2021 Chesapeake Bay Cruise

Chesapeake Bay Cruise - 2021

A sailboat at anchor while the sun sets on the Sassafras River. 

The Adventure Begins

I flew out of San Luis Obispo on an early flight to Dallas. Sitting on the left side of the plane gave me a panoramic view of the SLO area towards Pismo Beach. After an uneventful flight to Dallas and a lengthy layover,  I got on my second flight - it was to Baltimore.  When I arrived at BWI, Wes was waiting for me.

We spent the evening at Wes' home in Port Deposit. The following morning we got underway from Havre de Grace down the channel with an outgoing tide. We were fortunate with the tide but not the wind. We motored.

Our first anchorage was in Worton Creek. We celebrated being back on the water with a split of champagne.

 The next day we sailed south. We had a scenic view of the Bay Bridge as we sailed under it.  

Annapolis is always fun to visit. In this photo, the rotunda of the Maryland State House is visible at the end of the street.

Chick and Ruth's is a notable Annapolis landmark that's been around for many decades.

On the mooring, watching the schooner "Woodwind" sail through the harbor.

The following day we sailed south to Galesville and took a walk ashore.

We stayed in Galesville an extra day due to heavy rains. The next day the weather improved. We were rewarded with a superb sail (although temperatures were below normal - high 40's to low 50's). 

We arrived in Oxford (on the peninsula side of the bay) and anchored at our usual spot near the "Capsize" restaurant.

In the morning, we had a friendly visit from one of the local crab fishermen. 

Oxford dates back to the mid-1600's.  It has lots of interesting and colorful buildings.

After a couple of days in Oxford, we motored to Cambridge. It only took three hours to get there.

The inner harbor of Cambridge is a mix of commercial docks, a restaurant, the county building and townhouses. The harbor is shallow and provides excellent shelter from harsh weather.

Aero at anchor in Cambridge's inner harbor.

After our stay in Cambridge, with a shift in the winds, we headed back to Annapolis for another night on a mooring. Upon entering the bay, we were greeted by lots of race boats from small to over 30 feet. The fleet of racers often zipped right through the mooring field, passing us to our bow and stern. It was fun to watch and we were glad that the helmsmen were skilled and seasoned sailors.

The following day, with a favorable southern wind and tidal current, we decided to head up to Baltimore's inner harbor. From the bay, it's a long way to go to get to the inner harbor. But it's a unique anchorage, surrounded by high rises, restaurants, bars, an aquarium, a lighthouse servicing vessel and even a WWII submarine (the Torsk). 

We got there just in time before the weather started to turn on us.

After a couple of days in Baltimore, we weighed anchor and sailed north to the relative peacefulness of the Sassafras River. The weather was good and the water was warm enough for a dip around the boat. 

In the morning we motored north to Havre de Grace and finished another cruise of the Chesapeake Bay. In Port Deposit, we took a walk along the Susquehanna Heritage Trail and checked out Wes' vineyard. The Cabernet Sauvignon grapes looked healthy. Recently, Wes planted a dozen Sauvignon Blanc vines to complement the Cabernet vines. In the adjacent area of the vineyard, a very discernible, almost loud, buzz of the cicadas could be heard. Hopefully, they don't have an appetite for grape vines. 





At home, Wes opened up a bottle of his first vintage of Cabernet Sauvignon. On the label is a photo of his "château"  in Port Deposit. The wine tasted very good particularly for being so young in the bottle.

The following day it was time to pack it in and head home. We had finished yet another great Chesapeake Bay cruise - the 14th, I believe.

Chesapeake Bay Cruise - 2020

Chesapeake Bay Cruise - June 2020

With much of he world closed for travel due to the COVID-19 epidemic, our travel blog has been idle, awaiting a trip. The opportunity presented itself about a month ago.

Every year, one of the highlights for me is to visit my good friend, Wesley, in Port Deposit, MD and cruise the Chesapeake Bay. This was our twelfth cruise.

To get to the east coast, I flew from San Luis Obispo to Dallas with a connection to Baltimore. To say the least, it was somewhat of a surreal experience. Airports were deserted except around the gate area from which the flight left. Few if any bars, restaurants and general stores were open. Aboard, masks were mandatory and there was no food or drinks served. I actually felt relatively safe (whether it was warranted or not, I'm not sure).

My arrival at Baltimore was relatively normal, except that no stores were open at BWI. Wes was there to pick me up in his sporty BMW. We soon were on I-95 headed for Port Deposit, MD.

After arriving at Wes' home, we stretched our legs and took a walk along the Susquehanna River, that runs along Port Deposit. We had dinner and retired for the evening relatively early.

Wes had the boat ready to go - all we needed was ice for the coolers. We were underway by 10 am, with an out-going tide and a north wind helping us. Exceptional planning.

By late afternoon we were passing "down under" (the Bay Bridge, that is), approaching Annapolis.

