Tips + Trends

8 Questions to Ask Before You and Your Bestie Take That Vacay

You love your BFF to death, so of course you want to take a trip together. But taking a friendship on the road can subject it to new stresses, from money matters to sightseeing styles. You want to return home closer than ever, not silent, sulky and disappointed.

After you decide on a trip, but before you pack, sit down with your friend and answer these questions for each other to make sure you understand each other’s hopes and expectations.

travel with friends
Before you leave, get on the same page with your pal. (Photo: Getty Images)

1. What are your must-see/must-dos?

Will your trip to India be ruined if you don’t get to ride an elephant? Will your friend be devastated if you go to Cancun and don’t make it to Tulum? Look at the trip, look at the itinerary, and decide together what activities are nonnegotiable for each of you, no matter what serendipity throws in your path. From there, adjust your itinerary to make sure each of you can experience your must-dos.

2. Where shall we save, and where shall we splurge?

Are you willing to share a room to save some money? Are you an any-bed-will-do person or an Egyptian-cotton-sheets-only person? Do you live for fine dining, or is just plain eating enough? Where can you tighten up to save a buck? Compromises on spending should be easy to find when you know where you stand.

3. How will we handle money?

Will you split every cost 50-50, in the moment? Keep a general idea of what’s being spent and divvy up as feels comfortable along the way? Toss all receipts in an envelope and split the bill later? You don’t necessarily need to nail down a rock-solid plan, but a good way to build up money resentment on the road is to ignore the potential for problems.

Be mindful of each other’s budget, and find a respectful way to keep costs comfortable for both.

travel with friends
To splurge, or not to splurge? (Photo: Getty Images)

4. How tightly scheduled to you want to be?

Some travelers don’t want to waste a minute dawdling when there are sights to see, adventures to have, cuisines to sample. Others can happily while away an afternoon with a cold beer at an outdoor café. Both approaches are legitimate, just not always complementary, so talk this out ahead of time and plan how you’ll balance your styles.

5. Speaking of dining …

Food is definitely part of the fun of travel, but some people travel to eat, and others just want to grab a quick bite on the way to do something else. How important is the food experience to you, and how much time, money and energy do you want to put into it?

6. Museums or no?

Some people are passionate about museums; others find them a dreary waste of daylight. If you’re mismatched, going your separate ways for a few hours might be the best option. The same discussion can be had about shopping.

Research by the U.S. Travel Association puts shopping No. 2 on the list of favorite vacation pastimes, but not everyone wants to spend their days fondling souvenir T-shirts or even fine folk art. Chat it out. (Is a museum with a great gift shop the solution?)

travel with friends
Sometimes, it’s ok to part ways. (Photo: Getty Images)

7. All togetherness, all the time?

As much as you enjoy each other’s company, you might find that 24/7 togetherness can be exhausting or strain the friend–love connection. Will feelings be hurt if one of you spins off for a few hours of solitude? What if one of you wants to sleep in one day while the other is raring to go? If you can’t agree on how to spend your day, will splitting up be an option? Discuss.

8. What could ruin this trip for you?

Aside from the obvious — lost luggage or crime — what could poop your vacation party? Would it be having to do all the planning and make all the decisions? Not getting to do any planning or make any decisions? Spending too much money? Being abandoned for a vacation romance? Talk about it. Forewarned is forearmed.