The Nantucket Guide
General Tips
There is nothing like summer on Nantucket. My family has been coming to the island since the 70s and I’ve spend some portion of every summer of my life on the island. It is truly my happy place. A lot of Nantucket charm is the insider spots, the hard to find beaches and the unfinished moments, so I absolutely recommend not trying to overschedule your time on the island. Time is supposed to slow down on the island - enjoy it!
General Travel Tips
Nantucket is not the easiest place to get to - those of us who “summer” here admit it and it’s something you just need to accept. Get into vacation mode when you get to the airport and the delays will bother you less!
Via air, most people get to the island connecting through Boston, NYC or DC on either JetBlue, Delta, United or Cape Air (or Cape Fear as we call it!)
If you are in the Northeast, it’s worth looking into driving either to New Bedford or Hyannis and taking a ferry over. Do not, I repeat do not take the ferry from NYC to the island.
Nantucket isn’t called the Grey Lady for nothing. In any given week, there will usually be a mix of sunny and slightly more grey days. It’s good to prepare expectations (and pack your bags) accordingly! It’s okay though because there are plenty of things to do on the non-beach days.
Staying on Nantucket
Most people who come to the island are in rental houses (as many are coming with family). If you plan to be going out (whether to dinners or to bars) while on the island, within walking distance of town is key. If not, the properties out by the beaches give you more space and quiet. This will always be more economical if you plan a longer stay.
If a house doesn’t make sense because of numbers or trip duration, there are some lovely hotels and B&Bs (The Wauwinet, White Elephant, Life House, Faraway)! I can’t personally vouch as I always stay in our house but these are where we suggest friends to stay if they are getting a hotel.
Eating on Nantucket
Restaurants
FOR A NICE MEAL
The Nautilus (Town)
Nautilus is an Asian inspired in a tight space in town. It’s my favorite dinner on the island and I’m not the only one so it requires some advanced planning to get a table - it’s in high demand! The bartenders are really fun so the crowd tends to lean according to that vibe! The crab fried rice is amazing and the oyster tacos are my favorite but the whole menu is great! If you have a big enough group, the Peking duck is also really popular.
Proprietor’s (Town)
Proprietor’s is tucked on a side street in town and in an old house (lots of stairs, beware if you have a grandparent with you!). Their food is very vegetable heavy and lots of small plates and they have excellent cocktails. It’s a less talked about spot but the food is really inventive and delicious. As long as everybody is willing to try new things, this is a great spot and easier to get a table than some others.
Straight Wharf (Town)
This is one of the all time classic Nantucket restaurants. Eating in the main restaurant definitely requires a reservation (I’d recommend a few weeks out) but eating the bistro menu (more casual option next door) is more walk-in friendly. They have limited tables with water views so make sure to request that outdoor seating well in advance if it’s important to you. Expect white tablecloths (and equivalent prices) but they’re so good at what they do. The classic Clambake is a popular (lobster, clams, corn, potatoes, etc.) and chicken under a brick but I also really enjoy their pastas. Good for special occasions!
Ventuno (Town)
Ventuno is by the same people as Straight Wharf but is less coastal and more island. They have a huge menu and there’s so many solid options but it’s definitely best with 4+ people because there will be a lot of things you want to split here. The olives ascolane are delicious as are all of the pastas. If there’s a duck dish with hazelnuts (it’s seasonal, so won’t always be there), a tuna dish or the soft shell crab, I’d recommend it as well. It’s housed in a lovely old house tucked into town and has never dissapointed. I’m a bit of a regular to eat dinner at the bar :)
Via Mare (Town)
Via Mare is a fabulous dinner. It’s from the same group as Ventuno and Straight Wharf, so you know it’ll be good! It’s a more rustic Italian food option. The grilled green beans are a must and the fish items have always been fab. They focus heavily on fresh produce so it will rotate. Also, they have a great wine program here so definitely speak with the somm and enjoy. It’s also tucked into an adorable hotel with cozy decor, so is also good in the winter or off season!
