Crossing the Chesapeake Bay in November

Crossing the Chesapeake Bay can be challenging, but with appropriate planning and consideration for weather and how the boat responds to various weather conditions, it can be one of the most enjoyable cruises. We crossed from Onancock, Virginia to Hampton, Virginia for a long 8 hour cruise with excellent weather. 

Onancock, VA | The stillness of the morning hours are really special to see.

Our first night back at anchor on our journey south was amazing. We slept great thanks to a super calm night with little to no wind giving the anchorage a feeling of glass when we woke up. Unfortunately we had little time to really enjoy the stillness of the morning because Elliot woke up an hour after his alarm, something that rarely happens but speaks miles to how exhausted we were in preparing PIVOT to leave the marina days before.

Onancock, VA | The local watermen are already on their way back in.

Although we were faced with low temperatures in the 40’s (4.5 C), we thoroughly enjoyed seeing the Chesapeake during this time of year as the trees were colored in quintessential autumn colors of deep reds and oranges against the forrest green. As we made our way back out of Onancock Creek and retraced our breadcrumbs along the windy channel, we were greeted by two bald eagles that were perched on the very last channel marker. It was a sight to see, something we continue to look for as we traverse along the various waterways south. 

Chesapeake Bay | We spotted two bald eagles as we were exiting the Onancock channel and entering into the Chesapeake Bay.
Chesapeake Bay | Local watermen attending their crab pots.

As we made our way into the deeper waters of the Chesapeake Bay, the water became rougher and rougher. It was not the most enjoyable cruise, however, the sun was out and provided us a nice warm amidst the cool temperatures. We passed by several watermen going out for their daily catch, several large shipping containers from a variety of home ports, and too many to count crab pots scattered throughout the water. As the day continued, the water became more calm, giving us an enjoyable cruise for the second half of our day. 

We had excellent weather crossing the Chesapeake and were glad to take advantage of this weather window. I was at the helm for most of the day and Elliot was on his laptop editing a video. We listened to music and enjoyed the fall day on the Chesapeake. 

Chesapeake Bay | Jenn at the helm.

Due to our delayed departure, we were arriving to our anchorage an hour later than what we had originally hoped for, meaning we were arriving at sunset on the dot. Usually we plan our anchorage arrival time to be an hour or two prior to sunset so we have plenty to time to re-anchor if needed, read the water and local environmental conditions, and settle in before we loose all light. This particular anchorage was also challenging due to its shallow waters entering into the anchorage. There were several channel markers to help guide us away from any shoaling, but the reviews in Active Captain still made us cautious of the waterway. 

Arriving at sunset does have a few benefits including getting this incredible magic hour light to welcome us home for the evening. It’s quite stunning to see the sun lower below the horizon as you’re settling into your space for the night. Even Ollie enjoys watching the sunset. 


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