The Unpretentious Side of Nantucket

A couple of days ago, I posted this photo of myself in jeans and a t-shirt, saying that this was me getting “dressed up” on Nantucket, and that it was the first time I’d been out of my workout clothes all week. I mentioned that people often think Nantucket is “so fancy,” but that this is more the reality of someone who actually spends a summer here.

I did not expect the response! I received more comments and DMs than almost anything else I’ve posted this summer... maybe ever. The response was a resounding, “This is so true!” with so many of you messaging me to say, “this is the island vibe we love too,” or “I live in jeans and cut-off shorts here!”

There is no doubt a sceney, bougie side of Nantucket - the super-pretentious “#chadtucket” stereotype you see all over social media. Stereotypes usually exist for a reason, but this one has become so overpowering that people who don’t know the island well assume that vibe is the mainstream. As I said in my follow-up post, if that were true, we wouldn’t have a home here! That highly cringey slice of visitors does not represent most of the people who actually live on or love to visit this island.

I grew up on the Northeast coast and built my entire company, Cailíni Coastal, around my love for the coastal lifestyle. To me, coastal living isn’t fancy or pretentious. It’s the opposite. It’s bare feet, no makeup, wet hair, and casual clothes. It’s dressing up in breezy sun dresses and flip flops. It’s relaxation, joy, carefree, good, easy people and vibes. Coastal destinations that aren’t that (and there are many!) are personally just not my cup of tea.

As an outgoing introvert, I will take a small group and a night in over a party scene every time. In fact, my favorite days on the island consist of going to the beach as our only activity outside of the home. I prefer waking up early, being in bed by 10 pm, and spending my days with my kids, so I can’t even speak to the nighttime scene. But if you want a relaxed, unpretentious, and beautiful Nantucket experience, read on!

Location & Timing Is Everything

We live in Surfside, a couple miles outside of town, and it’s given us exactly the distance we need — close enough for an easy bike ride (often faster than driving once traffic picks up), far enough to feel like a real retreat. We spend about 80% of our time within half a mile of home, which means we can skip almost all of the in-town traffic in peak season. There are so many incredible places on the island that are away from the hustle and bustle of town. I just can’t speak to them because I personally have not spent enough time there to be a true expert!

If a quieter retreat sounds appealing to you, areas like Surfside, Cisco, Polpis, Dionis and Miacomet are great options. They offer the ideal balance: easily accessible to Town, but tucked far enough away to completely remove you from the summer crowds.

If you’re visiting without a car, especially for the first time, staying in town still makes a lot of sense because it’s walkable. The free shuttle (the Wave) covers the island, and Ubers are everywhere.

Since purchasing our home here, we have spent a lot of time visiting off season. It has been an eye-opening experience because my favorite months on the island are no longer peak summer, but early June and September. If your dates are flexible, June or September (just avoid the week that touches July 4th and the week of Labor Day) gets you the same great weather and open restaurants with a fraction of the crowds and traffic. I absolutely love the early fall too!

Embrace the “Dine-In” Experience

In peak summer, we actually prefer eating in more than we eat out. Weekend dinners almost exclusively happen at home. During the work week I have less time to cook complex meals, so we enjoy some home cooked goodness on the weekends. I’ll hit Bartlett’s Farm for most of the ingredients and stock up on organic produce for the week and pick up chicken and seafood from 167 Raw. Make sure to grab their guacamole! On nights we don’t want to cook, the 167 Raw food truck is a great takeaway option.

During the week, we’ll often order food from Pip & Anchor. Their chicken salad, their Vietnamese chicken salad, and their veggie egg sandwich on sourdough are all in constant rotation.

My newest favorite find though is Eat Fire Farm, a boutique grocer and farm shop on West Creek. It’s pricey, but on days when I have five hours of back-to-back Zoom calls and zero real breaks, their grab-and-go — smoothies, juices, a protein Greek yogurt parfait, grilled chicken — has been a lifesaver. Uber Eats isn’t really a viable option on-island, so this fills that gap perfectly. I usually go twice a week to stock up on lunches that get me through!

Strategic Dining Out

We still make a point of hitting our favorite restaurants, just strategically. Our first week back in mid-June, we went out three times just to get our regulars in: Galley Beach (we did a beautiful Father’s Day dinner there this year), Straight Wharf, and Oran Mor.

Straight Wharf Fish, which opened about a year ago, has become a real go-to for casual dining with our kiddos. They don’t take reservations. We’re early eaters, so walking in around 4:45 - 5pm usually gets us a table quickly. They have a great fish market in the front, and often times we’ll grab some fish on our way out to cook the next night.