Lola 41 (Near Town)
Lola is one of my all time favorite places but I’m not alone here. This is a popular spot. They open for reservations at 4p every day, first come first serve and it’s tough (I usually walk in and sit at the bar) The menu is half sushi and half a mix of just deliciousness. If you get a table (or a seat at the bar!), order the Lola Burger (I dream about the fois gras dipping sauce), a Tuna burger (and with two burgers you can get one order of classic and one order of truffle fries), a sushi roll (I really like the Honshu) and anything else that strikes your fancy. My family really likes the chopped salad and the bolognese but it’s really hard to go wrong here. Note: the burgers are dense, we normally plan for each person to have 1/4 of each type, in planning quantities. If you are here for the early seating it will be relatively calm but the later seatings, the music start to bump! (This crowd will be ordering cocktails and going out after - keep this in mind whenever you get a cocktail, they’re strong!)
The Pearl (Town)
An iconic older spot on Nantucket was renovated and reopened. A super cute interior with upscale asian-ish style food. The dumplings and lobster rangoons are very popular as is the wok fried lobster. The cocktails are delish as well. If you’re looking for a festive dinner out, this is a great spot!
Cru (Town)
Cru is upscale and the view truly doesn’t disappoint - it sits right next to the marina with all the huge boats! The food is very seafood forward (I recommend the lobster cocktail and the lobster roll as well as the calamari to start). I find it overpriced and a little too scene-y for me most times so I avoid on weekend nights and prefer weekend lunch when it’s calmer but the back bar is so fun in the evenings! There is outdoor seating but those aren’t the best tables - inside is all open air and is actually a better spot.
Galley Beach (Near Town)
Galley is potentially the most famous, iconic sunset on Nantucket. The restaurant spills out onto the beach on the north shore and has a beautiful view. That said, it’s absolutely priced accordingly and candidly, I don’t recommend it for a meal unless for an unbelievably special occasion. They have steak, lobster, etc. and you’re paying a lot for it! I more often recommend it for an early drink to enjoy the early sunset and maybe a small plate but to dine elsewhere. This is also a popular strategy, so keep in mind with your arrival time!
Sister Ship (Town)
Sister Ship is a new spot on the scene with a very Soho house vibe on the interior and a coastal menu. The bar is often lively and it’s definitely a fun spot for a dinner out or a drink on their stylish patio on a summer day. Unexpectedly, the lamb tagine (if they’re serving it the night you’re there is delish). Serving sizes are moderate so the tab does add up quickly though, especially with a few of their yummy cocktails!
Black Eyed Susan (Town)
Black Eyed Susan is a tiny restaurant with low key vibes that has excellent food. They’re BYOB and have a limited menu and only three seatings because they have only one chef who does the cooking for the whole restaurant. I’m constantly impressed with their food and consider a fun option for small group dinner (also clutch to know if you have wine snobs in the group so they can bring their own rather than racking up a tab at the fancier places)!
Gaslight (Town)
By the same team as Nautilus, Gaslight is a more low key asian meal. The restaurant is housed in a space that used to be a movie theater and this is one of the popular going out spots for late night live music in town. Great spot for a bigger group to get a bunch and share. Check the Instagram to see what live music might be happening the night you’re there!
FOR LUNCH
Sandbar at Jetties Beach (Near Town)
This place does my favorite Painkiller on the island. Sit with your toes in the sand and indulge in some good beachy fried food and a couple of summery beverages. This spot is low key and makes it easy to remember that you are at the beach after all. Picnic tables with umbrellas make a comfortable spot for the sun sensitive like me! It gets busy on weekend lunch times so if you can come a little earlier. They also do buck a shuck oysters in the early afternoon (although I prefer Fifth Bend oysters which cost a little more but are grown local on the island)!
Something Natural (Near Town)
Something Natural is an iconic sandwich spot on the island. It’s walkable from town up Cliff Road (where the houses are gorgeous!) but not immediately in town. A few key things: a “half” sandwich is plenty for one person unless you’re a very hungry boy; the bread options are Something Natural specific: White= “Portuguese”, Wheat= a couple options, I’d recommend “Herb”; the pre-made combos on the menu are worth trying but you can adjust your order however you like; the chutney is delicious but very sweet, plan accordingly. The peanut butter chocolate chip cookie is worth it! You order inside (or call ahead) and then pick up your sandwich from the window and they’ve got plenty of seating outside or it’s a great pickup if you’re on the way to the beach!
Henry’s Jr. (Central Island)
Henry’s is a lesser known sandwich shop on the island, probably because it requires a car to get to from town. They do great sandwich on more sub-style rolls. They’re chicken salad is delicious but it’s all pretty dependable! Another great grab and go option for the beach!
