The Ultimate Guide to Planning a Group Vacation

Have you been tasked with planning your next group vacation?  If so, we’ve been there, done that, and don’t envy you one bit because It’s a task of herculean proportions .  Whether it’s a family get-together of multiple generations or a mix of friends with kids, keeping everyone happy is going to be a challenge.

We’ve all been there. The festive get-together, a few glasses of wine or beer, and all that camaraderie that comes with the warm glow of friendship.

Someone says, “We should all go on vacation together” and so it starts.  Like adding Mentoes to a bottle of Coke, everyone bubbles over with enthusiasm, and by the end of the evening it’s a done deal.

Oh, and at some point amongst all the excitement you volunteered to organise it.

In the clear light of day, there’s a lot to think about and a slew of questions to answer. 

Where and when to go?

How much, and how to share out the cost?

How to meet everyone’s vacation wishes?

What to do first?

We’ve broken down the planning into different stages with some ideas on the things you need to think about, the information you need from the group and how to get this project off the ground.

Collecting and Sharing Information

Good collaboration is key. Before you even start you’ll need a place to share your research and there are plenty of platforms available.  The simplest is to use the tools Google provides.  They are free, easy to use and everyone involved gets access to them without having to sign up for new software they may never use again.  The group can use Google Maps to show where they want to go and even pinpoint particular property locations if they find one they like.

Sharing files and foiders on Google Drive is easy too.  Create a folder for the vacation and you can include checklists, photos, video and spreadsheets that everyone can access at any time.  There’s a range of sharing permissions to choose from so you can limit edit access and just allow comments on your most important planning documents, which is best if you don’t want Auntie Barb to delete all your hard work!

Trello Board

There are other organisational tools such as Trello, Asana and Evernote that offer a richer experience in terms of the ways they display information. Unless you are fully familiar with them and you don’t want to go off on a tangent to learn something new, then it may be best to stick with the simpler Google Drive option.


You’ll need a way to communicate with everyone. Emailing back and forth can be a pain and while you can get the group together on a Zoom call, any decisions made need to be accessible to everyone – including those that missed the call.

Slack is a tool primarily used in many small and large companies and is particularly useful for connecting with remote workers. It’s equally helpful for personal use and you can set it up as a personal chat room. And it’s free!

Set the Date

This is no different from planning any major event – all organisation stems from deciding on a date where everyone will be available.

Doodle is a great platform (with a free trial) for scheduling times when you are all available. Essentially a tool to allow workers to pick times when they can attend meetings, you can now choose the option of creating multi-day events.

Let your group know that once the date is set and your place booked there is no going back!

What Makes a Perfect Vacation

So you find this amazing property which has 7 bedrooms and will comfortably accommodate everyone. The waterfront is beautiful and you’ve fallen in love with the massive campfire area where you can all sit and toast marshmallows on a starlit night.

The only drawback is that it’s 15 kilometres down a country road and 30 minutes from the nearest store….and that’s after the 20 minute boat ride to get there.

And another thing….there is no wifi or cell service. Just a landline.

Nature’s Inspiration – Water Access – 7 bedrooms

This might suit you but will it be perfect for your friends who cannot start the day without a Starbucks coffee and whose teen children live on Minecraft and TikTok?

Determining a location that meets everyone’s needs is a good place to start and could be the topic of your first group Zoom meeting.

Give everyone a say in what makes their vacation perfect and create a list of Must-Haves, Nice-To-Haves and In Your Dreams criteria.

If one family has a dog, they will want a place that’s pet friendly; maybe those with small children want shallow entry to the water, and grandparents may demand an ensuite bathroom. A washer/dryer and dishwasher might be essential to some, while unlimited wifi is to others.

A games room or full bathrooms on different levels of a home, or a screened sun room could be nice to have but not a deal-breaker.

Getting these key issues hashed out at the start is super-helpful and makes it easier to select specific properties.

Set A Budget

This can be a tricky one so get it out of the way early on. If one family has 3 kids and another is just a couple plus a dog, should they pay equally for a property? After all, if the couple was going alone they would only need a one-bedroom place, but with a group they’ll be sharing the cost of renting a 3+ bedroom place.

