36 Hours on Nantucket

One of my favorite things to look forward to in the summertime is my annual weekend in Nantucket, Massachusetts to visit my friend, Emily. For years, she and her family have made Nantucket their summer vacation spot. As Emily and her siblings have gotten older, Nantucket has become more than a week-long holiday and has instead become their home, for she and her sister Julia now work and live on the island full-time.

I’ll typically make it out to see Emily towards the end of July. Sadly, due to our conflicting work schedules I’m only ever there for about a day and a half. BUT! That isn’t to say that I haven’t had the full Nantucket experience. For about 36 hours every summer, Em plays the ultimate hostess, tour guide, and bff by ensuring not a moment of my trip is wasted. As I reflect on my weekend on the ferry ride back to Hyannis, I’m always in disbelief at how much longer my stay had seemed due to our jam-packed schedule.

Because I enjoy my brief annual getaway so much, I’ve asked Emily to elaborate on our usual itinerary and share some of her favorite spots on the island. If you’re not already considering a trip to Nantucket this summer, there’s no doubt you’ll find yourself looking into it after reading Emily’s responses to some of the questions I’ve posed below.

Take a look!

First things first!!! What is the best way to get around Nantucket as a vacationer?

If visiting, I definitely recommend staying somewhere in town so you really don’t need to taxi or Uber since everything will be right at your fingertips. If you think you can handle it, I’d suggest renting a mo-ped. Always a good call. I also use Uber a lot, but keep in mind that taxis and Ubers have a surcharge at night, especially on big weekends like Wine Festival, Figawi, and Stroll. Biking is of course an option, although not the most practical. Also worth mentioning is the bus called The Wave. It’s not the most luxurious form of transportation but it only costs $1 per ride and stops just about everywhere on the island.

…And being an island and all, you can’t exactly ignore Nantucket’s stunning beaches. Which ones are your favorite and why?

My go-to beach is Fisherman’s. It’s definitely the ideal group beach rather than a quiet solo spot. Because it’s super wide and long, there’s plenty of room to hang with a bunch of people. It’s nice and flat so it’s perfect for beach games like spike ball, kan jam, and paddle ball, and of course, beach parties. The even better news is that there aren’t really any rules on the beaches here. Pretty much anything goes as long as you clean up after yourself. You can find some pretty big waves at this beach—it’s on the same stretch as Nobadeer Beach, which is a great spot for surfing. Even better, it’s within biking distance from town and has a decent-sized parking lot if you choose to drive.

If you’re looking for a more relaxing experience, I really enjoy Fat Ladies Beach and Radio Tower Beach. Located in the Miacomet area, these beaches are similar due to their close proximity and both are much less populated than those in the Fisherman and Nobadeer area. Although, they are not as easily accessible. These beaches are at the end of a mile-long dirt road right next to the Miacomet golf course. Nice for reading and solo tanning. Also some pretty big waves.

On the other side of the island, closer to town, there is Steps Beach. It’s on the sound side of the island so it’s pretty calm. Itty bitty waves, nice for swimming, nice sunsets. Typically pretty crowded in July and August.

But the best sunsets can be seen in Madaket! It’s a little ways out but it’s totally worth the trip. Plus, there’s a little casual restaurant called Millie’s. Quesadillas, tacos, and margaritas. Nice post-beach or pre-dinner spot.

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Anywhere else to grab a drink before dinner?

Nautilus is definitely the best place for cocktails. They are SO creative and SO delicious. Anything with tequila is a good call. Spicy margs on point. My current favorite is called ‘The Golden Goose,’ made with citrus vodka, grilled pineapple, and togarashi. The names of the cocktails are all super cute. I’m a fan of ‘Do you boys like Mexico,’ which is a combination of mezcal, hibiscus, orange & vanilla. Although, my favorite cocktail came out this year in time for Stroll and is appropriately named, ‘Strollin’ with the Homies.’ This one is vodka, hibiscus, and lemon. Talk about holiday cheer.

Cru is also a nice spot for cocktails, but more-so around 4pm and accompanied by a round of oysters. It’s super chic inside and I love that windows make up most of the walls. Cru serves champagne in coupes and has this really yummy punch presented to the table in a big, golden pineapple. Although it supposedly serves five to six, with the help of my sister Julia, one of Cru’s sommeliers, I finished it off in forty minutes alongside some oysters over the summer.

Once the 4pm oysters and punch have worn off, where do you suggest going to dinner? Any favorites off the menus?

VENTUNO!!! I know I work there, but I can assure you that I am not biased. The food is seriously so good. I think the menu probably appeals more to meat-eaters, but there are also really spectacular seafood options and always a great vegetarian pasta. THE PASTAAA. Homemade, fresh, hot pasta. If you come to Ventuno for dinner, get pasta. What’s great about these plates is that you can order either a half-portion or an entree. A lot of people tend to get pasta as their appetizer which is such a baller move. This summer I think my favorite pasta dish was the Radiatori: sauteed wild mushrooms, porcini sugo, and parmigiano. So. Fucking. Good. Another great dish was the Panzanella Salad that we served at the beginning of the summer. A Tuscan bread salad, this dish incorporated big, juicy bartlett’s tomatoes, ricotta salata, fresh herbs, olive oil and a vinaigrette dressing. My mouth is watering just thinking about it. And, of course, we have the classics: fried olives stuffed with pork sausage, ricotta and honey crostini, and our super famous meatballs. People come in specifically for the meatballs.

