21-Day Day 1: Rock Hall – anchor or marina

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Chesapeake Bay Itinerary


Day 1: Rock Hall – anchor or marina

Rock Hall is a quaint fishing town that sits picturesquely on the eastern shore. As a top cruising destination, it offers a bevy of marinas, interesting shops, a variety of restaurants and a burgeoning artist colony.

Waterman’s Crab House: 410-639-2261 Overlooking Rock Hall Harbor and the Chesapeake Bay, Waterman's Crab House Restaurant and Dock Bar is well-known for its award-winning steamed crabs, jumbo lump crab cakes and barbecued baby-back ribs.

Swan Creek has long been a favorite destination for cruisers because of its rural beauty. Located directly north of Rock Hall harbor, this well-protected creek offers a wonderful place to anchor.

Day 2: Baltimore Harbor – Inner Harbor Marina

The harbor itself is actually the end of the Northwest Branch of the Patapsco River and includes any water west of a line drawn between the National Aquarium in Baltimore and the Rusty Scupper Restaurant. You'll find a variety of things to see and do at Inner Harbor, all within walking distance. Baltimore's Inner Harbor is one of the most visited features of the city. Distinct in function and form, Baltimoreans and visitors alike enjoy Baltimore's Inner Harbor and the surrounding neighborhoods that offer a variety of fine dining, cultural experiences, and exciting nightlife.

Day 3: Chester River

The second-longest river on the Eastern Shore, the Chester River is bordered along much of its shoreline by beautiful, rolling countryside, and lovely estates. Nearly three miles across at its widest point, the Chester gradually narrows to about a quarter mile at Chestertown, with good navigating depths in a well-buoyed channel. Above Eastern Neck Island, the Chester fans out in four generous branches: Gray’s Inn Creek, Langford Creek, the main extension of the Chester that leads to Chestertown and the Corsica River. All are inviting.

Day 4: Mill Creek/Whitehall Bay

This quite little anchorage lies between the Chesapeake Bay Bridge and the Severn River. Be sure to pay attention to the winding, well-marked channel and on once inside you will find good depths for peaceful anchoring along with the famous Cantler’s Restaurant, known for some of the best steamed crabs in the area.

Day 5: Annapolis Harbor - downtown

Annapolis is the state capital of Maryland and is world-renowned as America’s Sailing Capital. You may dock, anchor, or take a mooring ball in this harbor. This small city is full of history, quaint streets with shops and restaurants. Also home of the US Naval Academy, a must see on everyone’s list.

Day 6: St. Michaels - anchor or dock

St Michaels, Maryland is a quaint waterfront village on the Eastern Shore, situated on a picturesque peninsula between Tilghman Island, Easton, and Oxford. Main Street has a lot of little shops and restaurants all walking distance. The Chesapeake Bay Maritime Museum offers the nation's most complete collection of Chesapeake Bay artifacts, visual arts, and indigenous water craft. Higgins Marina - Tons of restaurants to choose from, serving anything you can imagine. The Crab Claw is next door to the marina, and is a great spot for picking crabs while looking out over the harbor.

Day 7: St. Michaels - Wye River on the Eastern Shore

The river—divided into three branches—embraces the Wye Island along 21 miles of shoreline. You won’t find supplies or public facilities anywhere on Wye Island but secluded anchorages and a rich historical heritage are among the charms of the Wye River. The western shore of the Wye River is well developed, but its eastern shore offer more secluded anchorages. On the Wye East, big old houses, many dating back to colonial days, stand on the banks, greeting cruisers at every turn.

Day 8: Solomon’s Island MarinaZahniser’s Yachting Center - Full service resort marina and boatyard. Centrally located to town, swimming pool, restaurant, courtesy bicycles, grocery shuttle and more. There is a courtesy shuttle to Food Lion and CVS for ZYC guests. The Dry Dock Restaurant serves dinner, and brunch on Sundays. The ZYC Pool Bar and Café – serves drinks and light fare. Annemarie Gardens, the Calvert Marine Museum and several wineries are nearby.

Day 9: Deltaville- Dozier’s Regatta Point Yachting Center - has concrete floating docks, a Southern-style clubhouse and a courtesy car. Railway restaurant is across the creek from the marina or you can use the car and town is about 3 miles away.

Day 10: Portsmouth, Va. - Ocean Marine Yacht Center - is located just ½ mile south of mile marker zero on the Intracoastal Waterway on a 19 ½ acre site in Portsmouth, VA; just 15 minutes from the Norfolk/Virginia Beach International Airport. The new complex features a modern marina with all of the amenities, an indoor dry storage building, a complete parts department, and room for boats of all sizes. There are a ton of great restaurants a block away from the marina.

