Day 1: Rock Hall is a quaint fishing town and top cruising destination. It offers a bevy of marinas, shops, restaurants and burgeoning artist colony. Overlooking the 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 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. Enjoy fine dining, cultural experiences and exciting nightlife.
Day 3: Sail to Chester River, the second-longest river on the eastern shore. Chestertown has 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: The quiet anchorages of Mill Creek and Whitehall Bay lie between the Chesapeake Bay Bridge and the Severn River. Try the famous Cantler’s Restaurant, known for some of the best steamed crabs in the area.
Day 5: Annapolis is the capital of Maryland, and also considered to be America’s sailing capital. You may dock, anchor, or take a mooring ball in this harbor, then explore the city’s history, quaint streets, shops and restaurants. It’s also home of the US Naval Academy: a must-see.
Day 6: Quaint waterfront village, St. Michael’s sits on a bucolic peninsula. It is an important shipbuilding center especially noted for its Baltimore Clippers – the fastest sailing vessels of their time. Today, the town is a popular yachting center, the site of the Chesapeake Bay Maritime Museum.
Day 7: Sail into the Wye River on the eastern shore. The river’s branches embrace Wye Island with its secluded anchorages – you won’t find supplies or public facilities. Stately old homes, many dating back to colonial times, stand on the banks at every turn.
Day 8: Solomon’s Island is between the Patuxent River and the Chesapeake Bay. Zahniser’s Yachting Center offers a full-service resort marina and boatyard. Centrally located to town, it also features a swimming pool, restaurant, courtesy bicycles, a grocery shuttle and more.
Day 9: Cruise to Deltaville and visit Dozier’s Regatta Point Yachting Center with floating docks, a southern-style clubhouse and courtesy car. Dinghy to Railway Restaurant across the creek from the marina, or drive into town (about 3 miles) to sample other local joints.
Day 10: Ocean Marine Yacht Center is half a mile south of mile marker zero on the Intracoastal Waterway in Portsmouth, VA. This complex features a modern marina. Getting hungry?There are plenty of great restaurants minutes away from the marina.
Day 11: Bay Creek has the perfect blend of elegant homes, great dining, a word-class golf resort, plus a state-of-the-art beach club and fitness center – coastal living at its best. Bay Creek is a true escape and neighbors historic Cape Charles on the Chesapeake Bay, minutes away from Norfolk and Virginia Beach.
Day 12: Chesapeake Bay Marina at the Tides Inn Resort provides the beauty and tranquility of a secluded harbor and the facilities of a world-class destination resort. It’s on Carters Creek, 11 miles from Windmill Point.
Day 13: The channel to Onancock Wharf twists and turns, but it’s plenty deep and easy to follow. There’s no grocery in walking distance, but special arrangements can be made with the harbormaster for transportation. They can provide a list of restaurants in town, where you’ll also find plenty of shops and art galleries.
Day 14: Somers Cove Marina in Crisfield offers a swimming pool, picnic tables, barbecues and golf packages. If you’d like to pick up provisions, there’s a grocery store about a mile away. Excursions at Janes Island State Park and boat trips to Smith Island and Tangier Island are tried-and-true favorites.
Day 15: St. Leonard Creek is one of the most beautiful areas on the Patuxent River. This five-mile-long creek on the river’s north shore features marshes, rolling hills and wooded bluffs. At the mouth of Johns Creek is Vera’s White Sands Beach Club. Decorated with South Sea treasures culled from international voyages, Vera’s is a wonderful marina that welcomes all cruisers.
Day 16: It’s back to Solomon’s Island, a fishing village with numerous dining options, shopping and special events.
Day 17: Sail to Oxford on the eastern shore and bordered on three sides by the Tred Avon River and Town Creek. The friendly community offers a serene, boater-friendly atmosphere and walkable downtown with plenty of shops, restaurants and attractions.
Day 18: Cambridge lies about 13 miles from the mouth of the Choptank River. It was settled in 1684, and is one of the oldest towns in Maryland. Highlights include Richardson Maritime Museum, Meredith House, the Skipjack Nathan, Sailwinds Park, and the Choptank River Fishing Pier. Cambridge Creek offers ample anchorage.
Day 19: Herrington Harbour South and Herrington Harbour North on the western shore of Chesapeake Bay and offers overnight slips, several restaurants and lounges and a wide range of amenities. Make reservations in advance and then dine at Mango’s Bar & Grill for beautiful waterfront dining in a classy but laid-back atmosphere.
Day 20: The quiet anchorage at Galesville in the West River is the perfect penultimate destination for your charter. Spend some well-deserved time relaxing and taking in the natural beauty of the region.
Day 21: Make your way back to base with a sail lasting 5-7 hours – we hope to see you soon!
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