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!
Gorgeous couples. When are all of you getting engaged? Beautiful pictures and things to do. Also, love the outfits and swimsuit Caila and that blue outfit on you.
100% love this and you and Nick and the friends who connected you two. You all are dreamy together like the place you went for a couples getaway. Travel more together when you all 4 can. Come on the men pop the question to these amazing ladies.
Whoa stunning couples here. Also, have anyone every told u Caila that u look Actress Shay Mitchell and Pia Miss Universe? While Nick looks like musician Michael Buble.I want all ur looks girly. I think I will have to pick up some pieces and also try and book a vacation spot here with my husband.
Stunning! LOVE!
Beautiful couples full of love. You’re so gorgeous Caila. Thanks for information you shared and lovely pictures you.
Caila and Olivia y’all so beautiful. Those men are lucky. Those men better put a ring on y’all soon.
Amo sooo charming you all are and charming place too. Que Linda Caila que hombre tienes tan bien wow.
Love going to Cape Cod when I have a chance. So glad you, Nick, Olivia and her man went all together and looks like you all had so much fun and all. Beautiful couple you all make. I can’t say it enough you and Nick 😍 I will order that swimsuit and hope I look that amazing like you do In it.
You 4 should make an annual trip anywhere tog like this especially reading the story on you all together. It’s beautiful. Can only imagine if you all get engaged and married too. Which it looks it’s coming for all of you tog. Cool giveaway to this fantastic place. Thanks for always sharing quality and not like what others do Caila. It’s much appreciated.
What a giveaway place to win. You and Nick and Olivia and her guy are all dreamy couples.
Beauties
❤️
Great post and love all the pics! You and Nick make a striking couple!
Good new blog with some goodies. What dreamy couples you both make.
Goals
Truly beautiful
Awwwww
This will come in handy for my trip with my fiancé to Cape Cod in the future. As always you’re beautiful and also aces on the friends who brought you and Nick together.It’s cute story and you al should keep making travel plans together. Legit those men better put a ring on you and Olivia soon.
Amazing 💖
Natural happiness and love here WOW WOW love
Gorgeous the couples and Cape Cod looks like a place I should checkout with my husband. Caila Nick is one lucky man because you are a natural beauty. You and Olivia are gorgeous.
Effortlessly everything is beautiful.What moments you four created together.
Pretty.. Beautiful.. Lovely ❤️👍👌
Visiting this place looks so amazing and sailing in Cape Cod 😍 I won’t lie I’m ready to see you and Nick get engaged Caila. I think Olivia’s boyfriend should do the same with her.
That blue romper and paired with those earrings that pop just right on you 💙 I want it that look for me. Also the stripped shirt and swimsuit. Caila you are hair goals with such a stunning smile. Also you and Nick are precious together. He’s a handsome one too. Cleary you two keep falling more in love and it’s beautiful. Those friends you two have beautiful too they are and what they did for you two 💛
Beautiful and you’re a natural stunner 😍
You guys are so cute!
OMG looks like so much fun 🙂
Brianna | http://briannamarielifestyle.com/
It looks like so much fun! I have never been to Cape Cod but will definitely look into it for future trip! Love love love your outfits! You make anything look beautiful.
Maureen | http://www.littlemisscasual.com