Just off the coast of Massachusetts lies an island that feels like a step back in time—where weathered cedar shakes are the standard, American flags sway proudly from porches, and every corner seems to hum with a gentle kind of charm. Nantucket isn’t a place of billboards, chain restaurants, or noisy intersections. Instead, it’s an island of cobblestone streets, flower-filled doorways, and a pace that invites you to slow down. It’s where long lunches stretch into lazy afternoon strolls, meals linger long past dessert, and time feels both abundant and unhurried. If you’re looking for a place to truly unwind—while indulging in as much seaside dining, boutique shopping, and simple, soul-filling beauty as your heart desires—you must book a trip.
From the moment we arrived in Nantucket for our girlfriends’ getaway, it felt like slipping into another world. We pulled into town and were greeted by streets brimming with hydrangeas and that unmistakable coastal energy that makes you instantly breathe a little deeper. We checked into The Nantucket, our home base for the trip, and it set the stage perfectly—equal parts historic charm and modern comfort. We had minimal expectations and a very loose itinerary of eating, shopping, and then eating some more, which turned out to be just right and really let us enjoy the trip as each day unfolded.
Nantucket has a way of pulling you into its rhythm. There’s romance in the weathered cedar shingles and flowers spilling across sidewalks, but also a liveliness—friends lingering on patios, couples savoring sunset strolls, bikes weaving their way to the beach. Here are my best tips and notes from our trip—and how to capture a little Nantucket magic of your own—starting, of course, with booking a stay at The Nantucket.
WHERE TO STAY //
The Nantucket Hotel & Resort is the island’s only year-round retreat, blending historic charm with modern coastal comfort. With two pools, spa treatments, incredible dining, and a mix of suites and cottages that feel like home, it’s everything you could want in a stay—thoughtful details, plenty of comfort, and a touch of history. I also love that it’s family-owned and operated by Little Gem Resorts.
I first discovered Little Gem Resorts back in 2021 during a trip to St. Thomas & a day trip to Lovango. We loved it so much that we returned with our extended family in 2023. Now, I’ve had the chance to experience another gem in their collection: The Nantucket Hotel.
This grand, shingle-style landmark has been welcoming guests since 1891 (originally as The Point Breeze) and was lovingly restored by the Snider family in 2012. Today, it stands in the heart of Nantucket, just steps from cobblestone streets and a short bike ride to the shore, offering a rare kind of welcome that feels both timeless and effortless. With 44 suites and three charming cottages, it’s more than a hotel—it’s an invitation to slow down and experience the island in every season.
I went with three of my girlfriends and we stayed in the Cromwell Suite, which turned out to be absolutely perfect for us—and would be just as wonderful for a family. It felt like our own beach house tucked inside a luxury hotel, complete with nautical-yet-modern décor. The suite had everything: a kitchen and dining area, a washer and dryer, a cozy living room with a hidden Murphy bed, and a layout that was both warm and practical (no glass tables or slippery marble floors to worry about if you’re traveling with kids).
I’ll admit it—I’m a hotel snob. I care about the big things (nice linens, pretty aesthetics, a house car) and the little things (a morning coffee station, water carafes, plenty of bedside charging ports, even board games in the lobby). The Nantucket nailed every detail. The hotel also has a surprisingly impressive gym and locker room with a sauna, plus all the extras that make a trip feel special. Mornings can begin with a swim or workout, followed by breakfast at Sailor’s Valentine or The Breeze. Afternoons are perfect for spa treatments, yoga classes, or simply relaxing at The Nantucket Club. Evenings might mean cocktails at the lobby bar or a few rounds of pool downstairs in the game room. And the location? Unbeatable—steps from downtown yet still with that tucked-away feel.
It was the perfect stay for a girls’ trip, but I kept thinking about how much my family would have loved it too—swimming, playing, biking around town, and walking for ice cream until their hearts were content.
As a bonus, they’ve kindly extended a discount for you: use code COOP for 10% off bookings at all three of their properties—Lovango, Nantucket, and Martha’s Vineyard—for the 2025 & 2026 seasons.
WHERE TO EAT //
The food. Where do I even begin? Nantucket is a MUST if you love seafood as much as I do—I could happily eat oysters for every meal. But beyond the raw bar, the island is full of culinary gems and the menus are overflowing with crisp Caesar salads, salty fries, juicy burgers, and plenty of sweet treats in between. It really is a little slice of food heaven.
