We really don’t plan many things for our trip to Nantucket. To me the beauty is relaxing into a slower pace, visiting favorite spots and trying new ones, and just seeing where the day takes us. One thing that I really wanted to do though was go out on a sailing excursion with Endeavor Sailing. I’ve lost track of the number of times I’ve sailed with them and every experience is top notch. They really know how to tailor the experience for everyone, too, depending on the group.

I asked Mackenzie if she and her family would want to join us and they were able to make it with two of their boys. I think all three toddlers were a little skeptical of the boat at first, but by the end everyone was looking for fish, singing “Baby Shark” (mostly Jack…), and munching on Pirate’s Booty in pirates hats.

We picked the earliest charter of the day 10am, which was perfect for working around naptimes and capturing the best moods for everyone. Bonus was that the temps were a bit cooler than the peak of the day.

This very well may be our Christmas card this year! Kind of feels nice to have that mentally checked off the list…

Jack was living his best life. He’s been very into trains, but after this trip (and watching ferries come in and out of the harbor), I think boats are vying for a spot on his “most loved” list.

Honestly not bad for wrangling everyone in for a shot, right? I also have to point out that my first trip to Nantucket was 10 years ago with Mackenzie! We even took a ride on the Endeavor and I just can’t believe how much life has changed for us over the past (!!!) decade and to find ourselves in the same spot with a crew of boys later!

I’m wearing…. This sweater, these jeans, and these sandals. My hat is from Peter Beaton.

Jack’s lifejacket, sunglasses, and shoes.

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Hi I’m on Nantucket this week and am enjoying it for just the same reasons. Maybe I’ll bumb into you!

Loren Provins

Hi, this looks amazing! Do you have a link for Mike’s sunglasses?