5 things to consider when organizing a group trip

My tips for planning a group trip.

So if you read my recent post about cruisin’ through the Caribbean with Carnival Cruise Line, you’ll already know that it was a group trip: I had the pleasure of rolling with a crew that included Liebling, my mom, my auntie, and two friends.

This made for a relatively different travel experience for me. I’m a staunch advocate for solo travel; I love the independence, freedom, and learning that stems from traveling on my own. Whenever I don’t go solo, I travel with Liebling (ultimate travel buddy and master of maps) or with one or two friends (ultimate purveyors of laughable moments and memorable turn ups); rarely do I ever travel with a group this large.


However, after tackling the high seas with a team of six, I realize that in order for a getaway of this magnitude to run smoothly there are at least 5 things one must do.

Tips for a successful group trip:

1. Plan well in advance

The luxury of traveling solo dolo, à deux or even à trois, is that travel plans can be executed on a wing and a prayer. Flying off to an exotic locale at a moment’s notice is easy when only one or two additional people are involved. However, larger group trips require greater prep and co-ordination: with so many more people in the mix there are bound to be competing schedules, holiday constraints, and responsibilities (think dogs and kids).  This was the case for us, so we started planning for our July group trip around February: pinpointing dates when all six of us were able to travel proved the first major challenge of executing our getaway. Use Google Docs or a group planning website to plot out itineraries– they’re a lot easier than sifting through long email strings.


2. Sort out transport and accommodation

Once you and your team have determined exactly where and when you’re going, the next detail to sort out is how you’ll get there and where you’ll stay once you arrive. Again, when you’re by yourself or traveling in a small group, these details are almost negligible, but a larger group trip requires greater prep and consideration (see #1).

To wit:

  • Does it make sense to head to your destination on the same flight?
  • Once there, does it make sense to book an airport transfer together, or will every (wo)man fend for his or herself?
  • Should you book separate hotel rooms, or think about renting out a villa/house in which everyone can lodge together?

While the fact that we were on a cruise made accommodation a non-issue (a huge benefit of cruising), we still had the task of puzzling out transport and transfers. In the end, since four members of our team are based in NYC (me, Liebling, and my two friends Joy and June), I decided it made more sense for my mom to fly down to NYC from Toronto so that the five us could make our way to Texas together.  We headed to Houston on the same flight, then upon arriving, met my auntie, who had already flown in from Seattle.  All six of us then proceeded to the port of Galveston (where the cruise started) together in a minivan– a transfer we arranged prior to the journey.



 3. Realize you WILL move more slowly

When I travel by myself, I can get around fairly quickly, but when more people are involved it’s natural to move at a slower pace.  Your travel crew will inevitably be comprised of people who take longer to get ready than others, those who move more slowly due to age or lack of urgency, and those who stop to take pictures every second step.  The key is to recognize from the beginning that you will not whip through your sightseeing checklist at lightning speed; instead, try to adjust your itinerary (or expectations) accordingly.  The great thing about being on a cruise was that our group did not have to be joined at the hip at all times– since it was so easy to meet up at meal times or events on the ship we often did our own thing during the day.

group trip

4. Figure out the dollars and sense prior to going

Money can often be a sticking point on a group vacation: different budgets, spending habits, and methods of payment can take frustration levels from 0 to 100 real quick. To avoid losing your cool and unduly emptying your pocketbook, talk money and budgets with your travel buds before it becomes an issue.  Who will pay for what and when? Will tabs be split evenly?  How much money should people expect to be spending? Are credit cards needed, or is cash better? Should parties get foreign currency prior to travel or on the ground? Basically, what makes the most sense?  Having an open and honest dialogue about these details is key!

 group trip

5. Remember that everybody is different

Traveling with a group often means dealing with difference.  Remember that the members of your travel team are not a monolith: the larger the group, the more your interests, intentions, and personalities will vary.  My tip, as always, is to embrace these differences and encourage people to do what makes them happy: as I note above, your group is not a monolith, so there’s absolutely no reason they need to be joined at the hip for every tour or experience.  With that in mind, my recommendation is to pair up those with similar interests, travel styles, or personalities so that everyone has a partner or “road dog”– this will ensure nobody feels left out or left behind. On our trip, there were distinct sub-groups within our larger group: my mom and auntie (similar in age and outlook) hung out together most, followed by Liebling and I (naturally!) and Joy and June (they’re identical twins and built-in besties, after all).


Have you ever been on a group trip or travelled with a large number of people?  Do you agree with my tips?

This post was created for Away We Go with Carnival, the destination for getting in the getaway state of mind. Head on over.


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  • Reply
    Caroline Achieng Otieno
    September 14, 2016 at 3:37 pm

    You’re fortunate to get to travel with your family! My loved ones are so far away, and not that much into travel as I am..
    Great tips though.! Last time I traveled with a group, it was in Uni. Everyone paid for themselves but we kept on rubbing each other up in the wrong way, obviously because of personality and pace differences.

  • Reply
    Art Travel Eat Repeat
    September 14, 2016 at 4:46 pm

    This has absolutely been my experience. In 2005, I went on a trip with my college through Europe for Art History credits. While it was awesome to get college credits while traveling around and seeing Europe, I found the glacial pace of the group to drive me up the wall. Three days into the trip I had enough and decided to ditch the group. I still had to go to specific museums, but I slept in, got breakfast, took care of things like laundry, then wandered over to the train station, meandered around before going to the museum, and then group was still outside waiting to get in. That was the last straw for me and I did my own thing for the rest of the trip.

  • Reply
    September 14, 2016 at 9:03 pm

    I try to avoid traveling in groups as much as possible as it is a pain but your tips makes it more bearable. I guess it really depends on where you are going and who you are going with.

    I went with a group of friends on an all-inclusive trip before and while it was fun. It was a crazy! I became the group leader who organized everything for them.

    I only travel with my boyfriend now. He is the best travel partner for me!

  • Reply
    Kay Barriere
    September 14, 2016 at 11:48 pm

    I’m usually not too big on Group travel either, but, this is really good advice, Oneika. You mentioned the thing about coordinating flight arrivals and transfers which is often the one stage where major details go awry with Groups. And, yeah, its slower moving around with more people.

  • Reply
    Victoria @The British Berliner
    September 15, 2016 at 6:49 am

    Great tips Oneika!

    Yes, I’ve been on a group trip with an independent group travel company like Intrepid, etc, and it was fine! The trick is for the group to be small (8 people) and to know that you don’t have to go to everything together. Just let the group leader know what you’re doing, and then go ahead and do it!

    Re-with family, there’s only my husband, tween, and myself. I usually do all the travel planning (ho!ho!), but I take care to add things that hubby might like, and that son might like, ‘cos my personal travel style is utterly different, and then blend them together. Oh, yeah. When travelling with family SLOW DOWN!

    ‘Nice one!

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