I just got back from my first ever visit to Nantucket, Massachusetts! I’ve always wanted to go, but coming from Texas it always seemed like a fairly complicated place to get to. Now that I’m living in NYC, it’s an easy direct flight! I decided to plan a long weekend, and booked myself a stay from Thursday-Monday. What I loved about Nantucket was how small it was – it’s easy to get around (I walked nearly everywhere!) and while there’s plenty to do and see, it’s not an overwhelming amount. Easy to fit a lot in within just 3-4 days! The downside to it being so small is that it’s very crowded, especially on the weekends. Get reservations wherever/whenever you can (most places open up reservations 7-14 days prior – just check their websites!), or plan to go early and wait in line. Luckily any lines I did stand in, I was either seated immediately once I got to the front or it moved pretty fast. I had the time of my life and can’t wait to plan another trip back to the island! If you’re heading to Nantucket soon and looking for the scoop on the best hotels, my favorite restaurants and shops, and exactly what I did on this trip, here’s a travel guide for you to peruse!
WHERE TO STAY
Many who visit the island stay for a month or all summer long, so a rental may make more sense! But if you’re going for just a long weekend, consider one of these hotels!
THE BEACHSIDE – This is where I stayed! I loved how it was a 10 minute walk to downtown and a 10 minute walk to the beach in the other direction. It was perfectly positioned to enjoy both without a major trek either way! The only times I had to take an Uber were to the airport, to Cisco Brewers and over to Sconset Bluff (I’m not a cyclist lol). My room was well appointed and stylish, and the bathroom was large and well-lit! I especially loved the common areas and amenities – the pool and outdoor seating areas were fabulous, as was the lobby which features a coffee/breakfast bar in the morning and a little candy store in the gift shop. They also have a fitness center, but I didn’t manage to pop in on my trip.
THE HOTEL NANTUCKET – This hotel is the only year-round hotel on the island, so a good choice if you go another time of year! It is dog and kid-friendly, with plenty of activities, dining experiences and even a kids club.
THE WAUWINET – If you’re looking for a hotel with direct beach access, this may be the one! A classic luxury hotel with traditional, beachy interiors. Their restaurant, Topper’s, is very popular!
THE BRANT – Another beautiful boutique hotel on the same street as The Beachside but a little closer to downtown.
21 BROAD STREET – More of a bed-and-breakfast vibe in the heart of downtown!
FARAWAY HOTEL – Another great spot in the center of downtown, featuring a fun bar and restaurant called Sister Ship!
WHERE TO DINE & DRINK
CRU – A very popular spot for lunch or dinner, featuring a fabulous lobster roll and other delicious seafood specialties! We got in the already pretty packed line at 11:00am (they open at 11:30!) and luckily were able to be seated right away outside as a party of two. CRU is also a go-to for post-dinner drinks as the bar scene heats up at night! Fair warning, their drinks are deadly – so strong, I could only have half of the one I ordered!
THE NAUTILUS – Another beloved spot, it is almost impossible to score a reservation because the place is so small… but if you get in line 15-20 minutes before they open at 5:30 and you’re a small party, you can grab a spot at the bar. The bar is always first come, first serve! I managed to snag one of the last bar seats overlooking the kitchen and had the best meal! I ordered four dishes from the small plates section so I could try several things – the fried oyster tacos, the yellowfin tuna lettuce wraps, the Japanese street corn and the miso-marinated cod. Everything was amazing, but the dish I’ll be dreaming about is the Japanese street corn. It was INCREDIBLE! Definitely get it if you see it on the menu – it changes often depending on what ingredients are in season at the moment!
GALLEY BEACH – Hoping to dine on the beach? Add this one to your list. The reservations are kind of annoying to get, as you have to call a number repeatedly until they answer (two weeks in advance) – there’s no waiting room with music, just a busy tone that asks you to dial again. I swear I called the number 60 times before I got through! But I managed to snag us a reservation for 6:15 – you have the option of being on their patio or on the beach under the tent, and I chose the beach. It was so vibey to be able to sit with our feet in the sand as we sipped champagne watching the sun go down! I’d heard the food wasn’t that great, but I actually loved the halibut I ordered!
BAR YOSHI – I had lunch here at the bar on my first day in town and it was perfect! I sat between two locals (a bartender at CRU and a realtor) who were super friendly and gave me great insider tips for my trip. I’m used to sushi portions being fairly small, so when I ordered three dishes I was blown away by the oversized portions! I definitely couldn’t eat it all, but I am glad I tried a few different things on the menu. My favorite? The torched salmon roll stuffed with shrimp tempura and topped with truffle oil. Incredible!
TOPPER’S – If you’re looking for superior fine dining for a date night or special occasion, add this AAA 5-Diamond restaurant to your list!
SOMETHING NATURAL – Known for their housemade breads and sandwiches, this place is a go-to for takeaway! I ordered the famous Terry Terrific, which is famous on the island – it’s giving Ross’ Thanksgiving sandwich on Friends, featuring turkey, cranberry sauce, stuffing, etc. I got it on their house made sourdough, and it was, in fact, terrific! I took mine to go and enjoyed it by the pool at my hotel.
BLACK-EYED SUSAN’S – This was my last breakfast and it was incredible! There was a big crowd outside waiting for a table, but as a solo diner I was seated at the bar right away. I ordered the huevos rancheros and a side single buttermilk pancake! The huevos rivaled my favorite at the Rosewood in San Miguel, Mexico – they were phenomenal!!!! The pancake was so buttery and delicious too – just melted in my mouth. Highly recommend if you’re a breakfast person like I am! I sat at the bar, which was a very toasty spot overlooking the griddles – I’d try to request a table on the patio if you don’t want to be hot!
