Traveling with friends can be either a wonderful or awful experience.
The difference depends on 2 things: proper organization and choosing the right traveling companions.
It’s fantastic to travel and share new experiences with your partner, but it can be even more amazing when you are sharing these with a bigger group. Plus, with friends you always have someone to take a picture of you when you’re standing at that Instagram-worthy photo op under a waterfall!
We’ve done a few trips with friends and for the most-part they have been so much fun – save a few hiccups here and there.
There are some pitfalls you should try to avoid. Just like everything else in life, the outcome generally is better when everyone understands the guidelines and expectations of the group. This is in regards to deciding on things to do, booking in advance, staying on schedule, paying your share, and being accountable in general.
Just because you took the lead organizing a trip with your friends, it doesn’t turn you into their Mommy – and hopefully your friends understand that. It’s time for adulting now; which means everyone is responsible for their own time/money/enjoyment.
Here are the key elements to planning a successful, stress-free group trip:
- Pick Your Organizer
Designate a person who will put the trip’s details together and keep the group updated.
- Go with Low-Maintenance Traveler Friends
Avoid being miserable traveling with people who need constant attention and help.
- Agree on the Destination
Form a consensus on where the group will go and decide who is doing what, where, ahead of time.
- Make Sure the Budget Works
Be realistic with budget costs and make sure you’re being considerate of those who can’t afford the same things that others can.
- Be in Constant Communication
Make sure everyone is aware of all updates.
- Have Some Flexibility
If something doesn’t work out the way you expected, go with the flow and commit to still having a great time.
- Use Planning Tools to Assist
Let technology help you make your trip-sharing details easier.
back to menu ↑
How to Plan a Group Travel Trip
- Set Proper Expectations – While it is important to do this throughout the whole planning process, from the get-go you want to explain what you expect from your proposed group event. This means, explain how you like to travel, propose some rough ideas on what you might want to do, and what you expect out of others (will you be sharing a hotel, carpooling across country and expect the others to take turns driving?). Make sure your intentions are clear.
- Ask Who’s In – Discuss the trip with the people you plan on inviting and get an email distribution list going. As people opt-out remove them from the list so you’re not spamming everyone with travel updates.
- Group Votes – If you want a destination by committee, discuss the options together and take a vote on where the group wants to go and what they’ll want to do there. Otherwise, if you have your own itinerary in mind, just create it yourself and send it out. Often, people appreciate your willingness to come up with all the plans, especially if they don’t have the time to do the research themselves, so you may opt to pass on the voting since it can be frustrating to hear crickets at your requests. It’s also difficult when there are more people involved to come to a unified agreement.
- Initial Budget – Once you have a rough itinerary, use a travel website to get some rough estimates on how much you think the entire trip will cost. Send this out to everyone and inflate the price higher than the total based on if they’ll need to pay for food/drinks/excursions/transportation/miscellaneous shopping. Unless you are doing a cruise or an all-inclusive resort this will most likely be the case. Err on the side of over-budgeting to help your friends out, they won’t want to find out that they didn’t have enough money after they’ve booked the trip.
- Finalized Budget: Send a more finalized itinerary out with specific prices once you know the locations and possible excursions people are interested in doing. You might also want to look up some of the average cuisine costs, to get people’s mindsets prepared for what they will be spending on average. This might also shape some of where you decide to roam. For example, drinks in the less populated areas of Mykonos are under $10.00, while the more popular clubs in town will charge you easily over that price for a basic drink.
- Share your Booking: Give people links to airfare or the package you’re considering (or have purchased) to make it easy for them to make the same arrangements as you. Obviously, they may choose a different company to make their arrangements with, but this will give them a good starting point to match to your locations.
- Must See/Must Do Lists: Have each of your committed traveler friends come up with their list of “must see/must do’s” on their own. Also include a “nice to see” section. When everyone is done, share these collectively and see what overlaps. This is a good way to ensure they are getting their voices heard and what will be done collectively is agreed upon before hand. Then communicate and decide which ones you will buy before hand and which ones can be spontaneously purchased in town. Be careful with assuming there will be things like guided tours on islands, sometimes they have to be booked in advance. Do your research on excursions.
- Don’t Forget Transportation: While Uber has definitely made it possible to be WAY more spontaneous when it comes to getting around, if you are in a foreign country cars may be a little harder to come by. Read up beforehand on different methods of transportation, especially for things like island hopping, where Uber will not be useful. Factor these in and figure out if you need to book ahead of time.
