We’ve been on Nantucket for a little over a week and I’m so grateful for the change of scenery. Teddy is giving us a bit of a hard time adjusting to sleeping in his pack and play at night but he’s loving island life during the day — long walks in a different neighborhood every morning, afternoon trips to the beach, and outdoor showers every night before dinner! There’s so much out here that I can’t wait to show him and watching him experience all my favorite things for the first time makes my heart so full. One of the things I was most excited to do with him was sailing on The Endeavor, which we’ve done at least once a year for the last eight summers and even took some of our engagement photos on back in 2016. Seeing Teddy and his second cousin Hayes take it all in was so sweet, but I’m pretty sure Teddy was just as excited about being fed Ritz crackers by his Mimi as he was about being on a boat. In any event here are a few photos from our afternoon on the water!

children's ack sweater ellsworth and ivey

endeavor sailing nantucket

baby driving loafers elephantito

nantucket stubbs & wootton

nantucket sailing design darling

endeavor sailing

elephantito boys' driver loafer

baby nantucket sweater

nantucket stubbs & wootton and elephantito baby driving mocs

sailing nantucket sound

baby ack sweater

endeavor nantucket

ellsworth and ivey children's ack sweater

dog on endeavor sailing nantucket

Ralph Lauren cable knit cashmere sweater  //  L’Agence white jeans  //  Stubbs & Wootton bespoke Nantucket lighthouse slippers

Teddy’s ACK sweater  //  Teddy’s white chinos  //  Teddy’s driving mocs (Teddy is nine months and wearing infant size 2)

Will’s Stubbs & Wootton navy slippers  // Emily’s Ralph Lauren cardigan (similar)  //  Hayes’s Nantucket sweater

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P.S. Thank you to those who have expressed concern about the babies not wearing life jackets. I’m ashamed of having made this mistake and it will not happen again.

P.P.S. A few past sailing adventures here, here, here, and here.

P.P.P.S. You can use code DESIGNDARLING for 20% any full price Stubbs & Wootton order!

14 thoughts on “SAILING ON NANTUCKET

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  1. Perhaps a bit of an odd question, but any suggestions on where to get a good blow-out on Nantucket on a Monday?!

  2. I’ve just added this to my list for our visit at the end of the month! We live in Fall River and as many times as we’ve been to MV, we’ve never gone to Nantucket. Your guide has been great for helping us plan our little getaway. Thanks, Mackenzie!

  3. So cute! My cousin and I were introduced as babies and we’re best friends to this day. So glad your boys might get that chance too – not sure if you guys live close or not, but even if you don’t, it somehow worked out for me despite being two states away from my cousin.

  4. Have you tried a Slumber Pod for the Pack n Play? Our son is a month younger than Teddy and it’s been so helpful for us! There’s a little spot for the monitor and it makes it completely dark. I think it helps them go back to sleep if they wake up in an unfamiliar place!

  5. If you don’t already have one, a Pack n’ Play mattress makes a HUGE difference in sleep quality. Amazon has a bunch of them. Such a sanity (and sleep) saver when we travel with my little one!

    1. I have to second the pack-n-Play mattress. A total game changer. My son is over 2 and we still get use out of the pack n play as a result. We purchased one on Amazon.

  6. Cute photos.. but as a sailing instructor I’m horrified that you didn’t use life jackets for babies!