THE PROPRIETORS – A lively, bustling bar and restaurant downtown with great cocktails and food. I do not recommend sitting at the communal table, which I was subjected to with no bar seats available – I would have had way more fun at the bar and just should have waited for a seat to open up! I loved the crispy fried fluke I had for my entree – so so yummy.
CISCO BREWERS – A fun open-air venue featuring live music, food trucks, beer, wine and cocktails! We decided to go on a more cloudy day when it wasn’t optimal to be at the beach/pool. Highly recommend the frozen painkiller we got from the wine shed.
ISLAND KITCHEN – If I’d had time, I would’ve also gone to this breakfast spot just south of the downtown bustle!
BLOOM BAR – A newer spot to the downtown area, this spot acts as a cafe in the morning and turns into a bustling dinner spot at night! Very stylish interiors and fresh flavors. We loved the house-made fettucine, the farm greens salad and the shrimp & scallops francese.
BORN AND BREAD – An amazing bakery and coffee shop that is deserving of its line in the morning! Don’t miss their sourdough breakfast paninis.
SISTER SHIP – A fun spot for a drink before dinner! Grab a spot in their garden for the best vibes.
THE PEARL – A large restaurant in the heart of downtown that I got a lot of recs for! I had this one as a backup for dinner, but didn’t end up needing it!
STRAIGHT WHARF – This was another back-up on my list for dinner that I sadly never made it to! But I’ve heard it’s amazing.
THE CHICKEN BOX – Our wildest night was at this bar! They played amazing music, and that was BEFORE the band came on! Such a fun scene, but definitely on the younger side. I felt like I was back in college!
MILLIE’S – One reason I need to go back to Nantucket is that I never made it over to Madaket this trip! I just didn’t have enough time. But I’ve heard this restaurant is a great spot for watching the sun set over dinner! We actually tried some of their food from their truck at Cisco’s and loved it!
THE JUICE BAR – A popular ice cream shop in town with the craziest lines you’ve ever seen after dinner. Go in the middle of the day to skip that! Pro tip: try the watermelon cream – it’s fresh watermelon juice blended with vanilla ice cream… yum!!!
HANDLEBAR – I heard this is an amazing spot for coffee, but with the coffee bar in my hotel I never ventured over there!
PROVISIONS – If you’re downtown and looking for a Turkey Terrific like the one I had at Something Natural, this spot has a nearly identical sandwich that I hear is just as good!
THE CLUB CAR – Tried to go here after dinner Friday night and it was PACKED! Definitely plan to go earlier if you don’t want to experience it like a sardine.
19 RAW OYSTER BAR – I had this on my list to do for lunch one day, but didn’t end up having time! Next time I will try it!!
THE BEST SHOPPING
BIRDIE – I stopped by this last boutique on my final night and I’m SO glad I came across it, because it my be my favorite! On one side you’ll find women’s clothing and accessories, and on the other an impeccable selection of decor, platters, serveware, linens and other chic home goods. I wanted everything!!! I ended up getting this top (in a small!), this dress (in an XS!) and this touch table lamp in pink for my mahjong table.
GYPSY – Lovers of Khaite, The Row and Alaia will adore this incredibly well-edited boutique! They had Nour Hammour leather jackets, amazing denim, and plenty of styles in the quiet luxury category if that’s your look. I picked up a thick white cropped tee and some black culottes I’m not sure I can pull off… but I’m sure going to try!
CENTRE POINT – A collection of colorful clothing and entertaining finds! They had amazing serveware, cocktail napkins, trays, cutting boards, etc. I picked up these Lulu Powers multi-colored napkins – I thought they’d be a fun set to go along with my vibrant mahjong set when I host!
GRACE GEIER – the first boutique I popped into and loved! They carry contemporary labels like Hunter Bell and White & Warren, leaning into island, anchor and sea creature motifs. So many cute things! That’s where I found this lobster-embroidered sweater. Obsessed.
BODEGA – next to Milly & Grace, this boutique features a little bit of clothing, some accessories, but is mostly home and decor oriented.
MILLY & GRACE – A cute women’s boutique featuring clothing, accessories and beauty!
A SAILOR’S VALENTINE (TUCKERNUCK POP-UP) – Tuckernuck feels right at home on Nantucket, and their pop-up is adorable!
THE SHOP BY WHEAT – A unique collection of contemporary and designer labels, including some designer resale finds!
THINGS TO DO AROUND THE ISLAND
SCONSET BLUFF WALK – Bike or drive over to Sconset to walk the bluff overlooking the ocean! I walked on the path one way and on the street heading back so I could see houses from different vantage points. All so charming and beautiful!
STEPS BEACH – A beautiful public beach we went to one afternoon! Other beaches around the island to check out include Jetties beach, Children’s Beach, Dionis Beach, Surfside Beach, Madaket Beach, and Cisco Beach!
BRANT POINT – Check out the coast guard station and lighthouse before taking a walk down the beach! It’s named The Eighth Lighthouse, which is ironic because it’s actually the second oldest lighthouse in the country – it was established in 1746!
BARTLETT’S FARM – In addition to being able to pick your own flowers and veggies, they have walking tours, yoga classes and more events throughout the season!
RENT A BOAT/GO FISHING – I’ve heard renting a boat is another fabulous way to see the island from a different perspective. Or you can charter a fishing boat with a guide like Tom! If I were going to be there longer, I would have absolutely done that. Next time!
SUNSET SAIL – If I’d had more good weather days, I would have loved to be taken out on the water at sunset!
