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Travel Tips

How to Plan the Perfect Stress-Free Trip with Friends

Candice Walsh
By 
Candice Walsh
Freelancer
5 min read
Last updated 
June 29, 2020

Picture this: you and your friends have just arrived in Argentina. You’re ready for an amazing two-week trip, but before you’ve even had your first empanada, there’s tension as you start disagreeing about how to split funds and how to do everything you want when the group has wildly different interests and budgets.  

Trip planning can be a lot of work even if you’re traveling solo, but when you add a handful of other people to the mix, things can get even more tangled. The good news: a little work and some honest conversations before you depart—and even before you book your trip—can reduce the stress and help ensure everyone gets the trip they want. 

Here are twelve tips for planning an epic trip with friends. 

1. Choose the right friends, and set expectations from the start.

Let’s get the most obvious point out of the way first: You can be friends with lots of different people, but it doesn’t mean you’ll make good travel partners. Choosing your travel buddies wisely and being up-front on your expectations can mean the difference between a group trip you’ll always remember and one you can’t wait to forget. So how do you know you’ll be a match if you’ve never traveled together? 

Consider things like interests, budget, and personality. That doesn’t mean you need to be perfectly aligned on each of those things, but think about where you can appreciate the differences, and where they could cause friction. 

For example, if your art-loving friends expect you’ll do every activity as a group, but you’re just not into museums, you may get annoyed by the time they’re on their third hour at the Louvre. But on the other hand, if you’ve got independent friends who are cool with separating for an afternoon, you can do what makes you happy while they spend another 90 minutes admiring Etruscan antiquities. 

Have a frank discussion with your friends—and yourself—around the following: 

  • Will they want to map out each hour, or are they open to spontaneity? 
  • Do they want to go, go, go, and see it all, or do they prefer to take things slower? 
  • Are they night owls who want to party until dawn or early-birds who want to rise with the sun? 
  • Is their budget more street food and hostels or Michel-starred dinners and luxury hotels? 
  • Do they want to spend all their time as a group, or occasionally separate and do their own thing? 

2. Be upfront about your finances.

Money can cause a lot of resentment among friends, especially if you have different financial expectations for the trip. If you can only afford a hostel dorm but your friends want to stay in a resort, tell them. There’s no point in putting yourself in debt to please someone else.

From the start, be upfront about how much you can afford to spend—and how you would prefer to spend your money. While your friend may have the same budget as you, you might find out that while you prefer to splurge on a nice meal, they put their extra funds into shopping. 

Be clear not only on how much you can afford for the total trip, but also on how much you’re willing to spend per night for accommodations, what you’re comfortable spending on meals and activities, and how you prioritize your spending. Again, you don’t have to agree, but you should set expectations for what happens when you have different budgets and priorities. 

3. Consider how you’ll pick your destination. 

Deciding on a destination might actually be the toughest part of this whole trip planning process. How do you choose a place that everyone is happy with and can get to relatively cheaply?

One option: have each of your friends write out their top three to five preferred destinations, bearing in mind the length of time you have to travel and the budgets of everyone involved. 

You can easily do this over email or on paper. For a more tech-savvy way to do it, check out Kayak’s new Trip Huddle tool. First, you sign up and pick your destinations and preferred dates.

Kayak trip huddle tool.

Once everyone has added their input and voted, Kayak will recommend some hotels and vacation rentals for your group. It’s useful if you have a large group and would prefer not to scroll through hundreds of messages to keep up with the conversation. 

However you vote, compare everyone’s answers, and see if there are any common destinations. If there are none, think about the common factors. Did you all choose a beachy destination or a European city? This can help narrow down your choices.

Another option: decide based on airfare and go wherever you find the best deal. The group might have been thinking London, but if nonstop flights to Paris pop up for $250, they might say “oui” to a different idea. 

If you’re coming from different destinations, make sure you choose a place that’s realistic for everyone, especially given the number of days you plan to travel. For example, you might be up for a 3-day weekend in Hawaii if you’re based in Los Angeles, but for your friend in NYC, that may be too far to go for a shorter trip. 

When you join Scott’s Cheap Flights, you can select multiple airports to follow, so if you’re got friends spread across the US, you can see which deals apply from the most departure cities. 

>>Read our guide to the world's cheapest destinations.

4. Use the right tools to find airfare deals. 

Aside from joining Scott’s Cheap Flights, there are a few tools you can use to make it easier to find the best deals, especially if you are flexible on travel dates and destinations. 

Skyscanner has a handy “Search Everywhere” option that shows you the cheapest flights from your airport during your selected date range. 

