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How To Plan A Girls’ Trip Before Everyone’s Fall Calendar Fills Up

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Oct. 16 2026, Published 8:00 a.m. ET

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Talking about the trip without ever booking it can feel more exhausting than exciting. Discussion around a girls’ trip that doesn’t make it beyond the group chat is like a story with no climax. Between work deadlines, personal responsibilities, finances, and various schedules, getting everybody in the same place at the same time can feel like a job of its own.

It can become overwhelming finding the perfect travel dates, staying within a reasonable budget, and making sure that the trip comes together without any hiccups. As career women, a vacation should not be optional. You deserve time away from work and your home responsibilities. And more importantly, your friendships deserve more than “let’s catch up soon.” So before your fall calendar fills up, make time for your girls and take a trip!

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Don’t Make The Trip Optional, And Work Mandatory

Most think the planning stage of a girls’ trip is the hardest part, but in reality it’s the acceptance that you’re deserving of a trip. Many career women often focus on family and career as a priority, rather than self-care, personal time, and, in this case, traveling with the girls. 

When it comes to work, calendars get filled, and we focus on our tasks and deadlines. A survey based on 3,0000 workers reported that nearly 25% of employees didn’t take a single vacation day in the past year. We prioritize meetings and tasks before requesting vacation time. Even doing work on the weekends can consume our time as professional women. 

The problem is, we’re waiting for time to make itself. We’ll say things like “when my calendar frees up” or “when things slow down”. And honestly, that day might never come. So you have to make the time. Take matters into your own hands and request vacation time (even if you don’t have a vacation set yet) and let the planning follow afterward. 

A few days to simply enjoy yourself and friends doesn’t have to be a huge thing. A simple day trip, or weekend getaway, even a staycation allows for connection without waiting on the “perfect” time. 

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Let’s Get On The Same Page

An important discovery in group chats is that women tend to send flights or a TikTok video inspiring them to want to take a trip. But that shouldn’t be the first step. The first step is to see who can realistically go and everyone’s budget for an upcoming trip. Everything should be laid out to simplify the process for women with busy schedules. So instead of asking “when can everybody take a trip?”, maybe narrow down 2-3 travel windows and have the group vote on which one works best. That knocks out multiple, different answers and opinions that would prolong the planning. Then from there, the group can decide what type of trip this will be: weekend getaway, big vacation out of the country, or a simple day trip. 

And when it comes to the budget part, remember everyone’s idea of an affordable trip could be different. It would suck to plan an entire trip only to realize at the end, when it’s time to pay for things, your friends cannot afford it. 

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Plan The Details 

Once the basics are settled and agreed upon, this increases the chances of the girls’ trip making it out of the group chat. And the fun part is next, the details. 

Hotel or Airbnb? Driving or catching a flight? Sightseeing or fun excursions? And let’s not forget dinner reservations. These are important details to figure out but not the most challenging. I strongly believe in an itinerary with 1-2 options that the girls can choose from. Whether we stick to the itinerary directly or not, at least we’re not wasting vacation time trying to search places to go and things to do. 

Now you know your friend circle. Some people want to be included in the planning, and others don’t care as long as everything sounds good and aligns with their desires for the girls’ trip. Another helpful tip is to divide and conquer the responsibilities. One friend can find the living accommodations for the trip, while the other looks into activities and excursions for the group to do. And if your friend group is anything like mine, we have someone designated to find coupons or deals we can use to save on the trip, whether it be through Groupon or other apps. 

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Overall, stop leaving girls trip time in the “we should do this sometime” category. As a career woman, don’t wait for the perfect time to come along, you make the perfect time to spend with your girls. Just like you prioritize work and the various meetings and responsibilities. You can prioritize picking a date, requesting vacation time, and enjoying a girls’ trip. 

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Tyerra Drake
By: Tyerra Drake

"Tyerra Drake aka MissTDrake is a podcast host, journalist, corporate baddie, speaker, and entrepreneur whose vision is to empower women one step at a time. She has a degree in Mass Media and Communications. She has been featured in magazines and websites, such as VoyageATL and won ACHI Magazine Podcast of the Year 2022. In 2019, Tyerra launched her podcast Girls On Another Level (G.O.A.L) where she aims to progressively empower women who are catalysts for success. Expanding her media portfolio in 2023, Tyerra diversified into event coverage as a media correspondent, broadening her storytelling prowess. Her journey allowed her to interview several celebrities and influencers, amplifying her commitment to sharing inspiring narratives and offering guidance through impactful storytelling, covering events such as Essence Fest and HBCU Honors, while interviewing notable figures like Chrisette Michele and LeToya Luckett."

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