Girls Trips Travel Planning

How to Plan a Girls Trip Without Drama: Friendship-Saving Strategies

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The dream: you and your crew go on a girls trip and have a flawless, fabulous carefree time without a single glitch. The reality: different personalities may clash, everyone has varying expectations of a good time, and SOMEONE must do all the (sometimes stressful) planning. Therein lies the importance of learning how to plan a girls trip.

While girls trips can be amazing, they can also go sideways – especially if the right things aren’t considered up front. Staying with you beyond the trip, this type of poor planning ruins more friendships than you think.

On the successful girls trips I’ve taken, we’ve been aligned on the group dynamics, what type of vacation we’re in the mood for and what our budget is. They’ve been with ladies who are honest, kind and can talk through any hiccups together, and don’t mind letting people do their own thing when they want.

On the other hand, the trips that have been a bit less successful typically didn’t align on these things up front; were overly rigid in what everyone could or could not do; and didn’t have great communication amongst the group, leading to frustration all around.

My goal with this post is to outline practical strategies that actually work, so that your next girls trip is a success story!

This is the planning piece of a bigger picture. For destinations, budgets, and the whole framework, start with my girls trips guide →

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Before you Start Planning

Assess Your Group Dynamics 

Having a successful trip starts long before you board that flight or get in that car. Kind of like a good dinner party, you need to assess who is going, what the different personality types are and how they like to travel. If one person is expecting a backpacking adventure camping in the countryside, and another is expecting to return to a 5-star chateau after a light day hike, there’s going to be a problem. Is one person in need of a minute-by-minute itinerary, while another can’t be on time to save her life? If so, my magic 8-ball foresees frustration.

Identifying what the potential conflict areas could be, and determining if they are dealbreakers for anyone, is a crucial step. If everyone is still on board, thinking through how you can resolve conflict and setting expectations early will go a long way to having a successful trip.  

The Foundation Conversation 

These are the exact conversations you need to have up front. Discussing and aligning on the essentials are key. This will help folks understand and have ownership in how the trip is shaping up; and ultimately decide if it’s a trip they’re excited to take.

Essential Topics

  • What kind of vacation vibe are you looking for? Is this a relaxing beach getaway, a 3-day party, or a bustling city adventure?
  • What are accommodation preferences? Does a shared house make sense, or is this more of a private hotel room kind of group? Is there interest or outrage at sharing rooms with others?
  • How much time do we think we have, and what dates are feasible for folks?
  • Are there budget constraints or expectations we’re working with? Make sure people think in reality, not what they wish they could spend. Use the trip parameters as guidelines and talk about ranges. For example, I’d expect a 3-day trip to Mexico, including flights, hotel and food, to range between $1000-$3000. That can get people thinking about what’s realistic for them, so you can collectively set a trip cap. This cap may end up influencing where you decide to go.
  • Any health-related concerns for anyone in the group that need to be considered?
  • Are significant others invited to any part of this, or is it strictly girls only?
  • How do you want to handle it if someone wants to skip a group activity? Pro tip: I strongly recommend letting people opt out when the want to. Some people just need their own time, may not like an activity, or have something else they really want to do. Having them join an activity but be bummed out is worse than letting them do their own thing. It’s everyone’s vacation, after all!

How to Facilitate the Conversation

As the trip organizer, you can facilitate this session in a variety of ways. It can be via a survey, chatting one-on-one with each person, or getting the group together to discuss it live. Another idea is for folks to share their top 2 dealbreakers and must-haves, so you know what’s most important to everyone. I’ve found it works best when everyone gets on a call together, but I have had good results talking to everyone individually, then sharing out the consensus to the group.

Handling Conflicts

Being available and open to any questions or pushback is important here – you want to make sure you’re representing everyone’s needs accurately. If there’s an outlier – Judy wants to stay in a hostel in Honduras and everyone else is dead-set on wine tasting in Tuscany, you’re in a pickle. If the group is most interested in spending time with each other, then hopefully some collaboration on a third option can happen. Wine tasting in South American vineyards, perhaps??

