15th October, 2023

The Lost Cruising Season

This is Whiskers on the last day of our sailing season here in Katama Bay.  We were taking her back to the shipyard to be stored for the winter season. I was hoping to fill the sail blog with stories of our escapades while sailing her around the Cape and nearby islands. Unfortunately, cruising this season was not to be. For several reasons.

Scheduling was one problem. I thought that having our company arrive every other week or every two weeks would give us the freedom to cruise in between. What I didn’t factor in was enough leeway between visits in case of bad weather. What if we had visitors and we couldn’t get home in time to meet them?

And then there was the weather. Unpredictable. It was unseasonably warm and so much rain. If it wasn’t raining, it was too much wind. Whiskers is a whole lot of boat to handle in strong winds. Even with the sail reefed. It often takes both of us – me on the helm and Jay running the sheet – to keep her steady. Sailing for four to six hours a day in strong winds can get exhausting.

We did have many wonderful day sails. Some days we would ghost down the harbor, drifting along with the wind at our stern. This gave us time to relax and share the scenery with our guests. On the east side of the bay is the island of Chappaquiddick. It is remote and sparsely populated. On the west side is Martha’s Vineyard, with its many mansions lining the shore. It seemed like new construction sites would sporadically pop up, sprouting the latest, greatest building. As if there was an unspoken competition to see whose house could be the biggest. I wonder, who is it that needs a 26,000-square-foot house as a second home? One that they might live in for two months a year. But I digress.

Other times, when the wind was just right, we would fly down the bay on a beam reach. The sun was warm. The water sparkled. And the wind carried the joyous laughter of tourists swimming off their boats on the town moorings. Picture perfect.

When we reached Edgartown proper, we turned our boat east to head out to Nantucket Sound. But first, we had to contend with the Chappy ferries. Always a challenge.

There are two ferries. One on the Martha’s Vineyard/Edgartown side and one on the Chappaquiddick side. Each ferry holds three cars max, pedestrians, and bicycles. When fully loaded, they both leave at the same time, passing midway and docking on the opposite side from where they started. This takes all of three minutes at the very most. Meanwhile – and especially during the height of summer madness – powerboats, super yachts, miscellaneous ferries from the mainland, and sailboats – all weave in and around each other while timing their entrance through the ferry traffic in or out of the harbor. This used to give me great pause when learning how to sail Skipjack and maneuver through the boats. Not so much anymore. Besides, I know I have my faithful and trustworthy Captain Jay onboard to talk me through any potential mishaps.

The current can also be a factor. And it can be stronger and more unpredictable when there is a breach between Chappaquiddick and Norton Point at the south end of Katama Bay. This isn’t always the case. Sometimes the breach closes up and Chappaquiddick is no longer an island but is connected to Martha’s Vineyard. However, when the breach is open like it is now, it is not unusual to see the Chappy ferries swinging wide with the current. It can also make it difficult for Whiskers to move through the ferries when going against the current. That’s when we turn on the motor for a little boost. Just to play it safe until we get in or out of the harbor fairway.

Once we leave the ferries behind, the sea opens up to Nantucket Sound. On the perfect day, the wind picks up and we have a glorious sail as we pass Edgartown lighthouse to the left and the Chappy Beach Club to our right. The waves ripple across our bow and when we look down, we see the sandy bottom through crystal clear water. It’s nothing less than spectacular. So, maybe we didn’t get to cruise the Cape and nearby islands. But we sailed around Martha’s Vineyard, day after day.