A Guide to Nantucket


If you’re looking for the quintessential New England experience, Nantucket, or more lovingly known as ACK, is the place to be. Filled with history, picturesque homes, tasty dining options, and miles and miles of public beaches, what’s not to love? For me, I like how easy it is to bike around the island thanks to plenty of bike paths, the sailing culture, and also the practice of getting dressed up after your day on the beach for an elevated dinner with friends, and great bottles of wine.

There’s also plenty of events that would bring you to the island, like Figawi, Nantucket Food & Wine Festival, and the Nantucket Yoga Festival. You may also get wind of some intimate concerts hosted at the Box – a couple years ago I saw Matisyahu, and they have upcoming concerts with artists like G.Love, Marc Roberge, and Jamestown Revival. This is also a perfect place to snag a summer house for a week or two with a group of friends, cook family meals, take plenty of beach days, and unwind… whatever your fancy.

Brant Point Lighthouse, Nantucket
Brant Point Lighthouse, Nantucket


There are several modes of transport to the island, but if you don’t have friends with a boat or a private jet, you’re going to have to do a bit of planning in advance. In peak season, ferries and flights can sell out, so don’t sleep on grabbing tickets.

By Boat
via Steamship Authority, Hy-Line, or Seastreak

The way I travel to any of the islands (Nantucket & Martha’s Vineyard) most often is by ferry. I’m partial to the Hy-Line out of Hyannis, but Steamship Authority is a great option as well, and you’re only option if you’re looking to take a vehicle. If you’re coming from New York City, you can also take the Seastreak from NJ/NYC or New Bedford.

There are some things that you need to keep in mind. For example, if you would like to bring a car over, you need to book way in advance. I’m talking months in advance. In addition to big events and holidays, shoulder seasons, aka May and September, are also notoriously difficult for getting cars on and off the island respectively. Other things are that you can purchase a bike ticket for the ferries, which is usually cheaper than daily rentals (just remember to bring your own bike lock). You can bring wayyyy more luggage on the ferries for cheaper than if you’re flying. On a recent ferry trip, I packed a tent, my bike & biking gear, and a weeks worth of wine and outfits, as well as a cooler. If you’re staying in a summer house without all the amenities you get in a hotel, a ferry is probably the way to go to get all the items you’re going to want over to the island.

By Plane
via Cape Air or JetBlue

Traveling a bit lighter? Then flying is surely the way. I’ve traveled on both Cape Air and JetBlue, and they both work just fine. Cape Air is a fleet of little Cessnas, so if you’re a nervous flyer, best to go with a bigger company like JetBlue where the planes are more standard size. Downsides, are that flights out of Boston/NYC range from $150 – $350+ after fees and taxes, so it is a bit pricier than the ferry, and if you experience a delay on the island, the airport isn’t filled with tons of accommodations.

By Public Transport
to Hyannis

If you are planning on taking the ferry from Hyannis, and don’t have a car, there is another step you need to consider – the trip from the nearest major city to the port. If you’re coming from Boston, one option is the CAPEflyer. They only operate on weekends, and it isn’t a great option for longer stays, or if you’re schedule isn’t flexible. Round trip train tickets are $40. Another is Peter Pan Bus lines which drops off in the same spot, and a coupe other locations around Barnstable and Hyannis. One-way tickets start at $21.

It is also about a 15-minute walk from the Transportation Center to the port, so if you have a lot to carry, this could be a pain. There is a complimentary shuttle to the Steamship Authority that you have to call on-demand, but on busy days this can be slow and unreliable.

By Car
to Hyannis

So you have a car and want to drive down? They don’t make jokes about “Cape traffic” for nothing, so padding an extra hour isn’t out of the question. On a recent trip for the 4th of July holiday, we added an extra two hours, and had roughly 30mins to spare once fully unloaded and parked. Speaking of parking, it is helpful to book your parking in advance (Hy-line lets you do this). There are local lots around Hyannis, but they can fill up quick, especially on the weekend. If you’re traveling via Steamship Authority, they have lots off-site with shuttle busses. If this is something you think you’re going to need to take advantage of, you should add another 45mins or so onto your trip. Average parking costs around $15/day and can go up to $25/day on busy weekends, or during major events.

