How To Get Your Friend To Take That Crazy Trip With You

Libby Ryan

I’m obsessed with travel. I live and breathe flight deals and don’t hesitate to snap one up when I find my golden ticket to somewhere fabulous. And I always send those flight deals to my friends… who almost never book the flights with me.

Think about it: How many times have you and a friend, while sipping on drinks, daydreamed about the places you’d love to visit together? And how many of these dream trips have you actually taken with your bestie? If you’re like me, the answer is probably way fewer than you’d like.

So many of us end up never taking the trip at all because we wait around for a “yes” that never comes and waste that flight deal sitting on our wishlist. The unfortunate bottom line is that you can’t control or predict your friends’ lives and priorities. Sometimes they won’t have the vacation days or the money, and sometimes they’ll have to use those vacation days and travel budgets to go to weddings or familial obligations. But you can’t always wait for the one weekend in March when none of your friends have a prior commitment to see the world. You can, however, do everything in your power to clear the path for them to join you around the globe, should they choose to do so. Here are my methods.

Libby Ryan

Plan your adventure and share the dates.

These days, I’m on the road almost as often as I’m home. And I love it that way, but I miss my people.

My friends cheer me on from home, often with a woeful “I wish I could go with you” message. And even when I’m not traveling for work and I extend an invitation, it’s rare that one of my very busy friends takes me up on it.

So I go solo because I don’t expect my friends to jump ship from their normal lives and accompany me on every adventure — and there are some trips I’d actually rather do alone. But I’ve started sharing the dates of my planned travels as soon as I know them with any friend who I think I might like to share in that specific trip.

They don’t always join; most of the time, they just roll their eyes a little and congratulate me on finding such a great flight deal. But sometimes, someone can finagle a weekend in Scotland during your two weeks in Europe or a week in Colombia during a months-long tour of South America. It’s totally worth it to send the potentially irksome email, text or Facebook message telling your crew what’s up with your travel plans.

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Libby Ryan

Meet in the middle.

When I was in college, my best friend and I talked incessantly about backpacking through Europe together. But then she moved to Switzerland and I stayed in the U.S. It took us an entire year of being apart to realize that we could compromise. I wasn’t drawn to visiting Switzerland at the time (I know, but I was a broke college kid) and she wasn’t sold on trekking through Turkey, so we decided on Istanbul and Greece’s most beloved island of Santorini.

Your version of meeting in the middle could be meeting a European resident in Iceland, meeting up with someone living in Australia in Hawaii or even meeting a Los Angeles friend in Austin or Nashville. Just choose somewhere both of you have on your to-travel list that’s also not too far from where you both reside.

The next trick is to find flights in both of your price ranges. The meet-in-the-middle route is prime for those friends with a slight monetary discrepancy in their travel budgets. Let’s say Friend A has $200 to spend on a flight and Friend B has $500. Friend B can travel a little farther with no sweat and Friend A can still participate.

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Libby Ryan

Find a shared whim and jump on it.

The best shared trips are the ones where your crazy impulses match the crazy impulses of your craziest friend. If you both have the vacation time stored up and have the money for a bit of a splurge, egg each other on a bit and book that whirlwind trip.

My craziest friend and I swear by this method, especially after falling in love with the idea of visiting Svaneti, Georgia and trekking through the mountains. We didn’t wait for the perfect flight deal — we grabbed the first ones that fit our budgets. Waiting for the best deal ever is a big reason why many of my friends fail to embark on their dream trips at all. But the timing is never going to be perfect, you’re always going to notice the dent travel puts in your bank account and, yes, there might be something cool happening at home while you’re away. At least you’ll create your own once-in-a-lifetime memories to make up for it.

I traveled to Georgia to report on it for Swirled, and then my friend and I each took a week off to really immerse ourselves in the country. We climbed mountains, crossed suspension bridges, drank home-brewed moonshine and even hitchhiked to and from a glacier. And we came out of that trip even more obsessed than when we went in — never once did we regret using the PTO or spending the dollars.

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If you’re the friend who keeps getting invited on these types of ventures, what are you waiting for? If finances are what’s holding you back, set aside a spot in your monthly budget to save for travel. If it’s vacation time you’re worried about, have a candid chat with your boss about when you can take time off — and then take the time off. If you’re honestly just scared of the unknown, take one of your traveling friends up on their offers and join them on an adventure, taking advantage of all their hard-earned travel know-how.

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