How to Plan a Destination Classmate Reunion

February 24, 2024   1 Comment »

How to Plan a Destination Classmate Reunion

May 22, 2018 1 Comment »

high school 1988
Me in 1988

The year was 1988. We had big hair…lots of hair. I used to spend an hour each morning curling my already permed hair into even tighter little curls with a curling iron the size of my pinky finger. I really did want to be ‘Baby’ from Dirty Dancing even though I had stick-straight hair.

And of course, while everyone was listening to George Michael and Whitney Houston, I only had ears for the Beatles and John Lennon. I always had to be different – even at 18. It was the year we graduated and our entire lives living in the protection (and annoyance) of our parents were coming to a close.

I was a kid who spent a lot of time fantasizing about getting older and being on my own. I wanted to rush into adult life and all of the excitement that I hoped went along with it. When I finished high school, I really didn’t want anything to do with high school again. I went out of state to University where I knew no one, and never came back to my hometown except for the occasional quick visit.

Life goes on…

And when my parents moved, there was never a reason to go back. I had moved on – never to really return to that time. It’s not that I had a horrible high school existence – it was fine. I just was ready to move forward, not back.

I continued to pass on High School reunions because honestly I just had no interest in them and I had no desire to go back to Peoria when there were so many other places I wanted to go in the world with my precious free time. I didn’t want to go back to some formal event where I didn’t really get beyond a few niceties with people I hardly knew.

Through the years I stayed in touch with a few of my close high school girlfriends as they went through college, boyfriends, marriage, kids, and now aging parents. We exchanged holiday greetings and occasionally ran into each other on work trips or weird coincidences. There was talk about reunions from time to time. Some of them had gone to the earlier high school reunions, but I always successfully avoided going.

Class Reunion Ideas – You Don’t Have to Invite the Whole Class

class reunion
How About a Classmate Reunion?

But then my girlfriends came up with a class reunion idea I could get behind – a small, intimate high school reunion. We weren’t inviting the whole class or doing some big gala, it would be simple instead. No name tags were required. We’d just see the people we wanted to – my closest friends from high school, not the whole class; more aptly named a classmate reunion.

There was one more puzzle piece to this reunion that excited me – it would not be in Peoria, it would be at a destination we could all meet at and experience.

If you’ve heard of destination weddings, why not a destination class reunion?

How to Plan a Destination Class Reunion

I loved the idea of traveling somewhere new for a small class reunion – it met my need to explore new places and to see just the people who I really wanted to spend time with. However, even though this was a small group, it didn’t seem to make the planning aspect of it any easier! We all learned a lot from doing this first Destination Class Reunion; here are our best tips.

1. Plan Way in Advance

Getting 5 women’s schedules to mesh was harder than peace talks with North Korea. We were 5 women with busy lives – busier than I ever imagined. We started this planning process 2 years earlier and it finally came together this spring. I had a full travel schedule that took me out of the country quite a bit and when I wasn’t traveling I had work to do in Denver where I needed to sit still. The other 4 women all were raising kids AND working.

We started an email thread listing available times for each of us and one of us took the lead in pulling it all together to determine where there was overlap. We were only looking for a weekend – but 5 schedules to intertwine was harder than you think. We all had to sacrifice a bit, and eventually came up with a weekend that would work!

Class Reunion Planning Tip: Start a Google calendar and have everyone put in their available times to figure out what works best. It’s likely easier to put in the weekends that work as opposed to the days that don’t work based on my experience with our group.

2. Pick the Destination

We all live in different parts of the US (California, Colorado, Illinois, Kansas, and Wisconsin), and we talked about a number of areas we could all meet. The strategy here is to either pick a place everyone wants to go to (dream destinations like New York, New Orleans, or Savannah) or pick a place that is geographically convenient to everyone. You’ll want to make sure that flights are generally easy for everyone.

destination class reunion
How about Colorado for a destination reunion?!

For us, picking a destination in the middle of all of us seemed to work best. Since Colorado was still new to me, I lobbied for my new state. After all, I had barely had time to explore Colorado yet, so I thought it would be a great opportunity. Denver has a great airport so flights would be simple for everyone and we also had the mountains!

I thought it would be great to choose a mountain town where we could meet. Ski season was wrapping up in April and Summer season hadn’t quite begun yet; it was mud season in Colorado! Mud season is a time known for lots of rain and melting snow in the mountain towns, but also a time for fewer people, and good deals on lodging and restaurants in Colorado.

I chose Vail, only 2 hours from Denver Airport – it’s a beautiful drive into the Rocky Mountains and would have plenty of lodging options. Outdoor activities abound in Vail, but also a lovely town area with incredible restaurants and shopping for those more ‘urban focused’.

See a side of Vail in the summer you’ve never seen before – Piney Lake

3. Get Comfortable in a Condo

One thing that mountain towns have a lot of is condos! And since class reunions are about spending a lot of time together just hanging out and reminiscing, you want something spacious and comfortable.

We booked a big four-bedroom, four-bath condo at Antlers at Vail. It was right on the mountain along Gore Creek and had a giant kitchen with lots of great shared space to hang out and be comfortable. Plus, it had a fitness center and yoga classes offered through the nearby gym. Finally, it was right along a walking trail through town. They also had bikes we could use whenever we wanted and a great pool and hot tub!

