Nantucket: A First Timer’s Experience and Extra Special Babymoon

Nantucket is a destination that has been on my bucket list for many years for its charm and beauty. When planning a babymoon before our first baby arrives in January, Smylie and I added Nantucket to our shortlist of destinations. When we started looking at flights and travel logistics for each location, we realized Nantucket’s airport code, ACK, was the same as what our little girl, “Anna Carter” Kaufman’s initials will be! The other destination options were then tossed out the window, and we knew that Nantucket was where we had to go! Neither of us have ever been to the island, so we couldn’t wait to experience a brand new place together.


We were pleasantly surprised that we could fly through LaGuardia and straight in to Nantucket! We were initially under the impression that we’d have to fly into Boston then drive to catch a ferry, but that was not the case! Our travel day could not have been easier. The Nantucket airport is quaint and we had our bags in no time. If you’re planning to visit Martha’s Vineyard and other destinations on your trip, the ferry option is definitely worth researching!

Nantucket Airport


We took our trip on the third weekend of September and while Nantucket certainly wasn’t in full bloom with hydrangeas and roses at every turn, it was still as lovely as ever! The charm of the cobblestone streets in town was an idyllic New England experience. We had the most wonderful weather with temperatures in the low to mid 70s during the day and mid 60s at night. We had several locals comment that this was one of the greatest times of the year to visit. Some businesses had limited hours but everything was still open! Based on my research, Columbus Day seems to be when some businesses close for the season.
Town In The Fall


The Nantucket Hotel

Picture a hotel with a bed and breakfast feel, but with resort amenities-and that’s The Nantucket Hotel! After much research, Smylie and I were sold on the hotel’s spacious accommodations, the proximity to town, and access to The Nantucket Club, which is located at the hotel and includes a heated pool/hot tub and fitness center! In our room, we enjoyed the plush Frette robes, Nespresso machine, and kitchenette. Delicious complimentary breakfast is offered daily at the hotel restaurant, Breeze. They also offer complimentary beach chairs and towels, plus shuttles to/from Jetties beach, the ferry and into town.
The Nantucket Hotel Entrance
When first planning our trip, we were highly considering staying at The Wauwinet, which is on the far side of the island. After researching all that we wanted to do and see, we decided that accommodations in close proximity to town would be a better fit for us for our first time. We agreed that we are so glad we made that decision as we strolled into town multiple times each day. We also looked into The White Elephant, Greydon House, Union Street Inn, and Faraway, but ultimately chose The Nantucket Hotel and it was the perfect choice for our first Nantucket experience.
One thing to note about the Nantucket Hotel is that it is extremely kid friendly. Because our trip was after Labor Day, there were very few families visiting the hotel while we were there but I know that it is popular for families during the busy months due to its complimentary kids club and family pool. If you’re planning an adult getaway during peak season, it might be worth looking into The Wauwinet, which caters to guests 12 and older.


We took a cab to and from the airport and took an Uber to dinner two nights, but we walked almost everywhere else (with the exception of our bike day)! We chose not to rent a car because of the central location of our hotel, but if we were to rent a car, we would definitely rent a jeep based on the number of them that we saw on the island!


