Your Survival Guy’s boat-shoes-on-the-docks view of summer 2025. When the weather’s good, it’s still busy out there, especially in vacation hotspots like Newport, RI, and Martha’s Vineyard.
Last weekend, we took our boat, the Tom Sawyer, from Newport to Mattapoisett and then the next day to Edgartown, MA on Martha’s Vineyard. In Edgartown, it was tough getting a spot to dock, which is the risk one takes going without a reservation on the Fourth of July weekend.
Cruising to Edgartown and on approach, the first boat you typically see is a “mega” yacht so big it can’t possibly get close to the harbor due to water depth, and my theory: Security. Don’t worry, though, they’re fine. And if you want to see them, look for the 50-foot tender with triple 350 hp Mercury outboards, a crew dressed in white or black shirts, and two or three others in “regular” clothes.
Once you round the lighthouse and enter the harbor, you get a feel for the crowd size, you see beachgoers lounging beneath the matching umbrellas at the beach club. It’s Your Survival Guy’s barometer for predicting crowd size. The reading was high.
Hailing the harbor master on VHF channel 68, I was told to stand by. That’s when I realized the push-to-talk button on my microphone was stuck, and not only was I not receiving a response, but whatever I was talking about was being broadcast to everyone monitoring the channel. It happens. I hope they like Jimmy Buffett.
And let’s not forget that “Harbor Masters” are not typically in the friendliest of moods. It’s like talking with a police officer who pulled you over. “Yes, sir, just looking for a mooring.”
When he responded with “I can do that, but you need to log into Dockwa and do it,” I said to the rest of the boat, “Do they think I’m sitting at a desk?”
“Copy that,” I said. “But I can’t do that while navigating. I have an account. Can you look it up?”
“Stand by, Cap,” he said.
Minutes later.
“Cap, head beyond green cans 9 and 11 and head in to your left and you’ll see it, a white mooring.”
Taking the launch to shore, the queue of boaters we had to squeeze by on the dock was like getting out of an elevator when others are rushing in. The line from the dock stretched to the gangway.
Just a few steps away, the line at The Seafood Shanty, where we go for lunch, was out the door. When we got to our seats on the top deck, the service was prompt and a bit rushed. No big deal. You just have to know to slow things down a bit. The pressure to turn over tables is huge when the big money is made three months of the year.
After lunch, we visited one of our favorite clothing stores, The Great Put On, and visited with Nicole and her team. Then, back to the boat and home.
Action Line: Enjoy your summer. You and I think a lot about working and saving ‘til it hurts. But you also need to learn how to spend money. Make sure you get out there and enjoy the fruits of your labor. Spending money can be hard, but it should be fun. When you want help crafting a spending plan so you can have your lobster roll and eat one too, then let’s talk. Email me at ejsmith@yoursurvivalguy.com.
Originally posted on Your Survival Guy.
