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Quick Guide To Planning A Big Trip With Friends

There is nothing like going on a trip with a big group of friends. A chance to put the weight of daily responsibilities behind you and look forward to nothing but good times ahead. That is if you can actually get all your friends to commit to a date and stick to it. To help you rally your friends into committing to a big group trip, I have put together a couple steps to help you plan it and make it actually happen.


Start a group chat – Get everyone into one chat to talk about what dates work for the group and what destinations. This chat helps keep the trip on everyone’s mind, creates a place to share photos, builds excitement and FOMO. FOMO is the key element you want to create so your flakey friends will feel less inclined to drop out.

Set a flight reminder – I use Kayak, SkyScanner and the Hopper app for this. As soon as I have a trip in my mind I set a reminder to alert me when prices change. The earlier you do this the better chance you will have to get a good deal on a flight. The longer you wait to book flights the more risk you take on getting a good deal. Once you feel confident you found a deal strike while the iron’s hot. Being last minute and spontaneous costs money, trust me I know.

Find a place to stay – The more photogenic and amazing the place is, the more likely your friends will want to go. For this, I use AirBnB, or VRBO. You can filter the search results to treehouses, yurts and mansions with pools, to suit all your desires. Here is the crux, one person has to dive in with full confidence on the place. It is important that one person does this and then collects from the group. Just make sure on the group text that people are 100% in. Hold them accountable and write out names confirmed on a list with a full price breakdown. The group pressure will also help discourage flaking as they will have to let the entire group down to back out of the trip.

Plan to do a big grocery shop – The beauty of having a large group is that your place will most likely have a kitchen. Kitchens mean saving money. You can save money by making big group meals instead of going out to eat for every meal. Find the ones that enjoy cooking in the group and let them take the lead. Assigning one person as the lead chef makes everything run smoother and eliminates the ‘too many chefs in one kitchen’ problem.

Plan some epic adventures – Wherever you decide on going make sure to plan out some trip highlights. There is nothing worse than ‘group effect’ where nobody can make up their mind and you end up doing nothing. Be prepared and preplan at least one event. That event could be a kayak adventure to a cave, big hike through a national park, art tour of Montreal, eating tour of Toronto or surfing on the west coast. Wherever you end up, make sure you plan something epic to give the trip some substance and the group something to brag about when they get home.


Need some inspiration on where to plan your next big group trip? Check out these articles…

Surfing In Tofino
La Mauricie Camping Trip
10 Places For Eats & Drinks in Winnipeg
The Best Places To Kayak In New Brunswick

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