Over the next five years, one or more of my girlfriends will turn 40, which gives us the perfect reason to take an annual girls’ trip in honor of the birthday girl(s) and for the chance to reconnect in ways that texts and Marco Polos just can’t replicate.
Planning these trips is time-consuming, so we rotate who’s in the lead and who’s the support person to pull it all together. This year, we went to Santa Fe, New Mexico. My friend Lindsey took charge of planning the fun stuff, and I handled the logistics (hello, spreadsheets full of arrival/ departure times!)
This was an incredible trip—a refreshing, dare I say, life-giving trip—and I want you to have one, too. In this article, I’m giving you a behind-the-scenes look at how we make these trips happen. In my next article, I’ll share our actual Santa Fe itinerary, experiences, and helpful tips.
Now, share this with your friends, pick a date, and make it happen!
Our Operating Principles
“I do I. You do you.”
Since most of us in the group are moms and all of us are hard-working women, we revel in only having to worry about ourselves on this trip. There is no judgment on how anyone spends their time — whether they stay up until 4:00 AM or sleep for most of the trip.
Take the picture.
Besides posed group photos, one of us is always snapping candid pictures. When a trip is so full of fun memories, it’s easy to forget the small details. Plus, since most of us are moms and rarely get into photos ourselves, it’s nice to be in the center of the frame for once. These pictures—even though most of them will never see the light of day on social media—are special mementos from the trip. Everyone does their part to capture the moments.
Prepare to be silly.
What’s a girls’ trip without matching shirts, colorful wigs, or some other “look at me” marker? Just say, “When in Rome,” and see where the trip takes you.
Choosing Our Destination
Our group of friends is well-traveled and hails from all over the country, so it’s tricky to land on a location that excites everyone. Last year, we went to New Orleans, which meant late nights and basically acting like we were in college again. We’ve also done Vegas which was more of the same. So this year, we wanted to switch it up — do more daytime activities and go somewhere with a completely different vibe.
Lindsey crowd-sourced ideas (with a large group of girls, many locations turn out to be off limits for one reason or another) and we landed on Santa Fe. It was a relatively central location — we had people coming from both coasts and the midwest. The weather was perfect for a late September trip, and none of us had ever been.
Deciding on a Date
After last year, we designated September as our month to take a trip. Consistent timing year over year helps keep the trip a priority and lets us factor it into our busy schedules. But, truthfully, we might move it up to August next year because of work schedules, and not everyone who came last year was able to make it this year. That’s just life. But in general, we finalize the location and send out weekend options six months in advance. We land on the date that works best for the majority of people, and go from there.
Planning Our Itinerary
We’re all friends because we have a lot in common, but when upwards of 12 to 13 girls are invited on these trips there’s bound to be a variety of opinions on what to do while we’re there. For our crew, we have three priorities: downtime together, locally-inspired activities, and nightlife.
The Trip Lead handles the bulk of the planning but definitely collects suggestions from the group. We all ask around for suggestions, plus every city has its own Travel & Tourism website, and Trip Advisor is a great resource.
For Vegas, our priorites translated into a cabana by our hotel pool, dinner reservations every night, and ending at a bar or lounge for post-dinner drinks, and then sometimes a late night food spot after that, because Vegas. For New Orleans, we sunbathed at our rooftop pool, brunched in the mornings, ate beignets, took a horse and carriage ride around the French Quarter, and spent our nights on Bourbon Street and Frenchmen Street. For Santa Fe, we biked a margarita trail, went horseback riding, relaxed at the spa, and hired a personal chef to cook on our last night.
Choosing Where to Stay
Because we’re a large group, renting houses through Airbnb makes the most sense. It gives us communal space to all hang out together, allows us to eat some meals at home, and usually ends up being more cost-effective. The exception, of course, was our Vegas trip, because the goal of that one was to be right on the Strip.
The Trip Lead for the year researches lodging and makes the final call on where to stay, often in relation to the things we want to do while we’re there.
During the planning stage, the cost of lodging and proposed activities are shared so that people can choose what they want to do based on their budget. That means that when it comes to the actual trip, group expenses are generally divided up evently. The assumption is that everyone is okay with the cost of what we’re doing.
There’s an app called Splitwise that’s supposed to be great for dividing costs among a group of people. We’ve been doing group trips and activities for so long, though, that I still use a spreadsheet template — my friend Sarah introduced it to the group six years ago. Here’s the one from our Santa Fe trip.
We do our best to divide costs fairly, but it’s not a perfect science for a large group like ours (there were 11 of us on our most recent trip). Everyone goes into this trip with the understanding that there’s no perfect way to calculate costs to the exact penny. You’ll probably end up paying ± 10% of your true costs.
We are all very good about reimbursing each other once the final bill is tallied. If your friends are not as reliable, then, honestly, I’d advise against going on a trip like this unless you really don’t care how much you end up paying,
During the course of the trip, it is much easier to have one person pay for everything, at least for the big-ticket items like lodging, group activities, and meals. Later, when you’re trying to figure out who owes what, having most of the costs centralized saves time and ensures accuracy.
However, that puts a large financial burden on one person. Plus, other people sometimes want to pay to get credit points or because paying for things as they go makes their final tab lower, and that somehow feels better than dealing with a large bill at the end.
So, inevitably, after the trip, the Trip Support person (hi, that’s usually me) ends up with a hodgepodge of receipts, texts, and emails from everyone reporting what they spent on the trip. This gets entered into our giant spreadsheet so we can figure out who owes what to whom. We set a deadline to submit so that we can settle up in a timely manner. If you miss the deadline, you eat the costs.
If you back out of the trip after committing to the house and/or activities that we’ve paid for in advance, then you are still on the hook for those costs.
Everyone splits community expenses like the house, groceries, and Ubers that were taken by a few to benefit all (like going to the rental office to pick up keys or going to the grocery store for supplies).
You are not charged if you weren’t there — inevitably at the end of the night, the group divides up and some people go home and some stay out. The bar tabs from the late crew are only split among those who were there.
If some people in the group are on tighter budgets than others, it’s their responsibility to share their concerns and needs during the planning stage of the trip when big-ticket costs are being considered. Complaining at the end of the trip is too late for anything to be done.
Communicating with Each Other
We start a group email chain to announce the destination and finalize dates, and then we continue to use the email chain to share airline information, ask questions, and share the itinerary as it shapes up. Obviously, the Trip Lead and Trip Support person have lots of coordination behind the group emails, so make sure those two people can work together well.
We also create a shared spreadsheet where we keep everyone’s flight information, RSVPs for activities, and the expenses, like I mentioned above. Basically, if you can’t find what you’re looking for within the email chain, you can probably find the key information on the Google sheet.
As the trip gets closer, we switch to group text to share what we’re packing, just generally get amped for the trip, and to keep tabs on each other when we arrive.
As you can imagine, we end up with hundreds of pictures from the trip and rely on a shared Google album to store our collective photos—we have both iPhone and Android users in the group, so it’s an easy platform for both.
These trips do take some work to pull together, but it is always worth it. If you’ve taken girls’ trips like these, share your tips in the comments!