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   

What To Do When Everything On Your Trip Goes Wrong

Let’s be real -- no vacation is even close to as perfect as it seems on Instagram. More often than not something goes wrong - among other things, planes get delayed, it rains the entire time, and you don't actually get the Louvre all to yourself.  I've had more than my fair share of vacation mishaps, which most recently included arriving at my airbnb only to find that there was no running water.  

Although these situations are far from ideal, a few simply tips can turn them from trip-ruiners to simple speed bumps on an otherwise delightful vacation.  First, stay calm - stressing out just ruins the trip for everyone, and there’s usually a simple solution for most travel nuisances.  Second and most importantly, be sure to have a contingency plan before you travel, and use it to adjust your plans as needed.  And worst case, remember that no trip will go exactly as planned and sometimes that’s just part of the fun!


In my experience, there are two main ways to plan for and adjust to weather that just won’t cooperate.

The first is to incorporate some flexibility into your travel plans.  Do you have a drive you absolutely must do?  Be sure to that you can make a last-minute switch with another day’s activities if need be.   

The second is to set realistic expectations.  Though that $300 flight to Iceland in November may be tempting, keep in mind that there is a reason for the cheap flights and diminishing crowds - less daylight and colder, rapidly changing weather.  Although shoulder or low seasons can still be a great time to travel, it’s important to be okay with the fact that outdoor excursions may be cancelled due to poor conditions.  For this reason, consider trips to cities that can be enjoyed despite wind, rain, or snow - such as Paris, Venice, or Budapest.  If you’re lucky, you may even have the top attractions all to yourself!

Grey Days in Reykjavik 

Grey Days in Reykjavik 

Accommodation Mishaps

I’ve endured a lot with hotels and Airbnbs: broken heaters, no running water, and to top it off an exploded air freshener.  Nothing is worse than arriving to a hotel in winter in Canada to find your room smells like an Axe bomb went off and the hotels solution -- open all the windows. Great idea in December.  

These kind of things happen and as funny as it is to look back on them now not having an inhabitable place to stay is extremely stressful.  If you find yourself in a accommodation disaster, stay calm and reach out to your host or hotel manager.  Take pictures, write notes, and document all of the issues are running into. If the issue is still not resolved then escalate to whoever you booked the accommodations through, such as Airbnb or Expedia.  Their customer service is great & in my experience they’re very accommodating to resolve issues.

In a case when you're tight on time and the issue is not easy to resolve book another place.  I was recently traveling to Sydney & arrived at my Airbnb to discover that there was no running water. None of the bathrooms or sinks a work, and to top it all off we were dealing with an unresponsive host and it was late on a Friday night.  Instead of stressing out, we started a case with Airbnb.  After realizing quickly that this was not going to be resolved fast because the host was not responding, we booked an alternative accommodation on Hotel Tonight.  Airbnb refunded us the cost of our apartment and covered the difference in price for our hotel.

Hotel Tonight - Radisson Blu Sydney

Hotel Tonight - Radisson Blu Sydney

Flight Delays

Flight delays are the worst! Airports are chaotic to begin with so hours spent smelling Panda Express, hearing couples argue, and babies cry is a nightmare.  For short trips try to fly direct.  This prevents the risk of missing a connecting flight.  Traveling international?  Make sure you understand how long it will take you to get through the airport and make sure you leave a little extra time just in case.  Try to have layovers in airports that offer multiple flights to your end destination.

If your  flight is delayed talk to your airline’s customer service and be nice! These people deal with angry customers all day and a little kindness can go a long way.  I had an experience where my flight was delayed in Chicago due to snow.  The United Airlines rep was working with was able to reserve a seat for me on a later flight in case I missed my connecting flight.  

If you have a tight connection try to book an aisle seat and let the flight attendants know.  Usually they will be more than accommodating to help you get off the plane first so you don’t miss your connection.

If you do have a flight canceled or majorly delayed make sure you read your airlines policy.  Many airlines will give vouchers for flights, food, and even put you up in a hotel.

Connections in O'Hare

Connections in O'Hare


Getting sick is bad enough.  Missing a trip because of it is the worst. Despite the best thought-out plans, an unexpected illness can put a damper on any trip.  

To reduce the potential illness pack any medications you may need.  I’m allergic to shellfish so I always make sure I bring allergy meds just in case.  Purchase travelers insurance to mitigate the most of extreme case of missing your trip trip entirely due to illness. This happened to a friend of mine.  He luckily was able to get the entire trip refunded through RoamRight, which offers affordable insurance covering both cancellations and delays for around $60 a trip.  

Travel mishaps happen.  Keep your cool and remember it’s part of the adventure!

x Smack

City Girls in the Land of Fire & Ice

When I first started thinking about going to Iceland everyone thought I was going a little bit crazy.  My favorite response was the confused and semi-judgmental “really?” that I would get after I described my desire to travel to the land of fire and ice.  I totally get it.  Iceland is not your stereotypical Euro trip or Caribbean beach vacation.  It isn’t known for pristine white sand beaches or charming cobblestone streets.   However there is a certain allure to the minimalist design, Scandinavian architecture, and stark landscapes that I just had to experience.

It took some convincing, but I managed to persuade nine other people that Iceland is in fact the perfect place to spend Labor Day.  We were able to find some fantastic deals on Wow & Icelandair, which made the trip very doable.  After a few months of planning,  we packed our bags and were off.   Our flight was quick – 5 ½ hours – and we were pleasantly surprised that we got to see the Northern Lights from the air.

After taking a cab from the airport to our picturesque scandinavian Airbnb in downtown Reykjavik, our first stop was to find some latte’s.  It’s always good to take it easy the first day- especially after an overnight transatlantic flight.  So instead of road-tripping right away, we took a quick cab ride just outside the city.  Imagine five city girls at a horse ranch—armed with our mirrored sunglasses, Barbour jackets, and fishtail braids, and waiting to meet our Icelandic horses.  Luckily, the tour was geared towards beginners.  Icelandic horses are small, but they make up for their size in personality.  My horse Ivan loved having his ears scratched, head butting other horses, and speeding up whenever we were going down a hill.  I’d love to go horseback riding in Iceland again.  It was a wonderful way to experience the landscape and unwind after the flight.

Krista on her Icelandic Horse, Hafnarfirði, Iceland

After we finished our trail ride we were off to the Blue Lagoon, possibly Iceland’s single-biggest tourist attraction.  I was very skeptical that the Lagoon would live up to the hype, and pleasantly surprised when it did.   It was incredibly relaxing to float around the lagoon, drink smoothies, try out the silica mud masks, & sit in steam baths.  The Lagoon staff did a great job of keeping the Lagoon from being over crowded and there were many native Icelanders at the lagoon.

Our day horseback riding and enjoying the Blue Lagoon were the perfect introduction to our time in Iceland.  By the end of the day we were exhausted but excited for the week to come!

x smack


Blue Lagoon, Grindavík, Iceland

Blue Lagoon, Grindavík, Iceland

Ivan, Hafnarfirði, Iceland