Nantucket in Late September

I’ve been lucky enough to make it over to Nantucket a few times this summer. It really is my happy place. There’s something about walking off that ferry that instantly relaxes me– not an easy feat! This was my first late summer/early fall visit to the island, and I have to say, it was my favorite.

It wasn’t exactly beach weather, but it was still nice to visit the windy beach in sweatshirts and jeans watching the surfers wait for the perfect waves.

Traveling to Nantucket with a great group of friends doesn’t hurt either. I love this group of people so much… Garrett and I started going on ski trips with them a couple of years ago, and it’s been so fun to watch the friendships grow. I’m glad we made a summer trip happen in addition to our winter ski trip. Plus, this was an extra special trip for a specific reason (keep scrolling!).

Striped Dress Tuckernuck

Wearing: Ruffle Neck Stripe Dress (c/o) + Sneakers

Friday was such a beautiful day– I’m glad we got there early enough in the day to spend some time exploring the island in our rented Jeep and then meeting all of our friends back at the house.

We rented a four bedroom house (Gar gave a funny tour), and it was pretty affordable when divided between the four couples. It also ensured that we all had our space, but still under one roof where we could have breakfast together and hang out after dinner.

Nantucket Rental Property

Okay, so the best part of the trip… Garrett’s brother got engaged!!!! Everyone was in on it except for him, and it was the perfect morning. His boyfriend planned out the whole thing, and we had secret email threads and a whole plan in place. Seeing his reaction was so good. He didn’t know what was happening! So happy for them!!!

Cisco Beach Nantucket

We met them at Cisco Beach for a Downyflake doughnut breakfast. The eight of us crushed the two dozen doughnuts quite quickly while celebrating the couple!

Downyflake doughnut

After the proposal, I could have easily packed up my bags and caught the next ferry home. It was AMAZING! But the fact that we had 24 hours left to celebrate made it that much better.

Half the group went to Cisco Brewery, and the rest of us went to town to explore and shop.

Nantucket Harbor

We randomly ran into Casey Neistat downtown; more on that later, but trust me when I say that it was so cool.

Saturday was definitely on the chillier side of things, but it felt so nice. Truly a crisp afternoon where you could warm up in the sun and still be comfortable in a sweater and jeans.

Fall on nantucket

Ray-Ban Sunglasses

After shopping and grabbing a quick sandwich for lunch, we regrouped at the house and made our way to the Wharf to catch the sailboat! I thought it was going to be freezing, but the eight of us had such a fun time soaking up the sun. It felt like we were getting the very last taste of summer. Chartering a sailboat is a must when visiting Nantucket. You get such a fun view of the island, and it’s the best way to shop for your waterfront home. (Ha, a girl can dream.)

Nantucket Sailboat Charter

Wearing: Vineyard Vines Hat // Striped Sweater (c/o) // Jeans // Boat Shoes // Navy Vest

Sailboat Charter on Nantucket Sailing on Nantucket The next morning we had to leave pretty early, but I’m glad we got to squeeze in so much on Saturday! We started the super long commute home (it always feels 10x longer on the way back!) feeling so content and happy!!!

Sometimes I come home from a trip and feel like I need a vacation from the vacation, but I never feel that way with Nantucket!

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Congrats to Garret’s brother!

Renting houses with a bunch of friends is the best vacations! I spent summers on Martha’s Vineyard! Made me miss it even more this year!


I have loved following along on your trip through vlogs and everything. I have always wanted to visit Nantucket, and this has inspired me to really start planning and make it happen!!


you look AMAZING in that first boat picture! like change all your social media handle photos amazing!


I know what you mean about sometimes needing a vacation from a vacation; that was how I felt the last time I went to Disney World.

Visiting Nantucket off-season is so much better IMO. I’ve been once in May and once in October; the weather was still nice, and it was great to be able to explore without massive crowds everywhere.


First of all, congrats to Garrett’s brother!!! What an amazing surprise, it’s so nice that you guys were all in on it.

Second of all, AHHHHH I can’t believe you met Casey!! If I had seen you in his vlog and not known about you or what a big fan you were, I don’t think I would’ve been as giddy thinking about how you were trying to keep it cool during your cameo. 😛

Third of all, you are doing a really great job of convincing me to visit Nantucket, lemme tell ya!


1. It really was such a special morning! All of died!
2. Yea, ZERO chill was actually happening from me 😂
3. You HAVE to go!!!


Fabulous pictures! I am going to Nantucket next weekend for Columbus Day weekend and now I know what to wear- Navy of coarse! You two are so cute and love that you are on Youtube now!

Diana Pearl

Huge congrats to Garrett’s brother! Celebrating an engagment is always so much fun. Nantucket has been on my list forever, I need to go! Next summer, it’s a must. (And I love that dress in the top photo!)


Love these photos and seeing your adventures! Did you guys rent the sailboat for the afternoon or was it just a way to travel across town? A day on a sailboat in Nantucket is on my bucket list and I’d love to know how you do it!


I have been trying to find a sweater like the black nantucket one featured in your blog, do you know where I can get one?
P.S. I watched your video on youtube with Casey and I was so happy when you met him 🙂