What to Wear on Nantucket

Updated June 23, 2020.

It’s a very special What I Wore Wednesday! If you’ve been following along on Instagram and Facebook @quickwhittravel, you know I recently enjoyed a few days on beautiful Nantucket Island. I’ll be honest, I was a little insecure about what to pack. I’ve never been sailing, and I don’t think “athleisure” or all black is exactly an acceptable look for “summering on Nantucket.” But I think I came up with a pretty nice combination of pieces. Take a look!

*Many of the links below are Amazon affiliate links! This means that when you click the photos to shop with me, you’re supporting my small business at no additional charge to you!


Knowing I would be biking, boating, walking, etc., I needed an back-friendly bag to keep myself comfortable. So I chose my backpack/purse combo, which keeps things pretty secure since the main part of the bag is only accessible by a zipper against my back. I always put a jacket, reading material, snack bar, water bottle, sunglasses, credit cards, and cash in my carry-on, which will also be my purse for the trip.

Flying and Arriving

Because this was a short trip (48 hours, to be exact), I needed to be efficient about my clothing choices. I knew when I landed, I’d have time to drop my stuff off at the hotel, then go right for a two-hour bike tour! Later that afternoon, I scheduled a sailing cruise around the island, and I didn’t want to waste time changing clothes between activities (or lose the luggage space). I don’t have any white clam digger pants or a blue-and-white checkered button down shirt or boat shoes (that’s the boating outfit vision I have in my head–what about you?), but I do have an adorable white running skirt and blue polo! For efficiency’s sake I wore the running shoes to the airport and for the bike ride, and I changed into the water shoes for the boat tour.

Workout Wear

One of my favorite things to do in a new place is run outside! And the best kind of run is in a seaside town. Since I’d be there two mornings, I needed two workout outfits. It would be in the low-to mid-60s in the mornings (fantastic running weather), so I decided to use the same running skirt as the one above with two different tops.


These are my pretty basic toiletries, all travel-sized: hair mousse, toothbrush and toothpaste, floss, q-tips, hair ties, extra contacts, contact solution, contacts case, coconut oil, deodorant, and conditioner. I’m rocking that clearance sticker on the conditioner.

Basic toiletries.
Must read: Your Ultimate Guide to Solid Toiletries


This is the one item I actually got new before my trip. My mom got it for my birthday, and I thought it would be just perfect for a day out in classy Nantucket! I think of seersucker with a monogram as such a Southern thing, but it also seemed perfect for this trip–light, airy, and classic! And these Teva sandals are the most comfortable I’ve ever had.

The Flight Home

This little dress is one of the best–light, no wrinkles, quick-dry, and flattering! And it’ll go with my brown sandals or the water shoes. A morning walk along the beach might be a nice way to end a trip, don’t you think?

I hope this helps you pick your own luggage for a few days of summering on Nantucket! What would you pack? Find out my best tips and strategies on my Packing Page!

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