The “Rules” For Our Annual Girl’s Trip

There’s nothing quite like good ‘ol girl time.

Whether for an hour or three days, I’m a big believer that time connecting with girlfriends is good for the soul. Prioritizing that time can be hard with how busy life is, especially with a family, but it’s something we all agree is a huge priority in our lives. Which is why my girlfriends from high school/college and I decided to do an annual trip that is all about just that: Connecting!

The “Rules” For Our Annual Girl’s Trip

Our annual tradition kicked off two years ago.

We started it after my coworker Molly told me about a tradition that she and her girlfriends do. Every year they go on a girl’s trip, but there’s a catch: A different person from the group is in charge of planning it every year. That designated person picks a location, plans the trip, and then reveals to the rest of the group where they’re going. Molly and her friends have done this for 10 years, and after seeing some of their hysterical posts on social media, my girlfriends and I decided to adopt their tradition. Hence, our annual trip was born.

I love this idea for so many reasons.

I’m a firm believer that making quality time for your girlfriends is something that should be prioritized. Life seems to get busier and busier, and I think we can all empathize with how even a quick dinner can be so hard to organize. So, I love the idea of doing a weekend trip to really soak in time with one another.

This approach is fun because you actually create two times of the year to rally around: the trip reveal, and the trip itself.

The fact that it’s just the girls is really special. No hubbys, no kids. Though we of course miss our families dearly, it’s just a different trip when the whole family is involved. You don’t get as much one-on-one girl time, which is really the main point of the trip itself. Plus, lots of people make things like staying in one Air B&B house, or planning activities, super hard to navigate.

Here are the rules that we adhere to for our annual girl’s trip!

The trip is on the same weekend every year. We do the second weekend in October.

We like this timing because it’s after the crazy summer season, but before the holidays, and it also allows for a wide range of destinations when you think of the timing from a seasonal approach.

Having this established from the get-go is super important. When you start to move the date, things get complicated. We all basically know at the start of each year that this weekend is it, and that it should be prioritized no matter what! Unfortunately life happens — we know some years there will be things that people may need to prioritize over the trip like family weddings or even births — and we’ve all agreed that if that’s the case, we may look into other weekends if absolutely necessary. But if it comes down to it, that person may need to simply not go on the trip that year. And in that case we’d all of course be understanding!

The “Trip Reveal Brunch” is always in the spring.

Timing on that is super flexible! But having it in the spring again avoids the crazy summer season. It also ensures there’s enough time for everyone to book their flights, arrange for child care/details, etc.

This brunch is usually themed, and the organizer does a big reveal after we guess the destination based on the “clues” from the brunch. For example, this year’s brunch served grilled cheeses and maple syrup, and it was revealed we’re going to Vermont. For the brunch reveal I hosted, I answered the door with a southern drawl and served peaches and cream, then revealed we were going to Savannah. It’s so much fun to play into the theme!

For the trip, we’re flexible with what individuals need.

Last year, a girlfriend had an infant that she was still breastfeeding, so she needed her baby to come. She ended up also bringing her mom to help with her baby so she could have little breaks. This year, we had a girlfriend who needed to come a day later because she had just had twins and only felt comfortable leaving for a few days. Overall, we of course are accommodating to what everyone needs to do! The biggest priority is being together, no matter what that looks like.

One person is designated the trip organizer each year.

They’re responsible for picking the destination, arranging where we’re staying, organizing one activity per day, and hosting the trip reveal brunch.

Having a point person is a great way to surprise everyone else, and allows for so much creativity in the destinations. For example, this year we went to Burlington VT. I hadn’t heard much about it and honestly am not sure if I ever would have gone there on my own, but I’m so happy that was chosen because it’s now one of my top recommendations to travel to in the U.S. It was magical!

It’s also really nice for there to be a “point person” who runs things. Maybe it’s the past corporate marketer in me, but I’m a firm believer that every project needs one point person in charge or else things don’t get done as seamlessly. (Anyone else love a good RACI chart? Ha!)

The budget has been determined from the get-go.

None of us are in a position to drop thousands of dollars on a weekend getaway. From the upfront, we picked a budget. It’s the trip planner’s responsibility to plan the trip around that budget!

Trip duration is for a long weekend.

We all arrive on Thursday, and leave on Sunday. This ensures we can all prioritize it, and not have it be too extreme of a commitment.

On the last night of the trip, the next year’s planner is pulled by the person who planned the current year’s trip.

We have 6 women total, so for 6 years we’ll have a different planner. Once we get through the full rotation of people, we’ll start the rotation over again!

The trip planner isn’t responsible for EVERYTHING.

This is an important caveat! It’d be really hard to organize literally everything on the trip for all of the people. We decided that our trip planner is responsible for the high level things like destination, where we’re staying, and one activity per day. But the rest of us pitch in for things like restaurant recos, grocery shopping, etc.

For example, this year my friend Katie and I were the first ones to arrive, so we tackled renting the car and grocery shopping for the group. Super easy, and it makes the logistics a heck of a lot less daunting for the planner! We all take turns picking up bills at places, and use Splitwise while we’re on the trip, so all costs while there are even.

Another important note is that, though the planner takes flight costs into account while planning, we’re all responsible for booking our own flights!

I can’t tell you how special and fun these weekends are! I highly encourage anyone to make this happen, whether with your family or friends.

Speaking of destinations – where are your favorite places to travel to for weekend destinations? Would love to hear in the comments below!

PS – 5 reasons why every woman needs girl’s weekends + Things to do in Savannah, GA