However, if the destination is the genesis of the trip, and travel styles, budgets, or must-haves are too far apart to get there, this could be a good place for Judy to bow out and catch the next trip. I’ve found this happens a lot when a girls trip starts with a location or specific idea someone wants to do. It gets pitched, and those who are a) interested in that spot, b) can afford it, and c) align on foundation conversations are good to go. Others, myself included sometimes, say thanks but no thanks, I’ll see ya the next time around! As much of a bummer as that may seem, it’s much better than going on a trip you’re not interested in/will frustrate you/will put you into mega debt. Saying no now can save you a figurative and literal fortune later.

The Planning Process

Step 1: Establish Ground Rules 

Now that you have the foundation established, you can get into the actual planning. Before getting into the nitty gritty, it’s best to establish some ground rules. I know, I know, you’re wondering when we get to the fun part?!? But trust me, the more you do a few of these things up front, the more fun the planning – and more importantly, the TRIP – will actually be.

What kind of ground rules do we even need to worry about, you ask?

Ground Rules to Consider

  • Decision-making process – how will decisions be made? Is this being handed over to one pro planner, and everyone else will be informed of the outcome?  Are ideas being pitched to the group and everyone gets a vote? I’ve planned both types of trips, and both work. It really comes down to the crew and how much input everyone wants on the trip itself.
  • Roles – To that end, assigning roles in the group can be helpful. It can be as easy as Sophia does all the planning. Or, if you want to split it up, Sophia takes care of lodging; Margot is on restaurants; and Lisa is all about activities. Another approach is to have a ‘researcher’ and a ‘booker’, so the itinerary stays in synch. Again, lots of ways to tackle this and all can work. They key is making everyone feel like they are getting (or staying out of) as much of the planning process as they like.
  • Communication protocols – How and when everyone is synching up is a seemingly small but helpful thing to tackle. If you decide on a group chat, for example, and Sophia is blowing up the chat with every new restaurant she finds (honest hour – I’ve been guilty of this!) – that could really annoy other people in the group (I’ve also been in this seat, coming back to my phone with 300 unread texts – YIKES!). Maybe you all decide to only update once you have a proposal to look at; or to synch up once a week on planning. However you decide to communicate, make sure it works for everyone.
  • Financial arrangements and payment deadlines – This is a super important component, especially when everyone is going in on shared expenses. You’ve already agreed on budget guidelines in the pre-planning stage (please say you did this!), so the amount shouldn’t be a surprise to folks. If you missed that step early on, this conversation is even more important. Letting people know how much they owe, when it’s due, and what the cancellation policies are is crucial. I’ve had friends go in on an Airbnb, and someone had to drop out a month before the trip. Because the cancellation policy and final trip amount weren’t aligned on up front, it caused quite a kerfuffle, and no one ended up totally satisfied with the outcome. It put a wrench in what was supposed to be a wonderful getaway, so whatever you do, don’t miss this one!

Step 2: Budget Conversations That Don’t Ruin Friendships 

Speaking of budget, money can be a tough topic for people to discuss. How do you do that without it getting awkward? The best thing to do is take personal finances out of it. It’s not about how much everyone makes or how they choose to spend their discretionary income. As soon as you go there, it’s a recipe for intended or unintended insults. Instead, focus on the trip.

If you’re in range of the parameters you settled on up front and someone has missed the deadline, politely ask for a follow-up. You can remind them of the deadlines and ask when they’ll be able to pay their portion. If you’re ok floating for the other person, you have a little leeway. If, on the other hand, this puts you out financially, you can let them know that as much as you’d like to, you’re not in a position to cover their portion, even for a short while.

Strategies for Different Budget Levels

When you’re landing on the budget for everyone, there are different approaches you can take. If you all align on the amount, then doing an even split is an easy way to go. If not, I’ve seen and been on trips where a subsidy approach is applied. The higher earner(s) in a group subsidize part of the trip like lodging and food, leaving everyone else only needing to cover transportation and personal items. Any combination of this can work, as long as it works for the group.

