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Daydreaming about a joint vacation? Set some boundaries first


Sharing vacations and vacation properties with family and friends is a fabulous way to shave off costs. But, even the best laid plans can sometimes backfire both financially and personally, without clear boundaries. Here’s how to do it right.

Pick a travel partner with the same money mindset

Not everyone should vacation together, especially when there is a history of bad financial behaviours, such as squabbling over restaurant bills or “forgetting” to repay you for something.

The best travel buddies are financially aligned, meaning they have similar values around tipping, flight upgrades, travel insurance as well as budgets for food and accommodation. If a financial challenge (like a flat tire) arises while on holiday, savvy travel partners use respectful communication to come to a fair financial resolution.

Go Dutch

Hands-down, the best way to avoid conflict when travelling with others is to split everything evenly. Simply tell your service provider at your restaurant, hotel or amusement park that you require the bill to be equally split. If you have to prepay for tickets to a show, ask your travel partners to e-Transfer you their portion the same day the charges are incurred.

Whatever you do, avoid “I’ll pick it up next time” scenarios. Resentment will build quickly.

Distribution of duties

House swaps, through a company like, or Airbnbs, are a fabulous way to reduce accommodation costs compared to hotels. However, in the majority of these cases, your party will be on-the-hook for daily cleaning, cooking, dishes and laundry. Before you board your flight, establish a clear set of expectations around who is responsible for what.

Sharing property with family

Many Canadians jointly own all manners of vacation houses with their siblings, parents or children. But it’s necessary to determine who is responsible for paying the property taxes, cutting the grass, filling up the boat, buying groceries, and most controversially, managing the calendar of ‘who uses the property when.’ It’s generally best to appoint a leader within the family who can assign responsibilities, request appropriate payments and negotiate schedules.

We recently came across a Vancouver-based start-up, SharedKey, that automates the scheduling process, and will soon launch a budget tool to help families manage their vacation properties. The entire family can access the calendar and information about the property, right down to which days of the week the recycling and garbage bins are picked up.

Whatever style of vacation you choose, save your portion of the costs in advance. That way you won’t get slapped with massive credit card bill upon your return.