How To Start An Annual Girls Weekend Tradition

Have you ever wanted to plan a yearly girls trip?

New Buffalo Michigan Girls Trip

Shop The Looks: plaid blanket scarves c/o Mark & Graham // my friend Brittney’s yellow sweater {highly sought after in my IG stories!} // hats // more sweaters and knits! // my striped dress {old MDS Stripes}


Two weeks ago, my girlfriends and I went to New Buffalo, Michigan for our SEVENTH annual wine tasting weekend. We rent a Joanna Gaines worthy home; drink a million bottles of Pinot Noir; the charcuterie boards are flowing; knee highs and booties are wardrobe staples; and my face always hurts from laughing so hard.

Details: pink sweater // acrylic tray c/o


Mark & Graham made our weekend extra stylish this year by gifting us some fun accessories to compliment our festivities! Their famous monogram blanket scarves kept us toasty in the vineyards. It was a wee bit chilly! Their wood, marble and lucite cheese boards made the most delectable charcuteries. We drank out of our matching leopard wine glasses. And the leather pouches were the sweetest parting gift to keep our personal belongings organized {will be showing these later!}.

New Buffalo Michigan Girls Trip

Since I get a TON of questions every year on where we stay; where we go and how on EARTH we get so many ladies to dedicate a full weekend away, I’m spilling EVERYTHING right here. Email templates, our EXACT house, where we go, what we do…

Scroll below to get our process and a few highlights so you can easily duplicate it for your friends. Just copy/paste emails, then pick and choose which parts work for you. The sky is the limit here!

Details: Animal print monogrammed wine glasses


Before jumping in, I have to give a big THANK YOU to one of my very best friends, Jessica, who plans everything from soup to nuts every time. She takes time out of her busy schedule to plan it; puts her own credit card down; and organizes EVERYTHING. We’re SO fortunate she takes the lead and without her I’m not sure it would happen. We have such incredible memories because of it too. THANK YOU Schultzy!!! We love you!

New Buffalo Michigan Girls Trip
New Buffalo Michigan Girls Trip

High Level Details

If you just want the quick and dirty details, here ya go!

Where: New Buffalo, Michigan
When: Every October (first or second weekend). It’s beautiful here in the summer and spring too but the changing of the leaves gets us every time.
Our Exact House: The owner decorates it to perfection every season!
How Many People: It always varies but this year 9!
1st Night: We always stay in, snack on apps, eat dinner and play games…all in our PJs!
2nd Day: We usually get a driver to take us to the wineries. We used to hit up three or four vineyards but this year was two – haha!)
How: To keep it easy and affordable, everyone signs up for a meal/snack.

New Buffalo Michigan Girls Trip

Why It Works

“But Nicole! It’s impossible to just get coffee on the books, let alone an entire weekend!”

I HEAR YOU. Here’s why it works.

When we first started this tradition, there were only a few of us. It’s grown and evolved every year! Given this is our seventh, my best advice is to just plan it. Whether two or eleven people can come, you’ve got to start somewhere. As time goes on, it’s something you and your friends will prioritize and more people will want to go. Some of these ladies I ONLY see THIS weekend! But to give you an idea of how fun it is, so many of us have gone pregnant (AKA not drinking!) and we still have a ball. So don’t be discouraged if the first (or even second!) year is small. It will catch on – I PROMISE.

The second key factor is it’s planned several months in advance. Here’s the exact email Jessica sent out four months in advance so you can copy/paste it!

New Buffalo Michigan Girls Trip

Inaugural Email – Template

Sent 4 months in advance

Hello friends!

It’s that time of year again!! I looked at a few houses this morning!!! Both of our houses from the past two years are already booked – eeek! (It seems they book up earlier every year!) But fear not, I found this awesome place in the same complex!

Right now, we’re looking
at the weekend of October 11 – 13th. It’s Columbus weekend, but having Monday off might help some of us recover! 
I’m looking to get a firm headcount. Please respond by this
 Friday, June 21st regarding whether or not you are in and we can go from there! I want to get this booked ASAP, as places are going fast!

Have a great week everybody!!

New Buffalo Michigan Girls Trip

Meal Sign Up – Email Template & Google Doc

To keep it easy and affordable, we divvy up the food! Legit everything is handled from the time you arrive to the time you leave. Below is the email and sample sign up Google Doc {just duplicate it for your own girls weekend}. It’s always first come, first serve when it comes to sign ups. Then those who are in groups coordinate so there’s no duplicates!

Morning friends! I can’t believe the best weekend of the entire year is just around the corner!

Here is the meal sign-up for the weekend!
{duplicate and adjust for your own girls weekend!}

The meals to sign up for are: 1) Friday dinner, 2) breakfast stuff for the weekend, and 3) snacks for the weekend. To shake things up a little bit, we will be going OUT TO DINNER on Saturday to the Stray Dog! They don’t take reservations, so we’ll just roll up there when we feel like it!

Don’t forget – everyone is in charge of their own alcohol and water! Legit counting down the days….

New Buffalo Michigan Girls Trip

How To Begin On A Positive Note

Shop: marble and wood cheese boards

So I secretly love to make up a good game! Especially if it’s super woo woo. To kick off our first night, I wanted to think of a way to build each other up and re-connect. Mark & Graham’s monograms were key to pulling this off!

Here’s how to replicate it! {P.S. this works with any monogrammed or personalized gift}. I randomly placed a wrapped monogrammed scarf at every dinner table seat. Everyone sat wherever they wanted. Then the youngest person goes first by unwrapping the scarf at their seat. Whoever’s monogram was on the scarf, they had to say what they loved about that person and passed them their blanket. Then it was their turn to go next! We laughed. We cried. And cried again. And as a result, the entire weekend just flowed.

Our Favorite Wineries

Listing these in my current favorite order! But you can’t go wrong with ANY. This year we did Round Barn, Dablon and then planned to go to Journeyman. But were so tired we went to The Stray Dog for dinner instead!

  • Dablon: Hands down our new favorite winery! Some of the girls just got back from Napa and said it had a very similar feel! Very Restoration Hardware if you ask me and PACKED. So be sure to make a reservation.
  • Round Barn: Make a reservation in advance and be sure to visit the brewery house on top of the hill after! We usually buy a growler and drink it in the vineyards.
  • Tabor Hill: After your tasting, get a bottle and appetizer on their outside deck overlooking the vineyard.
  • Journeyman: A well known vodka distillery that’s known for their design too! Yes, I know it’s not wine, but who cares! Food is scrumptious and be sure to walk around the downtown Three Oaks. Their vintage stores are frequented by Chicago interior designers and where I got these 1950 glasses from!
  • Lemon Creek: A charming little vineyard that also has hay rides and a dog that lives on the property!

As for the rest, that’s where YOU come in! I hope you take this itinerary and run with it. Girl time is something money can’t buy and the older I get, the more I realize how rare it is. You have to MAKE IT HAPPEN.

If you have any questions or want to see the Instagram stories for more details, leave a message on my Instagram!

P.S. The perfect Bachelorette Party in Miami and my favorite trip to Nashville!

SHOP THE STORY