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!).

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.

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!!!

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!

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.

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.

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.)

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

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!