

Embarking on a sailing journey from Chesapeake, Virginia to Cape Charles is an adventure full of scenic views, historical landmarks, and some exciting stops along the way. This route, while relatively manageable, calls for careful navigation and awareness of the local waters, guaranteeing the safety of all aboard.
Before setting sail from Chesapeake, ensure that your vessel is fully prepared and all safety equipment is on board. Review local weather conditions, as the waters can change rapidly.
Navigational Overview:You’ll be departing from the southern tip of the Chesapeake Bay, generally heading east-northeast toward Cape Charles through the lower Chesapeake Bay and Virginia’s Eastern Shore.
1. Hampton Roads and the Elizabeth River: As you navigate eastward, proceed through the Elizabeth River and into Hampton Roads. This is a significant commercial waterway, so keep a sharp lookout for large vessels and follow the designated shipping lanes. The Norfolk area offers great sights including the historic USS Wisconsin at the Nauticus Museum, should you wish to take a detour.
2. Thimble Shoal Light: After passing through Hampton Roads, you will approach the Thimble Shoal Light. This navigational aid is crucial for marking the entrance into the Chesapeake Bay, and keeping it in sight will help you align your trajectory toward the lower bay.
3. Lower Chesapeake Bay: Continue sailing through the Lower Chesapeake Bay, where the waters are generally more open, but be wary of swell and shifting winds, especially if severe weather is in the forecast. Maintain vigilance regarding navigational restrictions, as there are specific channels and depths to follow.
4. Sheltering Options: - Craney Island: If you find the weather turning unfavorable, Craney Island provides a sheltered anchorage that is conveniently situated and relatively calm. - Deltaville: Known for beautiful marinas, if you can divert for safety, Deltaville can be a wonderful stop for refreshments and hospitality.
5. Point Comfort and the James River: As you continue, you'll pass Point Comfort, which is a scenic landmark. It is favorable to keep to the east of the shipping lanes here as they expand, where the James River meets the bay.
6. Bayling Stops as You Near Cape Charles: Before reaching Cape Charles, consider dropping anchor at the Bay Creek Marina or the Cape Charles Town Harbor, both providing excellent facilities and nearby attractions like beautiful sandy beaches, fishing opportunities, and local eateries.
Upon approaching Cape Charles, be sure to adhere to all speed limits and follow local navigation markers. This area offers a much-appreciated respite for boaters, featuring stunning landscapes and charming town amenities.
This route is perfect for intermediate to experienced boaters, ideally suited for those who have some familiarity with coastal navigation and local waters. It is a relatively simple route by Chesapeake Bay standards but still carries the responsibility of council with the vessels you encounter.
Above all, prioritize your safety and the safety of your crew. Make sure to have functioning life jackets, a first-aid kit, and adequate communication devices on board. Regularly check weather updates during your trip. Utilizing boating apps can greatly assist in navigation and weather monitoring; I highly recommend Savvy Navvy, along with others like Navionics and Windy, for comprehensive coverage of your journey.
This adventure promises beautiful scenery, engaging activities, and a healthy respect for the waters. Make sure your journey is both enjoyable and safe as you explore the best of what Virginia's coastline has to offer.