How to Plan a Stress-Free Group Trip

Exploring exotic cities, shopping at vintage stores, and skiing in Jackson Hole all seem so much more exciting with a large group of friends.  At times this can hold true, but it can also lead to disaster.  Based on experience, planning a successful group trip requires a little more thought than just inviting ten of your closest friends.  Picking the right group is tricky, but it can mean the difference between a tension-filled and a relaxed.  I’ve found that for group trips, a little extra thought can go a long way.

Determine Who to Invite

When group trips, I like to consider is what it’s like to shop with the people I’m considering inviting.  Yes…shopping.  Everyone has their own style of shopping that can be influenced by budget, taste, personality, and patience.  After all, if you are someone that loves to shop for vintage gems & wear no name brands you will likely not enjoy shopping with a label-obsessed friend.   

Like shopping, people also vary in their preferences of bars.  Some people love to club, others prefer a relaxed atmosphere.  I would not invite my friend that dislikes Dubstep and large crowds to a night out at Output in Williamsburg.  So why would I think it was a good idea to invite that same friend to a vacation in Berlin with a group of club-obsessed friends?

In addition to these first two considerations I also think about how the friends I want to invite get along & what it has been like to travel with them in the past.

Selfies with a fantastic group of friends, þingvellir National Park, Iceland   Photo Credit: Debbie Bang

Selfies with a fantastic group of friends, þingvellir National Park, Iceland   Photo Credit: Debbie Bang

Be Clear on Budget

Communicate budget early and be clear about anticipated costs. This may seem obvious, but when inviting friends it helps to give a rough cost estimate of lodging, flights, transportation, and incidentals.  If you think your group should go out for a nice dinner or two, include this also. Being clear on budget will not only help your friends decide if the trip works for them but also prevents awkwardness later on.

I learned this the hard way during a group trip to Paris, where our group of five couldn't agree on where to eat and how much to spend on meals.  Ever since, I’ve made a point to align cost expectations in advance in order to avoid conflict later on.

Set Deadlines

One of the most stressful parts of planning a group trip is getting everyone on board.   It’s very hard to pick a place to stay, book flights, and make reservations when you don’t know how many people are going, so setting firm deadlines can go a long way.

For trips that require air travel, I find that setting deadlines can help with indecisiveness.  I like to send out the flight I’m booking along with a deadline for booking it, leaving me with a firm count for an Airbnb or hotel. Basically, anyone that does not book their flight will not be guaranteed a room.

Although I may sound harsh, drawing a line in the sand can reduce a lot of stress on the planner and save everyone money.  Flights and lodging often get more expensive and more scarce as the trip date approaches, so deadlines can make things easier and cheaper for everyone.  Reservations for large groups at popular restaurants also get harder to book, so it’s important to act fast.

Portugal Airbnb, Porto, Portugal

Portugal Airbnb, Porto, Portugal

Use Your Group Size to Negotiate

When traveling with a group, I always take the time to negotiate rates.  Airbnbs, tours & entry to major sites can usually be negotiated.  I like to start by explaining my group size and situation (i.e. recent university graduates) and then ask if there’s any way to accommodate us.  I’ve found that most places are flexible and can offer a discount. This is especially true for Airbnb. When I was studying abroad, I explained we were college kids on a budget and X was the maximum amount we could spend. Sometimes hosts would not accept our offer, but more often than not they were willing to give us the place for the price we were able to pay just to make sure they booked fully.


In the end, it’s important to remember that whether you are the planner or a group member, this is everyone’s vacation.  While some group members may want to try different things and it’s impossible to accommodate every request, Google Docs can be a great way of planning and keep everyone on the same page.  I like to start a doc where everyone can share links and trip ideas for things that they want to do, and then gradually turn that into a rough itinerary that the group can talk about and change together.  Once the activities are compiled have everyone write their name next to activities they are most interested in.  Some activities will always get weeded out, but this method is the best way I’ve found of keeping everybody happy.  

It’s also important to realize that part of the group may want to do something different and that this is okay.  It’s easy to get fixated on getting everyone on the same page, but that can’t always happen.  Instead, allowing the flexibility for people to do their own thing is critical for a conflict-free trip.

The great and not-so-good group trips I’ve been on have shown me that well in advance of the trip is the perfect time to plan and pick the right group of people.  If you plan in advance, having a fun group around you that gets along can make your adventure a lot more fun.

x Smack 

þingvellir National Park, Iceland   

þingvellir National Park, Iceland