Cultural HistoryThe 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. |
Food & DiningBefore 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 or fish & chips at Galway Bay. Visit the Maryland State House – the oldest state capitol in continuous legislative use topped by the largest wooden dome in the nation.
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R E C O M M E N D A T I O N S
Summer Destinations
Suggested Itineraries: 7 Days South
Day 1: 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: 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 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 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 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: 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: 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!
Day 2: 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 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 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 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: 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: 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!
Suggested Itineraries: 7 days North
Day 1: 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 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: 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: 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: 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: 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: Make your way Annapolis Bay Charters today, talking over the adventures of the past week. Expect a sail time between five and seven hours – and expect to return soon! You’ll start to miss it right away.
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, all within walking distance. Locals and visitors alike can’t get enough of the fine dining, cultural experiences, and exciting nightlife.
Day 3: 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: 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: 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: 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: Make your way Annapolis Bay Charters today, talking over the adventures of the past week. Expect a sail time between five and seven hours – and expect to return soon! You’ll start to miss it right away.