What to Pack for Nantucket

Nantucket style is polished, colorful and never overly serious. The essentials:

• A convertible dress: The ultimate suitcase overachiever. Our Darling Convertible Midi Dress transforms from a coastal seashell midi into a flirty mini in one zip. Two dresses, one reservation-packed weekend.
• A lightweight jacket: Evenings by the water can get cool. The Este Convertible Jacket is lightweight, reversible and convertible, giving you multiple ways to wear it without overpacking.
• A breezy button-down: The Iman Barong Top is an easy travel-day layer with special heritage-inspired details, so it feels anything but basic. Wear it with shorts, over swimwear or again on the trip home.
• An easy cotton poplin dress: The Brooklyn Mini Dress is crisp, breezy and ready for coffee in town, biking around ’Sconset or an afternoon by the harbor.
• A roomy raffia bag: The Esperanza Raffia Tote fits the beach essentials, shopping finds and all the little island treasures collected along the way.
• Flat sandals: A must for Nantucket’s cobblestones. We love Larroudé sandals for easy days and dressier evening plans.
• Accessories with personality: Add oversized sunglasses, colorful jewelry or a basket bag when the itinerary calls for something fun.

Most importantly, bring the dress. Better yet, bring the convertible and get two.

Where to Stay on Nantucket

Life House Nantucket

For our first visit, we checked into Life House Nantucket, a historic boutique hotel tucked away on Cliff Road.

The house first opened to travelers in 1833, but today it feels more like the home of your most stylish friend. Botanical prints, layered textiles, cozy corners and a garden made for lingering.

It also made the dreamiest backdrop for our first Nantucket trunk show.

Allison, the property’s general manager and heart of the house, kept us laughing and made the entire Mestiza team feel instantly at home. We arrived as guests and left ready to move in. 

Coffee and Breakfast

Handlebar Café

A beloved downtown stop for iced coffee before a walk through town. Casual, convenient and always buzzing.

Born & Bread

Go for the fresh pastries, scones and breakfast sandwiches. The ideal place to pick up something delicious before the beach.

Lemon Press

Smoothies, juices, coffee and colorful breakfast plates in the center of town. It is fresh, pretty and perfectly placed for a morning of shopping.

Black-Eyed Susan’s

A Nantucket institution with more than 30 years of pancakes, eggs and cozy breakfasts behind it.

Maggie’s tip: Breakfast is walk-in only. Arrive early, but know that waiting in line is practically part of the tradition.

Claudette’s

No ’Sconset afternoon is complete without a sandwich from Claudette’s. Order it “with the works,” find a sunny spot outside and thank Maggie later.

Something Natural

Freshly baked bread, famously generous sandwiches and a garden hidden beneath the trees. Take lunch to the beach or stay awhile.

Bartlett's Farms

Stop at family-run Bartlett’s Farm for flowers, local produce and Maggie’s beach-day order: the chicken salad sandwich.

Dinner Plans

TOPPER’S at The Wauwinet

Sometimes the best dinner reservation requires a boat.

Take the Wauwinet Lady across Nantucket Bay for dinner at TOPPER’S, followed by cocktails and sunset on the lawn.

Maggie’s tip: Reserve both the boat and restaurant in advance. This is one evening worth planning around

More Dinner Favorites

• The Nautilus: Globally inspired shared plates, creative cocktails and one of the island’s most coveted reservations. Bring friends and order for the table.
• Galley Beach: Dinner with your toes in the sand and sunset directly ahead. Wear the dress you were saving for a special occasion.
• The Chanticleer: Seasonal dishes in a flower-filled ’Sconset garden that feels hidden from the rest of the island.
• Lola 41: Sushi, cocktails and a lively dining room. Book early or try your luck at the bar.
• Oran Mor: An intimate downtown choice for a slower, more romantic dinner.
• Millie’s: A Madaket favorite for a relaxed meal before or after sunset.

Drinks and Dancing

Cru

Head to Cru for waterfront cocktails, oysters and some of the island’s best people-watching. Do not forget to order the Crucumber.

Cisco Brewers

Live music, food trucks, oysters and local drinks make Cisco Brewers the island’s signature afternoon party.

Maggie’s tip: Cisco is a daytime activity. Arrive early on a sunny weekend before the crowd gets serious.

Box Mondays at The Chicken Box

Locals call it “The Box.” Casual, loud and slightly chaotic, Box Mondays are a Nantucket must. Go once—or twice. We’re not keeping attendance.

Honorable mentions: The Club Car for drinks inside its iconic railway car and Gaslight for DJs and dancing after dinner.

Where to Shop in Nantucket

Erin Hielle

Looking for Mestiza on Nantucket? Visit Erin Hielle to browse a curated selection of our colorful, vacation-ready pieces.

We love seeing how the boutique styles Mestiza for island life, from reversible swimwear to dresses ready for dinner by the water.

   

Honorable mentions: Explore the seasonal pop-ups, especially during Nantucket by Design. Visit Murray’s Toggery Shop for the original Nantucket Reds, Nantucket Looms for beautiful handwoven textiles and Mitchell’s Book Corner for an Elin Hilderbrand novel to read on the beach.

The Best Beaches in Nantucket

Miacomet Beach

Maggie’s pick for rolling south-shore surf and fewer crowds. Pick up sandwiches from Bartlett’s Farm, settle into the sand and stay long enough to require the outdoor shower afterward.

Honorable mentions:

• Cisco Beach: For surfing and more of a scene.
• Madaket Beach: For one of the island’s best sunsets.
• 40th Pole: For days you want calmer waves but also want to drive onto the beach with your oversands permit
• Surfside Beach: For classic ocean waves and a wide stretch of sand.
• Jetties Beach: For a harbor-side swim followed by a frozen drink at the beach bar.

The unofficial ACK afternoon routine: beach, rinse, repeat.

One Last Stop

The Juice Bar

The line is long. The homemade ice cream and warm waffle cones are worth it.

Order a scoop and take one final walk through town. Nantucket is especially charming when you are holding dessert.

Until Next Time, ACK

Our first Mestiza trip to Nantucket began with a trunk show, but every free moment became an opportunity to see a little more of the island.

With Maggie’s list in hand, we found beautiful beaches, memorable meals, charming shops and plenty of reasons to return.

Make the reservations, leave a little room in the itinerary and pack something worthy of dinner by the water.

Until next time, ACK.

XOXO,
Mestiza