Essential Tips for Traveling With Friends in a Different Tax Bracket

1. Don’t let them pay

Offering to pay for a meal might sound like a good idea if you make significantly more money than your friend. It’s generous, reduces the hassle of splitting a bill, and might appear to exhibit a degree of sensitivity. Well, don’t. Picking up the check is fine if you’re hosting a guest or taking an employee out for drinks. But on a vacation where everyone is supposed to be equal, picking up the check introduces a power dynamic, despite your honorable intentions.

You might say, “Don’t worry about it man, I’ll grab this one.” But what the budget traveler hears is, “I know you can’t afford this, man, and compared to you I’m basically rolling in money. So put that wallet away, you charity case, and let me handle it.”

Yes, you’ve been generous, but the line between generosity and pity is extremely fine. Your friend might accept your gesture, and even genuinely appreciate it, but they’ll also feel a pang of smallness that will persist — or grow into bitterness — throughout the trip.

By the same virtue, if your friend keeps trying to treat you to every meal, or constantly pick up the tab, don’t let them. It might sound harmless at first, but you’ll quickly start to feel indebted and even resentful. A successful vacation is rooted in equality. Nothing erodes that equality faster than one person paying for the other.

The exception to this rule is if one traveler offers to foot the bill for an experience both can enjoy, but which they would otherwise have to skip altogether due to cost. This could be dinner at a fancy restaurant, or a pricey excursion like swimming with dolphins. If the richer friend doesn’t mind spending the money to do the activity, you shouldn’t feel uncomfortable offering to pay as long as the other person understands it’s worth the double cost.

2. Balance the budget

Presumably, you’ll already have a rough idea of what your trip will look like before you depart. That means zeroing in on what things you want to reserve before going and which you want to book once you’ve arrived. Whether it’s a hot-air balloon ride, a safari, paddle boarding, snowmobiling, zip lining, or tickets to a bar crawl, excursions are the meat of your vacation. It’s also one of the most common parts of a trip where money issues come into play.

While your friend might have no qualms about dropping $100 to go zip lining during that hour of free time in Costa Rica, the budget traveler might prefer a short (and free) hike. While your friend might want to spend $40 on a bar crawl, and the built-in social circle that comes with it, maybe you’d rather hit the bars on your own and try your luck meeting people in the wild. Compromise is important.

A budget traveler should keep their funds in mind without descending into inflexibility (you’re on vacation, after all), while the more extravagant traveler should feel free to suggest and advocate for their preferred activities while remaining open to adjusting. Skimping on everything and eating McDonald’s for every meal is no way to have a fun trip, but blowing all your money on extravagences and pressuring your friend to do the same is also inadvisable. As with any relationship, each must understand the other’s situation.

3. Don’t be afraid to part ways

“Parting ways” doesn’t literally mean saying farewell to your friend mid-trip and having totally separate vacations, but it does mean diverging for a few hours to pursue separate interests or experiences. If you can’t agree on whether it’s worth it to enter an expensive museum, for example, feel free to go your separate ways for a few hours.

It’s healthy to carve out some alone time on a trip even when traveling with a partner or best friend. There’s no contract that says you have to spend all your time together. Agreeing on every single aspect of your trip would be great, but it’s unrealistic, especially when money comes into play. Rather than force a bitter compromise neither of you are happy with, just take a break from each other, spend some time on your own, and reconvene without resentment a few hours later.