I Planned A Trip With My Long-Distance Besties, & Here's How We Did It

Keeping in touch with your long-distance friends can be challenging. There's Skype and FaceTime, of course, but nothing beats actual face time with the girlfriends who know you from way back, when you lived in a forced triple in a college dorm. For me, these friends are Kathryn and Diana. I'm not trying to brag, but we're really good at planning trips. (Honesty time: they're really good at planning trips, and I'm really good at saying "yes" to going.)

In other words, there's something special about going on a vacation with your besties. First of all, you get to bond in a way that you just can't over the phone. Second, a true vacation will mean that no one ever has to work or run errands.

Historically, our trips have benefited from various levels of mooching and bootstrapping. We've done spring break at a family-friendly ski resort with Diana's parents, and we've accompanied her on two business trips to Arizona, sleeping three to a king-sized bed. We've visited moms and dads, aunts and uncles, and even grandmothers.

Recently, Diana relocated from Boston to Sydney, Australia -- and we're adults -- so we've decided to step up our game. Happily, PayPal and Airbnb have created a neat tool called " Meet Halfway ." They're offering $50 off an Airbnb stay of $200 or more if you book through PayPal, which seems like a no-brainer. Also, you're able to plug in your friends' locations, leading us to find our new vacation spot:

This is very close to Honolulu, so for all intents and purposes: We're going to Hawaii. ("We have to," I said. "It's for work," I said.)

Next up? A lot of decisions. Inspired by my super-organized friends, I present some tips for planning this kind of trip.

1. Figure Out Where You're Going

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Look! You've already done it. Of course, there might be other considerations for you. If someone is on a budget, consider booking something closer to her. If you're in far-flung locations, try to find a happy halfway point like we did. And as I mentioned earlier, visiting friends where they are is nice, but that means that your friend will have to host you. In this case, Kathryn and I didn't have two weeks to do Sydney right -- and we didn't want to make Diana host us on this particular trip.

2. Assign Responsibilities

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If this trip is your idea, prepare to do a lot of the initial research to get the ball rolling. Because I've traveled with this group, we pretty much know our roles. It helps that I'm traveling with a lawyer and accountant: Kathryn is an expert researcher, and Diana is excellent with finances.

...And yes, I will fully admit that I am the least useful of this group. I try to make up for it by being "down for whatever" and crowdsourcing the best places to eat, drink, and do fun things.

3. Become BFFs With Google Docs

Start with a blank document. This is the exploratory stage, so we're not quite ready for a spreadsheet. For a large group, a survey might work better, but with a small group, I like free-form questions and answers so everyone can share information. Also, surveys sometimes feel like work, so your response rate might be low.

4. Figure Out Your Budget, Part I

"What's the maximum we want to spend?" This, in my opinion, is the wrong question. Everyone makes a different amount of money, and also, it's hard to name a number without knowing the general cost of things. Because you're a good friend, you will have already done some legwork on pricing (flights, Airbnbs, transportation while you're there). Add that to your Google Doc.

5. Nail Down Some Dates

You've already asked your friends for no-go dates, so you can start narrowing down your research to a time period. My suggestion? Don't send out multiple dates; it gets too complicated. Pick three time periods that appear to work for everyone and comparison shop flights and lodging. Then... just send out one date and ask for a yes/no.

5. Book Those Flights!

Start an email chain with the flights that you're booking, and have your most meticulous friends ensure that you're doing it correctly. (Fact: I once booked a train in the wrong direction.) There's a lot of information out there about the best time to book a flight. In 2014, the Airlines Reporting Corporation analyzed 129 million transactions and found that the magic window is eight weeks in advance for domestic trips, and 24 weeks if you're flying internationally.

Though you might be trying to hold out for last-minute deals, a good fare is likely to rise considerably, especially as you get within one to two weeks of your trip. The ARC also found that Sunday fares were the cheapest, contrary to the "book on Tuesdays" rule that you've probably heard before.

Of course, these are averages and should be taken with a grain of salt. With that said... we take no chances in this group. We book early.

6. Find A Place To Stay

Airbnb allows you to search within a price range, so this will be another budget conversation with your friends. Find a few in the mid-range, a few in the lower range, and a few "um, this is the best Airbnb I've ever seen" options. Figure out what's worth the splurge and what aligns best with your priorities. If you book cheaper accommodations, you'll have more money to do activities. If you go all fancy-pants, expect to do a lot more lounging.

7. Plan Some Activities (Aka, Figure Out Your Budget, Part II)

Now that you know where you're going and how much the basics will cost, you'll have to set a budget for spending while you're there. Now might be the time for a survey! Add all of the activities you have been discussing and have your friends rate their level of interest. Then, do some research about how much they'll cost. For "big" activities, book in advance; for smaller activities, I tend to figure it out as we go.

8. Make A Loose Itinerary

Sample itinerary from our Arizona trip c. 2014

I say "loose" because for me, this is about hanging out with my friends, not seeing every single thing in Hawaii. Again, Google Docs are your friend because you can collaborate in real time.

8. Go On Vacation & Make All Of The Memories

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This is the fun part!

9. Settle The Bill

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Some people keep a manual ledger, some do "I'll get this, you get that," and some save receipts and settle at the end of the trip. It depends on your comfort level with splitting costs. If you want to be meticulous about it, PayPal makes it easy to send and receive money as you go, so there's no mystery or tension over who's getting dinner.

And that's it! Though we're still in the "booking flights" phase, we have something to look forward to for the next few months.

Conclusion: If you're thinking of booking a trip with your besties, just do it. You will not regret it. In the meantime, I'll be over here watching Blue Crush on repeat. Happy travels!

This post is sponsored by PayPal and Airbnb.

Offer terms: Book an Airbnb via PayPal using the coupon code MEETHALFWAY and get $50 off your stay of $200 or more! Offer valid for U.S. residents only. Bookings must be made within the offer period on eligible bookings. Must have a valid Airbnb and Paypal account, use the coupon code at checkout, and use PayPal as the sole method of payment. Limit one code per person. Restrictions apply. Learn more at paypal.com/meethalfway.