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Sailing the Upper Chesapeake


Last Updated on October 1, 2022 by Amy

We left Deltaville July 18th after forty days sailing around the Southern Chesapeake Bay. At this point, it was getting pretty dang hot and the lack of wind was taking its toll on us. We spent three days hightailing it up the bay to Baltimore.

Anchorage Marina

Several friends had recommended the Anchorage Marina to us. It’s located in Canton, on the waterfront of Baltimore with easy access to downtown. The facilities are lovely, and we couldn’t have asked for a better place to camp out for five weeks, plugged into shore power and enjoying the air conditioning.

The marina viewed from the office.

One key attraction of Anchorage Marina is the monthly rate. We paid $13 per foot per month! That did not include electricity, but even with the extra charge that’s an amazing rate and no wonder several cruising boats book months of dock time in the summer and leave their boats behind while they fly home or travel.

The facilities were all very clean. It’s a big marina – it was a quarter mile walk for us to leave the docks, but there is a bathroom block out on the dock, plus a swimming pool, Adirondack chairs, and grills.

I grilled as often as I could, and definitely enjoyed the view of sunset from those chairs!

Every Sunday there was a breakfast social in the boater’s lounge and Saturday nights were a live band out on the dock. The staff, especially Dockmaster Wayne, were very friendly and accommodating.

Starry Horizons happily tucked in on the T-head.

Exploring Baltimore

The city has a history of high crime rates, though we felt comfortable where we were. The inner city has been developed quite a bit in recent years.

Our favorite attraction, one that was just a step off the dock for us and something we enjoyed nearly every day was the Waterfront Promenade. This pedestrian area covers more than six miles around the inner harbor of Baltimore. We used it to join dozens of other runners in the mornings, a walk in the evenings through the busy restaurants of Fell’s Point or Harbor East, or to explore the waterfront attractions such as the historic ships USS Torsk submarine and the USS Constellation tall ship, or concerts at the MECU Pavilion.

Lacing up for a morning run.
USS Constellation

Canton and Fell’s Point both have tons of restaurants, and we also made a point to try out the best ice cream shops in Baltimore – Bmore Licks, Taharka Brothers, Pitango, and The Charmery. My favorite (non-dairy) was Pitango.

Ice cream and a view: we walked all the way to Federal Hill in search of The Charmery ice cream.

Baltimore has great access to travel. While Starry Horizons stayed behind in Anchorage, we took the train to Washington DC and spent a week exploring the capital.

What didn’t we do: well, a lot. We didn’t get to a baseball game (the heat deterred us). We didn’t make it to any of the museums (Covid). We also didn’t make it out to Fort McHenry. Ah well, things to do next time.

Rock Hall Landing Marina

Toward the end of August we were getting anxious for the heat to break and to start the move south. We finally left Anchorage on August 23rd and motored over to Rock Hall.

Less than twenty nautical miles away from Baltimore, Rock Hall is a quintessential small town in the Chesapeake. There are multiple marinas and definitely more marina slips than residents (1,500).

First we docked at Rock Hall Landing Marina for three nights during the week – a cheaper weekday rate and stay two get the third night free. There’s a West Marine and a local grocery store (Bayside Foods).

It’s easy to walk into town, but the marina offers bike rentals. We did bike around and outside of town for fun one morning.

Swan Creek

After three nights we moved around the town to Swan Creek to anchor. As we’ve found in most places in the Chesapeake, the weekends get crazy in the marinas. The anchorage was much quieter, with a few boats coming in for the weekends but mostly we were by ourselves during the week. It was quiet and protected enough for us to enjoy sunsets and paddleboarding.

A gorgeous sunset in Swan Creek, Rock Hall.
Paddling Swan Creek.

We stayed on anchor nine nights. The holding was good and we rode out a nasty summer squall there.

Time to batten down the hatches.

There’s More!

We didn’t cruise that much of the upper Chesapeake, and I know there are a lot of amazing places we missed. Many people recommended the Sassafras River, and there’s an entire Facebook group dedicated to Upper Chesapeake Sailing.

On to the Middle

The Middle Chesapeake region is the one we sailed the most.

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