Galley Beach, Lola 41, and Cru are ones I don’t even attempt in July and August. They all offer incredible food and vibe, but they often have an ultra scene in peak season. We save them for quieter times on island instead. I had lunch at Cru for my 40th birthday last October, sitting on the water with the boats still in — quiet, crisp, and honestly one of the best meals of the year.

Brant Point Grill, the restaurant at White Elephant, is our special-occasion family spot. Both our daughters have had birthday dinners there or we’ll go when we have another family with kids visiting us. They have a big lawn for the kids to run around on while we catch our breath, and a front-row seat to watch the ferries come into the harbor. It feels quintessential Nantucket in every way, but is super family friendly and not stuffy.

No list is complete without Millie’s. We live near the Rotary, so we do takeout from there at least twice a week. It’s same great food as the Madaket location, but more of a takeaway spot. The Madaket location is fantastic, it can just get very crowded in summer. We did make it out to Madaket earlier this year too; we were the first outdoor table of the season back in May!

Most nights, though, we’re just cooking simply at home — mac and cheese for the girls, something separate for my husband and me.

The Provisions Ecosystem

Bartlett’s Farm is a staple for us, but timing matters — go early or late on a weekday or weekend. Weekends, especially midday, get packed. One of our year-round neighbors gave me the best tip: on the Fourth of July, the beaches are slammed but the grocery stores are empty. She was right and I suspect that’s true for other busy beach days. We always add a stop at 167 Raw for fish and chicken on the way home.

For filling in the everyday basics (ie: we don’t want to brave the large supermarkets), Nantucket Meat & Fish is our go-to — turkey and cheese for the girls’ camp lunches, bagels, bananas and eggs, etc. I dont love Nantucket Meat & Fish for produce because nothing is organic (which is still so surprising to me). So for quick organic produce needs, Pip & Anchor is small but excellent. They always have staples like strawberries and blueberries.

Stop & Shop covers whatever’s left — but I’ll be honest, it gives me anxiety even early in the day or late at night come July and August. My husband has officially taken over Stop & Shop duty for the summer, and I am not mad about it.

For coffee, Roastd is everywhere on-island now, but our go-to is their airport location — it’s the biggest, with a small market, great food, and gelato for when the kids want ice cream without a special trip.

The Great Debate…The Best Ice Cream

Speaking of ice cream, I know this may be a triggering comment to some people, but personally do not understand the Juice Bar hype. It’s good ice cream, but the amount of time people wait for that ice cream does not equal how good it is, in my opinion. If Ice Cream has a “scene” Juice Bar is the scene.

Just around the corner is a place called Jack and Charlie’s. That has been our family’s favorite for years. I personally actually think it’s better, and the line is not nearly as long. I think the longest we’ve ever waited was 15 minutes, and that’s rare.

If we do get ice cream in town, Jack and Charlie’s is our go-to 100%. The Juice Bar as a business is an excellent case study in impressive guerilla marketing. People see the line, they just assume it’s the best. They hear the buzz, so they wait, but once you’ve tried it once, you can check that box, walk a couple streets over, and get equally as good, if not better, in my opinion, ice cream for way less of the wait.

Our favorite ice cream option out of town is The Surf at Surfside Beach. It’s a short bike ride from our house. What’s great about it is not that the ice cream itself is so out of this world, but that it is right on the beach. Our girls also love their acai bowls. We grab our cones and then walk down to the beach. It’s one of our family’s traditions, and it’s almost always quiet!

Seek the Quiet Shores

We’re creatures of habit and mostly stick to the quieter local beaches near Surfside rather than the island’s more popular spots. Steps Beach is a real favorite of ours, but it’s enough of a trek in peak season (and gets crowded on top of it) that we save it for quieter stretches of summer instead. There are so many amazing beaches that are quiet and we have not even scratched the surface of exploring them all!

The Workout Anti-Scene

Yes, even the workout classes can be a scene and need to be navitated! When I’m working out, I want to get really sweaty alongside a mix of people who are just doing their own thing. I’m competitive with myself, not the people around me. I also draw a hard line at studios that let people set up their phones to film during class. The last thing I want is to end up in the background of a stranger’s Instagram story looking like a sweaty mess…no thank you!

