For Baked Goods: Born & Bread

My favorite scones of all time can be found at Born & Bread. This bakery makes excellent loaves of bread, coffee, sandwiches, you name it. The store has such great energy and it’s always buzzing with locals.

35 N Centre St

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For a Special Evening Out: Sister Ship

Sister Ship’s whimsical decor gives the impression you’ve stepped into the home of a maritime traveler. I love coming here for a delicious evening cocktail and dinner (they source locally!). My go-to is the Faraway Mermaid, with mezcal, Curaçao, lime, & jalapeño infused agave.

29 Centre St

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For Neapolitan Style Pizza: Pizzeria Gemelle

Gemelle is open year round for takeout and it’s my absolute favorite pizza on island. Gemelle, Via Mare, and Ventuno (the latter two are open in the warmer seasons) are all run by the same owner so you know the food is going to be deliziosa.

2 E Chestnut St

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For Locally Sourced Groceries: Pip & Anchor

If you feel like cooking at home, you should stop by Pip & Anchor for the most delicious and fresh, locally sourced produce. The watermelon radishes are insane - I eat them by the bag. They also sell an assortment of yummy natural wines to pair.

14 Amelia Dr

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For Surfboards & Cool Finds: Stoke ACK

Home to colorful surfboards, vintage clothing, coffee table books and more, this store has quickly become my favorite in town. I always seem to walk out with a new purchase when I visit and you probably will too!

48 Centre St

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For High Times: The Green Lady Dispensary

For those who partake, I recommend stopping by The Green Lady. It’s female and minority-owned and everything is locally grown. The Chocolate Firecracker Bar is delicious and guarantees good times.

11 Amelia Dr

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For a Scenic Walk: Sanford Farm

This is one of my favorite nature walks on the island. I usually go with my family and walk all the way until you eventually hit the ocean. It’s gorgeous no matter what season. Insider tip - the ACKTrails app by the Nantucket Conservation Foundation lists all of Nantucket’s amazing trails.

118 Madaket Rd

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For Shopping in Town: Ralph Lauren

Ralph Lauren is one of the only fashion stores that remain open year round and I have to recommend it, not only because I used to work there, but they always have gorgeous finds and the storefronts are such a delight. Make sure you check out the glass case of vintage Native American jewelry.

16 Main St

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For a Cultural Experience: African Meeting House

A National Historic Landmark, the African Meeting House is the only public building constructed and occupied by African Americans in the 19th century still standing on Nantucket. The building is the island’s most vivid reminder of a thriving 19th-century Black community. The Museum presents cultural programs and interpretive exhibits on the history of African Americans on Nantucket.

29 York St

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For Drinks with Friends: Cisco Brewers

Cisco Brewers is like an island institution at this point - it’s been around for years and everyone’s a fan. Some of my favorite memories were made at Cisco and I can’t recommend it enough. Make sure to check out the live music line up on their site. Their drinks are fantastic and made on island!

5 Bartlett Farm Rd

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For a Rejuvenating Yoga Class: Supta Yoga

Supta Yoga’s studio is spacious, high-ceilinged and filled with plenty of natural light. They teach a variety of transformative yoga styles and offer donation based community classes and meditation, in effort to make yoga & meditation more accessible on island.

9 Amelia Dr

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See Annabelle on Instagram at @annabellegiletti.