Road Trip Across America: Nantucket

Nantucket is an island with a personality all it’s own.  It is equal parts sophistication, New England charm, and laid-back beach destination, with a rich history in colonial commerce and whaling.  When traveling to Nantucket, packing well is essential.  You need the right high/low mix to take you from bike rides and the beach to a night out on the town.  That, and it all needs to fit in the perfect weekender bag since you have to take the ferry or a little puddle jumper plane to get there.


Pick a bright color or a fun pattern. No boring black here.

Beach cover-up
Opt for a beach cover that can also double as a sundress.  An item that can serve a double duty is key when packing light.

Aviators for biking and beach time, and some ultra glam cat-eye sunglasses for strolling downtown.  Remember, the sun doesn’t set until almost 9pm in the summer.

Flip flops
Cute enough to mix with your dresses, but functional enough to go to the beach.

Panama hat
I am loving these right now.  They are wide-brimmed enough to offer sun protection, but without the hazard of a floppy sun hat blowing off your head during your bike ride.

Maxi dress
Glam it up for night with a breezy maxi dress.  Pick a great color that can also transition into fall.

Denim jacket
The nights can get chilly on the island, and a denim jacket is a perfect travel solution.  Cuff the sleeves and throw your hair up in a loose topknot for instant evening-chic.

Wedges or flat-forms
Get some height for night, but still navigate the cobblestone streets like a pro.

Gold tones look great on sun-kissed skin.  Stack bracelets up each arm, add a great cocktail ring, and you are ready for evening fun.

Throw it all in a nautical-themed canvas weekend bag and you’re ready to board the ferry or hop on a little plane, “Wings” style.


Nantucket has some of the most beautiful beaches on the east coast, and a great way to see them is by bike.  There are a ton of bike rental shops in town and you really can’t go wrong with any of them.  Rent one for the day and hit the beach.  My favorite is Surfside Beach. It’s a nice bike ride from downtown, has a long, beautiful beachfront, and a little snack shack so you don’t have to pack a huge picnic.

Rent a 4×4 Jeep at the airport and drive out to the Coskata-Coature Wildlife Refuge. It’s a magnificent, coastal safari as you drive over the sand and dunes in this wildlife sanctuary. Make sure to look for seals popping their heads out of the water.  Note: this is not for novice 4×4 drivers, but it’s well worth the adventure.

For a little island, Nantucket boasts some major shopping. I particularly love seeing how shops curate and display their goods. We’re talking fabulous interior design inspiration. Two of my favorites are Trillium and Belongings.

When you’re all beached out, Cisco Brewers is another great day adventure, and the perfect bike destination should you indulge in a few beverages.  They usually have live music and a great patio connecting their three tasting rooms: one for beer, one for wine, and one for vodka.  They have the best bloody Mary mix I’ve ever tasted…hands down!

As the sun begins to set, throw on your maxi dress, and begin your night on the town with a cocktail at Dune. It’s right downtown and has a cute, little outdoor patio. For a fancy dinner, my favorite place is the Boarding House, or for a more relaxed, Tex-Mex dinner, I love Corazpn del Mar.

No night is complete without a visit to The Chicken Box.  It will take you back to your college days with live music, dancing, foosball, beer right out of the bottle, and more fun than you can imagine.

See ya on the island!

Sarah Winchester is a commercial photographer and graphic artist. For more of her work and tastes of Nantucket, check out her blog Sarah Winchester Studios

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