Cook’s Cafe (Town)
Cook’s is an unexpected little spot right next to a bike shop. They do great smoothies and wraps! My favorite is the Bangkok Chicken (it is a little spicy!). Smoothies are very sweet - don’t expect a health option here!
Millie’s (Madaket)
Millie’s is out on the West side of the island and leans a little on the Mexican vibe. They have great fish tacos and excellent cocktails! You can also try their food if you’re at Cisco Brewers (sans the cocktails, but there are plenty at Cisco). If you’re looking for a change of pace from town or a low-key sit down lunch, this is a great option!
Lemon Press (Town)
Lemon Press is the most trendy lunch spot - this will feel like any australian coffee shop, juice and acai bowl you’ve tried in your home city. It’s conveniently right on Main street but as such, can get crowded. If you’re desperate for health food item, vegan food, a juice, etc., they’re a go-to! They’re also surprisingly good for dinner but a much chiller vibe than many of the other food spots on isle.
Corner Table Cafe (Town)
Corner Table Cafe is tucked underneath the Nantucket Culinary Center and has a ton of grab and go food, salads, sandwiches, dips, etc. that are way better than the premade food at the grocery store. If you want a mix and match lunch for the ferry or plane home, this is a great spot or just for variety other than sandwichees
Sayle’s Seafood (Central Island)
What is better than fried seafood. I dream about these fried clams, oh my goodness. It’s greasy fried food but you can’t get any fresher than this seafood. I’ll go grab orders of fried clams and fried scallops (bay, of course, which are local and smaller but more flavor dense than you get with the larger kind) and share them with friends!
167 Raw (South Shore)
Outside of this seafood shop is a cute little yard and a truck selling delicious fish tacos, ceviche etc. If you want to eat before the beach or are craving fish tacos, it’s a great spot! It’s also just around the corner from Cisco Brewers so if you want to eat before you drink, it’s nearby!
FOR BREAKFAST/COFFEE/TREATS
Born and Bread (Town)
This place does the best breakfast sandwiches on the island. There is a line every weekend morning but for good reason, their bread is insane and so any sandwich is only improved by the experience. They also do great coffee and pastries for all of your early morning beach town needs!
The Bean (Town)
Tucked on a side street, the Bean is a classic Nantucket coffee shop that’s gotten on trend with the coffee vibes. You can get anything you’re used to in major cities here.
Handlebar Cafe (Town)
A tiny walk out of town is a small coffee shop that people rave about! Grab and go spot for a hit of caffeine.
The Juice Bar (Town)
Let’s get one thing straight - this is not a juice bar, this is an ice cream shop. The best ice cream shop. Their flavors are unbelievable, the cones (or cone cups, where a cone’s material is wrapped into a cup) are handmade and an absolute must and the scoops hand-scooped by local teens. The line wraps around the block after dinner and even occasionally mid-afternoon. I recommend Green Monster or Crantucket but you truly can’t go wrong. Nantucket rite of passage.
Nantucket Bake Shop (Central Island)
The Bake Shop has been in a a bunch of locations but the treats have stayed exactly the same - the florentine cookies (spun sugar dipped in chocolate) are unbelievable but everything’s good. Unexpectedly, they also do delicious granola!
Sconset Market (Sconset)
This is the corner store in the “town” of Sconset. It’s an expensive spot to grab a random grocery but what you’re actually going for are the brownies. They are so unbelievable that my mom spent one summer attempting 42 different replicas to match the secret recipe (yes, 42 different times)! The muffins, ice cream and iced coffee are also delicious but don’t leave without a brownie.
FOR GOING OUT
Cisco Brewers (South Shore)
If you’re of drinking age, Cisco is a must visit (and of any age but it’s most appealing for the young adult crowd)!They make beer, wine and liquor and they have a great courtyard at their location that attracts a crowd for live music, drinks and food from food trunks. You’ll see people coming from town and fresh off the beach alike. It’s always a great vibe and one of my favorite places. It does require a car to get to (or they run a shuttle from town on a regular basis) but you will want to enjoy the libations, so make sure you’ve got an assigned DD before you walk in the door! Kids (and dogs) are also allowed!
Chicken Box (Central Island)
This is the Nantucket institution when it comes to bars - it’s a Nantucket dive bar (i.e. it gets grimey and sweaty and the decorations are nothing fancy and yet the crowd still shows up in seersucker, white jeans, Lilly Pulitzer and Jack Rogers. It’s very popular, especially on Friday nights so if it’s in the thick of summer, plan to arrive there before 10pm if you’d like to avoid a major line. Also, they often have covers (but have an ATM if you need cash). Plan to drink dive bar style (lots of Bud Light or Cisco on draft). They also have live music on most weekends which is one of the fun parts of the experience. I usually plan to spend one of my “going out” nights here and the other one out in town, because transit does take a bit!
