How To Make Traveling With Friends Easier

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There’s something about this time of year that has me itching to travel. Whether it’s the inspiration for planning my annual birthday trip (soon to make a comeback) or a desire to play tourist in someone else’s town, my need to escape is strong. But as I’ve learned with years of group travel, there’s an art to making traveling with friends easier. So today I’m giving you my top tips as well as recommendations for my favorites apps to make things as smooth as possible.

How To Make Traveling With Friends Easier

SET GROUP EXPECTATIONS

Before any planning can take place, you need to know what kind of trip you’re wanting as a group. If you’ve got a group of two girls who want to do all the hiking things and 3 girls who want to see museums, drink lattes, and shop – you might need to do some extra research or plan more than one trip.

Knowing up front that hotels and traveling to your location are often the largest shared expense, be honest upfront about what kind of accommodations you’re wanting and how much you’re willing to cover to make that happen.

It’s also the time to really narrow down the when/how long you’ll travel for. Learning upfront that only two people of 5 will be free for an entire trip with everyone else floating in and out means you can be the most respectful of everyone’s time and budget.

Have A Key Planner

I feel like most friend groups end up with this person naturally – the one who corrals the group. It’s also easy to put the pressure on one person to make it all happen unnecessarily. If you have someone in your group who loves to plan, make sure they are okay with taking charge and check in with how they can be supported. The other part of having a key planner means less assuming someone is taking care of a part of the trip and more accountability as well as backup making sure all the things you want to do are getting booked.

SET DEADLINES

There’s a few deadlines I like to set when I’m in charge of planning a trip:

The Must Know If You’re Going Deadline – This saves you time when looking at accommodations as well as making sure you’re not wasting time researching for extra people (i.e. tickets for small groups are often easier to find vs trying to find availability for 6)

Rough Trip Plan Deadline – Everyone approaches traveling differently. For example, I have friends who LOVE an intense itinerary. They are amazing resources when I go somewhere new. However, I’m very much a person who likes to have the freedom to find what I didn’t know existed.

A rough plan deadline gives everyone the ability to plan/pack/shop accordingly so that you aren’t totally winging it. But it also prevents fewer people from dropping at the last minute due to budget constraints. Additionally, it will empower you to book the things you MUST reserve ahead of time.

Must Book X By Deadline – It’s helpful to know upfront if what you’re booking will require payment or a deposit upfront or if you can reserve and pay later. I like to map this out for everyone so they can adjust their budgets accordingly. I’m also not a big fan of putting the financial burden on one person.

Give Everyone Time To Do Their Own Research

Once you’ve picked a location, I like to ask everyone for the 1 thing that is a must-do on their list. With a smaller group, this is a quick conversation. With a larger group, it’s going to take a minute. For example, planning a trip to Paris. There are SO many ways to see the Eiffel tower. And presumably, it’s on everyone’s list to do. Giving everyone the chance to bring something to the table will mean that it’s a trip you’ll all enjoy. Plus, you never know what new experiences you’ll have because of it.

How To Do 30A On A Budget, tips featured by top US travel blogger, What Savvy Said

SET A BUDGET

So I like to do this in detail with a two-part process before we start booking things to give everyone realistic expectations for the cost of the trip. The first part is asking everyone what their overall budget is for the trip with the specifications of covering the cost of hotel, travel, food, and activities. If one person is planning to spend 60% of their budget on shopping while there and another person 10%, it’s going to change how things go. Clarifying this up front saves headaches.

Part 2, I like to make a detailed daily budget. I’ve found it’s a great way to make sure everyone is aware of unknown costs. It can also help everyone save and plan accordingly. To do this, I make a rough plan of each day noting the cost per activity as well as where we expect to eat with an estimated total for how much is expected to be spent per day on essentials. 

I also like to note what is booked ahead of time vs what will actually need to be paid for on the day. You can take it a step further and do a monthly cost sheet with deadline booking dates beforehand. Essentially, this helps avoid the procrastination effect and keeps everyone aware of the cost as well as allows people to speak up if there needs to be a change. Plus, it helps make sure everyone enjoys the trip because no one has a reason to complain about the money.

