Last year my wife Elizabeth (aka The Admiral) and I completed the DelMarVa Loop adventure on our 1999 Formula 34PC and it was covered in a three-part series in PropTalk. Thanks to everyone who let us know how much they enjoyed reading about our journey. We hope you find our 2021 Inside the Chesapeake Bay Loop journey as much fun to read even though we planned a trip with a lower likelihood of drama on the water.  

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It is a lot more fun to cruise the Bay than drive cross the Bay Bridge or travel down I-95. Especially when you get to experience places like Solomons Island from the water. Photo by Aram Nersesian

Note to readers: We used Dockwa to make reservations at all the marinas along the way, and the email confirmations with maps and additional info were quite helpful. We also know that telling friends your cruise schedule a week in advance is a cardinal sin for boaters.

In 2021, we decided to do something different for our annual cruise. We missed seeing our friends during the Covid lockdowns, so we made plans to connect with several of our closest friends by traveling on our boat to their homes on the Bay. After all it is a lot more fun to cruise the Bay than drive across the Bay Bridge or travel down I-95. Our friends live in Oxford, MD, and Reedville and Williamsburg, VA, so this meant we were going to be making what we called an “inside the Bay loop.”

First Stop: Oxford

The Bay was relatively calm when we departed Annapolis on September 25 with the usual crowd of sailboats going nowhere fast. We chose to give the sailors lots of room and not rock their boats out of deference to our sailing roots and friends. Our course was taking us towards the eastern side of Poplar Island or the inside passage. We slowly cruised into the narrow and shoaling Knapp’s Narrows channel. It gets a little unnerving as the depth sounder goes from nine to eight to seven… and stops at four and a half feet at low tide.

After exiting the narrows, our port transmission alarm sounded as we entered the Choptank River. We idled back and checked and added some transmission fluid. The alarm went off for about five minutes and then came back on. We called our Eastern Shore based mechanic Tom Turner, owner of Turner Mobile Marine, to ask him to meet us in Oxford to check it out. This was déjà vu all over again (to quote Yogi Berra) as Tom met us in 2020 in Oxford to repair the water pump. Anyway, we headed up the Choptank River with the alarm blasting away until we reached the Tred Avon River and turned off the port engine. That is why we have twin engines, right?

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We met up with friends Steve and Barbara Hayes who recently purchased a home in downtown Oxford. Over drinks we enjoyed catching up on old times, our kids, and our plans for the rest of the cruise down the Bay.  

We had made a reservation at Safe Harbor Oxford (they provide excellent welcome information by email in advance of our arrival) and hailed them on our arrival. We were directed by the owner to a fixed pier on the far side of the property. This made for a lengthy hike through the parking lot and Strand Road to the very nice bath house facilities. 

We got cleaned up and called our friends and former boat partners and Alexandria neighbors Steve and Barbara Hayes, who recently purchased a home in downtown Oxford. They arrived in a few minutes by car. We departed the marina and Steve proceeded to give us the VIP tour of the town and surrounding area to show us there was plenty to do in “sleepy” Oxford. After a 15-minute tour, he took us back to Fandango to get cleaned up for dinner. Fortunately, we got to share some delicious appetizers and drinks at their home before going out. We brought Annapolis Seafood’s lip-smacking crawfish salad and delicious smoked Bluefish to show that boaters come prepared. It complemented the incredible crab dip and crackers they offered. Over drinks we enjoyed catching up on old times, our kids, and our plans for the rest of the cruise down the Bay.  

We drove to Latitude 38 on the one road leaving town. It was pleasing to see the white table cloths on the tables and the excellent service diners appeared to be receiving. The bar was full of locals. Three of us ordered the softshell crab half-dinner and one order of the duck special. Everyone loved the gourmet meals and fond remembrances of past sailing days.

Tucked into our queen-sized berth for the night, we drifted off to slumber land in the heart of Oxford. The wind piped up at about 3:30 a.m., blowing 15-20 from the northwest, and it pushed us against the dock. So, I went out to put a bumper on the rail in my best underwear. No further bumping and plenty of ZZZZ’s the rest of the night.

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We called our Eastern Shore based mechanic Tom Turner, owner of Turner Mobile Marine, to ask him to meet us in Oxford to check out a transmission problem.