Skyscanner search everywhere

The Google Flights Explore map is similar. Input your departure airport(s) and it will show you the cheapest places on the map you can fly to either during specific dates, or during a date range like a weekend, one-week, or two-week trip during a specific month. You can type in a specific region or move the map to narrow down your options. 

Google Flights Explore map

>> Read our complete guide to finding cheap flights. 

5. Start planning far in advance.

The more people involved, the slower the planning process can be—and speed is your friend when it comes to snagging cheap flights. Two to eight months in advance is the sweet spot for the best airfare prices, you’ll want to start looking for flights as early as you can, especially if your dates and destination are fixed or you’re traveling over peak season like the summer or holidays. Start tracking prices by setting up flight alerts so you’ll get notified when the price dips. 

If your dates and destination aren’t fixed and you’re open to wherever there’s a good deal, chat with your friends in advance about what dates you’re all free so that you can cut down on the back-and-forth and quickly jump in a great deal when you see one. And remember, the 24-hour rule means that in most cases you can cancel a flight within 24 hours of purchase so you don’t miss a deal while waiting for your friends to confirm the dates. 

6. Use apps to keep your finances sorted.

It’s important to keep track of everything you’re splitting as a group, whether it’s the flights, hotel rooms, activities, or meals. You can create a simple spreadsheet to do this, or use an app like Tricount or Splitwise.

Tricount was developed for roommates to keep track of split expenses, but it’s completely customizable so you can use it for your travels instead. Splitwise works the exact same way. If you want to keep it simple, Venmo is also a great option for sending money quickly to your friends (but it’s not available everywhere just yet). 

>> Check out our list of the best travel apps.

7. Check refund policies carefully and don’t get stuck with the bill. 

It’s a cautionary tale often repeated: a group of friends plan an epic trip, with one friend making the reservations on her credit card. One by one the other friends cancel, until the friend who booked it all is left sleeping solo in a nonrefundable room for six. 

Book refundable hotels and tours as much as possible, and for anything nonrefundable, have each person book individually when you can. When you can’t, such as sharing the cost of a room, get payment upfront and be clear than any nonrefundable payments are just that: nonrefundable. Anyone who cancels at the last minute, will be out their share of the nonrefundable costs. 

If you’re booking Airbnb accommodations, you can use Airbnb’s “Pay Less Up Front” option to make a partial payment, giving you time to collect everyone’s share before the rest of the payment is due. 

If you’re traveling with a very large group and need several hotel rooms (usually at least 10) you can call the hotel and reserve a “room block.” This holds a certain number of rooms up until a specific date, but doesn’t require you to cover all the costs. When your friends book a room as part of the block, they pay individually. Any rooms not booked by the cutoff date are released, so you’re not personally on the hook if you end up needing fewer rooms than you thought. 

10. If you want to book your seats together, it may cost you.

If members of your group are each booking their own airfare, you’ll have to take a few steps to make sure you’re all sitting together. 

  • Book early. Waiting until the last minute to book not only increases prices, but it increases the chance you’ll be left with only middle seats to choose from. 
  • Don’t do basic economy. The cheapest rates come with fewer perks, like not being able to select your seat until check-in. While there’s a chance you could still get seats together at that point, if you want to guarantee it, upgrade to main economy, or pay extra to choose your seats in advance, if allowed with your fare. 
  • Show up at the airport early. If none of the options above work for you, arrive early at the airport. You can speak with the attendant at check-in to see what seats are available, and if there are several seats altogether, he or she will likely be happy to accommodate you. 

11. Take some time for yourself. 

As mentioned above, it’s unrealistic to think everyone wants to do the same activities all the time, and taking some time apart from your group can help keep everyone stress-free. 

If there’s something you want to do and your friends don’t, there’s no harm in stepping out on your own—so long as that expectation was set at the beginning. A little bit of space ensures you get to do everything you want, and it can help you appreciate your time together even more. 

>> Read our tips for solo travel.

12. But don’t be afraid to let your friends push you out of your comfort zone. 

Maybe you’re not normally into the idea of cliff jumping in Hawaii, or tackling a via ferrata in Switzerland, but there’s a big difference between not wanting to do something, and wanting to do it but feeling apprehensive. 

In the latter case, a little encouragement from braver friends may be all you need—and if you decide it’s not, you can always hang out nearby or snap photos of their adventure.  

That’s the joy of traveling with friends. When it’s bad, it’s stressful and tense, but when all goes well, not only will you have an amazing adventure, you may wind up growing in unexpected ways. 

Last Updated 
January 7, 2020
How to Plan the Perfect Stress-Free Trip with Friends
Candice Walsh
Freelancer

Candice Walsh is a destination marketer and freelance travel writer and blogger living in Canada. Her work has been featured in Canadian Traveller, BBC Travel, Westjet Magazine, The Independent UK, and more.

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