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5 Ways to Stay Sane When Planning a Trip with Friends

You haven’t eaten because your friend didn’t wake up in time for breakfast. Now your train is delayed and you missed out on the one tourist destination you really wanted to see. This is not the vacation you wanted when you imagined planning a trip with friends.

For friends to stay friends before, during, and after a trip, it’s vital to have both complementary travel styles and clearly defined expectations. This checklist for planning a trip with friends will minimize headaches and maximize quality time.

Questions to Ask Before Planning a Trip with Friends

Ask yourself these questions before committing to a trip with friends: 

  • Do your travel styles align? Figure out if you’ll be happy doing the same activities, staying in the same type of accommodations, and generally moving at the same speed. Comparing travel styles also means considering transportation preferences; for instance, are you OK with taking a connecting flight to save some money, or do you only travel nonstop?
  • What is the most important thing you want to get out of the trip? When planning a trip with friends, think about what you most want to get out of the trip. Are you longing for plenty of low-key beach time, or do you want to see every museum on your route? Figure out what your goals are before you agree to a trip with another person or group.
  • Do you have the same budget? Money is a big deal when it comes to travel. Don’t book a trip with someone if you know they’ll want to spend significantly more (or less) than you overall.
  • Do you have the same budget for different things? Your budget also encompasses what you’re willing to spend money on, like splurging on a hotel room vs. staying in a hostel, or going out to a nice restaurant vs. saving money on food by cooking in your vacation rental.
  • Who will take charge of booking and reservations? There’s a lot of leg work that goes into planning a trip with friends. If you don’t have the time, patience, or organization to take charge of these details, don’t volunteer to plan the whole trip.
  • How many vacation days are you willing to use? Before you book a trip, make sure you know how many days people are willing to take off from work so you know how flexible you can be with dates.
  • Do you want to book everything in advance? Some people like to travel with flexibility, while others prefer to have a set plan, so discuss this beforehand.
  • Do you have the same level of physical fitness? Many trips include long days on your feet or some sort of physical activity. If your friend is notorious for lagging behind, you might not want to go on a walking tour or volcano hike with them. Make sure you’re on the same page about just how much activity you want to do on your trip.

Things to Consider When Planning a Trip with Friends

Here’s what to discuss when you’re planning a trip with friends:

  • Type of accommodations. Don’t book a five-star hotel if you’re trying to save on accommodations. But also keep in mind that hostels and budget hotels aren’t everyone’s cup of tea. Make sure you agree on what type of place you’ll stay at and a rough budget.
  • Type of transportation. Decide if you’ll fly, drive, or take a train ahead of time. It’s important to weigh the cost benefits of each option, i.e. saving money by taking a long train ride or spending more to get to a destination quicker.
  • What you can’t miss at the destination. Make a list of what you each want to do at the destination and allow time for everyone’s top activities.
  • On a road trip, who will be driving? Driving for hours on end is tiring. If you’re taking a road trip with a group, plan on switching off and taking breaks. If you’re renting a car, make sure everyone who is driving will be on the contract.
  • Eating schedules. Some people need to eat first thing in the morning while others can go hours before needing a meal. Discuss this ahead of time to avoid any hunger-induced arguments.
  • Sleep schedules. Jet lag and fatigue will vary by person. Make sure you don’t plan a bunch of activities right when you land if people want to rest or nap during the first few days of your trip.
  • How you’ll split up costs. Decide ahead of time what you’ll split expenses for, including meals, accommodations, and transportation.
  • What you’ll pay for individually. Decide ahead of time what you’ll pay for individually, such as flights, tickets, alcoholic drinks, Wi-Fi, travel insurance, etc.
  • Tipping habits. Read this handy tipping guide together before you travel so you’re on the same page about tipping expectations in your destination.

Tips for Splitting Expenses

Splitting expenses is one of the biggest problems you’ll encounter when planning a trip with friends. Use these tips to help alleviate money tension:

  • Book on Airbnb. You can now split the booking costs on Airbnb. This is a great way to split expenses on accommodations without anyone fronting the whole reservation.
  • Use rideshares. One of the reasons people love Uber and Lyft is because of the built-in split cost feature. No more keeping track of who paid for which cab.
  • There’s an app for that. There are countless expense apps out there, but tricount is a great tool when planning a trip with friends.
  • Jar fund. Another alternative to tracking expenses is to create a “jar fund.” All members of the group contribute a set amount of money that goes onto a credit gift card. You can then use the card for meals, drinks, and other agreed-upon expenses.
  • Book accommodations or trips where you can pay in installments. This way if one person has to front the costs for accommodations, you can either divide the payment with installments or book with no deposit down so the other members of the group can pay the person back ahead of time.
  • Take out cash. It can get annoying if one person is always borrowing cash for tips or not exchanging enough money, so visit the bank before your trip.

Important Tips for Traveling with Friends

Following these tips can help keep everyone on the same page and prevent offense:

  • Know what annoys them, and tell them what annoys you. When I travel with friends, I let them know that I always need to have something small to eat in the morning before we go out and do anything. The sooner they know that something will bother you, the better.
  • Raise issues before anything builds up. You’re more likely to reach a breaking point or get angry if you let little annoyances build up.
  • Be flexible and have patience. This helps you realistically manage expectations. Group trips are all about give and take. And hopefully if you go out of your way to go to a restaurant someone really wants to go to, then you’ll get your moment, too.
  • Don’t say “we’ll figure it out later” when paying. Keep track of expenses when they occur by using an expense app.
  • Pack well. Make sure you both pack things like chargers, adapters, proper footwear, and outerwear. It can get annoying when your friend asks to borrow your phone charger for the 10th time when you’re also trying to use it.
  • Have your alone time. Take some time every day to separate yourself from the group if you need to. It can be as simple as walking to a coffee shop or going to a museum by yourself.
  • Take turns. It can be exhausting if you’re always the one in charge of navigating or choosing a restaurant. Switch off being the group leader.
  • Limit phone time. Take time to be with your friends rather than on your phone. This also goes for taking photos: While it’s great to have your friends as photographers, it’s annoying to take 40 photos at every single monument.

Trip Planning Help for Traveling with Friends 

If planning a trip with friends is too overwhelming for your group, look to these alternatives.

  • Go on a cruise. Cruising is a great way to travel with friends. There’s no planning involved once you’re on the trip, and everything is priced per person. Plus, you’ll have plenty of time to do your own thing.
  • Go on an organized tour. If you don’t want to do a cruise but want something preplanned, look at a guided tour. Intrepid Travel and G Adventures have great options for younger people, as do Contiki, STA Travel, and EF Ultimate Break.
  • Look into all-inclusives. If you want some flexibility with your trip, book an all-inclusive resort so your drinks, meals, and some activities are included in the up-front price.
  • Use a travel agent. This isn’t the cheapest option, but a travel agent will be able to plan and book a great itinerary for your group travel while keeping in mind everyone’s budget and must-do activities.

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