
Monday, October 6 – We Fancy
| Start: Cambridge Municipal Yacht Basin, MD (dock) | Miles: 36.5 nm |
| End: Lake Ogleton, Annapolis, MD (anchor) | Time: 7hr8min |
| Weather: Pleasant, light & variable wind | Waves: 0-1 ft |
Sailboats galore! Once we got back in the Chesapeake, there were countless sailboats heading in all directions. We took our time sailing downwind before taking a beam reach (wind at an easy 90° from our bow) into Annapolis. Our boat doesn’t have great sails for downwind, but we weren’t in any rush. To clarify, we weren’t in any rush after we found out our friends on Kosmos left at 4 in the morning and would handily beat us to Annapolis.
Our anchorage for the night was a lake separated from the Chesapeake by a short, narrow ditch. Getting to that canal was treacherous with all of the crab pots littering the approach. I’m glad that some of them had flags highlighting their buoys, but we had never seen pots this densely packed. Leanne perched on the bow like Captain Morgan pointing at the never-ending stream of mines.
The lake was small, but had enough space for Blue Heeler. The shore was lined with $3-$5 million houses, each with their private dock for their multiple boats. It strikes me sometimes that we can anchor in anything from secluded river bends to posh lakes where $5M houses with envy-inducing lakefront property end with private docks housing a few of their luxurious boats. This anchorage was the latter, and I felt like Uncle Eddie in Christmas Vacation, showing up with our nice-but-not-posh sailboat with torn canvas, and boys who just want to pee off the back of the boat, just 100 feet from the end of their docks. “Hey Clark, I brought you something from the landfill!”
Tuesday, October 7 – The Boat Show, New Friends, and Visitors
| Start: Lake Ogleton, Annapolis, MD (anchor) | Miles: 3.5 nm |
| End: Annapolis Yacht Basin, MD (dock) | Time: 51min |
| Weather: Pleasant | Waves: 0-1 ft |
Three and a half miles should be easy, right? Welcome to the boat show! Our dock was next to the Annapolis Boat Show, one of the largest boat shows in the US. We studied the charts before leaving, and had our approach. But when we pulled into Spar Creek, we were overwhelmed by the number of sailboats anchored/moored in the creek, with some illegally anchored in the channel. It was a challenge just to find space to weave between them. We got to the end of the channel, but it looked nothing like the map. Where was our dock? I’m panickedly asking Leanne where we should be going while weaving through anchored boats, and avoiding two boats turning around in front of us. In retrospect it’s almost funny how much panic can happen while moving at 2 mph.
The source of our confusion: apparently, (and I knew this from my delivery captain John Herlig, who told me he worked on the Annapolis Boat Show dock team) the boat show installs miles of docks around the show boats. And that isn’t shown on any chart. We realized this, and Leanne navigated us to our marina.
The marina has given us a tough slip assignment. We need to go down an aisle, turn left in a narrower aisle, then back into the first slip on the left. That second aisle is 47’ across and our boat is 45’ long. It felt like Austin Powers attempting the u-turn in the powered cart. I can tell we’re getting better because (1) there was no yelling, and (2) we barely even kissed the piling opposite our slip. We got safely into the slip with the help of Eric from Cosmos and the marina dock hand pulling in the ropes.
This kicked off an awesome week in Annapolis. We went to the boat show twice; first day to scope out what was there, and the second day to buy things we wanted (my favorite being solar-powered dinghy lights).
Buying groceries in Annapolis proved to be a challenge. Leanne made an online order at the nearest Kroger store. I drove our dinghy 2 miles to a dock, then walked 2 miles to the Kroger. I showed up to pick up groceries, and the app asked which parking stall I was in, so I stood in Parking Stall #1 with a grocery cart, looking like a fool while shoppers quizzically looked at me. I loaded the groceries into oversize duffel bags, took an Uber to my dinghy, and drove them back to the boat.
Also in Annapolis, we met up with dozens of sailing families as part of a friend’s birthday party, the Nauti Kids WhatsApp group, and Totem’s (our cruising coaches) dinner hangout. This was such a good time to connect with other cruising families who are heading down to the Bahamas like us.
Towards the end of our stay, my parents and sister flew in and spent 5 days with us. We explored the beautiful downtown Annapolis. Who knew Annapolis was briefly the nation’s capitol?! We also went bird-watching on Kent Island across the Bay from Annapolis. My mom was excited to see migrating birds, but we didn’t see anything exotic. We stayed an extra day in Annapolis due to high winds, but we enjoyed ourselves.
Next stop: the famously quaint St. Michael’s, what our guidebook describes as “an annual must for Chesapeake Bay sailors”

