All the Details On Our Family’s Multi-Generational Trip + 10 Tips For Yours

Empty Nest Blessed by Suzy Mighell
group of people gathered around fiona from shrek at starlight mountain theatre in garden valley idaho
The whole group with the one we all came to see!

Whew! We’re just back from a five day, nine-person, multi-generational trip in the mountains of Idaho. We took a group ranging in age from 21 to 81, and we made memories to last a lifetime. The best news of all? We still love each other!????????

Today I’m going to tell you where we went and why, and I’m going to share my tips on how to navigate a multi-generational trip. I’m going to be honest about what we did well and what we would do differently next time.

I’ll also share my looks from the trip. (But, of course????!) Everything fits TTS unless indicated. As always, click the pink links or any image for more information.

Tip #1: Know These Things Before You Go

We’ve vacationed with our family a lot. (but never with nine family members!) Here are a few things we’ve learned over the years:

  • Honor your differences. Whether your family is into the Enneagram, Myers-Briggs, Strengths Finder, or what have you, understanding different personality types, strengths, and temperaments will help you enjoy one another while minimizing irritation. (Even if you just remember who’s an introvert and who’s an extrovert, it’ll help!)
  • Everyone’s idea of a relaxing vacation is different. Some people like active vacations where they immerse themselves in activities that they would never do at home. Some people like to read in a lounge chair by the pool for hours. Still others like to spend time in deep conversations that the pace of normal life doesn’t usually allow. All of these are valid! Others may not relax the way you do, but they’re probably still relaxing in their own way.

Tip #2: Unite Behind a Common Purpose

What’s the main purpose behind your multi-generational trip? Are you celebrating a 50th wedding anniversary? Is someone having a milestone birthday? Are you going to share a common experience that you love, like fishing, hiking, or sightseeing? It’s important to keep the common purpose in mind as you plan.

woman and man on either side of fiona from shrek at starlight mountain theatre in garden valley idaho
Our daughter, Becca, played Fiona in Shrek the musical.

Black Long Sleeve Tee | Black North Face Fleece Jacket (40% off) | High-Rise Floral Jeans (60% off – now $39.99!) | Black Allbirds Wool Tennis Shoes (Amazon alternative HERE)| Necklace (Similar less expensive HERE)| Earrings

The primary purpose behind our multi-generational trip was to support and cheer on our daughter, Becca, as she performed in several productions at Starlight Mountain Theatre in Garden Valley, Idaho. Several members of our family had never seen her perform at a professional level, and we knew she would feel so loved if we were all there to encourage her. (She did????!)

shrek and fiona at starlight mountain theatre in garden valley idaho
Our daughter, Becca, as Fiona, with Shrek.

Where We Went and Why

Way back in January, our daughter, Becca, who is a working (and self-supporting!????????) musical theater actress, booked a summer stock contract at Starlight Mountain Theatre, an outdoor theater in beautiful Garden Valley, Idaho. When she booked it, we immediately planned a multi-generational trip, booked an Airbnb that would sleep all nine of us????, and started booking flights.

When THE COVID hit later in the spring, Becca was touring the country in a show with a children’s theater, which was canceled. She fully expected the summer contract would be canceled as well. But with no cases in remote Garden Valley, and most Idaho cases centered in Boise (1½ hours away), the contract was delayed, but remained in place. She reported on May 15th and jumped right into rehearsals.

group of people gathered around the wardrobe from beauty and the beast at starlight mountain theatre in garden valley idaho
Becca played the Wardrobe in Beauty & the Beast.

In late June, we headed out to Garden Valley, Idaho to see her as Martha Cox in Disney’s High School Musical (Watch the movie version HERE.), as Fiona in Shrek, the Musical (Watch the Broadway version HERE.), and as the Wardrobe in Beauty and the Beast (Watch the Broadway version HERE.).

woman wearing lilly pulitzer luxletic pullover in dallas love field airport
Travel Look – Headed to Idaho! It was warm the day we arrived, so I wore a short sleeve tee and removed the pullover when we got there.

Hot Pink Short Sleeve Tee | White Jeans | Half-Zip Luxletic Pullover | Earrings | Customized Tote Bag

flycaddy on the back of an airline seat
Even before THE COVID, I never traveled without my FlyCaddy! It goes over the tray table of the seat in front of you, providing a clean, convenient spot for your in-flight essentials. It’s made of stretchy fabric, so when you open the tray table, you not only have a clean, covered surface to use, but your in-flight essentials stay in place!

FlyCaddy | Phone Case | Rose Gold Monogrammed Pop Socket | Kindle| Kindle Cover (Similar) | Customized Tote Bag

Tip #3: Do Your Research

We were traveling to an area of the country we were unfamiliar with, and going to a remote, rural area made getting info about our destination challenging. It quickly became apparent that we were going to have to play it by ear somewhat and be flexible. In a big group, some people are bound to prefer that kind of trip, while others do not.

