“What’s the worst that could happen?”

This is my friend Lesley and I’s motto. As in, “Would it be insane for us to take our kids on a boat ride on the open ocean to a small island for a self-guided walking tour?”

“Yes. But sounds like something we would/should do.”

“I mean, what’s the worst that could happen?”

Two crazy mothers
Thank you to our long time sponsor, Bad Idea Jeans™

And so began our boat trip to Star Island.

FullSizeRender (10)
A three-hour tour, a three-hour tour* (*including one hour on the island)

The boat ride was lovely, interrupted only by the constant cries of, “I’m hungry!” by our poor, starving waif children. Luckily, Lesley had a hiking backpack full of cereal bars to hold them over.

Where everyone’s a star! (Even if you refuse to pose like one, George.)
We could only get them to run because we promised them food in that shelter.

We only had one hour shore leave and the kids spotted a playground right away, so they were as singled-minded as sailors during fleet week, except substitute playground for floozies. We told the kids we’d spend the last 10 minutes at the playground, which left us just 50 minutes to test out this antique revolving door, desecrate this graveyard, interrupt this duet, and run in and out of four little cabins without breaking various antiques.

We also felt it was worth taking the time for Lesley to make this epic lay up on the Pelicans’ practice court.

Pelicans scout, call me.

At long last, we reached the Promised Land.

Swings! Tires! A tire swing (slightly off camera)! 

Raise your hands if you love Star Island!

Respect, Eliza

On the way back, we were the last ones on the boat, just like we were on the way there. But unlike on the way there, it was socially acceptable to have a beer.

Cheers on surviving 2/3 of the trip, Lesley!

And also, something about our one-step-away-from-complete-anarchy charm won over the crew, because they let each of our small children steer the boat, even though they literally couldn’t see over the steering wheel.

Angling for Favorite People Ever, the crew guys then said yes to Hazy’s preposterous request that she get to work the cash register in the store, but sadly, no one bought anything for the rest of the trip.

Come on, somebody buy a G-D bag of Cool Ranch!

Due to a slight snafu (cough, cough, Lesley telling me we were spending the day on the island), my car ended up blocked in by all the cars of the people on the all-day island plan. But when life hands us lemons, Lesley and I use those lemons to garnish our lobster rolls at the Beach Plum, voted the best lobster roll in New England. That’s right; we loaded up the car seats into Lesley’s car and took ourselves out for lobster rolls, mac & cheese, and ice cream.

The lemons were just an expression, guys.
Found our mascot for the summer. p.s. These ice cream cones are heavy.

We also killed some time at this killer beach. I’m very grateful to Lesley’s family friends, who have a beautiful home on this private beach, about two hundred yards away from the public beach, which was packed about 10 umbrellas deep. We had this one all to ourselves, and it was absolutely perfect.


These kids went on more boat rides than a Bachelorette date.

You know when you get really tired and all you want to do is put on an avant-garde play and charge people for admission into an imaginary dance club? Yeah, me neither.

After much rosé was consumed,the imaginary nightclub got shut down due to zoning restrictions, and someone peed in the bathtub (I won’t name names), we finally got the kids to bed.

The next morning, I slept in while the kids (and Lesley) answered the siren call of Elena of Avalor.

If you’re not familiar with Elena, it’s basically Sofia the Second (The First is its gateway show).

Then we spent a little while enjoying the adorableness that is Newfields, NH. Lesley and her husband Paul live in a Charles Wysocki puzzle where Lesley brings her mug over to the General Store next door and fills it up with coffee, while her awesome dog Ollie goes behind the counter for a treat.

Of course, it wouldn’t be a visit to Newfields without seeing our old pal, Slowpoke. Slowy was as magical and slow as ever.

After dutifully jotting down the series of highways that Lesley told me made more sense than Waze’s directions, I promptly took one in the wrong direction and ended up following Waze the rest of the way. But first, we stopped for the kids’ 12th (!) ice cream of the summer, with make your own sundaes at Friendly’s.

This is also where George told me, “Waitresses aren’t real.”

Thank you for an action-packed day and night, Lesley. There’s no one with whom I’d rather be woefully unprepared for the worst that could happen.

Where should we go next? And relatedly, where’s the best ice cream in New England?


6 thoughts on ““What’s the worst that could happen?””

  1. Kimball Farms is on our summer idea list. I think my favorite ice cream is Christina’s in Inman Square though admittedly I haven’t been there in years. Maybe we should go this summer!


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s