Facebook Copy-color Created with Sketch.
Instagram-color Created with Sketch.

Explore

I'm Kiley Smith, an experienced makeup artist with over 20 years in the industry, based in Fairfax City, Virginia. 
My passion lies in creating natural, radiant makeup looks that enhance your beauty, ensuring you feel confident and stunning with a flawless finish. 

I'm Kiley smith

Hello!

Beach Bag Beauty: Cape Cod & Nantucket

Travel

August 19, 2026

back to blog

My makeup bag essentials, the shops I couldn’t leave without visiting, and everywhere we ate this summer on Cape Cod and Nantucket.

Every summer my family heads to Cape Cod to spend time with my best friend Samantha — we’ve been friends since we were little, and now our families vacation together every year. Sam and her husband own Weatherwood Cottage, a sweet 18th century cottage in Centerville — one of the oldest homes in town — and it’s become our home base for these trips, and for packing my beach vacation makeup essentials before busy beach days. It sleeps nine comfortably, has the dreamiest outdoor shower, and sits just a few minutes from Lake Wequaquet, Craigville Beach, and Hyannisport. If you’re ever looking for a place to stay on the Cape, I cannot recommend it enough.

This year’s trip meant three beach days, a hop over to Nantucket, and — of course — a full kit of my favorite beach vacation makeup essentials. Here’s everything I reached for, what Sam fell in love with when we played with products before dinner one night, and all the little shops and restaurants that made the trip.


My Beach Vacation Makeup Essentials

Between three beach days, heat, and many trips in and out of the water, my SPF and makeup had to perform. These were the MVPs:

Mascara

Sunscreen — Face

Sunscreen — Body

Everyday Sunscreen (Under Makeup)


Getting Ready With Samantha

One of my favorite parts of these trips is the pre-dinner getting-ready ritual. It takes me right back to our sleepovers as kids, playing dress-up for hours. I show up with a big bag of my favorite products, and Sam and I take our time together, playing with makeup before heading out for the evening.

This year Samantha used the under-eye brighteners I’ve been raving about for ages, and she’s officially obsessed:

She also tried my year-round go-to blush, Westman Atelier Baby Cheeks Blush Stick in Coquette. Sam usually reaches for the shade Petal in the fall and winter, but I think I may have talked her into picking up a second shade for spring and summer too.

The other product she couldn’t stop talking about was the Thrive Causemetics EmpowerGloss Ultra-Glossy Lip Serum — just a sheer wash of color with so much hydration. Honestly the perfect beach day lip.


What I Picked Up on the Cape

What I Picked Up on Nantucket

A note on Nantucket shopping: everything on the island tends to run pricey — shops often charge $500+ for sweatshirts, sweaters, and dresses simply because they’re on the island. Murray’s Toggery Shop (the original home of Nantucket Reds) offered some of the more reasonably priced pieces, so if you’re looking to bring a piece home, I’d start there.


Where We Ate on the Cape

The Pheasant in Dennis accommodated everyone with food allergies well (almost everyone in our party had an allergy or preference — shellfish, gluten, vegetarian) — it had a loud atmosphere but served genuinely delicious food with good service. My one note: the tomato and peach salad needed more peaches and was a touch bland.

Fancy’s Market in Osterville was our go-to for sandwiches to bring to the beach. We love everything on the menu, but the Mediterranean, the Ivan, and the Caprese are the standouts. A Del’s lemonade (pink and regular) plus a bag of Cape Cod chips are non-negotiable beach day musts, too.

At Mattakeese Wharf, a waterfront seafood spot, we had lobster bisque, fish and chips, pasta in a beurre blanc sauce with capers, and scallops in butter. Very chill atmosphere-not the most amazing food but a fine casual dinner. Iwould go back just for the incredible Lobster bisque and my family loved the calamari.

Anejo Mexican Bistro, located in Hyannis (with a second location in Falmouth), is a spot we continue to return to. We love eating under the gigantic beech tree patio. Their food is wonderful and service is always top notch.

Ice Cream on the Cape

Ice cream happened nearly every evening — rotating between Four SeasIce Cream Smuggler, and Steve & Sue’s Par-Tee Freeze.

Where We Ate on Nantucket

We had the largest shrimp cocktail I’ve ever seen at Cru, along with lobster rolls, a crispy haddock sandwich, cucumber salad, and a summer tagliatelle. Loved everything — my only note was the coleslaw could’ve used a bit more sauce. That same trip we also tried Bar Yoshi, which was just okay.

Ice Cream on Nantucket

The Juice Bar is an absolute must — they make their own waffle cones (essential, according to my husband) and their own ice cream in-house. I got the watermelon crème, a milkshake of fresh watermelon juice and vanilla ice cream, and it was incredible.

We also stopped at Jack and Charlie’s, which had gluten-free waffle cones — such a treat, since I honestly can’t remember the last time I had one since being diagnosed in 2020. My one disappointment: they don’t make their own ice cream, they use Gifford’s.


Around Nantucket

Beyond the shops and food, we spent time exploring the island itself. The Nantucket Whaling Museum was a highlight — I learned so much about the island’s whaling history, the famous lightship baskets, and scrimshaw. They have an amazing rooftop terrace where you can get a wonderful view of Nantucket. We also wandered through the historic Nantucket Atheneum, and as book lovers, it was so fun to see all the old historical texts on display.

There’s so much to see just walking around — the adorable historic homes (my favorite is one called “Hunky Dory”), hydrangeas absolutely everywhere, and flower box displays that were honestly to die for. We ducked into more shops and bookstores than I can count.


That’s a wrap on this summer’s Cape Cod and Nantucket trip — thank you to Samantha, Reid, and Oliver for having us at Weatherwood again this year. We have plans to go back to Weatherwood in December and next summer, and we’ll also be visiting Martha’s Vineyard and Nantucket. If you try any of these products or make it to any of these spots, I’d love to hear about it!


Getting Married on Nantucket or Cape Cod?

I’m now booking destination weddings on Cape Cod and Nantucket! If you’re a bride getting married in either location, I would love to hear from you. Get in touch and let’s talk about your big day.


Leave a Reply

Your email address will not be published. Required fields are marked *

share this post:

Facebook Copy-color Created with Sketch.
Instagram-color Created with Sketch.

Explore

I'm Kiley Smith, an experienced makeup artist with over 20 years in the industry, based in Fairfax City, Virginia. 
My passion lies in creating natural, radiant makeup looks that enhance your beauty, ensuring you feel confident and stunning with a flawless finish. 

I'm Kiley smith

Hello!