Let’s get real. Keeping up with the day-to-day (juggling jobs, families, commitments, etc.) is already time-consuming, and now your friends want to plan a trip? Pshh, unlikely. We hear you and we’ve been you.
But it’s possible, we promise! No more “would love to get together, let’s plan a girl’s trip” and then crickets in your text thread. Take these steps, chunk out the work, and then enjoy that vacation with your besties–you deserve it!
First things first, it’s time to figure out the details that come before you even start planning the trip. Buckle up, ladies, this is where you ask the hard questions, identify the group, and nail down the details.
Identify the group – Our biggest piece of advice is to start small, especially if you haven’t traveled with this group before. The more people you add, the more personalities and interests you have to navigate. Keep in mind that everyone’s travel styles are different – you may have the foodie, the shopaholic, the adventurer. Make sure you’re identifying styles that work together to ensure you have a good trip.
Get commitment – Make sure everyone is on the same page with the dates they need to decide by. Depending on the length of your trip, PTO requests can become a factor, and there’s nothing worse than planning a trip with the idea of splitting costs for accommodation, tours, etc., between a certain number of people and then realizing that fewer people are splitting a bigger bill.
Meet early & often – This doesn’t need to be rigid. Hit a happy hour and make it fun, but talking about the trip often to make sure that everyone is on the same page is critical. Before heading to Thailand, we met about once per month via Zoom since we were based in different locations to make sure we were booking things early, chatting through what we wanted to do and see, and giving ourselves homework to work on in between meetings.
Ask the hard questions first – Make sure you’re asking for people’s budgets and preferences. Even if money talk can be uncomfortable, it’s important to understand where everyone’s comfort level with spending is because it can get really awkward while you’re traveling if someone is being pushed beyond their means. If someone’s must-dos clash with someone else’s, it’s easier to talk those things out before you’re in the moment and someone is upset. Be open, be honest, be flexible.
Planning Time:
Alright, the hard part is done. You’ve identified who you’re going with and gathered the commitments. Now it’s time for the fun part. While planning can seem overwhelming, we promise it can be a blast if you break it up and let your imagination guide you to your dream trip.
Start a shared document – This is a spot where everyone has access to dump research, share links, and post questions. It can be referred to during meetings and will be your ultimate tool, as it can be tough to keep everything straight. It doesn’t have to be fancy, we used a simple Google Doc that we could all edit in real time.
Let everyone have a say – One of the things that made our Thailand trip the best is that each of us got to pick 1-2 things that were a must-do. These were non-negotiables, and it let everyone get their perfect trip instead of one person taking the lead. This also helps get the itinerary started.
Get the big things done first and work out the details later – Whether you’re meeting at the final destination, trying to get a group flight, or planning a carpool, transportation is the key piece to figure out first. If you’re flying, you want to make sure to get tickets early to:
- Make sure everyone has a seat.
- Make sure that ticket prices don’t soar, leaving someone unable to join.
- Help keep your timelines similar so no one is just sitting around waiting.
- Determine the budget you have left over for activities.
Identify the accommodation that works best for your travel needs – Depending on how big your group is, an Airbnb might be the easiest option for housing everyone under one roof. Proximity to activities, transportation, and amenities that are important to the group can also be key factors in determining what’s best for you. This is where your homework will come in. Give yourselves a few weeks in between meetings to research options and post in the shared doc. Post your top picks and come back to the next meeting ready to vote on your favorites.
Break up the work – Identify point people for each category. For example, on one of our recent trips, we had one person responsible for booking the hotels, so they had all the documents in one place and would be the expert for this area. We had a different person in charge of booking transportation and another on activities. This allows you to become a mini-expert in your area without the stress of trying to keep all aspects straight – think of this as a giant group project. 🙂
Track your expenses – Some locations make it a lot harder to split your bills, and it’s easier to take turns paying. You also might want to book group tickets, split accommodation, etc. Keep track of everything in an app like SplitWise or a spreadsheet where everyone has access. This makes it super quick and easy to figure out who owes whom at the end instead of trying to Venmo back and forth constantly.
Enjoy your trip: Congratulations, you’ve made it out of the group chat, and you’re heading on your dream girl’s trip. Here are a few things we’ve learned over the years to make sure it’s everything you imagined and more.
Be flexible – It’s a group trip, so you may not get to do every single thing you want to do in your own way. If you want to do other activities, you may have to go solo or identify a smaller group. You may have to compromise or be open to trying things you may not have before. Maybe you’re not a foodie, but you realize you actually like taking food tours. Or maybe you’re not a shopper, but you’re willing to do it for a short time. Make sure to communicate often.
Know yourself and your limits – It can be easy to get caught up in the excitement of a new place. Maybe your group is go, go, go, but you need some time to take a break and smell the roses. It’s still your trip, and you want to enjoy it, so make sure to communicate if you need breaks. Honor your body and your travel mindset, and don’t be afraid to speak up. It’s better to take short breaks throughout than end up missing the big stuff. We promise, it’s more of a big deal in your mind than it actually is to your group.
Post-Trip:
Start a group album – Make sure you’re sharing your favorite memories with everyone, so that it’s a great way to reminisce. We started a group album because we ended up snapping photos of each other during the trip. This was a super easy way to share without having to text a bunch of photos.
Pro Tips:
- Make sure you have a group of committed girls. The biggest reason the trip doesn’t leave the chat is because people lose interest, don’t respond, or talk about it with no real plans. If you have 2+ passionate people, you just have to start tangibly making decisions and setting deadlines.
- Remember, you don’t have to travel just with your besties. You can end up becoming great friends on trips because you had similar interests and made memories. Similarly, you can travel with friends you’re close with on the day-to-day, but find out that traveling together is not your jam. That’s ok. You can have different friends for different seasons.
- You’re going to see the best and worst of people on a group trip. Maybe someone’s hogging the bathroom or was grumpy during an activity. Don’t sweat the small stuff and give everyone some grace.
Congratulations! Your trip was a success. You made it out of the group chat, and you had a blast. Looks like it’s time to start planning the next one 🙂
About Sippin’ Sangria
Caroline and Lexa are a traveling duo who have visited several local, U.S., and international destinations together. Through these adventures, they’ve learned the ins and outs of traveling with friends and love connecting with other female travelers. When they’re not booking their next flight, Lexa and Caroline plan trips – honeymoons, girlfriend getaways, weekend trips, etc.
🧃 Like the cool friend who always knows where to go.
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