After catching sunset at Madaket Beach, Millie’s was the perfect, casual dinner spot after a travel day. We ordered chips and queso to start, then I had the lobster salad and Smylie had the shrimp quesadilla. Tasty food in a laid back atmosphere was the perfect combo for our first night.
Millie's Lobster Salad
Grabbing a sandwich before heading to the beach in Nantucket is a must and so many people rave about the sandwiches at Something Natural. Smylie ordered a ham sandwich on Portuguese bread and I had a loaded veggie sandwich on herb bread. The sandwiches are huge and ordering a half was plenty. I was not familiar with Portuguese bread until reading about Nantucket – it’s a delicious sweet bread that is very much worth the hype!
Something Natural Sandwich
Dinner in a rose garden? Count me in! Chanticleer is located in ‘Sconset a picturesque little town on the east side of the island. I made an early dinner reservation here so that we could do the ‘Sconset Bluff Walk (more on this later!) before dinner. We enjoyed dinner on the patio (next to a heater) and ordered the Caprese Nicoise, halibut, and lamb bolognese. It was all delicious and the atmosphere was lovely! If you prefer to dine inside, they also have 3 dining rooms, each with a different vibe.
 Chanticleer Chanticleer Food
The Juice Bar is a Nantucket staple and while they do have juices and smoothies, the main event is the homemade ice cream! You can’t help but notice the smell of freshly made waffle cones as you walk by. We stopped here after dinner two nights of the three we were there. “Dirty Grasshopper” (Crushed oreos folded in chocolate mint ice cream) was my favorite flavor I tried! 
The Juice Bar
Lemon Press is the kind of place I look for in any city we visit – a restaurant with healthy food options and a cool vibe! As soon as I read about this organic eatery and cafe, I immediately added it to our must-do list! The Grey Lady Latte, Lavender-Infused Espresso + Vanilla, was just amazing as it sounds (if you’re a lavender fan)! Smylie had the breakfast sandwich with sausage on a Portuguese roll and I had the breakfast burrito as a bowl. We enjoyed every bite! Take a seat for breakfast or lunch or stop by and order a coffee, cold-pressed juice, smoothie or grab-and-go snack from the counter.
Lemon Press Lemon Press Food
We biked to Cisco Brewers to hang out and have lunch one afternoon. With food trucks and live music often, it’s a great spot to spend the afternoon/evening. I do not enjoy beer, but I appreciate a brewery that has cocktail options (when I’m not pregnant!) and Cisco has their own line of spirits. I ate a yummy lobster roll from the Lobster Trap food truck and Smylie had a wood-fired pizza from Eat Fire Farm plus a Whale’s Tale Pale Ale. A very fun vibe!
Lobster Roll
In all my trip prep, I learned that The Nautilus is a hotspot and tricky reservation to secure. This quaint restaurant, known for shared plates with Asian flare, seats around 40 people and very few reservations are released each night. Reservations on Resy were released 7 days in advance of the day we planned to dine at 10 am EST (during the time of our trip) so I had that day circled on my calendar for weeks. I was on at 10am on the dot and was able to score a reservation, but I’m not kidding when I say there were only 4 time slots available and they went FAST! Walk-ins are welcome, but be prepared to wait a little while and most likely sit at the bar (not a bad thing)! The food was TOTALLY worth the hype and this may have been my favorite meal of the trip! The cocktails all sounded amazing and they even made me the best mocktail I’ve had during pregnancy! We shared the early Fall salad, oyster tacos, blue crab fried rice, and Dan Dan noodles. I kept reading review after review that mentioned the oyster tacos and I was apprehensive at first but they were unbelievable- tempura oysters, nori wrap, sushi rice, chile BBQ, wasabi aïoli – YUM! The blue crab fried rice was outstanding too!
Nautilus Blue Crab Fried Rice Nautilus Oyster Tacos
On our last morning, we walked into town to grab coffee at Handlebar Café. I had one of the most delicious Americanos I’ve had in awhile. I am kicking myself that I didn’t bring home some of their coffee beans!
Handlebar Café
Sandbar is a casual, family-friendly restaurant/bar on the the beach! With a menu of sandwiches, salads, burgers, and tacos, there is something for everyone on the menu. We sat at a picnic table on the sand and had shrimp tacos and a Cuban sandwich. While it wasn’t crowded while we were there, I know it’s PACKED during the summer based on photos I’ve seen! 
Other restaurants that caught my eye when researching:
167 Raw Food Truck (I LOVE enjoying their lobster roll when in Charleston)
Born and Bread (the ABC grilled cheese)
The Wauwinet for sunset cocktails


Beach Day at Steps Beach
There are beaches all over the island, but Steps and Jetties Beach were a short walk from our hotel. I had seen photos of the beautiful approach to Steps Beach, a steep staircase that descends to a beautiful beach with turquoise water. We set up our beach chairs (which we brought from our hotel), enjoyed our sandwiches from Something Natural, and relaxed in the beautiful weather! I was pleasantly surprised that it was warm enough for us to be able to sit out in our swimsuits in September.
Steps Beach
 ‘Sconset Bluff Walk
This was one of my very favorite things we did on the trip! The bluff walk is a public footpath with stunning homes on one side and gorgeous oceans views on the other. We did this walk at golden hour before our dinner reservation at Chanticleer. Because we were dressed for dinner, we did not do the full 2 mile out and back trail, but it is a very easy and scenic stroll.
Sconset Bluff Walk
Bike Day
Per our hotel’s recommendation, we rented bikes from Young’s Bicycle Shop, which is just a short walk from the hotel. Bikes can be reserved for a half day, full day, or even a full week. They must be reserved 72 hours in advance and it takes no time to do so on their website. There are several bike paths on the island, and we chose to bike out towards Cisco Brewery. From there we biked a little further to Bartlett’s Farm – a family-owned farm with a garden center and market. We found Barlett’s Farm produce on many menus around town! I gathered major fall decor inspiration from walking through the garden center, which was filled with pumpkins and some of the most beautiful mums I had ever seen! We also popped into the market and I bought a loaf of Something Natural Portuguese bread to bring back to Birmingham with us (yay for a basket on my bike)! We then biked to Ladies Beach to enjoy a little beach time before heading back into town!