- Finalize It: When everything is agreed upon as far as where people are going, what they are doing, when and with whom, make sure someone (detail-oriented) documents the heck out of it all, down to the finest details of exact times and locations – maps are a beautiful thing here. Get familiar with where you will be using TripAdvisor forums, Google Satellite views, a travel agent, someone who has been there before, or your local friends in the area… You want to know things to avoid, what to wear, what to expect weather-wise, EVERYTHING. Don’t be afraid to let your obsessive-compulsive neurosis blossom into full bloom here. It’s important that you are as organized as possible, because these trips are usually a little chaotic all-by-themselves without a lack of organization.
back to menu ↑
Stuff happens. Travel plans can get thwarted easily with flight delays, natural disasters, or any combination of events (oversleeping, your Uber had a flat tire). Being prepared is necessary and important even when you’re not traveling with a group, but it’s especially important if people are waiting on you that you have an agreed upon emergency plan for every place you go.
At a minimum, your entire group should know these 2 things:
- Contact Info – This might be the most important thing for an emergency – make sure you not only have all of your friend’s contact info and itineraries in your phone, you also have this on printed paper. I know right, so archaic? Foreign land wifi/cell strength can be spotty, and technology can be unreliable – what happens if your phone ran out of battery in the middle of a foreign city? You may actually have to use a land line at that point, and what’s the name of that hotel they’re in? Good thing you have this weird fibery sheet in your hand with that information.
- MeetUp Spots – We had an incident on a cruise we took with friends where we thought someone was “lost” and some of the group was losing their mind trying to find her, to the point of almost asking the boat to turn around in case she had fallen overboard. It turned out she had gotten separated from the group and just went back to her room and went to sleep. Funny enough, no one thought to check her room. To avoid this, have a plan in place in case someone from your group gets lost – say that if you can’t find each other by a certain time, you’ll be at X location (maybe the hotel you started from) by X time. Then, you will know if you should be worried enough to organize a search party.
back to menu ↑
How to Stay Organized and On Track
- Updates: Once you have a “locked in” group, send regular updates anytime new information is discovered (prices change, dates change, or excursions are researched). You will want to keep in touch every now and again to remind people that the trip is approaching and to get them prepared. It’s easy to get consumed with work/life and forget, especially if you’ve been a good planner and booked this well ahead of the date your group is leaving.
- Before you Leave: Right before the trip, send out all the itineraries to everyone going along with your meeting points/emergency contact info, etc. Also include a list of packing must-haves – you can use our list of recommended items to pack for a trip so that no one forgets anything. You don’t want to spend your first hours in Italy searching out an electronics store because someone didn’t bring their laptop cord.
back to menu ↑
Travel Apps for Group Traveling
Here are some of the best apps for group travel or keeping track of your expenses as a group.
I think this is my favorite group travel planning app of all the ones I have tried so far. Reason being, it’s easy to use, intuitive, and has most of the features you would want in a tool like this. You enter your information, invite friends to join, and then the group can vote on the activities they want to do, post group messages, photos, and track and split expenses easily. The only downside is that there is no website access (I find that easier to enter all the info into, then access through the app), so you end up having to enter everything through the app, which can be tedious. Available on iOS/Android
This app will help you find friends in your network when they are traveling or reside in the same location you are. It will also keep track of your itinerary and you can add items as needed. If you are looking for a very simple itinerary holder/itinerary share app, this will do the trick, and has no ads which is a big advantage over the other apps with ads. You can send your itinerary to their email and they will add it to your calendar, which is great, as it saves you the pain of entering it in manually. The highlight of this app is that it connects to Facebook so you can see when your Facebook friends’ locations overlap with your own if you’ve allowed that in the settings. Available on iOS/Android
I love the features of this app – but I installed it and the ads became an annoyance to the point where I uninstalled it after a few minutes. This app comes with incessant video ads that you can’t stop and they show up on every screen. However, you can pay for an ad-free version, it looks like the pricing models are $4.99 or $9.99, but it was confusing as far as if that’s monthly or yearly, and it also wasn’t clear on what you get at the different price points. It might be worth it to pay for this if you and your friends travel often. This has a survey tool where you can poll your friends on where they want to go and what they want to do, expense tracking and reimbursement options, and photo upload capabilities in the cloud, where you can share these with friends. Overall pretty cool functionality, if I could stomach the constant ads or wanted to pay the fees. Available on iOS/Android