Since we only had two and a half days on the island, we couldn’t possibly try it all, but we managed to squeeze in some incredible meals. Below is the list I kept on my phone to share with my girlfriends—a mix of where we ate, where we wished we had time to go, and a few quick notes to help you plan your own food-filled adventure. It’s not exhaustive, but it’s the kind of cheat sheet I always wish I had before visiting a new spot.
- Sailor’s Valentine – This is the restaurant at The Nantucket and was our favorite dinner of the trip!! We had pasta, salmon, oysters & several delicious apps and it was the only dinner spot we went to with delicious desserts.
- Cru – We went for dinner but I would go for lunch. It’s right on the water with a lot of outside seating and I feel like it’s more of a lunch vibe.
- Galley Beach – We went for dinner. It is a very nice experience with an elevated menu. It’s located right on the beach which people say is a must if it’s pretty. It was rainy and foggy the night we went and there was a huge tent set up for a wedding blocking the view of the ocean. I vote go if it’s sunny and maybe call ahead to see if there is a massive wedding tent erected.
- Nautilus – Went for dinner based on a TON of recommendations. Maybe it was an off night but we did not enjoy. We actually sent two dishes back and so did the table next to us.
- Brotherhood of Thieves – Grabbed a mid-shopping burger here one day for lunch. Delicious and a fun moody basement vibe.
- Bar Yoshi – We went for lunch and give it 5 stars. Amazing sushi, apps, dishes and drinks!
- Billies – Had happy hour apps there one day and it was amazing. We ordered oysters, fries & the wedge salad and they hit the spot. It’s brand new and BEAUTIFUL inside.
- Breakfast – We ate breakfast each morning at The Nantucket & it was delicious!!
Other spots recommended to us that we didn’t make it to this trip:
- Born & Bread – Breakfast (We walked by and it looked amazing)
- Juice Bar – Ice Cream (We regret not making this happen)
- Toppers, Black Eyed Susans, Chanticleer, Straight Warf, Lola 41 – Other spots that were suggested to us.
- Claudette’s – Sandwiches in Sconset if you bike the bluff
- Lemon Press – for a causal bite (it’s right in the middle of all the best shopping)
- Club Car – Recommended for after dinner drinks. Walked by one night and it looked lively & fun but we were tired & went back to watch reality tv in our jammies.
- Cisco, Millies & Lola 41 – Also recommended for drinks. We didn’t make it to any of them… are we sensing a pattern?? I think we were home by 7 or 8 each night binging chick flicks and/or reality TV. No regrets.
WHAT TO DO //
- Eat, eat some more and eat again (see above).
- Morning walk to Brant Point and up to Steps Beach.
- Bike to Sconset and do the Bluff Walk (You can reserve e-bikes from Young’s Bike Shop).
- Explore town, the wharfs & shop.
- Book a boat trip for the day. We didn’t do this but if we go back with the family we 100% will.
- Shop, shop, shop (see below).
WHERE TO SHOP //
- Boutiques You Can’t Miss // Our favorite shops were Millie & Grace, Erica Wilson, For Now, Cara Norman and Wheat—all charming stops with a great mix of fashion.
- Brand Stores // The Veronica Beard boutique is one of the best I’ve ever stepped into, and you absolutely can’t miss Ralph Lauren. Other favorites include Doen, Ellsworth + Ivey, Faherty, and Southern Tide, all with beautiful island storefronts.
- Vintage & Antiques // For one-of-a-kind treasures, check out Nantucket Antiques Depot, Trinity Collection (a must for vintage bags), Craftmasters of Nantucket (great ornaments and leather goods), plus Sylvia Antiques and Lynda Willauer Antiques.
- Souvenirs & Gifts // Nantucket Bookworks feels like stepping into the set of You’ve Got Mail, with an incredible selection of books and thoughtful gifts (especially for kids). Pinwheels Nantucket is another great spot for little ones, Townpool is a cheeky souvenir shop, and Millie & Grace doubles as both a boutique and a go-to for fun gifts for tweens and girls.
WHAT TO WEAR //
Shop my entire suitcase here and visit my LTK and ShopMy for more outfits!
Sweater // Jeans // Shoes // Shoes on Amazon // Sunglasses // Bag