Front porch nook at Life House, Nantucket


Life House Hotel
10 Cliff Rd, Nantucket, MA 02554

There are several magical properties on Nantucket, but one of the newest players on the island is giving them all a run for their money. Opening in the midst of a pandemic, Life House is a breath of fresh air in the Nantucket Hospitality scene. Boasting thoughtful decor, and plenty of nooks inside and out for curling up with a cocktail or a good book, and an incredibly courteous staff, you cannot go wrong. The property is ideally located a short walk from the harbor, and with it, some of the island’s best dining options.

Their complimentary breakfast (pictured below) and happy hour are good excuses to wake up slow and take a breather before partaking in evening activities respectively. If you need help coordinating anything on the island, their staff is equally as friendly as they are helpful, and they even helped me secure a couple reservations during my recent stay.

Breakfast at Life House Hotel Nantucket
Breakfast on the patio at Life House, Nantucket
Dressed in cream on the front porch of the Life House, Nantucket
Front porch looks at Life House, Nantucket; outfit links: Sunglasses, Vest, Trousers, Slides
Desserts from Dune Restaurant on Nantucket
Desserts from Dune, Nantucket


Dune (pictured above)
20 Broad St, Nantucket, MA 02554

Upscale food with an approachable vibe is the best way I know how to describe this island favorite. Locals and visitors alike love to treat themselves to a meal created by Chef Michael Getter, formerly of 21 Federal, and it’s not hard to see why. The menu is constantly changing with seasonal ingredients, but don’t leave without their signature Chocolate Pot de Crème. In the heart of the historic downtown district, this is an ideal place to make a reservation after a day of shopping or on the water.

Duo of Ceviche from Bar Yoshi Nantucket
Duo of Ceviche from Bar Yoshi

Bar Yoshi (pictured above)
21 Old South Wharf, Nantucket, MA 02554

One of the newest additions to the harbor restaurant scene, Bar Yoshi is the perfect place for a dinner date, or fashionable lunch. Sit on the patio and people watch, or pull up at the beautiful and cozy bar for a few cocktails to start your night. The “I Am a Daiquiri” and “Geronimo Margarita” are two of my favorites on their current menu. For food, you can’t miss with the ceviche duo, udon noodles, or the yakitori. Keep an eye on their specials. You’ll see ingredients like soft shell crabs, uni, and other seasonal favorites.

The Nautilus
12 Cambridge St, Nantucket, MA 02554

With growing popularity now that they have a Boston location as well, this is a hard reservation to get. If you can snag a table for dinner, this small plates place will leave your taste buds dancing through the menu. Oyster tacos, steamed pork buns, and blue crab fried rice are dishes you can’t miss. If you want to go big, the whole roasted peking duck is a show stopper as well. Don’t skip the wine list, and make sure to touch base with the somm to try something new.

Hamachi Crudo from Proprietors

The Proprietors (pictured above)
9 India St, Nantucket, MA 02554

A celebration of family style dining can be found in this old whaling hub on the island. Opened in 2013, it remains one of the more popular spots to share global tastes with friends & loved ones. In the phone above you can see one the favorite dishes of the evening (actually two), the hamachi crudo and chicken liver pate. In addition to being a great locale for dinner, it is also a brunch favorite. The lobster and mushroom pancake is a crowd pleaser, and you can’t skip out on the cocktails – good any time of day. They’re usually closed on Wednesday in the summer, so plan accordingly.

1 Straight Wharf, Nantucket, MA 02554

Could I even write a dining section without mentioning Cru?! This is the spot to be seen on boozy, rainy days, where you drink oodles of sancerre and eat a copious amount of oysters. If you want to go all out, get a Grand Cru Plateau with some caviar, and add in a few Alaskan king crab legs for good measure. If you’re still hungry after all of that, go big or go home with a lobster roll; chilled obviously. And, if coconut pavlova is on the menu, order it and thank me later.