The next morning, we woke up to hot, black coffee and warm banana bread in the cabin. Elizabeth and I walked to the distant Safe Harbor office and bathhouse. All buffed and polished, we hopped on the free bicycles and pedaled all over the scenic and flat Oxford streets to see and appreciate the many beautiful, old, and historic homes.  

As if on cue, Tom Turner of Turner Mobile Marine showed up at 9 a.m. to check out the transmission issue we had the previous day. In short order, he drained and refilled the transmission fluid and offered that he thought the clutch may be slipping. We had plenty of fuel to reach Solomons Island, so we didn’t top off our tanks since the price of fuel was nearly a dollar more than Annapolis.

We had a leisurely departure from Oxford at 1 p.m. with the winds still blowing 15-20 kts from the northwest. The seas were one to two feet on the nose coming out of the Choptank River. We couldn’t wait to get to the Bay and turn south. Once we reached the R10 buoy, we changed course to the southwest, and the wind and waves shifted to quarter stern for the first time in what seemed like years. (Our 2020 entire trip around the DelMarVa Loop had blasted us with headwinds and waves.)

Perfect Timing in Solomons

As we approached the Patuxent River, we enjoyed the spectacle of seeing dozens and dozens of racing sailboats with the graphite black sails racing in the distance. Our timing was perfect to see some of our friends racing in the Screwpile Lighthouse Challenge. Since our destination, Safe Harbor Zahnizers, does not sell fuel, we pulled into Solomons Yacht Center to top off.  

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Enjoying the Screwpile Lighthouse Challenge Regatta party at Safe Harbor Zahniser's in Solomons.

Fandango took on 115 gallons ($4.14/gal a savings of 75 cents/gal from Oxford). We thanked the dockmaster Maria and she helped cast us off, as we headed up Back Creek to Zahnizers. Dockmaster John gave us lengthy dock location instructions over the radio. 

John was a true professional dockmaster and we knew it when we saw him. His tie-up assistance was first-class. Lines tied properly, water and electric hook-ups made, and a full rundown of marina services and bathhouse locations. Fandango was washed with plenty of soap and our new lamb’s wool brush pad to clean the glass. The Admiral came up on deck with two delicious Mount Gay and Regatta Tonic drinks with lime as our just reward for a good trip across the Bay. The Screwpile Lighthouse Regatta band party just happened to be hosted at this marina, so I bought the Admiral an official race hoodie so she could blend in with the sailors.

We saw our dear friend and SpinSheet editor Molly Winans taking pictures and we mugged for a pic with her. We left the party to shower, which isn’t a requirement at sailor parties. After getting cleaned up we sat in the cockpit of Fandango enjoying our grilled flank steaks (prepared at home) with stuffed potatoes with sour cream from Annapolis Seafood Market, and a nice bottle of cabernet. Following dinner, the Admiral stroked the ivories on her Yamaha keyboard and was jamming into the night under candlelight. It really doesn’t get any better than this!

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What a small world! Running into old friends in Solomons. 

After a nice breakfast and shower the next day, we checked out bikes at the marina office for a ride around Solomons and a little exercise. While the Admiral was deciding what bike to select, a woman in a mask walked up and told her to select the red bike. The Admiral looked at her as though her voice sounded familiar, and asked “are you from Philadelphia?” It turns out she was Leslie Hayes the mother of one of our daughter’s closest, high school friends when we lived in Wayne, PA, about 15 years ago. What a small world and another connection with a friend on our journey.

We rode the bikes to the end of the island taking in all the sites—the educational and cultural Chesapeake Biological Laboratory Visitors Center, Isaac Solomons home, Our Lady of the Star Catholic Church, the famous Tiki Bar (closed but ready for a thirsty crowd), and finally a loop back north to Spring Cove Marina and back. Definitely a great ride and one of our favorite ways to get exercise before several hours underway the next morning.

We departed Solomons Island under beautiful, sunny skies as the fleet of sailboats headed out to the racecourse on the Bay. It was a pleasurable cruise at 18 knots with two-foot seas on the stern pushing us south to Reedville and the Wicomico River. 

About the Author: Paul “Bo” Bollinger is the executive director of Chesapeake Region Accessible Boating and has been sailing and powerboating on the Bay with Elizabeth, family, and friends since 1984.

Check out the next installment of this journey, Inside the Chesapeake Bay Loop: Part II.