I Just Took A Trip With 5 Friends, And Here's What I Learned About Making The Planning Process Easier

By Allison Berry

I'm not sure if you and your friends are anything like me and my friends, but we have a tendency to enthusiastically say we want to do things without always following through. Most of these plans involve travel, like planning big trips together, or finally visiting each other in our respective cities. Just when I was finally coming to terms with the fact that the New Orleans trip we'd been talking about would never become a reality, my friends and I decided to actually book a flight to New Orleans.

So there we were, for the first time in seven years of friendship, actually showing the desire and determination to make an elusive friend-cation happen — but how exactly were we supposed to get six women from three different states to one city for five days of fun and relaxation? Spoiler alert: It took a lot of patience.

I know I'm not the only one who's found themselves caught in the crossfires between actually wanting to plan a big adventure with your friends and not actually wanting to plan it, and that's exactly why Elite Daily has teamed up with Venmo to offer up a few of the ways that my friends and I finally turned this dream into a reality.

First Order Of Business: Start A Group Chat

Ashley Batz/Elite Daily

My girlfriends and I mostly live in different cities, so we started a group text months before our actual trip. That chat became our to-go place to do everything from offer our opinions on house rental options, to coordinating shared payments with each other, and even just getting excited about our trip.

In hindsight, having one spot where all of our communication went down made it way easier for for us to hold each other accountable for so many moving pieces. Then when the actual trip came around, it became the place where we shared all of our photos with each other, and how our different groups stayed in touch while we were out doing other things.

Determine Early On Who's Paying For The Rental


Speaking as the Designated "Just Pay Me On Venmo" Friend, I was happy to put our rental home on my credit card and have my friends send me Venmo payments for their share, but if I were to plan this trip again, then I would for sure have volunteered myself sooner. Especially since we were planning to visit New Orleans during a popular local festival, places were getting booked fast. If we'd started our planning with a payment strategy, we could have found something with more than two beds.

Thankfully, Venmo just came out with the new Venmo Mastercard® that can make this process even easier. The card is tied to your existing Venmo balance and can be used anywhere in the US where Mastercard® is accepted, so if I'm putting a rental home on the card and having my friends pay me their shares on Venmo, then there's no need for me to stress about transferring funds from my other bank accounts to cover the immediate cost. The app also lets you split charges made to your Venmo card, which makes that ever-awkward "when r u going to pay me" text slightly less awkward.

Set Your Vacation Expectations Sooner Than Later


After weeks of looking for flights, booking concert tickets, and finding a place to stay, my friends and I all had a moment where we realized we each had totally different vacation styles. While myself and couple of my friends tend to be the type to want to flesh out an itinerary in advance, others are happier playing it by ear. Neither vacation style is better than the other, but it was helpful to find this out before we all arrived in the same city with drastically opposite expectations.

Resist The Urge To Overbook Yourselves


Remember that group chat? The only downside to having quick and easy access to each other is that we came up with a massive list of things we were all excited to do. This, paired with the fact that we all had different hopes and dreams for our trip to the Big Easy, helped us decide to only book one or two activities per day. Things like dinner reservations and ghost tours that required tickets were booked in advance, but for the most part we tried to keep our days as open as possible.

Encourage Everyone To Be Honest About Their Budgets

Han Burton/Elite Daily

I have my friend Kaylee to thank for this one: After spending three years living abroad in Spain and spending a ton of time traveling around Europe, she confessed that her worst trips were the ones where her fellow travelers weren't honest or realistic about how much money they could spend. "It was weird when one person with a lot of cash didn't understand why other people weren't interested in doing things that cost more money," she told me.

With this in mind, Kaylee kept the money conversation going from the start, making sure to suggest activities and attractions at every budget level. It was such a considerate thing for her to do for us, and I'm definitely going to be keeping this tactic going next time we're planning a trip together.

This post is sponsored by Venmo.

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