As a general rule, if you all decide to vacation together, then you will all be getting a larger and probably higher standard of accommodation overall – not just a greater number of bedrooms. There may be access to a bigger kitchen, entertainment areas, and more amenities than a small cottage would offer. So, a simple 2, 3 or 4-way share based on the number of families involved is an equitable way of setting the budget for the price you are willing to pay for a property.

On the other hand, your catering budget could be set out per person….more of that to come.


Now you know how much you can spend and have a list of the non-negotiables, the task of finding a location becomes a little easier. You may have already discounted the idea of a water-access cottage and know you need to be within 15 minutes of a general store or within easy access of medical facilities if there are older members in the group.

There may be individuals who want to get back to the city occasionally so find out the maximum distance people are prepared to travel.

For waterfront properties, do you want a private location in a lot of acreage or are you happy with enough area for the kids to play and a sizeable dock? Does there need to be access to a boat launch or a marina nearby to rent a boat?

Research the different areas and create a list of features and benefits of each. For example, cottages in Eastern Ontario can be more reasonably priced but have fewer local attractions, restaurants and stores than in the higher-populated Muskoka region.

There’s more bang for the buck in areas north of Bancroft but it’s a 3+ hour drive to get there.

Getting the location right can make or break the whole experience so get acquainted with the different regions and share your results with your group.

Living Arrangements

While you might have entertained your neighbours in your own home, and been to their house for a barbecue or cocktails, have you really thought about living in close quarters with them for a week?

Without getting too detailed, you have no idea what their morning habits are – how a shared bathroom might work, and whether nocturnal noises will pass through the thinner walls of a country cottage.

If you know each other well enough to spend time on vacation with them, you should be able to discuss these things openly.

Does anyone snore?

Are there early risers or night owls who might disturb the others?

How long is a typical morning bathroom ritual?

For one family, a cottage vacation might mean the silence of nature, listening to the call of a loon on a still night, while the others may see cottage living including The Weekend on full volume on the outdoor speaker.

Sleeping Arrangements

Do not leave allocating bedrooms until you arrive at the cottage. That’s the fastest route to a friendship going down the tubes as resentment builds because one couple got there earlier and bagged the master ensuite, leaving the other families to fight over the 8′ x 6′ bedrooms.

From your earlier planning details you’ll know who wants the larger bedroom to accommodate a pack’n’play for the smaller human; which couple needs easy access to a washroom for nightime visits, and who likes the idea of a pullout couch in the sunroom. You have all this documented so there should be no argument at a later time….well, there’s less likelihood of it anyway.

Many listings now have 3D video walkthroughs that show the floor plan of the property and it’s easy to see where all the rooms are in relation to each other.

Set The Ground Rules

Living together in close proximity can be challenging when different families have different ways of doing things, so setting the base rules of co-habiting before you go is a way of avoiding issues when you get on vacation.

My sister recalls having her daughter and 2 children stay at her cottage along with a niece and her family. Her daughter had a laissez faire attitude to kids bed times – after all she said, ‘they are on holiday’. The niece on the other hand stuck rigidly to home rules.

This resulted in evenings when two little faces were pressed against the inside of a bedroom window watching the other same-age kids enjoying dusk time on the beach and a campfire. The outcome was antagonism between the two moms and a frosty air in what should have been a happy summer time.

Ground rules should cover bed times, internet usage, outdoor music, meal times and any other things that one family commonly does that could impact the others.

When you end your perfect vacation with friends and/or family, you want to be able to say, “That was the best ever – let’s do it again next year” rather than “Never again…what were we thinking?”

Good planning and organisation is going to get you closer to a better outcome, maintain family harmony and friendships, and achieve your goal of having a dream holiday with the best possible memories.

CottageLINK Rental Management
Toll Free: 1-866 323 6698

Our Hours:
Mon-Fri 9-5
Sat-Sun 9-5

Business Address:
PO Box 39036
Columbia PO, Waterloo, ON, Canada N2T 0A7

Email Sign Up

  • This field is for validation purposes and should be left unchanged.