Cru (Town)
What is a fancy dinner spot at the dinner hour becomes a happening bar in the evening (only at the back bar). There’s not a ton of square footage and this is squarely a “chatting bar” but it’s got a great playlist and they pour heavy. Crowd is more young 30-somethings than 20-somethings (which for most of us is a good thing!). If you’re looking for an easy but delicious local cocktail, try a Triple 8 cranberry and soda (no juice involved)!
Ventuno Back Bar (Town)
In the back of Ventuno, there’s a patio set up with a bar and some low key tables. It’s not technically a different place but there is a totally separate entrance on the side street. It’s totally low key, they’ve got good music and it's usually not too crowded. One of my favorite spots if you’re with a group!
Tree Bar (Town)
Tree Bar sits right next door to Ventuno Back Bar. This is also not an official spot, it’s more a second use for the patio area from Queequeg’s. A small space but does get some traffic (probably because of the location).
Club Car (Town)
Club Car is a more put together spot for dinner but in the evening there’s a live piano player who takes requests and you can bet that singalongs ensue. It’s actually in an old club car so space is tight but this is a Nantucket classic!
What to do on Nantucket
FOR PRETTY DAYS
Beaches
Of course, if you’re coming to an island there must be a beach trip in your future! There are 55 miles of beach on the island (last I checked) and all public! Most require a car to access (and a decent sense of direction as there isn’t signage) but there’s a few that are walkable from town or via a bike.
If you like calm seas and/or are with little kids who need shallow water… you’ll want to go to a North shore beach, likely Steps Beach, Jetties or Water Tower. Downside of these beaches if the North shore (which is on the sound instead of the Atlantic) does get more shells so its not as walkable.
If you like creature comforts… Surfside Beach has a snack shop and an accessible bathroom but is a popular beach and does get busy. Or Sconset Beach also has an easily accessible bathroom, this beach just takes the drive to Sconset so takes longer to get there.
If you want a lifeguard… Miacomet Beach on the South shore allows you waves but with the sense of security of a lifeguard!
If you like to surf… you’ll want a South shore beach. Cisco and Nobadeer (or the adjoining areas) are the most popular with the surfing crowd!
If you have a big group… Any of the South Shore beaches will be your friend. You’re probably better off going one or two entrances over from the main beaches for more space.
My favorites are some of the unnamed beaches near Cisco Brewers (a few entrances over from Ladies Beach) but anything near Cisco and Miacomet is normally a good mix of space, waves, views without huge crowds!
Cisco Brewers
Whether or not you’re going to a South Shore beach, mid to late-afternoon at Cisco is the place to be. In the mid-summer you will see plenty of Nantucket bachelorette parties and weekend trip groups. My favorite is a beach trip from 1-4p and then an hour or so at Cisco with friends but it’s also great in the off-season in a little more cozy vibe. It’s both fun but totally low key and there’s a drink/food option for everybody (in addition to a great selection of beer, they also do great cocktails and wine + food trucks)!
Bike Ride to Sconset
If you’re looking for a very active option, you can bike the distance out to Sconset (or if you prefer, back from Sconset). It will take at least 1 hour (depending on how in shape you are) and there aren’t really stopping points along the way (although there is a bike path). That said, the middle part of the journey looks out over conservation land which is a really beautiful look at the more natural part of the island!
FOR RAINY DAYS
Shopping in Town
There are lots of great spots in Town to poke through, ranging in category and price point, and all very walkable. I’d recommend 28 Centre Pointe, Milly & Grace, Skinny Dip and Island Cashmere but lots of places in the island have good treasures if you’re willing to look around a bit. Note that the best time to shop is actually on really sunny days when most people are at the beach. If it’s rainy, you won’t be the only one with this idea!
Whaling Museum
Nantucket became what it looks like today from back when it was a major whaling community. This sounds incredibly far off from daily life today but the Whaling Museum does a great job at educating on this history. One of my favorite parts about this history is that it means Nantucket has actually been a long time feminist community (since a lot of the men would be gone for years on their voyages, the women ran the town) and some very notable feminists such as Lucretia Mott.