Wester Ross Glazed Salmon from Keepers Nantucket
Wester Ross Glazed Salmon from Keepers

Keepers (pictured above)
5 Amelia Dr, Nantucket, MA 02554

Looking for more of a local’s joint? Head to the middle of the island for this cozy spot serving up the best in comfort food. I would say that Keepers is the most family friendly on the list, so if you’re traveling with a big crew, this is a good bet. Highlights from their menu include the mac & cheese topped with BBQ pulled pork, wester ross glazed salmon (pictured above), and the crispy broccoli. They have a bike rack at the restaurant, so if you do bike there, and don’t feel too full to bike home, you’re good to go on that front as well.

Lola 41
15 S Beach St Ext, Nantucket, MA 02554

Part bistro, part sushi spot, I am sometimes a bit confused at the identity of this place, but fact fo the matter is, they crush both concepts under one roof. I’m more partial to their sushi menu, particularly their wagyu beef carpaccio, hand rolls, and the Tsukiji speciality roll. This is definitely a place to order as you go, enjoy splitting items with friends, and ball out on some killer wine. If you can’t make it to Nantucket, they have a sister restaurant (Lola 42) in Boston’s seaport.

Sips on the lawn at The White Elephant


In addition to the aforementioned restaurants, there are a few spots that are worth swinging by for a drink or two… or four. They all have different personalities and purposes, but the key takeaway is they are more known for their sips than their snacks.

The White Elephant (pictured above)
50 Easton St, Nantucket, MA 02554

Need a hangover cure? Look no further than the lobster Blood Mary’s on The White Elephant lawn. Looking over the harbor, this is a fashionable place to spend your Sunday mornings recovering from your Saturday night. Yes, you can get food, but frankly, a few drinks with this view should more than do the trick.

The Chicken Box
16 Dave St, Nantucket, MA 02554

A whole different vibe than most of the island, The Box, is a watering hole enjoyed by everyone on the island. As I mentioned in the beginning of this post, they’re host to some great bands, and is a place where you can sip a Bud Light without fear of judgement. Yes, you will definitely run into more than a few “chads”, but that’s the risk you run anywhere on the island. Stick with your crew, or make friends with the band, and you’ll be good to go.

Galley Beach
54 Jefferson Ave, Nantucket, MA 02554

Ahhhh, the views at Galley Beach are just *chef’s kiss* making it one of the hottest tickets in town. This is by far one of the best places to catch the sunset on the island. Bear in mind, a good portion of the tables are in the sand, so dress appropriately. If you are hungry, they do serve a full menu, but I would go for cocktails/wine + raw bar here before moving onto a more formal dinner spot.

òran mór
2 S Beach St Ext, Nantucket, MA 02554

The food here is great, so you might be wondering why I added this to the “Where To Drink” section. Frankly, their bar program is superior. They have a very small, intimate bar (I think it seats no more than 5 or 6 people), and it is a perfect romantic spot to sip with a hot date. My current favorite drinks include the Mr. O’Brien Flies to Mexico and the Red Sky at Night…

Cisco Brewers
5 Bartlett Farm Rd, Nantucket, MA 02554

Yes this place is a bit of a haul from the harbor, but they offer shuttles every 25 mins or so from 23 Federal St., which is good if you don’t have a car on island, or are not wanting to drive after a day in their beer garden. With multiple bars and food vendors, this kid & dog friendly mecca in the middle of the island is a place for every walk of life. You may run across a couple bachelor/ette parties, but just find a picnic table on the other side of the compound and you’re in the clear.


There are four primary bike paths on the island: Surfside Road Bicycle Path, Polpis Road Path, Madaket Road Bicycle Path, and ‘Sconset Bike Path. Between them all, you can see the best that the island has to offer. Between all the New England island destinations, I find Nantucket to be the most bike friendly, not just because of the bike paths, but because drivers are really keeping their eyes peeled for you on the road, and they’re not honking at you like they would on say… Martha’s Vineyard *cough cough*. If you are someone who needs lots of water or bathroom breaks, be sure to plan your bike rides accordingly. There isn’t usually a stretch longer than 7-8 miles without either option, but depending on how fast the slowest person in your group is going, good planning can make the difference.

Pack a bike lock with you wherever you go – not necessarily because there’s a lot of bike theft on the island, but because bike racks get busy and a lock can keep your bike upright with lots of comings and goings; preventing things from getting busted from more casual cyclists. Usually bike shops will also let you pump your tires at their storefronts if you’re friendly, but it’s always good to be prepared with everything you need to keep your bike suave for longer stays.

