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Day 1: Sail 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. Note that due to Herrington Harbour South’s popularity, it’s best to reserve a slip in advance. Call to book one early. After you dock, head to Mango’s Bar & Grill which offers beautiful waterfront dining in a classy yet casual atmosphere.

Day 2: Sail to Oxford

Oxford is located on the Eastern Shore and bordered on three sides by the Tred Avon River and Town Creek. Oxford’s allure is the quiet small town where townspeople make visitors feel like old friends. Oxford works hard to maintain its serene, boater-friendly atmosphere and boasts a small, easily walkable downtown with enough shops, restaurants, and attractions to satisfy any visitor.

Day 3: Sail to Cambridge

Cambridge lies about 13 miles up-river from the mouth of the Choptank River. Cambridge is the county seat of Dorchester County, Maryland. Settled in 1684, Cambridge 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. Town attractions include several museums (Brannock Maritime Museum, Richardson Maritime museum, and Meredith House), the Skipjack Nathan, Sailwinds Park, and the Choptank River Fishing Pier. Cambridge Creek offers ample anchoring room for those looking for a protected spot to relax.

Day 4: Sail to St. Leonard’s Creek

St. Leonard Creek, about seven miles upriver from Solomons, has been said to be the most beautiful on the Patuxent River. 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 5: Sail to Solomons Island

Solomons Island is a picturesque island town nestled in the joining of the Patuxent River and the Chesapeake Bay in Calvert County, Maryland. Once a renowned seafood packing house supported the local economy, but now tourism is its mainstay. Solomons remains a fishing village — alive with workboats and an active charter fishing fleet. It’s also a place to escape and to learn about the Bay’s past, present, and future. Solomons’ mile and a half long town offers numerous dining options, shopping, and special happenings. 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 Southern Maryland tradition with crowds in excess of 10,000 people at the event. We recommend the house drink: the Mai-Tai.

Day 6: Anchor in St. Michaels

St Michaels, Maryland is a quaint waterfront village on the Eastern Shore, situated on a picturesque peninsula between Tilghman Island, Easton, and Oxford. St. Michaels 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 offers numerous things to do and see. The Chesapeake Maritime Museum is the nation’s most complete collection of Chesapeake Bay artifacts, visual arts, and indigenous watercraft. Interpretive exhibitions and public programs cover the range of Chesapeake Bay maritime history and culture including Native American life, Anglo-American settlement, seventeenth and eighteenth-century trans-Atlantic trade, naval history, the Bay’s unique watercraft and boat building traditions, navigation, waterfowl, boating, seafood harvesting, and recreation.

Day 7: Sail Back to Annapolis

Expect a sail time between five and seven hours.