Caila and I have been wanting to go on our trip together with our guys for forever now, so when Vineyard Vines reached out about a weekend trip to The Cape, we knew it was fate 🙌🏼

A little back story on our crew. Caila and I had been Instagram friends for a while and finally had the chance to meet in person a few years ago at fashion week. We met when I first started dating Conner, whose best friend and roommate at the time in NYC was Nick. They were roommates in college and played on the Harvard football team together. After the first double date set up with us and Caila & Nick, the rest was history. It was so good getting to spend quality time all together this past weekend in Chatham. It was the most low-key (in the best way) romantic getaway.

I’ve spent years pinning photos of New England and dreaming about what it would be like to vacation there in the summer, but this was my first time ever experiencing it. Spending the weekend at Chatham Bars Inn felt like living in a fairytale. The resort is one of Cape Cod’s most beloved destinations with its charming seaside ambience, modern comforts, and luxurious atmosphere. The private quarter-mile beach covered in blue and white striped cabanas is the most picturesque thing I’ve ever seen. And the rooms were huge and absolutely beautiful. Definitely the first time I’ve ever stayed in a hotel room with a sauna and a steam shower!

The view during our daily walk down to the beach was so iconic, it was my favorite shoot location from our trip. I decided to shoot this adorable white eyelet dress from the VV collection here and I love how the photos turned out!

The food at the resort was absolutely incredible. A highlight of the trip was definitely the breakfast buffet (fave meal of the day)- it was the most breakfast display 🙌 The dinners were the most memorable part of the trip because of the romantic candlelit ambiance, delicious menus, and of course the good company.

Nothing really beats a cabana day at the pool at Chatham Bars Inn. After Caila and I convinced the boys to take some pictures, we relaxed in the cabana while sipping watermelon margaritas and eating fish tacos. The life! I love all of the swimwear options for both guys and girls on at Vineyard Vines, I linked all of our suits below.

We spent the weekend with Nicole and Erick from the Vineyard Vines team who immediately felt like old friends and made the trip even more of a good time. We took a day trip to the Chatham Bars Inn Farm – 8 acres of farmland that provides all of the produce for the restaurants on the property. We were lead through a personal tour of the grounds and snacked on veggies as we walked through the property.

Erick set up a little photo moment for us at the farm to shoot these Vineyard Vines outfits. This gingham dress is so adorable and comfortable! I love how classic the boys looked all weekend in their preppy outfits 🙂

From sailboat rides to sunset cocktails, I couldn’t have asked for a better group to experience it all with. I can’t thank Vineyard Vines and Chatham Bars Inn for the most authentic, first-hand Cape Cod experience.

A highlight for Conner was taking the Jeep out along the beach to fish and drive along the shore. These are definitely some of my favorite pictures from the trip! I love the comfy VV looks we wore for this one. I think we could get used to this life, MUCH different than NYC city life haha!

Vineyard Vines partnered with Chatham Bars Inn to launch their 200 square-foot poolside pop-up where customers can shop for items from vineyard vines’ exclusive Cape Cod custom product line and for other summer items. I got the cutest Chatham Bars Inn sweatshirt to remember this trip 🙂

Can you see yourself vacationing here? Vineyard Vines is kicking off the opening of the pool shop with a Good Life Sweepstakes for an Endless Summer Getaway to Cape Cod including a 4-day, 3-night vacation at Chatham Bars Inn with breakfasts, dinners and a spa treatment as well as a $2,500 travel gift card and a $2,500 vineyard vines shopping spree! You have to enter, this is one of the most memorable trips I’ve ever taken!

To enter, visit by July 7, 2019.

Thank you to Vineyard Vines for sponsoring this post and for the trip of a lifetime, thanks for all the wonderful memories!

Every Day Should Feel This Good 😉🐳

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Showing 5 comments
  • Kelly

    Wow! I am so in love with this post and all the beautiful imagery. Sounds like such a dream summer getaway. I’ve never been to Cape Cod but spent all my summers growing up in Northern Michigan and this post has me itching for my trip up there next month!!

    xoxo – Kelly

  • rachel

    Gorgeous couples full of love. Great place to for couples to getaway together. When are both men going to ask both of you ladies for hand in marriage?It better happen soon. You two are keepers here me guys don’t wait wife up Olivia and Caila asap they are a dime and so rare. Do them right.

  • Reply

    I love Cape Cod so much and have vacationed there quite a few times. It’s so beautiful and nautical. Your outfits are so cute and I’m so happy you had a great time!

  • Brianna

    Aww that looks like so much fun!! 🙂
    Brianna |

  • anna

    This weekend I was in Leicester with friends. If you are planning a trip to Leicester and need a multi-seater car, I recommend renting one at Here you will find the best deals on car rental at Leicester airport

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