Tiny Town Tour Part 2: Norfolk to Annapolis

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After 3 weeks of settling into Norfolk / Portsmouth, we realized that it was only September and there were still a few months of warmth to be had. We had been told that sailing the Chesapeake Bay was phenomenal, under the right conditions, and that there are so many cute little towns to go to and explore. Neither Justin nor I had any clue as to where to go first, so I took to the internet and started asking around to devise a plan. I became interested in The Chesapeake Bay Loop which visits towns on the east and west side of the bay. We tentatively decided to head north along the Eastern Shore of the Chesapeake with adjustments to be made if weather/hurricanes came our way. After spending too many miles in the ICW, we were very excited to shake out the sails and turn off the motor for a while.

We had a heck of a send off as we left Norfolk. While we were still getting ready to leave at the dock, we turned on the VHF radio to hear that Carrier 1 was leaving the Norfolk Navy base and heading out into the Atlantic. Not gonna lie, we sped up our process of leaving the dock in the hopes of getting to see it underway. What we didn’t consider, as we were motoring toward the base, was that a carrier never sails alone, they are always part of a strike group of destroyers and support vessels. FYI: When they call you on the radio by name asking for you to say out of the way, you do as you’re told. We were passed by 4 ships and there were still more leaving the Navy base as we cleared out of their path. 

Cape Charles, VA (population 1,178)

We chose a nice calm weather day to make our way out of Norfolk and through Hampton Roads, the body of water where the James, Nansemond, and Elizabeth Rivers join the Chesapeake Bay to flow into the Atlantic Ocean. Big winds and tides can make for very choppy conditions and an uncomfortable sail but we made it through without any troubles. We happily sailed into Cape Charles Marina after 8 hours and 37.5nm on the water. The marina is all about the location as it is the only marina that directly accesses downtown. Its restrooms and showers are semi-public and were not clean during our visit and they do not have laundry. There is an onsite restaurant, The Shanty, which has great food and friendly people at both the inside and outside bars. This little town is as south as we could get on the eastern shore of the Chesapeake and is known to be quite a tourist destination. We loved shopping up and down Mason Avenue and partaking in the local libations: Cape Charles Brewing Company, Buskey Ciders, and the Cape Charles Distillery. We were told by people in town that we had timed our trip just right since we docked right after Labor Day. They said that the marinas were full and you almost couldn’t enjoy the restaurants or shops due to so many tourists being in town. Yay us!

Onancock, VA (population 1,263)

We traveled roughly 50 nm and 9:21 hours further up the eastern bank of the Chesapeake Bay to reach the Onancock Wharf & Marina. The weather and waves were so calm that we couldn’t really sail, so we motored and did boat projects along the way. I cleaned half the stainless railings of rust and Justin replaced our shorepower cable hookup after it started showing signs of burn. The last hour or ~5 nm were a bit nerve wracking as it was through the Onancock Creek and the channel was very narrow and shallow. The harbormaster said that we would be fine with our 5’2 depth but it made us quite anxious to have our depth sensors reading 6-7’ at times. I don’t remember if we came through at high or low tide but we made it through and told our autopilot to follow our same route as we exited the creek a few days later. The marina has large and clean bathroom/shower combos 1 washer/dryer which were FREE. We enjoyed this sleepy little town which only had a few stores and restaurants within walking distance. There were more options and a grocery store further up the road, about 3 miles from the marina, which would be a nice bike ride. 

Crisfield, MD (population 2,475) Our 9th State!

As we sat on the boat in a rainstorm in Onancock, we were also watching what was going on in the Atlantic with tropical storms and hurricanes possibly churning our way. Though we wanted to continue our trek up the eastern shore of the Chesapeake, we decided to make our way to the western shore for a bit more protection. We decided that we would head toward Solomons, MD. The distance wasn’t right for us to do a full overnight sail so we did a day hop (29 nm / 5 hours) to Crisfield and stayed at Somers Cove Marina for a night before we moved on. We were one of two boats in the 100 available transient slips. It did look like they had a good portion of liveaboard boats down the other docks in Somers Cove. There were multiple bath houses with older but clean restrooms and showers. They had a large coin laundry facility as well, though we didn’t use it. The town is known as the “Seafood Capital of the World” and hosts annual events and festivals and is the hub for ferry trips to the Smith and Tangier Islands In the middle of the Chesapeake. Though it is going through a revitalization process trying to be a tourist destination, there isn’t much of a main street or restaurant options near the marina and the area overall seemed a bit sketchy after dark. I could see going back for an event or as a place to go during a storm as the marina is well protected on all sides.

Solomons, MD (population 2,650) 

After our night in Crisfield, we left with the sun and sailed past the Smith Island toward the western shore of the Chesapeake to the Solomons Yachting Center, motor-sailing almost 8 hours to go 45 nm. We were excited to get to a more interior location since Hurricane Lee, Margot, and Nigel were expected to head toward the US. We were not quite so excited with our dockage as we were on the outside of the marina on the T-Head to get hit by boat wakes and the waves produced from a southeast wind (the only direction that the marina was vulnerable to). The bathrooms/showers are also attached to the onsite restaurant but they have a decent coin laundry facility which wasn’t too expensive. We toured the Calvert Marine Museum and went through the Drum Point Lighthouse which was approved in 1854, finally built in 1883, decommissioned in 1962 and moved to its current location in 1975 to be restored. We pretty much walked the length of Solomons itself for shopping and restaurants and a bit into its neighbor Johnstown for a restock on our celebratory champagne and to get a few supplies at West Marine. It would be an easy bike to go a bit further to reach a grocery store. We liked the vibe of Solomons a lot as there were plenty of restaurants that you could take your dinghy to, multiple marina options and a few DIY boatyards. The locals and tourists were very laid back and helpful. We’ll probably stop here again, but at a different marina or anchorage.

Annapolis, MD (not a small town!)

With the multiple storms still brewing out in the Atlantic, Lee, Margot and Nigel, we decided to continue to make ourselves more safe and head on up to Annapolis, MD. It took us 10:32 hours to sail ~55 nm up the Chesapeake. We had great wind and loved seeing other sailors out once we reached the mouth of the Severn River to access Annapolis.

We decided to make Annapolis our home base while we visit with family, go sightseeing, do boat projects, and wait to follow the other snowbirds back down south for the winter. It feels like we’ve been here forever and yet not long enough and can’t wait to show you what we’ve been up to in a future blog. Skål!

A good Navy is not a provocation to war. It is the surest guarantee of peace.

President Theodore Roosevelt, 2 December 1902, second annual message to Congress