In Annapolis, Wes brought out a special bottle of champagne that his daughter, Janette, had given him for the cruise. It was a bottle of Veuve Clicquot, one of the best. We indulged.

Looking towards the naval academy.

The following morning, we left Annapolis and headed for St. Michael's, a historic town on the peninsula (east) side of the bay.

St. Michael's is a lovely town and anchorage that over time has been gentrified. Among the amenities in town are restaurants, bars, a maritime museum, a winery and a brewery.

Christ Church in St. Michael's was founded in 1672.

Anchored at St. Michael's we met Benoît and Inès, a Frenchman and his German wife who are chefs at the German embassy in Washington D.C. They wanted to take a walk around town but had relied on there being a water taxi - none were operating. So Wes let them borrow the dinghy. We later had a drink with them on board their Beneteau 38.

Benoît and Inès getting accustomed to rowing.

In the morning, we weighed anchor and headed for Oxford. 

A beautiful late afternoon in Oxford. 

Wes even got the Seagull to run.

The weather was in the 80's and the water was comfortable for a swim.

A waterman baiting his lines with clams to catch crabs.

We were searching for a place to quench our thirst, but this bar was closed.

We had a couple of brews at the Capsize Restaurant.

There was no lack of good dinners and Bordeaux wines.

Solomons with the Tiki Bar lit up. 

After three days in Oxford, we departed and crossed the bay to Solomons. We spoke to the crew of another sailboat anchored near us, Seven on the Seas. They were a young couple (Paul and Jessica) with their five children, ages 7-14, sailing around the world. They purchased the boat in Turkey and sailed it through the Mediterranean, across the Atlantic, through the Caribbean and were now cruising the Chesapeake Bay. From afar, the kids appeared to be well behaved and enjoying themselves. What a life-changing experiencing for those kids.


We spent the night at Solomons and, in the morning, left for Turkey Point. Wes' high school friends, Mike and Ann, have a small trailer near Turkey Point - it's just a few feet from the bay. After several hours of motoring and sailing we anchored in front of their trailer. As we anchored, we spotted Mike, busy checking his crab pots for dinner.

Mike, Ann and I. We had oysters followed by a fish dinner.

Mike and one of his crab pots.

Great view of the bay.

It was a feast prepared by Courtney's Seafood Restaurant!

After dinner we sat around a fire pit overlooking the bay.

Wes and I came ashore the following morning and had breakfast with Mike and Ann. Afterwards, we pulled up the hook and were on our way to Reedville, VA.

At anchor at Turkey Point.

The following day we said our good-byes to Mike and Ann and got underway to Reedville. As we approached, I got the idea to call a friend, Bob Riddle, who both Wes and I knew from when we worked in Iran for Bell Helicopter. Bob was home and yes, he was able to come over for the night from Richmond, VA (about an hour and a half drive).

Rowing Bob to the boat.

Wes and Bob had not seen one another  in 41 years. I, however, had kept in touch with Bob and seen him on a number of occasions. It was a good reunion.

After a night of reminiscing about life in Tehran and all the good and unusual experiences we encountered in Iran, I rowed Bob ashore and he was off. It was really a pleasure to spend the evening together.

Soon afterwards, Wes and I weighed anchor and left for Tangier Island.  But once we got out into the bay, we found out that we would be fighting a strong northerly wind, just the direction we were heading. We decided to turn back to Reedville and await more favorable winds.

A rainy day in Reedville

We anchored at another spot near Reedville, in front of Jennings Boat Yard. We ended up staying there for three days due to weather - rain and high winds. We amused ourselves with long walks, lunch at the Fairview Marina and looking at a number of forlorn yachts on the hard.There were Cal-40's and even bigger boats there.

These were some of the smaller boats that have been abandoned by their owners. 

On the third day the weather improved and the wind swung to the south. Perfect. We weighed anchor and headed for the Solomons.

More fine dinners, more fine wines.

Solomons is a fine stop-over for a night. But it's really an odd place to anchor. Loud cigarette boats often come by on their way to the Tiki Bar as they vroom-vroom around in their macho boats.

In the morning, with light winds from the SW, we went to Annapolis, arriving there in the late afternoon.

One of the Woodwind schooners that take people sailing around Annapolis.

Lots of evening chats over a glass of wine.

Looking towards the naval academy as a large yacht comes by.

We had light winds from the south after we left Annapolis for Havre de Grace. Towards the afternoon, the wind increased a bit and we noticed an ominous looking squall coming from behind us. For the most part we managed to outrun it, only getting doused with a light rain.































After returning to Havre de Grace, we drove to Wes' home in Port Deposit. The following day we took a drive to Elk Neck State Park. We had wanted to walk along the Turkey Point trail (another Turkey Point), but it was crowded. Nearby we found another nice hiking trail.

Wes' home in the background.

Elk Neck State Park

Elk Neck State Park

The following day I flew home. The airport was not busy.