**Pilotage Plan: Annapolis, Maryland to Chestertown, Maryland****Overview:** This route from Annapolis to Chestertown is a beautiful journey that caters primarily to leisure boaters. It offers a blend of serene waterways, picturesque views, and the chance to explore local landmarks while keeping safety as the utmost priority. Ideal for experienced cruisers and leisurely boaters alike, the trip weaves through Chesapeake Bay’s scenic landscapes, winding your way through the Eastern Shore's charm. **Starting Point: Annapolis, Maryland** Coordinates: (Long -76.4815, Lat 38.9624666667) Prepare your vessel by checking weather conditions, ensuring you have enough fuel, and verifying all safety equipment is on board. Annapolis, known as the "Sailing Capital of the U.S.," provides ample resources for provisioning and last-minute gear checks. Before leaving, take a moment to enjoy the historic charm of Annapolis, the sailing capital itself.**Route Planning:** Depart from Annapolis and navigate eastward through the Chesapeake Bay. 1. **Chesapeake Bay Navigation:** Keep a close eye on the navigational markers. The Chesapeake Bay is well-marked with buoys and channel markers, which you will need to follow closely to avoid shallows, especially in areas near the eastern shore and near Sandy Point State Park.2. **Sandy Point State Park:** This is a great place for a brief stop-off if the weather permits. Located just south of the Chesapeake Bay Bridge, the park boasts sandy beaches and picnic areas. If conditions are right, consider anchoring briefly to enjoy the scenery. 3. **Sandy Hook and Herring Bay:** As you continue eastward, watch for Sandy Hook, where Herring Bay opens up on your starboard side. Keep your speed in check in this area as congestion can vary, especially with fishing activity.4. **South River:** After navigating through Herring Bay, make a turn into the South River. Be alert as you follow the river up; the waters can be narrow and winding. The banks here are lined with local waterfront restaurants and private docks, perfect for a meal or a rest stop.5. **Broadneck Park:** This is another potential site for whale-seasoned boaters to stop if you’re seeking leisure activities. Enjoy hiking trails or a picnic, but be cautious of shallow waters as you approach the shore.6. **Approaching Chestertown:** Leaving the South River, direct your course back toward the Chester River, paying careful attention to the navigation aids along this stretch. The Chester River is navigable but subject to tides, so consult local tide charts to avoid grounding.**Points of Interest Along the Route:**- **Historic Purcellville & Highland Beach:** As you near the Chester River, consider a short exploration of Highland Beach for a glimpse of local history and waterfront homes dating back to the early 20th century.- **Chestertown Marina:** Upon approaching Chestertown, the marina is a great place to secure your vessel. The downtown area is rich in colonial architecture and is famous for its arts community and sailing regattas throughout the year.**Shelters Along the Route:**In the event of unexpected weather changes, look for the following sheltered bays:- **Herring Bay** provides substantial anchorage.- **Broadneck Bay** offers several docking facilities.- **Lankford Bay** is an additional alternative known for its protective waters.**Important Navigational Considerations:**- Be mindful of the winds, particularly when you are exposed during portions of the Chesapeake Bay.- Maintain a proper lookout for other boats, especially in more congested areas like the South River, as recreational fishing is prevalent.- Familiarize yourself with any local boating regulations, such as speed limits in certain areas and designated idle zones.**Suitable Boater Profile:**This route is particularly well-suited for recreational sailors and power boaters who prioritize safety but also appreciate the balance of exploration and calm cruising. It allows for leisurely travel, with beautiful views and opportunities to enjoy charming stops along the way.**Apps for Navigation:** For enhanced safety and navigation, consider using boating apps such as:- **Savvy Navvy** for detailed marine charts.- Other popular navigation applications tailored specifically for local waters.This trip offers a safe, enjoyable, and scenic adventure while also allowing for the chance to explore some of the best sites that Maryland's Eastern Shore has to offer. Happy and safe sailing!