The condo was the perfect answer to having a space that was conducive to just hanging out together. With the kitchen, we could cook if we wanted to or just hang out on the many couches or balconies reading old yearbooks and talking.

Plan your weekend in Colorado Springs: where to eat, stay, and adventure

4. Bring Yearbooks and Pictures

Did you know that Friend Appreciation Day is April 11th? What’s that, you’ve never heard of Friend Appreciation Day. That’s probably because I made it up when I was 17 years old. Yes – that’s right, I made up an entire holiday and my girlfriends and I celebrate it every year. We’d dress up in our best dresses and I’d drive to pick up all of my best girlfriends (I’d even bring them flowers!) and bring them to my house for the evening. My mother and I would cook a special multi-course dinner for everyone, and then we’d have a sleepover.

Part of the fun of a class reunion is reminiscing about old memories, and I had totally forgotten about Friend Appreciation Day until we started looking through pictures – then it came rushing back to me!

class reunion tips
Then and Now

Pictures jog memories, so someone will need to be responsible for bringing the yearbooks! Even though I don’t have many material goods in my little studio apartment, for some reason I do have my 4 years of high school yearbooks. I dug them out from under my bed and brought them with me to Vail. In addition, each of us dug up old photos from parties, dances, and sports.

“There were after-game dances?” I asked Tiffani in disbelief as I was looking at the yearbook pictures of people partying in the gym.
“Yes, they were held in the gym,” Tiff answered.
“After every game?” I followed up still incredulous.
“Yes,” she answered.
I looked around at everyone else and asked, “Did you guys ever go to after-game dances or know about them?”
I got blank looks and “no’s” all around. Granted – Tiffani was likely the most popular out of any of us. She was a cheerleader in high school while the rest of us were jocks and generally just good students who weren’t necessarily popular. And clearly, the rest of us had not been aware of after-game dances. We all laughed about this and continued to flip through the yearbooks.

The yearbook trip down memory lane was hilarious as we tried to remember class mottos and teacher’s names. There were many questions about “whatever happened to…”, “who dated x”, and plenty of laughter about fashions. For some reason the fashion our senior year was Puritan–esque; big floppy collars as if we were pilgrims. Not sure what we were thinking…

5. Plan Some Active Activities

Luckily we were all quite active yet. Maybe that had something to do with we were all into sports in high school. But I was happy everyone was up for getting outside and really enjoying the best of what Colorado and Vail had to offer.

We started the mornings off with yoga and a little zen. It’s funny how the times have changed, in high school we all did morning aerobics – the newest fad in the 80s. Now here we were taking our 48-year-old bodies and doing downward dog. I wonder what the next fad will be – forest bathing?

In addition to yoga and walks along the creek, we also got out and did one of Colorado’s most famous hikes – Hanging Lake.

Mud Season Hiking Tip: During mud season make sure you check with the front desk or locals about what trails are open. Some take longer to open due to the mud and melting.

6. Have a Few Planned Discussions

Make sure that you leave ample time to just sit around and talk. We had a number of topics where we sort of went ‘around the circle’ to catch up on our respective lives.
We had topics about careers/jobs; it was fascinating to hear the routes that everyone went and ended up in after college. It reminded me once again that life is full of twists and turns.

Another popular topic was to go through the status of our extended families. After all – in high school, you become pretty familiar with the parents and siblings of your friends. So a ‘where are they now’ update is necessary. Kids are of course a really popular topic too. I honestly thought I might not have much to add in that department but I actually surprised myself and was not only fascinated hearing about all of their kids, but also sharing some about my nieces who are the closest thing I have to kids!

And of course, since we were remembering the 80s I had to tell my story about meeting our heartthrob – Andrew McCarthy!

high school reunion ideas
A blast from the past…our high school heartthrob…

7. Have a Music Playlist

The whole weekend was about reliving the 80s, so it’s great if someone has an 80s playlist. I just looked on Spotify and found an 80’s playlist. Soon we were all reminiscing about Prince, Madonna, and Michael Jackson while singing along.

8. Bring Old Movies

The condo had a huge flat-screen TV and luckily we brought old movies from our high school years. We made our favorite teenager junk food from the ’80s (popcorn and M&Ms) and watched John Hughes movies.

destination reunion
Snacks from 1988

As I watched a young Molly Ringwald lament about people forgetting her birthday, I thought about how much better this small destination experience was than the typical high school reunion. I never would have been able to live through a night of dinner and general niceties of answering the same questions over and over again – where do you live, how many kids do you have, what do you do, etc. Kill me.

Instead, we had a small, intimate, experience in the beautiful Colorado Rockies where we could relax and really get to know each other again. We were all transported back to the 80s in a good way while making a transition to the present and getting to know each other again. It wasn’t niceties; it was real.

I actually surprised myself with how much I enjoyed being around the kindred spirits that helped shape me. I had forgotten how much we really did have in common and shared. As we drove back to the airport, we all agreed that we would do it again. So the planning begins again…

Planning Reunions in Colorado

You can use this destination idea for any kind of reunion actually! I planned a family trip / reunion in Colorado a few years back and it was perfect!
Consider Antlers Vail Resort and their spacious condos for a reunion!



I was a guest of Antlers Vail Resort during my stay, however all opinions expressed here are my own.

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