I’m working on putting together a comprehensive travel guide for Nantucket so you can find all my favorite recommendations in one place. I’m hoping to have it ready sometime this month (can you believe it’s August already?) but in the mean time I wanted to share one of our very favorite activities on the island, chartering a sailboat with Endeavor Sailing. This is the third summer I’ve hired them to take family and friends out on the harbor and it truly never disappoints.

Two weeks ago we ventured out to celebrate my Grandy’s birthday (she’s such a champ) with my fiancé Will, siblings Reilly and Grayson (poor Camden had to work), cousin Sarah, and friends Ali, Amy, Carla, Hadley, and Patrick! I was insanely lucky in that Ali, Amy, Patrick, and Grayson are all great photographers so I mostly sat back and relaxed and let them do their thing. It also happens to be Ali’s birthday today so send her some birthday love!

mackenzie horan wears the club monaco zephine sweater while sailing on nantucket

brant lighthouse from endeavor sailing on nantucket

mackenzie horan and will beuttenmuller sailing on nantucket

endeavor sailing in nantucket harbor

amy stone mackenzie horan and ali schilling on nantucket

design darling sailing nantucket

endeavor sailing nantucket

amy stone on nantucket

mackenzie horan and amy stone sailing on nantucket

nantucket sailboat charter with endeavor sailing

sailboat ride nantucket

design darling wears a striped off the shoulder club monaco zephine sweater

sailboat rides nantucket

Ray-Ban clubmasters  //  Club Monaco striped off-the-shoulder sweater  //  J Brand white skinny jeans

When deciding what to wear for a sailboat ride, a nautical striped shirt is really a no-brainer. It gets a little windy on board so this striped off-the-shoulder sweater from Club Monaco was perfect for the occasion! I also wore this ruffled off-the-shoulder sweater out to dinner at the Summer House one night — Club Monaco gets it right every time.

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