The Workout Anti-Scene Yes, even the workout classes can be a scene and need to be navitated! When I’m working out, I want to get really sweaty alongside a mix of people who are just doing their own thing. I’m competitive with myself, not the people around me. I also draw a hard line at studios that let people set up their phones to film during class. The last thing I want is to end up in the background of a stranger’s Instagram story looking like a sweaty mess…no thank you! Because of that, I absolutely love Nantucket Cycling and Fitness. The crowd feels like it’s primarily made up of locals - truly chill people who are just there to work hard in a wide range of ages and fitness levels. So even though the classes are hard, it’s a complete judgment-free zone. The instructors are amazing, and they offer a wide array of classes, from cycling to dance cardio. Personally, I am a huge fan of their Burn and Bootcamp classes - they are insanely hard - and Lisa (who is the owner) is my all-time favorite instructor! I try to go two or three days a week early in the morning. I am not a huge yogi, but I definitely appreciate slowing my body down and stretching (especially since I don’t do it enough!). A couple of years ago, I connected with an incredible local yoga instructor named Emmy. She has come to our house several times to lead private sessions when we host friends and family, or sometimes just for my husband and me. It is a wonderfully unique experience that we treat ourselves to on occasion. Emmy also teaches regularly at Supta Yoga, which is a fantastic, unpretentious studio if you want a great flow without the scene.

A Homebody’s Rhythm

Our weekdays are pretty uneventful, in the best way. Camp drop-off, sometimes a coffee run to Roastd on the way home, then a full workday for both of us. I try to sneak in a walk when I can — down to the beach and back — and it’s one of my favorite parts of the day. We have an ad hoc babysitting setup with a few amazing local girls who take the kids from 3 to 6 so we can finish up the workday. Then it’s dinner at home, usually something I make or Millie’s takeaway. After dinner, we try to get down to the beach as a family. Sometimes a bike ride, sometimes we drive down with the dogs. Even just 30 minutes. It’s the most peaceful part of the day!

Weekends are about maximizing time outside: beach, pool, and usually a mix of both! For an easy lunch, 45 Surfside is a regular for us, and The Surf at Surfside Beach — open till 8 on weekend nights, with picnic tables right on the sand — is a family favorite when we don’t feel like cooking. The 167 Raw food truck is another great takeout option. My husband is a big Cisco Brewers fan; I enjoy it too, though I’ve mostly caught it packed, so I’m a little less enthusiastic than he is. We bring the dogs everywhere, including the beach.

This weekend we did Dreamland’s drive-in movie for the first time - our girls LOVED it! It was a very nostalgic and fun experience for my husband and I as well! As newer Nantucket homeowners, we intentionally didn’t book a house full of guests this summer. We wanted the time to make local friends and just be the four of us, and it has given us some of our best memories with the kids yet!

Hosting, Homebody-Style

When visitors do come, we lean into a few island staples: the Critter Cruise (when kids are part of the visit), a yearly must for the kids, plus a dinner or two in town since everyone enjoys a night out every now and then.

When we host, we always get our wine, spirits, and cheese from The Brix — a shop run by two women from Boston who are endlessly knowledgeable and always kind. Their charcuterie boards make entertaining completely effortless; I preorder one anytime we have a group over.

We all love to ride our bikes, and when we have visitors its no exception! We’ll ride to lunch, the beach, etc. Youngs in town and Easy Rider in Surfside are great places to rent bikes.

This year, this beach picnic table we bought for casual sunset dinners in the sand has become a favorite! Our beach dinner was a highlight of our last set of visitors’ trip!

The Recap

The island is actually quite large, and to be honest, we have barely scratched the surface! But because summer traffic gets so congested, we tend to stay fairly central to where we live. It’s easy, it’s relaxing, and it allows us to truly experience Nantucket without the scene.

Here is a quick breakdown of our favorite summer routines, plus the things we skip.

Our Summer “On Repeat” List

• Morning walks and bike rides to the beach.

• Sunsets dinners at the beach with takeout from 167 Raw or Millie’s.

• Eating at home, outside (I am loving this recipe right now!).

• Hosting casual nights at home with charcuterie and wine from Brix.

Our Summer “No Go” List

• Town on weekends: we plan around it entirely in July and August.

• A revolving door of guests: we intentionally kept our schedule light this year to focus on our family of four and making local friends.

• Peak-season Cisco Brewers: It is amazing in May, June, and early fall, but too crowded for us mid-summer.

• Holiday weekend beach crowds: We stayed home on the Fourth of July and had the best time.

• Trendy Restaurants: Galley Beach, Cru, and Lola 41 are great in the off-season, but they are a total scene (and a skip for us!) in summer.