How I Spent 52 Perfect Hours on Nantucket, Part One

Nantucket Travel Guide, What to Do on Nantucket // Pearl Girl

Waiting at our gate for our flight to Nantucket, my friend Charlotte said a colleague had told her that “Nantucket is pleasure.” After spending a long weekend on the island, I have to say that I’m in complete agreement with that description. Nantucket isn’t very big, but every mile is gorgeous, summertime perfection. Not to mention, I visited with three of my close friends, Natalie, Charlotte and Ivy. If you were in a sorority, they are my “little”, my “big” and my “grand little.” We’d never traveled together as a group before, but it was so much fun — I see many more trips together in our future.

I honestly just have so many photos I want to share from my time on Nantucket, so I’m going to break this up into two posts. (You’re probably going to read through this and think ‘This is only half of the photos you’re sharing?’ Yep, I took a lot of photos!)

How We Got There

We flew in on Saturday morning, on the new direct service to Nantucket from LaGuardia on Delta. If you’re looking to get to Nantucket from Manhattan, I’d highly recommend this option, as trekking up to the Cape + taking the ferry seems like quite the trek. Flights can get pricey, so book in advance — we booked ours in February, and paid less than $200 round trip!

The Nantucket airport is actually adorable. It’s so tiny. Right after we left the plane, a truck drove up the bags and dropped them off right there. And when you’re flying out, you honestly can get to your flight five minutes before you’re supposed to board and make it there on time.

Where We Stayed

We rented a guest cottage on the property of a larger house through AirBnB, which is totally the way to do Nantucket. I’ve seen several other bloggers talk about staying at a hotel, which also seems lovely, but staying at a house was amazing. There was a patio with a table, chairs and a grill, which we put to use on Sunday. It was so cozy and felt more home-y than staying at a hotel. And honestly, nothing beats cracking open a Fisher’s Island Lemonade on the patio.

How We Got Around

We were far away enough from the downtown area that we didn’t want to bike everywhere, and didn’t really want to rent a car and deal with the hassle of parking, either. Thankfully, Nantucket has Uber! We never waited long for a ride, and all the drivers were super friendly! I’d say most of them cost about $12-15. If you’re splitting between multiple people (or switching off who orders the Ubers!) it’s totally doable. (And then, of course, you can have a few glasses of wine without worry!)

What We Did

We arrived on Saturday around noon, and headed over to the house we were staying in. After quickly changing and settling in, we hoped in an Uber to downtown. We were all pretty hungry, but knowing how expensive food on Nantucket can get (#IslandLife) so we just grabbed a slice of pizza and sandwiches (not both for each of us!) down near the water on Broad Street. Then we grabbed ice cream cones at the Juice Bar, which has the best waffle cone I’ve ever eaten in my life. However, Natalie had a smoothie, which was also so good. You can’t go wrong!

We had a reservation at 4 p.m. with Endeavor Sailing, so in the meantime, we walked around and popped into all the different shops in downtown Nantucket. A few favorites? Skinny Dip, which I also visited in Charleston, Murray’s, a preppy paradise with lots of Nantucket reds, and Margaux, a brand that carries beautiful ballet flats. However, my favorite item I purchased on the Straight Wharf, in a tourist-y shop called Nantucket Peddlers, where I got this red sweatshirt! We all ended up buying them, as they were $30 and the perfect Nantucket souvenir!

Our ride on Endeavor Sailing was amazing: 90 minutes on the water, and you can just sit and relax while the boat staff takes care of everything. One important tip: BRING DRINKS. As the boat was pulling up from their last ride, we saw the passengers holding red cups. And we realized, you can BYOB to this boat ride! We were about five minutes from departure, and Natalie literally took off towards the nearest liquor store (which was about five-ish blocks away) and then came back equipped with a four pack of Fisher’s. (Bless her.) The ride wouldn’t have been the same without it.

That night, we went to dinner at Cru, which is right on the water and had a great lobster roll. It’s on the pricier side, but this was our only really nice meal out, so we didn’t mind! Afterwards, we made a stop at Stop N Shop downtown to pick up groceries for the rest of the weekend — another perk to having a house!

The rest of my Nantucket photos and recap will be up on the blog early next week — along with another Nantucket outfit!

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  • CelebratingthisLife

    I can’t wait to see the rest of the photos! It looks like you had an amazing time. I’m sitting here jealous, this is a dream vacay! Thanks for letting me live through your adventure 🙂 xx Rox-Anne Celebrating This Life

    • It was a wonderful weekend! Thanks so much for reading 🙂

  • Brooke Reagan

    OBSESSED with all of these photos!! I want to goooo!


  • Mollie Sheperdson

    This all sounds like so much fun! I’m heading there on Sunday and I can’t wait! Definitely need to check out the sailing company!

    xx Mollie

    • Have SO much fun! I’m so in love with Nantucket. Definitely check them out, it was such a fun way to spend an afternoon!