Travefy used to be good, if not great, it sounds like… but as of October, 2018, they have removed most of the functionality that people loved – I am not sure why. What sounds like it was originally a very useful group travel planning tool has turned into a very simple app where you can enter and share your itinerary, but that’s about it. You no longer have the option to do group polling or track and share expenses which is one of the main drivers of the people installing this app. I also noticed there doesn’t seem to be any way to automatically import itineraries, which is something that makes an app like this much more useful. I tried it then uninstalled fairly quickly, when the activity search did not seem to bring back any good results, and they were not in my language. Available on iOS/Android
Worth mentioning as it has really good ratings, however I can’t try it since I don’t have an iPhone and they don’t have an Android app just yet. If you (and all the people in your group) use an iPhone, you may want to check it out. Available on iOS
TripIt is a pretty slick app from its parent company Concur, with a way of instantly uploading your itinerary so that you don’t have to enter it manually. You have the option to share your itinerary with a group, but this is not specifically a group travel app, so it is lacking in features such as photo sharing, messaging, expense sharing and voting. A nice feature of this app is that you can access your information even while offline, so if you are searching for your reservation number you don’t have to connect to an email that’s not coming up while you’re in a foreign country. Pro version ($49/yr) also offers additional features such as finding upgraded seats and instant notifications on flight changes, etc. Available on iOS/Android
Although not a travel app per se, this can be very useful for free communication with your travel group. Most people use WhatsApp for its free phone capabilities, but there are other features you should know about for group travel. You can set up a specific group for each Travel Group you go places with, and you can talk, chat, upload documents, and even drop your current location on a map for the rest of the group to see where to meet up. For instructions on how to add Google Maps pins to your WhatsApp conversation, read this how to on installing and using it. Available on iOS/Android
This app is for people carpooling with friends or family to a drive-able vacation destination and want to share driver duty. It will help you find the best routes and suggests things to do along the way such as restaurants or landmarks. You can calculate all the legs of the trip to determine how long it will be until the next stop. Available on iOS/Android
Great app for sharing expenses on a trip, the only thing that would make this better is if you had a total accumulated balance instead of a balance only for each individual entry. You can see who paid for what items and then divide up the reimbursement amounts – you can also do this unevenly which comes in handy in the case of splitting bills with people who have kids, etc. Available on iOS/Android
If you are sharing the cost of things with your group such as AirBnB rentals, cab fare, food, etc., it can get a little sticky as far as who pays for what. Splitwise makes keeping a running tally of who owes what easy and also integrates with Venmo for payment purposes. Converting foreign purchases however, is kind of a pain, and requires that you log into their website to do so. Available on iOS/Android
back to menu ↑
Ways to Prevent Group Travel Misery
- One Organizer To Rule Them All – You will most likely want a type “A” personality leading the charge, one and only one is important; someone who can put together the entire itinerary with all the details accounted for. These people can be painfully annoying at times (I know because I think I might be one of them), but will make your travel life so much easier with their OCD-ness. Be careful if you are leaving travel plans to someone who is a last-minute, fly by the seat of their pants type of person, as the whole plan might fall apart – if there even is one.
- Expectations – Make sure the expectations of the group are understood and agreed upon by all. For those who want to travel together but do things more independently, it might not work out to travel with a group which plans to do everything together. If your idea of a vacation is relaxing on a beach all day while the rest of your party wants to get up at the crack of dawn and see all the landmarks of the city, make sure you have been clear on what you plan on doing with and without the group.
- Physical Requirements – It’s important that you understand the level of energy you will need to exert during activities on the trip, and that if your friends plan on accompanying you to these activities they are able (and willing) to keep up with you. If you plan on swinging through vines on the jungle like Tarzan, just make sure your traveling companions want to be Jane, or maybe they have something else in mind to do at that time. Research on excursions is important, you don’t want to find out at the bottom of a volcano that your friends aren’t physically able to make the climb and expect you to stay back with them. Most excursion companies will tell you the level of activity required for the event.
- No Drama – Collectively commit to having a “drama-free” trip. Although this may not be completely mitigated with this verbal contract (it’s not legally binding, after all), it should be the common goal everyone agrees to, for the enjoyment of the entire group. In our past group travels we have experienced a few temper tantrums or couple’s fights that put a damper on the rest of the group’s fun (and wastes valuable vacation time). It’s so much better to avoid these if possible.
Following these tips, you should be off to an amazing adventure. Wishing you all Happy and Safe travels!