How to travel with a friend or in fact, anyone

Scrolling through TikTok and Instagram to see the memes of being the friend who hikes or walks 30,000 steps a day makes us want to head out on vacation. Then we check our travel bank account, which is still recovering from the last time we went on vacation.?

You might be wondering why I’m talking about travel now when it’s getting colder in the northern hemisphere. You know why. You’re probably planning on getting away during low season where it might be slightly cheaper; you’re looking at a warm getaway early next year, or you may have holidays to burn because you can’t carry them over to next year.

You might be dreaming of getting away from it all. I know I am.

Travel post-pandemic has gotten more expensive for various reasons. NerdWallet’s 2024 Summer Travel Report found that travel will be more expensive even though hotel prices and airfares have dropped by an average of five per cent.

The reason is because restaurants, recreational activities and the travel extras cost more. Your flight may be cheaper but if you want to check some luggage, that will cost you. If it’s heavy, it might cost you extra.?

People still want to travel but they’re looking at different ways to save money. We love a good solo trip, obviously, but we’re not made of money as I recently told my youngest nibling. (That’ll be the next newsletter).

One option is to travel with a friend. You know each other and can get along. But that’s not enough to make sure your trip is successful. If you don’t want to end up screaming at each other at 11 p.m. in France, Greece or Italy while the locals view you with annoyance or amusement, there are some things you need to do.?

Discuss your budget and spending limits

Discuss and agree on a total budget for the vacation, including accommodations, food, activities, and souvenirs. Both or all of you need to agree on how much you want to spend, especially if you have different salaries. Do this before you start booking flights and hotels to make sure everyone agrees on the money. Set daily or weekly spending limits to ensure both friends are comfortable with the overall expenditure.

Doing this early means you know how much you should save or even if you should go on this particular vacation.?

The rule of thumb is: the longer the vacation you’re taking, the more hours you should spend talking about it.?I suggest you book time and sit down to do this. I did with a friend and it was one of the best decisions we made because we did not fight about money.

Payment splitting

Decide how expenses will be split. Will it be 50/50, alternating payments, or proportionate to income. Who will cover what? If you want to see something, do they have to go with you? All of these situations should be discussed before you start booking excursions.?I wanted to visit the Ferragamo museum in Florence. That wasn’t in our plans but it was there. I offered to pay for both of us as it was affordable.

You can use apps to track the shared expenses, collect the receipts and write who paid for what on the back of them, or agree that one person picks up the cost of one thing and the other person picks up the cost of the next thing if it’s a comparable amount.?

You don’t have to split it down to the last five cents since that can be very aggravating. So if you’re happy to be in the range of $5-$10, agree to that. You can buy them a coffee later if you really want to even out the split.?

Accommodation preferences

We’re fans of hotels for several reasons: you don’t have to clean, strip the beds, and take out the recycling before you leave; there’s the breakfast option so you don’t have to cook and let’s face it, room service. Even if you never use it, it’s just nice to know you can.?Plus we’re not contributing to unaffordable rentals in high-tourist areas.

But your friend may like the freedom of an AirBnb, which is why you need to discuss the type of accommodation both of you prefer and agree on a price range.?Whatever you do, make sure everyone has a proper bed.

Activity costs

One of you wants to visit every single museum and the other wants to visit every single store and winery in the area. First, know that you probably won’t fit every single thing into your vacation. It’s a vacation, not the Amazing Race. Sit down and prioritize activities based on mutual interests and budget constraints. This is important because a lot of places don’t offer refunds if you change your mind.?

Each of you create a list of must sees and dos: you get one each a day. Rank them from must-sees to ‘meh, if we have time, it’d be nice to check it out.” Then agree on the activities you want to do, find out their costs and plan for them.?

Keep in mind you do not have to be attached at the hip. You can meet up after to debrief.

How much cash to carry?

Most major tourist spots will take debit or credit cards but it’s always a good idea to walk with some cash in case you go to a smaller town or if you’re buying something small like a coffee or a glass of wine. Plus, it’s good to have just in case your wallet or bag gets stolen. Summer travel often means more pickpockets.?

Do all the talking upfront and be honest. Both of you want to have a good time and who wants to have the awkward conversation about money while you’re in a restaurant in a foreign country with the locals, your fellow travellers and the serving staff avidly listening to you argue??I know I’d be listening.

This week’s readings:

A study by the American Academy of Matrimonial Lawyers (AAML) has reported a 62% increase in the number of clients requesting prenuptial agreements. More than half of the attorneys surveyed in the AAML study cited Millennials as the driver of those requests.

How do I reverse lifestyle creep? (The Cut, paywall)

Women of Influence and CIBC released Canadian Perspectives: Women, Money, and Wealth. There’s a ton of information in it including how Canadian women will control nearly $4 trillion in assets by 2028. (Women of Influence and CIBC)

Cash-strapped and anxious Canadians planning to spend less this holiday season, BMO says . (Financial Post)

The Bloc’s plan to add billions to Old Age Security doesn’t make sense. Just ask Canadians. (Globe and Mail, paywall)

Canadians lack financial literacy, confidence in managing money: survey (Investment Executive)

Small change:

Skyscanner released its Travel Trends 2025 including the top ten places for Canadians. It includes Okinanwa, Japan and Madeira, Portugal.

The Canadian Institute of Actuaries released The Evolution of Employer-Sponsored Long-Term Disability Plans