Nautilus is a close runner up food-wise. It’s known for its delicious Asian-influenced small plates. All so good. My favorites are the scallion pancakes and the blue crab fried rice. It’s such a great place to eat because you can try a lot! It’s a fun date spot, but I prefer going with large groups for optimal sharing. If you’re looking for something a little more filling, not to worry. Nautilus serves larger plates in addition to the smaller ones that are ideal for sharing. For example, the scallion pancake is small but the blue crab fried rice is the size of an average entree. Right now they are serving lunch, and the Korean short rib tacos are too bomb.

Let’s maintain that Golden Goose buzz. What places offer the best nightlife?

Ventuno’s back bar is bumping, always. It’s busy even through the off-season in December. But in the summertime it’s like a big, crazy dance party.

Cru also gets busy at night. Kourt K even stopped in for a drink over the summer.

And then, if you’re really tryna get after it, be sure to hit The Chicken Box. I literally blackout every time I go to the box. It’s a total dive bar but it’s so much fun. Pool tables, darts, gambling… and basically the only music venue on island. A lot of great bands play including Cherub, Galactic, and The Revivalists. So much fun!!!

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Emily and Me at Ventuno’s back bar, July, 2016

And after an evening of incredible food and maybe one too many cocktails, please tell us: Where can we get a great cup of coffee to bring us back to life come morning?

The Handlebar Cafe! It’s the cutest. Their coffee is honestly the best in town. If you try all of Nantucket’s coffee shops you’ll really be able to taste the difference. Unsurprisingly, The Handlebar Cafe is kinda like, bike-themed… the wifi password is ‘ridemybike’ and there is an actual bicycle hanging on the wall. Not only are the girls who work behind the counter really sweet and helpful, but they’re also willing to make you anything you ask for. I always get iced lattes in the summer and hot ones in the winter. One girl, Tanya, makes a specialty maple latte that isn’t on the menu, so you’ll have to ask. It’s my favorite. I like to bring my work and sit outside—there is the cutest secret garden in the back with mosaic tables and a darling little trellis. Located right on the edge of town, it’s definitely my favorite coffee spot. Handlebar does it best!

Next up: Brunch. Any recommendations?

Proprietors has brunch every Sunday, which is always a fun time but the food is definitely on the heavy side. Decent cocktails, but always a really good crowd and great bartenders, which can make all the difference. Anna is super fun and nice! Located in a beautiful old Nantucket house, this brunch spot is right in town.

I also like going to Island Kitchen. I think they have it goin’ on. Good food and interesting specials like peach cobbler pancakes. Not to mention they serve the most delicious freshly squeezed orange juice, which tastes even better with champagne. They also have nice outdoor seating surrounded by pretty flowers in the summer. It’s typically pretty busy but I’ve never waited more than 15 minutes for a table.

Black-Eyed Susan’s is awesome. Great breakfast food right in town. Always busy. Keep in mind that they will not seat you unless you have your entire party waiting with you. However, it is sweltering inside throughout July and August. They don’t have AC and they pack you in there pretty tight. It’s certainly a small space, but they have great food and quick service. The blueberry dutch cakes are to DIE for—two fluffy pancakes with blueberries and jarlsberg cheese. Although you’ll see plain dutch cakes on the menu, just as to add fresh blueberries. And make sure to ask for a little jar of maple syrup, the real stuff, and just dump that bad boy on the cakes as soon as they arrive. Hands down my favorite breakfast dish on island. I like to pair it with something savory and typically order the spicy thai scramble and add tomato to cool it down a little.

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Brunch at The Proprietors Bar & Table, July, 2015

And if we were to squeeze in a little shopping? What are the best boutiques in your opinion?

My favorite is Salt, right on Water Street in town. Super trendy stuff. Awesome jewelry and bathing suit selection. They carry Boys And Arrows bathing suits, which are like, my fav ever. Milly and Grace is also very cute. It has an anthropology vibe going on. Cute homegoods and really cute clothes. Of course, both of these places (and everywhere else on Nantucket) are super expensive. But that doesn’t keep me from shopping because I have a real problem.

Oh! Ladybird Lingerie is one of my new favorites. They have more than just lingerie, including loungewear and robes and stuff. Very cute.

Now that you’ve gotten the inside scoop from a local, book that quick summer getaway and get your butt to the beautiful island of Nantucket. With an incredible selection of beaches, restaurants, and shopping, Nantucket is the perfect destination—I guarantee it’ll be some of the best 36 hours you’ll have all season.

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