After three years of talking about taking a couples trip together over games nights, dinner parties, and picnics, Olivia & I were determined to get our guys out of the City and make it happen this year! Since we both live New York, we wanted a destination with sun where we could unwind from the bustle, but also close enough so the guys wouldn’t have to take any time off from work. So… when Vineyard Vines suggested a couples getaway to Cape Cod, Massachusetts – we were absolutely thrilled with the idea!
(P.S. click here to read the back story of how Olivia and Conner set Nick & me up 😊)
THE VINEYARD VINES STORY
Best known for their smiling pink whale, to me Vineyard Vines is a quintessential staple of northeast prep-leisure style. (Haha totally made up prep-leisure, but I’m really liking the sound of it for my weekend suitcase 😆) Founded on Martha’s Vineyard by brothers Shep & Ian when they left their desk jobs to start making ties that represented the Good Life, Vineyard Vines designs classic pieces for your closet that you can wear at any age. I am in love with their collared shirt dresses for me and performance button downs for men. This summer you will find them pool side at the Chatham Bars Inn, as they have an adorable pop-up shack to style you for your weekend away.
Since Vineyard Vines embodies the Cape Cod lifestyle, they took the lead on our visit & planned a dream…
CAPE COD COUPLES WEEKEND ITINERARY
DAY 1
MORNING
✈️ Fly into Hyannis Airport around Noon
🐚 Check into the Chatham Bars Inn
🥗 Enjoy lunch and a view at The Veranda
Afternoon
🚲Bike to the Chatham Light House
🌅Sunset cocktails at The Bayview Bar
🐟Dinner at The Sacred Cod
DAY 2
Morning
🥐Room service breakfast
⛵Harbor Seal watching Sailboat Cruise
👙Visit Vineyard Vines Pop-up Pool Shack
🥗Lunch at the Beach House
Afternoon
☀️Relax by the Pool
🚤Champagne sunset cruise on BarTender boat
🍽️Oceanview dinner at Stars
🥤Night out at The Squire
DAY 3
Morning
⛳Early Golf, 🎾Tennis, or 🏏Croquet
🍳Gourmet buffet breakfast at STARS
🥕Tour of the Chatham Bars Inn Farm
🌳Explore town of Chatham – 5 minute walk to Main Street
🚘Drive to afternoon flight out of Boston Logan International Airport
Where SHOULD WE STAY?
When time is short… the distance from your room to the beach should be too!
A member of the Leading Hotels of the World, the Chatham Bars Inn is an iconic oceanfront 25-acre resort makes you think Everyday Should Feel This Good. With those greeting you dressed in Vineyard Vines and a smile, you’ll be shuttled to your cottage in a private car provided by Lexus. Then say goodbye to your shoes as you spend most of your stay with a watermelon margarita in hand at the beach, pool, or next to you as you nap under your cabana.
Address: 297 Shore Rd, Chatham, MA, 02633
CHATHAM BARS INN BEACHSIDE RESORT
photo credit: New England Inns & Resorts
WE STAYED IN THE SPA SUITES THAT HAD THEIR OWN LITTLE SAUNAS INSIDE!
photo credit: Jetsetter.com
MORNING HARBOR SAIL TO GO SEAL WATCHING
MY SWIMSUIT

COUPLES SUMMER SWIMWEAR

A VISIT TO THE CHATHAM BARS INN FARM
Meet our sweet Cape Cod travel companions! Vineyard Vine’s Nicole Sutliff & photographer Erick Dent
MY FAVORITE VINEYARD VINES LOOKs

Vineyard Vines is giving away a trip to the Cape!
Vineyard Vines and Chatham Bars Inn have partnered this summer to bring Cape Cod traditions to life with a 200 square-foot poolside pop-up shop and they’d love for you to come visit it!
To celebrate the opening of the pop-up shop, Vineyard Vines is hosting a Good Life Sweepstakes for an Endless Summer Getaway to Cape Cod. This trip will include 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!
I don’t want you to miss out on the fun, so enter below before it’s too late!
Enter to win here: https://www.vineyardvines.com/capecod
by July 7, 2019
Vineyard Vines Pool Pop-up Shop at Chatham Bars Inn

Biggest thank you to Vineyard Vines for sponsoring this post and gifting us a memory we’ll never forget!