Cape Cod: New England's Summer Playground
When you hear “Cape Cod,” you might picture lobster rolls, weathered shingles, and Kennedy-level leisure. But when you get called there for a business retreat? You pack your bags, charge all the devices, and get ready for the most beautiful kind of “OOO.”
Hosted by my amazing business coach, Amanda Writesman of The Bridal Theory, this business retreat was the perfect blend of networking, content creation, and coastal fun. Plus, we got super lucky with the most incredible weather of 75 and sunny the whole week. Here’s what we did:
Where We Stayed
We stayed at The Chapter House, think historic character meets boutique vibes, right in the heart of Yarmouth Port. The staff was incredible, attentive, and truly went above and beyond for our group!
Night 1:
The retreat kicked off with a breezy welcome night on the lawn. Dressed for “white garden chic”, we gathered under the stars for cocktails, conversation, and a catered spread from the iconic Old Yarmouth Inn (seriously, the crab and lobster alone are worth the trip). Think relaxed elegance with just the right amount of Cape Cod charm.
We ended the night in cozy sweaters around the fire pit with glasses of wine in hand.
Day 2:
Started out the day with breakfast and coffee (I got an oat milk chai latte with rose) from Lighthouse Keeper’s Pantry each morning.
After a morning work session, we spent the afternoon soaking up views at Wequassett Resort, where lunch felt more like a coastal editorial shoot.
From the dock below, we hit the water with Down Cape Boating for a private sail—think salt air, sunshine, and serious main character energy.
No trip to the Cape would be complete without an ice cream stop! We took our little sweets break at Ice Cream Smuggler. For those that are dairy-free, this place had great options!
Dinner brought us back to the Old Yarmouth Inn (dress code: old money honey!) for another round of Cape Cod classics, followed by a golden-hour visit to Grey’s Beach, where the sunset over the boardwalk could make even the busiest brain take a deep breath (aka me).
Day 3:
Breakfast/coffee again from Lighthouse Keeper’s.
Morning consisted of a tour of Thacher Hall, a local landmark of a church turned event hall with timeless charm, followed by a literary detour to the cozy and well-curated Parnassus Book Service and popping in an out of a few shops.
Afternoon croquet on the lawn gave us some retro fun (and photo ops), with headshots scheduled right before golden hour—because what’s a retreat without fresh content? Photos courtesy of Mary Kate Steele.
Our final dinner at the Pelham House brought ocean views and fresh seafood, and we ended the night barefoot on the sand with a bonfire and s’mores. Yes, business was discussed. But between the boat rides and beach walks, it felt more like a soul-refreshing escape.
Whether we were brainstorming over coffee at Chapter House, setting out on the water in a sailboat, or chatting in the glow of the Pelham House sunset, every moment felt intentional—and a little magical. Cape Cod, you’ve officially raised the bar for work trips. Until next time, we’ll be dreaming of salt air and s’mores.
Credits for night 1 dinner:
Host: The Bridal Theory
Catering: Old Yarmouth Inn
Planning- Event Planning by Sara
Florals- EH Blooms
Paper: Scribbles and Swirls
Rentals: Sparrow Lane Rentals, Peak Events, Northeast Tent and Party
Samantha Shammas, Author
A true travel enthusiast, Samantha has been going around the globe her entire life and has visited over 40 countries and counting. With a lust to wander, she’s always excited to visit new places and soak in inspiration for her artwork.
