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Annapolis, North

7 day Boat Charter Cruising Program


Before embarking, seeing the sights of Annapolis is a must. Stroll down to “Ego Alley” at Annapolis Harbor, and then grab a sandwich at Chick & Ruth’s Delly on Main Street. Visit the Maryland State House – the oldest state capitol in continuous legislative use topped by the largest wooden dome in the nation. The Chesapeake Bay takes its name from a Powhatan word, “Chesepioc,” or “Great Shellfish Bay.” The French founded Annapolis as a settlement called Port Royal in 1605, and Captain John Smith became the first European to explore and thoroughly map the Chesapeake Bay in 1609, writing in his journal that “heaven and earth have never agreed better to frame a place for man’s habitation.” With so many delightful creeks, coves, rivers, towns and villages to visit, Annapolis makes for a dream sailing vacation.




Day 1: Rock Hall

Rock Hall is a quaint fishing town and top cruising destination. It offers a bevy of marinas, shops, restaurants, and has a burgeoning artist colony. Overlooking Rock Hall Harbor and the Chesapeake Bay, Waterman's Crab House is well-known for its award-winning steamed crabs, among other delights. 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

Baltimore Harbor includes any water west of 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. Locals and visitors alike can't get enough of the fine dining, cultural experiences, and exciting nightlife.


Day 3: Chester River

Sail to Chester River, the second-longest river on the Eastern shore. The Chester is bordered along much of its shoreline by rolling countryside and grand estates. Nearly 3 miles across at its widest point, the river gradually narrows to about a quarter mile at Chestertown, with good navigating depths in a well-buoyed channel. Beyond Eastern Neck Island - which features a wildlife refuge - the Chester River fans out in four generous branches, all of which are inviting.


Day 4: Mill Creek and Whitehall Bay

The quiet anchorages of Mill Creek and Whitehall Bay lie between the Chesapeake Bay Bridge and the Severn River. Be sure to pay attention to the winding, well-marked channel. Once inside, you'll find good depths for peaceful anchoring and with the famous Cantler's Restaurant, known for some of the best steamed crabs in the area.


Day 5: St. Michael

Another quaint waterfront village, St. Michael's sits on a bucolic peninsula. It became an important shipbuilding center especially noted for its "Baltimore Clippers" - the fastest sailing vessels of their time. Today, the town is better known as a popular yachting center, and the site of the Chesapeake Bay Maritime Museum. The museum houses the largest collection of Chesapeake Bay artifacts, visual arts, and indigenous water craft.


Day 6: Wye River

Sail into the Wye River on the Eastern shore. The river's branches embrace Wye Island along 21 miles of shoreline. You won't find supplies or public facilities anywhere on the island. Secluded anchorages and a rich historical heritage are the main attraction. Stately old homes, many dating back to colonial times, stand on the banks at every turn.

Day 7: Annapolis Bay

It'll take about 5 to 7 hours to sail back to Annapolis Bay Charters, giving you plenty of time to cement the beautiful scenery in your memory. But don't worry - the Chesapeake will always welcome you back!



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