Talk about an unexpected adventure. When Peyton suggested we take a trip to Newport, Rhode Island in August of 2021, my first reaction was somewhere between “Heck yeah!” and “Why there, of all places?”

For someone who, at the time, cherished my days of PTO, taking a chance on a new city took a little convincing. After all, you’re talking to the girl who scours the menu every time we visit our favorite Mexican restaurant, only to order the same tried and true—albeit pretty boring—chicken fajita quesadilla every time. Not to throw shade on 30A (my beloved quesadilla, in this scenario), but that definitely would have been the “safer” option for our end-of-summer getaway—and I’m so thankful that my extroverted husband convinced me to try something new.

After spending several days bayside in the World’s Cutest B&B and eating our body weight in fresh lobster, it became official: the New England life is the life for me.

We wasted no time mapping out our plan to hit each and every recommendation we were handed, with in-depth Yelp research of our own. (Our method while traveling: Pack in every reservation we possibly can, over-plan down to the minute, and then hold loosely to plans in the end.)

After flying into Boston and spending an evening there (also a first!) we picked up our rental car and took the scenic route to our end destination. We ended up opting to stay in the tiny town of Jamestown, which is about a 5 minute toll bridge away from the center of Newport, which ended up being a huge cost saver and a great getaway from the buzz of the city center. It turns out that even small towns like this draw sizable crowds this time of year! Jamestown also happens to be the filming location of our collective favorite Wes Anderson film, Moonrise Kingdom, so we carved out some time to hunt down some of the most iconic spots for a photo opp, while blasting Vampire Weekend and Jonathan Richmond songs, of course.

There were so many highlights of the trip, it’s hard to pick a favorite. However, the private sunset boat cruise through the harbor was easily a Top 20 life moment for both of us. The only true competition with that experience might be the beach picnic we set up below Taylor Swift’s Holiday House in Watch Hill, which was only about an hour drive away. (I mean, best husband ever to breathe life into that dream of mine.)

I could go on about this trip for pages, but instead, I’ll leave you with a list of absolute must-do’s, as well as some favorite images from our time there—both in film and digital!

Newport Favorites
Castle Hill Inn
Del’s Lemonade at Easton Beach
Simpatico
Grapes & Gourmet
The Breakers
The Black Pearl
The Clarke Cooke House
The Landing
The Lobster Bar
Diego’s
Coffee Grinder
Midtown Oyster Bar
The Mooring
The Lounge at The Chanler