Last year, Jill and I attended a Breakthrough T1D event where I got carried away bidding on one of the auction items. She kept looking at me with big eyes as another bidder and me one-upped each other. I won, and told her, “It’s for a good cause.”

That auction item was a trip to Portland, Maine on a private plane. Life got in the way and we kept delaying scheduling it, until we finally pinned down a date: Last Saturday.

Jill and I are go with whatever feels right kind of people, so we invited our sons, her nephew, and friends Matt and Kelly to ride along. We had a kinda-sorta plan: Catch our ride, eat lunch, and see the town. We had a rental minivan and my four year-old memories of Portland to guide us.

We left rainy Plattsburgh around 9 am and were on the ground at rainy Portland by 10. This was the smallest plane the others had ever flown on, so there was a bit of nervousness as we took off. Jill warned me in advance not to joke about crashing, the probability of crashing, or not crashing. I kept my mouth shut, but I keep thinking of this:

After landing in Portland, Jill and I picked up the minivan and we set out for downtown, where we spent a couple of hours roaming around the Old Port area, shopping. I had one shopping goal: Replace my raggedy state flag of Maine trucker cap, which thankfully no one has yet confused with the “appeal to heaven” flag. If that happened, I’d have to throw it away. Mission accomplished.

We picked the Eventide Oyster Company for lunch, and Jill’s cousin Daryle, who lives nearby, met us.

Yes, that’s a lobster roll, but not your average lobster roll. The lobster is bathed in brown butter, and the whole delicious mess is on top of a steamed bun. I could have eaten a lot of these, but I restrained myself. Jill and Daryle ordered the scallop waffle-taki, which is just what it sounds like and might be even more delicious than the lobster roll. You can’t go to an “oyster company” without eating oysters, so Matt and I took care of a dozen from three local-ish farms.

We followed lunch with a walk back to Beal’s Ice Cream. My tip for you: Get the ginger ice cream. I’m now reverse engineering the recipe.

We had time to kill, so the next stop was Fort Williams and the Portland Head Light, on Cape Elizabeth.

I’ve been to this park a few times, and it never gets old. It’s only a few minutes away from downtown Portland, but until you spy the houses next door, it feels wild and remote.

Good things can’t last forever, so I texted the crew and announced our return. Forty minutes later we were onboard and headed home to Plattsburgh. The chill level was significantly higher on this leg of the trip.

By 5 pm we were back at our house, where our antsy little dog was anxiously awaiting us. Between the great company, laughter, food, sights, and convenience, this may be my favorite day trip ever.