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Annapolis, South

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: Herrington Harbour

Begin by sailing to Herrington Harbour. Herrington Harbour South and sister marina Herrington Harbour North are both located on the western shore of the Chesapeake Bay and offer overnight slips, several restaurants and lounges, and a wide range of amenities. Due to Herrington Harbour South's popularity, it's best to make reservations. We recommend Mango's Bar & Grill for beautiful waterfront dining in a classy but laid-back atmosphere.


Day 2: Oxford

Sail to Oxford, located on the Eastern Shore and bordered on three sides by the Tred Avon River and Town Creek. Oxford's allure is that of a quiet, small town where townspeople make visitors feel like old friends. This community works hard to maintain its serene, boater-friendly atmosphere and boasts a walkable downtown with plenty of shops, restaurants, and attractions.


Day 3: Cambridge

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. The elegant 19th-century homes lining Cambridge's shaded streets hail from a time when the town was an economic and social center-a heritage also proudly preserved in its maritime museums - Richardson Maritime Museum, Meredith House with its Heritage Museum and Gardens, the Skipjack Nathan, Sailwinds Park, and the Choptank River Fishing Pier. Cambridge Creek offers ample anchorage for those looking for a protected spot to relax.


Day 4: St. Leonard Creek

St. Leonard Creek is considered one of the most beautiful areas on the Patuxent River. This five-mile-long creek is on the river's north shore, and features a mix of 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 5:Solomon's Island

Solomon's Island is picturesque island town nestled in the joining of the Patuxent River and the Chesapeake Bay. Once a seafood packing house supported the local economy, but now tourism is its mainstay. Solomon's remains a fishing village as well, alive with work-boats and an active charter fishing fleet, but it also offers numerous dining options, shopping, and special events. Be sure to visit The Tiki Bar, the first completely open air bar in Southern Maryland. The annual opening of the Tiki Bar has become a firmly entrenched tradition, drawing crowds near 10,000. The house drink is the Mai-Tai, but look out - they're strong!


Day 6: 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 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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