On one side it is a high end women’s boutique carrying brands like Ulla Johnson, Rhode, Veja, etc. and the other side is dedicated to needlepoint including canvases, supplies, and finished needlepoint work.

This shop is dripping in fresh cut flowers and therefore smells absolutely wonderful! In addition to gorgeous flowers, they also have beautiful gift and home decor options.
Flowers on Chestnut
I LOVE Hill House nap dresses – specifically the Ellie style – and they’ve been great during pregnancy, too!  Having only ever shopped the brand online, it was so much fun to see all of the styles in person! I caught this pop-up on one of their last open days, but as much as the founder loves Nantucket, I have a feeling it will be back open next season!
This boutique for women carries brands like Loveshack Fancy, Tata Harper, and Loeffler Randall.  Here you will find clothing, shoes, accessories, gifts, and clean beauty products. I loved this shop!
Mitchell’s Book corner is a cozy, local book shop and it’s the perfect place to pick up a beach read. Elin Hilderbrand, known for her fiction novels about Nantucket, often does book signings here. We purchased Anna Carter’s first children’s book, ACK! The Nantucket Duckling.
Murray’s is home of the “Nantucket Reds” – a fabric “Inspired by the red sails dotting the coast of Brittany France.” “After repeat washing and exposure to sea breezes these distinctive pants soften and fade.” Murray’s has a men’s, women’s, and children’s department. Smylie found several things he loved including an ACK hat in Nantucket red that he plans to wear in the delivery room – so sweet!
Murray's Toggery
If there is a Ralph Lauren store, we always pay a visit, and the Nantucket location was so charming! 
Polo Ralph Lauren
This shop was starred on my list because they carry the most precious ACK sweaters for children, and we were excited to buy one for Anna Carter! They have a great selection of women’s clothing, men’s clothing, and gifts as well.

Our first time to Nantucket was incredibly special. While we are far from experts, we thoroughly enjoyed everything that we did. We hope to take Anna Carter back one day as it is such a family-friendly destination. It’s also perfect for a romantic getaway or for a girl’s trip! Hopefully next time I’ll be able to enjoy the extensive raw bar options and Smylie hopes to play golf at one of the three courses when we return. I’d love to go back in the summertime, when everything is in full bloom. Renting a house and picking up fresh seafood to cook from the little markets and produce to enjoy from the farm sounds like a dream, too!

Our 3 Night/4 Day Itinerary

Day 1
Flew into Nantucket Airport at 4pm
Checked in to the Nantucket Hotel 
Walked into town
Back in time for wine & cheese at hotel – an amenity available when the hotel restaurant is closed
Jumped in an Uber to Madaket in time to catch a sunset on the beach
Casual dinner at Millie’s
Day 2
Early morning walk around town
Breakfast at hotel
Popped in some of the shops in town
Grabbed beach chairs and towels from hotel
Walked to Something Natural for sandwiches with our beach gear in tow
Afternoon at Steps Beach
Took an Uber to ‘Sconset to do the Bluff Walk
Dinner at Chanticleer
Ice cream at Juice Bar
 Day 3
Breakfast at Lemon Press
Stopped in a few shops in town
Rented bikes from Young’s Bike Shop
Took the bike path out to Cisco Brewery for lunch
Biked to Bartlett’s Farm and then to Ladies Beach
Dinner at The Nautilus
Ice cream at The Juice Bar
Day 4
Coffee from Handlebar Cafe
Breakfast at hotel
Last minute shopping in town
Lunch at Sandbar at Jetties Beach
Walked to Brant Point Light House
Flew home from Nantucket Airport in the late afternoon

There’s a little sign on the bluff walk that says “If you’re lucky enough to be on Nantucket, you’re lucky enough” and I feel very fortunate to have experienced this beautiful place!

Always finding joy,


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