Start Here: Nantucket

Our friend (and fellow travel advisor) Julie Sommer has been summering in Nantucket since she was teeny tiny. If I was going to Nantucket, she would be the very first person I’d go to for recommendations. Nantucket = Julie. Julie = Nantucket.

So we asked her to give us her recommendations for ACK both as a semi-local and an advisor. With one caveat. We asked her to only recommend ONE place per category; hotel, bar, restaurant, activity, shop. She said sure, but then gave us an exclamation - ONLY ONE!?? So here it is, her best of the best spots for this idyllic destination.

Take it away Julie…

A little about me: I'm Julie Sommer, owner of Jewel Travel Co., and I've been going to Nantucket since I was 5. My family has a house there, so my childhood summers were all biking to the beach, ice cream at the Juice Bar, and sunsets at Madaket. It's just as good year-round too (Daffodil Festival and Christmas Stroll are non-negotiable traditions in my house). The island has changed a lot in the past 30 years, but it's so rooted in its history and traditions that at its core, so it's it's still the same if you know where to look. That's exactly why showing someone around for their first time is one of my favorite things to do. One ask if you go: please follow the local trash rules (they're very specific) and respect the folks who live there year-round! The island is so much more than an Instagram aesthetic.

White Elephant. A bit of a splurge, but I can't think of a more quintessentially Nantucket place for a first timer. The perks (courtesy car, advisor amenities) add so much value, and there's a little something for everybody: the hotel itself, Cottages that are great for families, Residences in different locations with multiple layouts (some are lofts in town along the boat basin), and lower priced rooms in the Inn. It was renovated a couple years ago and it's gorgeous. Sunday brunch at the hotel restaurant is one of the best on the island (especially if you love a bloody mary). Pro tip: its sister property is the Wauwinet out in Sconset, a charming, more traditional, adults-only hotel. The restaurant there is Topper's, and when you book dinner you can reserve a $35 spot on the Wauwinet Lady, the boat that takes you from the White Elephant out to the Wauwinet. Such a beautiful way to see the island, especially at sunset.

(For less of a splurge I love the Faraway Hotel right in town. Note there can be street noise in the rooms due to its location, but it has a cute courtyard bar called the Sistershi. Get The Mermaid. It's next to Born & Bread, which has the best sandwiches you'll ever eat. There will be a line, but it's worth it.)

I have to break the rules and give you two (a day option and a night option), because it would be a rookie mistake to leave out Cisco Brewers. People call it the happiest place on earth and they're not wrong: a brewery, a distillery, and a winery around a courtyard, food trucks on the side, and a big stage with great live music. Take the WAVE (the free public transport) or their free shuttle. Pro tip: the vibe is apres-beach, so no need to dress like you would for dinner in town. Cutoffs and a tank is all you need.

For happy hour, my favorite is Proprietors. There are a lot of cucumber drinks on the island (shout out to the CRUcumber), but this cucumber cocktail takes the crown in taste and presentation. Really fun vibe, great variety, and the bartenders are so good that you can tell them the flavor profile you like and they'll invent something amazing for you.

And for a proper night out, the Gazebo on the wharf is always a fun time. It's literally a gazebo and a total dive, but you could be drinking next to a billionaire and never know it. Rumor has it this is the last year of their world-famous mudslide, so get there before the end of the year if you want one!