Annapolis Sample Itinerary

Your destinations on the Chesapeake Bay are boundless. Our base is in the heart of Annapolis right in the middle of the sailing capital of the world! The Chesapeake Bay, at about 200 miles long, is the largest estuary in the United States. There are coves and inlets all along the shoreline, small quaint towns to explore and plenty of places to anchor or dock with history all around you as you explore national landmarks.  

Make sure to allow time to visit downtown Annapolis at the beginning or end of your charter. Here you will find Main St. and small side streets loaded with shops, restaurants, galleries, and the Market House. And if time allows, take a stroll through the Naval Academy. Whatever you choose, you cannot go wrong in this historic town. 

Sailing Itineraries are helpful when planning your charter. You can choose the North or the South route. North takes you to historic Baltimore Harbor with nice quiet anchorages along the way. Sailing the South route will take you to places such as the legendary St. Michaels and the historical landmarks in Oxford and Cambridge. 

So many destinations on the Bay to explore makes Annapolis a great choice for your charter vacation.

Sail South (North Winds)


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 work-boats 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.

Sail North (South Winds)


Day 1: Sail to Rock Hall

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. 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: Sail to Baltimore Harbor

The harbor itself is 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 the 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: Sail to 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 options to explore.

Day 4: Sail to Mill Creek/Whitehall Bay

This quiet little anchorage lies between the Chesapeake Bay Bridge and the Severn River. Be sure to pay attention to the winding, well-marked channel and 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: 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 6: Sail into the Wye River

Sail into the 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 offers more secluded anchorages. On the Wye East, big houses, many dating back to colonial days, stand on the banks, greeting cruisers at every turn.

Day 7: Sail Back to Annapolis

Expect a sail time between five and seven hours.