COMMUNICATE COMMUNICATE COMMUNICATE

Let’s be real, life happens. Between Covid and big life changes, there’s been more than one trip canceled or rearranged in the last few years amongst my friends. If you can’t make it or something needs to change, tell someone sooner vs later. It’s no fun for the group if they are stuck with a large bill or unable to book things because they are waiting on one person. Be honest and respectful. Just communicate.

USE A PLANNING APP

When I started doing the planning for a potential Paris trip this year, I stumbled onto the Wanderlog app. It’s quickly become one of my favorites. I love it for several reasons: everyone has access to it. This is a great way to share travel plans with friends and family who want to make sure you’re safe.

It also lets you map the travel time between locations as well as see a map of everything you’re wanting to do ahead of time. For example, there are quite a few places we are wanting to visit during our next jaunt to France. In order for us to get a better idea of how many stops would work for this trip vs our next time abroad, we plugged everything in to get a better idea of how many excursions were close together so we could make the most of our time.

Wanderlog is great for getting recommendations and just being an amazing travel planning partner. Hands down one of my top tips for making traveling with friends easier.

How To Make Traveling With Friends Easier

CREATE AN OUTFIT GUIDE

I will be the first to admit I’m notorious for traveling to colder climates and not having all the right pieces. But it got me a gorgeous fur coat in Paris so I won’t complain. Along with my daily budget breakdown, I like to do an outfit packing breakdown. As the resident fashion friend of the group, it helps everyone to feel their best as well as make sure they know what to bring.

So for each day and location, I’ll note the outfit/vibe. Most of my friends aren’t heels gals but no one wants to only pack t-shirts and leggings when you’ve got a nice dinner planned. If there’s a plan to add in workouts or maybe an extra outfit swap, I try to put that in as well. The idea is that everyone feels their most comfortable and beautiful because they know what to expect. Plus, who doesn’t love a packing guide?

OPT FOR HOTEL OVER HOUSE

I’ve been a boutique hotel girl for years and thankfully hotels.com has helped me find some of my favorites. But truthfully, I’ve landed on a hotel over house standard after a few trip mishaps over the years. Ones where we didn’t know if everyone would show so we opted for a place that sleeps 6 but wouldn’t be too costly if only two came. And everyone showed up. It was a tight fit.

Or the trip where it started as 6 with two hotel rooms and ended up as 3 in one room two weeks before. It happens.

I love that with hotels there’s less of a financial burden if people need to cancel last minute as you can secure a lot of them without needing to pay upfront. It’s also a bit more flexible if you need to add someone last minute or have someone bail. Plus, I’m a sucker for having points and a gym.

SOMETIMES LESS IS MORE

As much as I love traveling and meeting up with my friends, I also know that sometimes the easiest trip is 3 or fewer friends. And if there’s a large group, there’s always the option to do smaller group activities so everyone can enjoy the trip they are on. Don’t fret if the big group thing isn’t happening or it’s too much. At the end of the day, those you are getting close time with are the people you’re meant to be within that moment and that’s perfectly okay. Enjoy the moment as it’s being presented! You’ll be much happier in the long run.

Wherever your travels take you, I hope that you have the most wonderful time! And if you have any tips for how to make traveling with friends easier, let us know in the comments below. Ps. If you’re looking for a packing guide, be sure to check out mine here. And if you want to stay up to date on all the latest adventures, be sure to sign up for the weekly newsletter! Until next time. Xoxo, Savvy

PPS. As an added bonus, I’ve included a list of questions below to ask up front to make planning your trip even easier. Happy planning friends!

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Questions To Ask To Make Traveling With Friends Easier

Where Do We Want To Go?

How Do We Want To Get There?

How Much Are We Willing To Spend?

How Will We Get Around?

What Is Your Ideal Place To Stay?

What Do We Want To Do On This Vacation?

What Is Our Goal? (See lots of things, go to the spa, relax, eat?)

How Long Do We Want To Go For?

What Do We Need To Pack?

How Far In Advance Do We Need To Book & Budget Things?

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