Address: 9025 Cuckold Point Road, Sparrows Point 
• Hours: 11 a.m.-9 p.m. Tuesday-Wednesday; 11 a.m.-11 p.m. Thursday-Saturday; 8:30 a.m.-8 p.m. Sunday; 3:30-9 p.m. Monday  
• Phone: (410) 477-8100 

Waterfront experiences worth pairing with dinner 

A waterfront meal is only part of the experience. Maryland’s maritime attractions, harbor cruises and sailing excursions make it easy to turn dinner into a full day on the water. 

Chesapeake Bay Maritime Museum 

Located in St. Michaels, the Chesapeake Bay Maritime Museum is one of the state’s most beloved waterfront attractions. Visitors can tour historic vessels, explore waterfront exhibits and learn about the region’s rich maritime heritage. The museum’s waterfront campus offers beautiful views of the Miles River and serves as a perfect complement to a day of dockside dining. 

• Address: 213 N. Talbot St., St. Michaels 
• Hours: 10 a.m.-5 p.m. daily 
• Phone: (410) 745-2916 

Watermark Annapolis Harbor Cruises 

Watermark’s sightseeing cruises offer one of the best ways to experience Annapolis. Narrated harbor tours provide views of the U.S. Naval Academy, historic homes and bustling waterfront activity while sharing stories about the city’s maritime history. A harbor cruise followed by dinner along Ego Alley makes for a quintessential Annapolis day. 

• Address: 1 Dock St., Annapolis 
• Hours: 8:30 a.m.-5 p.m. Monday-Friday  
• Phone: (410) 268-7601 

St. Michaels Harbor Shuttle 

Part water taxi and part sightseeing tour, the St. Michaels Harbor Shuttle gives visitors a unique perspective of one of Maryland’s most picturesque waterfront towns. Cruises highlight local history, waterfront homes and Chesapeake Bay wildlife while providing beautiful views of the harbor and surrounding waterways. 

• Address: Mulberry St., St. Michaels 
• Hours: Noon-9 p.m. Monday-Thursday; noon-10 p.m. Friday; 9 a.m.-10 p.m. Saturday; 9 a.m.-9 p.m. Sunday 
• Phone: (410) 819-9606 

Sail Selina II 

For those seeking a true Chesapeake Bay sailing experience, Sail Selina II offers public sails and private charters departing from St. Michaels Harbor. Guests can relax aboard a historic sailing vessel while taking in views of the Miles River and open Bay waters. Sunset sails are especially popular during the warmer months. 

• Address: 100 N. Harbor Road, St. Michaels 
• Hours: 9 a.m.-9:30 p.m. daily 
• Phone: (410) 849-9864 

Annapolis Canoe & Kayak 

For a more active adventure, Annapolis Canoe & Kayak offers kayak and paddleboard rentals that allow visitors to explore Spa Creek, Back Creek and portions of the Chesapeake Bay. Paddling through Annapolis provides a unique view of the city’s waterfront restaurants, sailboats and historic architecture. 

• Address: 311 Third St., Annapolis 
• Hours: Seasonal hours vary 
• Phone: (410) 263-2303