Day 11: Cape Charles - Bay Creek Marina - This is coastal living at its absolute best. Located on 1,729 gorgeous acres at the southwestern tip of Virginia’s Eastern Shore, Bay Creek is a unique community—the perfect blend of beautiful homes, great dining and a word-class golf resort, plus a gorgeous new state-of-the-art Beach Club and Fitness Center.

Here, getting away from it all means getting closer to the life you’ve always imagined—relaxing by the beach, casting off for a day of fishing, or playing golf at the first resort in the United States to feature both Arnold Palmer and Jack Nicklaus Signature® courses. With the completion of the spectacular Beach Club and Fitness Center you can follow a full workout on their state-of-the-art equipment with a refreshing dip in one of the pools. Kids or "kids at heart" can enjoy the 52-foot waterslide and splash pad. Bay Creek is a true escape, yet it neighbors historic Cape Charles on the Chesapeake Bay and is minutes away from Norfolk and Virginia Beach.

Day 12: Tides InnThe Tides Inn - Chesapeake Bay Marina, with new floating docks; provides the beauty and tranquility of a secluded harbor along with the facilities of a world-class destination resort. Located on Carters Creek, 11 miles from Windmill Point, the floating dock marina accommodates up to 24 vessels, ranging from small weekend cruisers to 150-foot yachts. Additionally, our Lodge Marina, located a water taxi ride away from the Tides, provides 36 slips and accommodates boats up to 150 feet.
Day 13: Onancock - Onancock Wharf - ask for the bulkhead. About 5 miles from the “No. 1” marker. The channel in winds a bit, but is deep and easy to follow. No grocery in walking distance but special arrangements can be made with the harbormaster for transportation to nearby grocery. A complete list of 10 or more Onancock restaurants is available at the Harbormaster’s office. There is also public transportation using Star Transit.

Day 14: Crisfield - Somers Cove Marina – At marker R10 or G11 continue 45 degrees towards the water tower. To the port side will be a 2-story city pavilion and condos with a blue roof. To the starboard side with be the H. Glenwood Evans and Son Seafood building. Continue through the channel, and the marina office and fuel dock will be to the port side of the marina. The marina offers a swimming pool, picnic tables, barbecues, and golf packages. Nearby is Janes Island State Park. There are boats to both Smith and Tangier Islands. There is a commuter bus pick-up at the marina gate to the grocery store a mile away.

Day 15: St. Leonard’s Creek - Patuxent River (Anchor or dock at Vera’s)

St. Leonard Creek, about seven miles upriver from Solomons, has been said to be the most beautiful on the Patuxent. This five-mile-long creek is on the river’s northern shore. The shoreline is a mix of marshes, rolling hills and wooded bluffs. At the mouth of Johns Creek is Vera’s White Sands Beach Club. This fanciful place looks like a Polynesian island misplaced on the Chesapeake. Decorated with South Sea treasures culled from international voyages. Vera’s is a wonderful marina that welcomes all cruisers!

Day 16: Solomon’s - Spring Cove Marina - is considered to be one of the finest marinas on the Chesapeake Bay and a perfect family getaway destination.  You will enjoy Spring Cove's pristine, upscale facilities and the friendly, efficient staff. 
Day 17: OxfordCampbell’s Boatyard -The three-boatyard and marina facilities of Campbell's Boatyards offer a complete range of services, from custom boatbuilding, restoration, and repairs to winter dry storage and slip rentals. Since 1993, Campbell's Custom Yachts has been building only the finest custom boats - whether a 31-foot cocktail cruiser or a 42-foot luxury yacht - for those boat owners looking for exceptional quality, construction, and service. The experienced Campbell's crew is on hand to serve you in a friendly, relaxed atmosphere while continually providing the quality craftsmanship and attention to detail that has earned us a reputation for excellence in marine service.
Day 18: Cambridge - Cambridge Yacht Club- There is a very nice restaurant and bar right at the Yacht Club. The town has many nice shops and great restaurants. You can take a cab over to the Hyatt Hotel and get a day pass for the pools. Go to the spa and enjoy food and drinks at the many bars and restaurants.
Day 19: Herrington Harbor South – Entrance into Herrington Harbor is through a well marked but narrow channel on the southern end of Herring Bay. Watch for G1 in Herring Bay for channel entrance. There is a trolley that runs on weekends between Memorial Day and Labor Day for $0.25. Route goes through Chesapeake Beach. They have a nice beach on Herring Bay with canoes, kayaks and other beach toys for rent. There is a fitness center. You can eat at the restaurant right at the marina Mango’s Bar and Grill or you can use many of the grills around the marina and eat on the beach.

Day 20: West River -Galesville / West River Marina town/Rhode River Quiet anchorage off West River

This area offer nice quite anchorage.
Day 21: Return to Port Annapolis Marina.

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