Cape Cod in 2015

“I’ll plan it!” said no one ever. The idea of a family vacation is fun but the thought of planning it is a stressful burden no one is ever happy to take on. Scheduling, researching blogs, booking accommodations, considering everyone’s preferences and budgets all over too many phone calls, group texts, email, and social media. And that’s before considering what the kids want. The overwhelming list of things to think about can be as long as the number of people in your extended family.

It’s been over three years since my last family vacation and according to Wait But Why’s post, I most likely have 300 days left to hang out with my parents. Sad but likely. So Tim and I decided to make a family vacation not only a reality but also a stress-less one by using DIEMlife®.

Here’s how we streamlined the planning of our family vacation without anyone losing their minds.


1. WE MADE IT A Quest®
There’s a kind of power that comes from putting your goal in writing or on record somewhere. We titled this one “Family Beach Vacation” and added a short description and a bunch of Milestones. We checked off each Milestone as we completed it.

Description: “Enjoy the rolling tide with family and friends. Add your favorite photos of previous beach vacations to the gallery to keep us motivated. Booking updates coming soon!”
-Choose a date
-Choose a location
-Book a place to stay
-Create a list of needed items and decide who is bringing them
-Create a list of things to see and do
-First night reunion and confirm plans for the vacation
-Return home with a lifetime of memories

Under Settings, we selected the Invite-only option so only those we invited will be able to see the details.

In the Invite-only option, we added in the names of our family members and invited them to the Quest®. All they had to do was click “Start” to join it after they logged in or signed up!

Over twenty of us are going on this vacation. Can you imagine all of us trying to have a well-moderated and productive discussion in person, over the phone, or by group text about anything? Once everyone accepted our invite, we used the comments to plan the first two Milestones. This allowed us to take turns asking and answering questions (without talking over each other) and made it really easy to lock down the date and location of our vacation. We’re still using the comments to plan the rest of the details using Milestones. This helps us figure out other group decisions like who’s coming for which dates and where to eat for our big family dinner.

Date and location, check and check. Next up, accommodations. One of our siblings stepped up and helped make the booking for the house we’re staying in. Instead of us paying her back in different ways like Paypal, Venmo, QuickPay, check, and cash, everyone paid her back in the Quest® by using the “Back Me” button. We were able to quickly send her money and she didn’t have to deal with the headache of keeping track of who gave her what where. We’re going to do the same for during and after the trip for shared meals and activities. It’ll help us organize who owes who what.

It’s T minus three weeks from our vacation. Photos of the beach, of where we’re staying, of things we want to do, and our past vacations are being uploaded and the excitement is building. And when our family vacation starts, there will be new memories shared in the photo gallery for us to revisit in the years to come. If it’s cool with our family, maybe we’ll make this public so you can see them too!

In the past, planning family vacations would cause undue stress. This is the first time we’ve done this efficiently and with almost no drama. C’mon, it’s family. There will always be a little drama.

If you and your family have avoided planning a get together because of the drama, try making it a Quest® next time. We think you’ll spend less time feeling frantic and scattered and more time thinking of what new memories you want to create with your loved ones.

Let us know if you try this out and it works!