If you have a group that wants pretty different experiences, you can always split up into groups. One group does a budget-option hotel/hostel, while another does a more upscale location. You meet up for activities and meals, enjoying the benefit of each other’s time without breaking everyone’s bank to do it.

Creative Solutions for Inclusive Planning

There’s also a variety of ways to cover the upfront costs of trip planning. You can of course have your main planner pay for everything and let folks know what everyone owes at the end. This works well if you have one person booking everything and they also have enough on hand to front the costs. This isn’t always the case, though.

In situations where someone may not have enough to temporarily cover the expenses for the group, you can ask folks to chip in an upfront amount – could be $200, $500, really depends on the expense of the trip. You can also have different folks book different items, dividing the upfront costs up a bit. One person books the hotel, another books the activities, etc. As with much of this, there’s different styles that work for different groups, so chat through it together and see what works best for you.

Step 3: Destination Selection 

Sometimes picking the destination is easy – the trip idea may have come about because of a specific interest or desire to see a place, then inviting others to join. I keep trying to get a trip together to go swim with whale sharks in Baja, and humpback whales in Moorea. They haven’t happened yet, but I’m keeping the dream alive!

In other cases, the group wants to get together but needs to decide where. First is aligning on time of year, length of time and budget, which you did up front. All of these impact where you can go. If you only have a 2-day weekend, you may not want to fly all the way to Japan (though if you do, more power to you!).

I’d start with scope – are folks up for international destinations, or do they want to stay domestic? Then tie in the type of trip they’re looking for. Is it a casual beach vacation, an adventure vacation, a little of both? That can help you hone into a short list. People may have places they’ve wanted to go and it’s great to throw those out. You just need to compare those against the needs and interests of the group.

Also be cautious of dismissing anyone’s concerns too quickly. Trip planning should get people excited about the trip, and if someone doesn’t feel heard, they can feel alienated and actually lose interest in even going. Not the outcome you want.

Step 4: Logistics Without the Drama 

I’ve found the best way to minimize drama is minimizing control over the itinerary or the group – to an extent. Ever heard of Mel Robbins’ “Let Them” theory? If people want to drive separately or fly in on their own and meet you at the accommodation, let them. If someone wants to skip an activity or a dinner, let them. Forcing them to adhere may meet your idea of an ultimate trip, but not theirs.

Of course, if you must be somewhere that has a hard time requirement – catch a flight, make a dinner reservation, join an activity – it’s ok to expect promptness. If people can’t make it within the time needed, make it clear you’ll have to go without them. Ruining a day or a trip for everyone isn’t worth it – and will likely make the late person feel even worse.

Picking rooms can be another area of tension. To avoid this, be clear on how many rooms there are, how similar or different they are, and whether people will need to share. If there’s a big difference in rooms, you can draw names to see who gets which ones; have some pay extra for a space (if it’s significantly better), or use the better accommodations to treat someone on the trip – eg, the birthday girl, the recent divorcee, the mom who hasn’t had a minute alone for the last 4 years, etc. With many groups I find people are flexible on rooms and don’t mind so much, but I have heard of trips where this causes a lot of consternation, so having a plan will help you in a pinch! Whichever way you go, communicating and keeping the group up to speed is key.

Timeline & Organization 

A planning timeline can vary greatly. Some trips have come together a month before, while others we talk about a year ahead of time. Typically, you’ll want to have the initial conversations, pick your destination and do your big bookings like flight and accommodations 6 months ahead of time. 3 months ahead is a good benchmark for activity research, planning out the daily itinerary, and getting final count of who’s coming. One month out, your fun countdown can begin! What to pack, confirming transportation and bookings, etc gets you ready for a great vacay!

During the Trip: Maintaining Harmony 

You made it! By this point, you’re relaxing on the beach with a margarita in hand. Everyone is getting along swimmingly, and due to your fantastic planning, nothing has gone astray! So how do we keep it that way?

