Category: Chesapeake Bay shakedown 2026

The BoatUS tow boat arrived first thing in the morning with hot coffee for Roger! We weighed the anchor and they handed us a tow line to pull us across the bay to Cape Charles. It went much faster than expected and we arrived at the home dock around noon.

After a hot shower we hopped into an uber and I was dropped off at the Norfolk, Virginia airport for my return back to Austin, Texas.

Roger is now tasked with several big tasks to resolve. I wish him the best.

• The starter issue was resolved by a local tech by replacing the starter. It is believed that the previous starter was damaged by the salt water splashing down from the anti-siphon valves.
• The engine had vaporlocked when we tried to start it with the malfunctioning starter.
• The antisiphon valve and connections were replaced and secured.
• Jib still needs a revisit to the sailmaker.

Sadly, the above issues took too long to complete preventing in the planned participation in the Greater Chesapeake Schooner Race, so that will have to wait until next year. I look forward to my next adventure with Roger and Ulysses, she is a beautiful solid vessel.

Daybreak broughs us a new problem. Looks like the starter isn’t firing, we weren’t sure if it was the starter or that the alternator just wasn’t charging the battery yesterday. We called Boat US for support and they arrived faster then expected and they diagnosed that the starter was the issue. We bridged the starter and bingo we had her up and humming. We were headed back into the Chesapeake by 09:00.

Since we weighed the anchor a little later than we wanted, the decision was made to run the motor a little harder than we did the day before. The bilge pump process was the same as before and kept up with the ingress. Around 12:30 the motor ceased to operate. Luckily the wind picked up a bit just before noon and we were able to set the sails. Roger was smiling heavily even with the setbacks once we got Ulysses moving along under sail.

Unfortunately, the tide shifted and dropped so we were unable to make our way south, it was decision time. We changed our course and slowly sailed to Ingram Cove and set the hook in slightly protected waters of about 15-20′ depth. We coordinated with Boat US and scheduled a tow for the following day to get us across the Chesapeake to Cape Charles, about 40 miles away.

After a solid breakfast we cast off the lines around 09:00 and topped off the fuel tanks before pointing the bow down the Chesapeake.

The wind was almost non-existent, so we ended up motoring the entire day. With the engine running solidly we noticed water above the floorboards about 2-3 hours into the trip. Looks like the float switch on the bilge pump wasn’t firing. First, we pumped out the water, then set to locate the ingress point. The anti-siphon valve on the engine water intake has failed and it was pumping a large amount of water into the bilge. After diagnosing and inspecting this, we determined that while running we could stay ahead of the water by manually running the bilge pump for ~10 minutes every ~30 minutes. We made it safely to Solomons Island and dropped the anchor shortly before sunset.

We were greeted by this fun little boat after setting the hook.

Ulysses is a 1986 Cherubini 48 Staysail Schooner. She has been on the hard for the last year and a half, she was splashed earlier this week. Now that she is in the water, we spent the 27th and 28th looking her over and checking things out, repairing or replacing as many things as we could. First, we found that the freshwater pump was dead so that was our first trip to West Marine, easy fix. When hoisting the sails, we noticed that the sail shop had done NOTHING to repair the jib that they had in possession for the last YEAR, it will need another visit to the sailmaker very soon. The main staysail went on easily, and we found that the outhaul wasn’t rigged properly, that will need fish tape or poles to run it inside the main staysail boom. Starting the engine was an issue, after replacing the battery, we found that it wouldn’t fire without some starter fluid sprayed into the intake. After the trip it was discovered that the flow plugs had a bad wire and weren’t powering up.

It looks like everything is ready to sail so our plan is to cast off the lines in the morning after a solid breakfast.