Free People Maxi + Family Friendly Nantucket Diary

Last month, we made it to Nantucket in time to catch perfect summer weather and a spectacular display of hydrangeas all over the island! The last time we visited was for a weekend of food, drinks, and over-indulgence. Needless to say, with our newest member of the family in-tow, this trip had a slightly different itinerary and vibe to it : )

It’s not often when I purchase something at full price, but this Free People dress (multiple colors) is what my maxi dreams are made of! There is a lot of fabric which moves and swirls beautifully, yet the skirt portion is very breezy and lightweight, which is rare with such full skirts. There is no stretch and no zipper so the torso is cut a little loose and straight in order to fit over your head comfortably. The shoulder ties can be adjusted and tied higher in order to shorten the dress length (which is petite friendly). I wore it a few times with either my tan slides or my Castaner wedges + straw picnic purse and lost track of the number of compliments around town!

I’ve had these espadrille wedges for a couple years now and they’re well made and pretty comfy for the height! Mine are the 80mm height, and they also make a lower 60 or a taller 100 depending on what your feet can handle. Not sure if their sizing changed over the years, but I’m usually between a US 5 and 5.5 and fit their size 35 with a little bit of room to spare.

what we did

While Nantucket does have a variety of beaches, our favorite part about the island is how the main town area is completely walkable and you can explore all the old cobblestone streets and little boutiques and artisan shops, then pop out to other areas for mini excursions (beaches, the brewery, smaller villages).

Brant Point Lighthouse
This is a cute photo opp and the closest lighthouse to town. We went for a picnic, but it was more of a local fishing/drinking/smoking hangout than the last time we visited.

Siasconset Village
About a 15-20 minute drive from downtown. Our friend took us here to peep the quaint cottages and do part of the ‘Sconset Bluff Walk, which is a little path that winds through the backyards of some gorgeously manicured oceanfront homes. Apparently, this area is even more full of blossoms earlier in the season with flowery vines growing all over arches and trellises. Afterwards, we treated ourselves to ice cream at the one general store in town.

Children’s Beach
This was steps away so we stopped by each day! Not really a beach, more of a stretch of sand on the harbor. Lifeguards and the lack of waves make it good for children, though. There is also a park with playgrounds that is popular with families.

Mom & Dad’s Night In
Nick stocked up at Epernay Wine & Spirits, a cute wine and cheese store with reasonable (for Nantucket) prices half a block from our door. They had a good selection of craft beer and wine (“better than a lot of places on the mainland” according to Nick) which we enjoyed at home with some HGTV and cake from Something Natural!

Where we ate

With a little one in tow, we found ourselves opting for less formal dining and mostly picked up food at casual local spots.

Something Natural
About a 15 minute walk from our hotel in a residential neighborhood, but it’s a nice stroll down a street of hydrangea adorned homes. They bake all their breads and goodies and serve generously sized sandwiches (note: their “half” sandwich is basically a whole sandwich and a “full” is huge). The carrot cake and curry chicken salad on Portuguese bread was great, and we heard the lobster salad and roast beef are also solid. Very family friendly with affordable prices and lots of outdoor picnic tables on a grassy lawn.

Straight Wharf Fish Store
A simple and straightforward seafood shack, mostly selling fresh fish but with a small prepared food menu. We got gumbo + grilled fish sandwiches, if you’re looking for non fried seafood options.

Oath Pizza
Another kid friendly (picnic tables outside) and affordable option, especially compared to the $6 slice of pizza by town center. I think they use a smaller than usual oven, though, so not as good as regular Oath locations.

Stubbys (specifically for the Jamaican Specials)
A few of our friends scoffed when I mentioned we went here (apparently its where drunken young people go seeking fried grub at 2am), but none of them had heard of or tried the Jamaican menu. I learned that their chef of 10 years started making specialties from his home country a while back, alongside his homemade hot sauce. The jerk chicken and oxtail plates served with rice and beans were not bad, and adds some welcome cultural diversity to the food options in town!

Brant Point Grill
The menu is pricey, even for Nantucket, but it’s a fair option if you’re looking for an upscale yet kid friendly restaurant. They have a huge covered patio that looks out onto the harbor and a lawn area with cornhole and other games. Almost every table at 5:30pm had kids who were roaming free on the grass, while the parents enjoyed their dinners at a (relatively) leisurely pace.

Lemon Press
Wanted to mention this spot, as it was recommended by several friends as a healthy breakfast option in a cute ambiance. We were planning to go here on our last day but ran out of time! Another popular recommendation was Nautilus for dinner, which was packed when we tried to go.

Where we stayed

Thank you to The White Elephant for hosting us this visit – we’d seen parts of the hotel when here previously for the wine and food fest, and got to explore the property more and soak in just how family friendly it is! The location is amazing, right in the heart of town so we didn’t need our car. We stayed in a 1-bedroom Residence, which looked new and had a sofa bed in the living room, kitchenette with big dining table, and in unit laundry (something I never appreciated as much as I do now, with an infant!).

Nori was greeted with a full-size crib, complete with elephant-print sheets, a baby toiletries kit, and a little stuffed elephant. She also adored the off-roading red wagons and the bubbles by the pool. It never felt like the place was overrun by kids, though, however we did go mid week. The hotel also has plenty of complimentary bicycles for guests to use while exploring the island, along with chair, umbrella and cooler bags available for beach trips.