Daily Decision Making 

With all the planning in the world, there will still be decisions to make each day. Check is as you go and see how people feel. With an open, casual vibe, people should feel comfortable saying what they’ll join or opt out of. As you plan, also make sure free time or down time is baked in. I’ve made the mistake of making itineraries so packed, people need a vacation from the vacation. Leaving some breathing room creates good balance. It may also make people more likely to join the group activities since they’ve had some solo time baked in. The key is not to take your itinerary so seriously, or to get offended if people don’t want to join something. More than likely, it’s not about you. And if it is, maybe some time apart is a good thing! 😉

Money Matters on the Road 

You’ve covered the big expenses, but how do we decide what to go in on as a shared expense, and what to keep separate, while we’re on the trip? A good rule of thumb is to share expenses on the things that everyone will partake in. Think shared accommodations, group transportation, common groceries, etc. Pay individually for expenses that are only for a single person, such as flights, personal shopping, etc. Gray areas can be meals, room charges, spa treatments, and the like. For these, I’d recommend splitting evenly if there’s equitable expenses across the group. If the costs are only for a few people, I’d recommend splitting it based on usage.

Now, you may have a friend who wants to treat you all to a dinner, or you may be a group that doesn’t worry as much about who spent what – the convenience of an even split is worth it to you. That’s great! Either way, you need to feel out your group and know what’s going to work best for them.

Expense-Tracking Assistance

If you end up splitting costs somehow, I highly recommend an app like Splitwise to track expenses. It allows you to create a Group, and everyone can enter the expenses they incurred. The app will automatically divide it amongst the group, taking your math skills out of the equation. Even better, it minimizes the payments you need to make by netting out everyone’s total. So, rather than paying $100 to Judy, $500 to Sally, and receiving $300 from each of them, it will show you as settled up, and the amount Judy can pay Sally ($200). As the trip goes on you can add meals, groceries, etc and settle up at the end. I’ve used this on nearly all my recent girls trips, and it makes tracking and settling up such a breeze!

After the Trip

The Settlement Process 

If you’ve used the Splitwise app, settling up is simple! Ask everyone to have all their expenses entered by a certain day – let’s say a week after you get home. Once that’s done, people can go in and settle up with those they need to. For any forgetful folks, you can send them a request in the app or shoot them a friendly text. Usually, people just get bogged down in the return home and aren’t trying to dodge you! I’d recommend having everything wrapped up within 2 weeks after the trip, a month at the latest. No matter how busy you are, being respectful of other peoples’ finances goes a long way.

Preserving the Memories (and Friendships)  

Another thing you can start on the trip is a shared iPhoto album. It doesn’t work as well for non-iPhone users, but it’s a great way to share photos and memories during and after the trip. Tag each other in social media posts (if you’re the social media kind) and keep the good vibes going even after you get home.

This can also be a great time to start talking about the next trip. Everyone is still riding the high from this one, longing to be back on that beach, so why not tap into that and chat about what a next vacay could look like, and when it could be.

Whether or not you decide to take another trip, you’ll have strengthened your bonds together and will likely have inside jokes and memories to build on now that you’re back at home.

Conclusion

You survived! You planned an amazing trip, communicated clearly with the group, and had an amazing time. While putting this much thought into planning may seem excessive, the investment you make really pays off in not only a seamless trip, but in preserving your friendships. I’ve seen bonds go sideways because of trip mishaps and miscommunications, and I don’t want to see that happen to you!

Hopefully this gives you a good approach to follow when you tee up your next girls trip. Already have a trip plan in motion? Start putting some of these to use and see what works for your group.

If you’ve already used these tips on prior girls trips, I’d love to hear your stories and take-aways. What would you do again, what would you change? Similarly, if you haven’t taken a girls trip but are still overwhelmed by the planning of it all, contact me for custom trip planning guidance!

Wherever you go and however you get there, I want you to have a trip to remember.

Happy travels, kindreds!

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