Today I’m en route to Nantucket with Ali and her husband Patrick where we’ll be joined by my friend Amy and all my family members who are up there working for the summer! It’s kind of a haul to get there from Dallas but I can’t wait to be up there with all my favorite people. Will is joining us in a couple days in time for a sailboat ride on Saturday to celebrate my Grandy’s birthday. SO EXCITED!

I’ve gotten a lot of emails about what to pack for a trip to Nantucket and it really depends on what you plan to do once you’re there. There’s definitely a big dining out scene in town if that’s your jam but our plans tend to be pretty casual — blueberry muffins and iced coffee for breakfast, sandwiches on the beach for lunch, grilling out in the backyard or heading to one of a few spots in town for dinner. (You can see my favorite restaurants here, my list of things to do on Nantucket here, and all my posts about Nantucket here.) I think it’s the perfect place for striped shirts, white jeans, Jack Rogers, a straw clutch, maybe a pair of espadrilles for a night out. Here’s my packing list for a casual summer weekend on Nantucket:

design darling nantucket packing list

one  //  two  //  three  //  four  //  five  //  six  //  seven  //  eight

nine  //  ten  //  eleven  //  twelve  //  thirteen  //  fourteen  //  fifteen

First, there’s no such thing as too many stripes. If Nantucket had a uniform, this would be it. I live in Saint James shirts that can be worn with shorts or over a swimsuit during the day and then with jeans when it cools off at night. If you have fun dinner plans, this scarf top would be to die for with white skinny jeans and gold wedges or you could tuck this silk camisole into a fab striped skirt.

Second, a warm weather vacation is the perfect occasion to bring out your chicest statement jewelry. I’m definitely biased but our turquoise tassel earrings and new oyster shell necklace fit in perfectly on the cobblestone streets of Nantucket.

Which brings me to my third point — shoes. Cobblestone streets and high heels are a recipe for disaster. If you love a little height (I’m 5’1″, I get it) go for espadrilles or wedges and leave your heels at home. Not only will they save you precious space in your carry-on (particularly if you’re flying Cape Air 😳) but you’ll save face not tripping down Main Street en route to cocktails. During the day you’ll be most at home in a pair of Jack Rogers or a stylish flat sandal like these gold pineapple pretties.

Lastly, I pack everything in my Steamline luggage, which is hands down the most complimented item I own. Then I’ll bring an LL Bean boat tote or my new monogrammed straw basket as a carry-on and voilà! I’ve toted all my essentials and managed to bring a bag that’s perfect for beaching and boating.

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  1. Please advise on the best attire for a visit to nantucket at the end of october? we will be on island for 4 days
    Many thanks in advance

    1. Hi Leanne, I would bring several sweaters as you will likely have traditional New England fall weather with temperatures dropping lower at night. I would also bring a trench coat or a jacket as well as a scarf in case it’s chillier than expected. Other than that, a pair of boots or booties and jeans and you should be good to go! Have a great time!