Sankaty Head Light, Nantucket
Sankaty Head Light


Sankaty Head Light (pictured above)
Baxter Rd, Nantucket, MA 02554

A bit out of the way, this lighthouse is a great cycling destination on the island. This lighthouse first went into service in 1850. Due to erosion, the structure was actually moved 400ft in 2007. Talk about a serious undertaking!

Walking across the popular bridge in ‘Sconset

‘Sconset Foot Bridge (pictured above)
Easton St, Nantucket, MA 02554

All of ‘Sconset is picturesque, but this footbridge is a particularly popular spot for photos. The left exit off the bridge pictured above actually goes to a house, so be courteous to those taking their morning walks when snapping a shot on this frequented walkway.

The “Rose House” in ‘Sconset

The “Rose House” (pictured above)
Mitchell St, Nantucket, MA 02554

No, this house doesn’t have an official name, but ask anyone who has been on the island, or frankly looked up Nantucket on Pinterest, and they’ve probably seen this house. It is also located in ‘Sconset, so be sure to plan accordingly if you’re going for the bluff walk and footbridge snaps.

A "grey lady" on Cliff Road, Nantucket
A “grey lady” on Cliff Road

Innishail House (pictured above)
11 Cliff Rd, Nantucket, MA 02554

One of the ultimate grey ladies on the island (where Nantucket gets its nickname) is this glorious home. If you’re lucky, you can see the red, white and blue antique cars uncovered out front, adding to even more charm. If you’re staying at the Life House, it’s right across the street.

Brant Point Lighthouse, Nantucket
Brant Point Lighthouse

Brant Point Lighthouse (pictured above)
Easton St, Nantucket, MA 02554

A much more easily accessible, and crowded, lighthouse to visit is Brant Point. It’s the light that you see when you’re coming in on the ferry and can either be adorned with a daffodil wreath, like the first image of this post, or an American flag, like on the shot above. Either way, it’s a pretty cute spot to grab a photo.

Madequecham Beach, Nantucket
Madequecham Beach

Madequecham Beach
12 Madequecham Valley Rd, MA 02554

With miles and miles of open-to-the-public beaches, it’s hard to pick a bad one to take a photo at. Madequecham happens to be one of the quieter options on the south side of the island, making it easier to take those beach photos without having to edit people out. Honorable mention would be Steps Beach, but boyyyyy does it get busy there.

Morning tea at Life House Hotel, Nantucket
Morning tea at Life House Hotel, Nantucket


Packing for Nantucket is equal parts a joy and stressful. Even though it’s further north, you still have to treat it like an island; the weather can change at a moment’s notice. Keeping in mind everything from a sudden temperature drop to a random day of rain will save you a lot of heartache. But, the weather isn’t the only thing you need to factor in; there’s also the social engagements. Nantucket is known to have a certain unspoken dress code, that may come with a certain level of formality. Button ups, neutral tones, and fabrics like linen, seersucker, and cashmere. Think elevated basics with clean lines. Also keep in mind what activities you’re going to be doing – sure standard beach attire is a no brainer, but what are you packing to go out on a boat, or for a bike ride across the island? A few practical items can go a long way. My top five items to pack:

  • The Schiffer Button Down from Lysse. It doesn’t wrinkle and is super breathable.
  • A neutral sweater, like this one from Mango. I get so many compliments on this one.
  • A flattering shirt dress. You can find this Veronica Beard one in three colors in my closet.
  • Sandals that are indestructible and can go from day to night. I’m partial to these ones from Aquatalia; they’re waterproof and super comfy.
  • Stay dry in a rain coat. The jackets from Penfield are great quality and keep you nice and dry.
  • BONUS: A swimsuit (even if you don’t think you’re going to swim). My favorite swim brands are currently Aerie, Albion Fit, J.Crew.

If you couldn’t tell, Nantucket truly is one of my favorite little gems to visit. I hope these recommendations help you to plan your next trip, and if you have any questions, comment below and I’ll be sure to share any other tips you might need to have a successful visit to this New England getaway.

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