Cruising Itinerary: Baltimore, MD, to Tangier, VA

The Chesapeake Bay is a spectacular cruising ground covering more than 64,000 square miles along the Mid-Atlantic and home to 150 major rivers and streams. The Chesapeake region offers tons of options for boaters from urban areas like Baltimore and Washington, D.C., to smaller historic towns like Oxford and St. Michaels. The vibrant tiki bars, fresh seafood, historic sites and waterfront events will keep you busy.

‍

‍

Starting Point: Baltimore, MD

Harbor East Marina

The best of Baltimore is located just steps off the docks in the upscale Harbor East neighborhood. Within walking distance of the marina, enjoy fine-dining restaurants, world-class hotels, hip lounges, quaint pubs and shopping. Guests can also walk to the Inner Harbor and nearby Fell’s Point and Little Italy neighborhoods. Plan your visit around an Orioles game at Camden Yards or Trawlerfest boat show held each fall at the marina.

WHAT TO DO

The waterfront promenade is ideal for jogging, biking, or strolling the pier for picturesque harbor views. Discover sea wonders and scientific marvels at attractions including the National Aquarium and Maryland Science Center or just steps from the marina catch a movie at the newly renovated Harbor East Cinemas. Harbor East beckons shopaholics with its array of upscale boutiques, including renowned names like Sassanova and Madewell.

Restaurant Recommendations: Upscale restaurants include Loch Bar, The Bygone and Maximón located directly next to the marina. Also nearby: Ouzo Bay, Azumi, Cinghiale

‍

‍

Leg 1: Baltimore to Annapolis, MD

Estimated Mileage: 28 NM

As the city of Annapolis boasts the title of both Maryland state capital and U.S. sailing capital, this historic waterfront is a premier destination on the bay. Cruise Spa Creek to Ego Alley and dock at Annapolis Town Dock marina located in the heart of downtown.

Where to Dock

Annapolis Town Dock

The marina is a 220-foot strip of alongside dockage at the end of Ego Alley, one of the best places to boat and people watch. Keep an eye out for many special events such as the annual Blue Angels flyover in May or the Annapolis Powerboat and Sailboat Shows in October.

WHAT TO DO

Slowly tread Ego Alley’s narrow waterway and admire the impressive array of boats along City Dock’s promenade or take a short stroll up to West Street to find shops and historic attractions. Head over the bridge to the quiet Eastport neighborhood to enjoy relaxing restaurants or visit the Annapolis Maritime Museum. Rent a paddleboard or kayak and explore the calm waters of Spa Creek, which flows adjacent to Town Dock. Set sail on a local sunset cruise or charter rental and watch the sky transform into a palette of vibrant colors.

Restaurant Recommendations: For fresh seafood, dock and dine at Choptank located on-site at the marina, or nearby at Chart House, Carrol’s Creek Café or Boatyard Bar & Grill

‍

‍

Leg 2: Annapolis to St. Michaels, MD

Estimated Mileage: 25 NM

This charming Eastern Shore town is a boater’s favorite along the bay. Walk the red-brick sidewalks along the picturesque streets of St. Michaels to see Victorian homes and shops and restaurants. The Chesapeake Bay Maritime Museum (CBMM) is a local staple with exhibits, restored vessels, hands-on boatbuilding workshops and events.

WHERE TO DOCK

St. Michaels Marina

This facility offers 55 transient slips for vessels up to 220 feet and amenities, including fuel and pool access, and is within walking distance to shopping and restaurants.

WHAT TO DO

Enjoy scenic river tours aboard Patriot Cruises to see waterfowl and historic estates along the Miles River. The St. Michaels Harbor Shuttle will take you on a tour of the waterfront, or rent kayaks or SUP boards to venture down local harbors and creeks. In addition to exploring exhibits, events and workshops at CBMM, do not miss the Thursday night summer concert series held in Muskrat Park, next to the marina. Stroll along Talbot Street where you’ll discover an array of distinctive shops owned by welcoming locals.

Restaurant Recommendations: Foxy’s Harbor Grille, the Bistro, Ava’s Pizzeria & Wine Bar, Theo’s Steaks

‍

‍

Leg 3: St. Michaels to Oxford, MD

Estimated Mileage: 33 NM

Founded in 1683, Oxford is one of the oldest towns in Maryland. The charming, tree-lined village is a quiet antidote to the hustle and bustle of city life. For the most efficient route, cruise through Poplar Island straits and Knapps Narrows. The Oxford Market’s local convenience store is the only spot in town to buy any essentials for provisioning.

WHERE TO DOCK

Safe Harbor Oxford

This marina offers transient slips for vessels up to 120 feet with amenities including a ship’s store, fuel and marine services, plus complimentary pump-out and Wi-Fi.

WHAT TO DO

Visit notable landmarks such as the Grapevine House, a historic home dating back to the 18th century. Book charter fishing trips led by experienced captains who know the best spots along the Tred Avon River. Delve into Oxford’s history and learn about the role the town played in American maritime commerce. Sift through artifacts at The Oxford Museum, embark on a self- guided tour of old-fashioned homes and establishments, or take a ride on the oldest ferry on the Bay, the Oxford-Bellevue Ferry, operating since 1683!

Restaurant Recommendations: Doc’s Sunset Grille and the 300-year-old Robert Morris Inn

‍

‍

Leg 4: Oxford to Solomons Island, MD

Estimated Mileage: 26 NM

Solomons Island is the perfect weekend getaway along the western shore of the Chesapeake Bay. Situated on the Patuxent River, several landmarks and attractions showcase the island’s rich maritime heritage.

WHERE TO DOCK

Harbor Island Marina

This marina boasts over 100 slips for boats up to 65 feet. Amenities include a DIY boatyard, clean showering facilities, a lounge, cable, Wi-Fi and a gift shop filled with fun knickknacks to remember your stay on the island.

WHAT TO DO

Enjoy the beauty of the Patuxent River as you cruise the island in your own boat or a local rental. Book a fishing charter from Harbor Island Marina and try your luck at catching striped bass, bluefish, perch and other species abundant across the bay. Take a leisurely stroll around the island or visit shops, art galleries and historic sites like Drum Point Lighthouse and the Annmarie Sculpture Garden.

Restaurant Recommendations: Sip and savor island charm at The Tiki Bar & Grill with tropical décor and live music or The Lighthouse Restaurant and Dock Bar offering a cozy ambience.

‍

‍

Leg 5: Solomons to Tangier, VA

Estimated Mileage: 43 NM

Home to working watermen who rise before dawn to go crabbing and oystering, this hidden gem represents true Chesapeake Bay culture. With a total population of about 400 and a unique dialect, most locals can trace their ancestry back to a handful of families. Daley & Sons is the only grocery store on the island.

WHERE TO DOCK

Parks Marina

Parks Marina is just across the harbor channel from the many crabbing shacks built on stilts along the shore. The marina offers 25 slips and guest showers.

WHAT TO DO

Embark on island boat tours to discover the region’s stunning natural landscapes and maritime culture. Experience the traditional Chesapeake pastime of crabbing and witness skilled watermen as they unload their catches, providing a glimpse into the island’s iconic heritage and close-knit community. Visit landmarks like the Tangier History Museum or beachcomb serene shores where you can search for sea glass, shells and arrowheads.

Restaurant Recommendations: Lorraine’s, Muddy Toes Cafe, Four Brothers Crab House & Ice Cream Deck