Bob and I did what we could, putting together an itinerary—with everyone’s’ flight info (we were on different flights), and links to anything we could find links for: our cabin, area restaurants, places to shop, etc. I would recommend doing this! The mistake we made was stopping there!! Looking back, we should have done some kind of family Zoom meeting beforehand to make sure everyone was on the same page. More on that later.

woman wearing black sweatshirt with blue heart standing on deck of a cabin in the woods
This is the deck on the back of our cabin!

Blue Polka Dot Heart Sweatshirt | Jeans (Similar – 55% off) | Black Allbirds Wool Tennis Shoes (Amazon alternative HERE)| Earrings

Tip #4: Anticipate Potential Problems

woman wearing whbm floral jeans sitting on wooden steps
In the lighting, my white tee, sweater, and tennies look silver! They’re white!

White Crew Neck Tee (2/pack) | White Crewneck Pullover Sweater (Similar)| Floral Jeans (60% off and still available in all sizes!)| White Allbirds Mesh Tennis Shoes (Similar Amazon Alternative HERE.)| Faux Pearl Cluster Stud Earrings ($7.99!)|Necklace (Similar less expensive HERE) | Apple Watch

We checked with our Airbnb host about WiFi, and he told us the WiFi in the cabin was excellent. He did not tell the truth! It was a challenge the entire trip! The good thing was that it kept us off our phones and talking to each other! The bad thing was that when people had work emergencies (or wanted to post something on Instagram ????????‍♀️), it was extremely frustrating!

We knew from talking to our daughter that we would have poor cell service in the mountains of Idaho, but none of us realized how poor it would be! (We basically had none outside of our cabin or in the town.) This made communication a constant challenge! Looking back, we probably should have anticipated this and brought walkie-talkies just in case.

two women dressed in tie-dye shirts standing on the deck of a cabin in the woods
This is my beautiful sister-in-law, Laura! She is an extraordinary woman!

My Tie-Dye Sweatshirt (Comes with matching bottoms, not pictured.) | 9″ Pull-On Jeans Shorts | Tennies (Similar) |Necklace (Similar less expensive HERE) | Pearl Stud Earrings |Laura’s Tie-Dye Vneck Tee

Tip #5: Know Your Group

We went with a group that ranged in age from 21 to 81! Everyone in our group was an adult, so everyone had personal preferences for everything from food and drinks to activities and bedtimes. We agreed that we wouldn’t cook dinners – there were enough restaurants nearby, and nobody wanted the stress of working within dietary restrictions or preferences.

Even though we were all there to see and support Becca, looking back, we realize that everyone in our group had a slightly different mindset about the trip. For some in our group, it was their family vacation for the summer. Others in the group had specific activities they really wanted to do. Still others wanted as much “togetherness” as possible. Bob and I wish we’d been more aware and more mindful of these varying mindsets. We could have done that with more advance communication. More on that later.

woman in pink marley lilly pullover sweatshirt

White Crew Neck Tee (2/pack) | Monogrammed Half-Zip Pullover ($10 off right now)| Jeans (Similar – 55% off) | Navy Allbirds Tennis Shoes (Similar Amazon alternative HERE) | Pearl Stud Earrings

Tip #6: Someone Has to Lead

Bob and I were the trip organizers, and we decided early on that in a big group like that, someone’s got to lead at least some of the time. What we didn’t want was to get into a “cruise director” mindset!???? Our idea was that everyone on our trip was an adult, so we should let everyone be an adult and pretty much do their own thing. We knew that (because our family enjoys one another), there would be open invitations for everyone to join one other for anything from hiking to fishing. (Which happened!????????)

Since we had specific activities every night (Becca’s shows), it provided some structure to our days. We let everyone know when we would be leaving for dinner and kept track of the show tickets, etc., but that was pretty much the extent of our “leadership.”

Looking back, I wish we’d delegated more. Since we were going with a group of adults, we should have asked the people who really enjoy planning vacations for help! Those who enjoy researching restaurants could have been in charge of that. Others who love activities could have researched those and made some plans. The people who love games could have been in charge of bringing those. And so forth.

group of adults gathered around a table at a restaurant

All was humming along fine until we tried to do an all-day, full-group activity! We planned to drive about two hours through the mountains to a beautiful, clear lake we’d heard about and wanted to see. Immediately, there were differences in opinion about what time to leave, where to eat, etc! We did have a great meal at a cute restaurant, but by the time we got to the lake, it was so crowded, we couldn’t find a parking place. We basically had to turn around and head home. Everyone was disappointed.

woman wearing marley lilly y'all sweatshirt posing by a pine tree
Our cabin had the prettiest river running right behind it and we loved sitting on the deck and just listening to the sound of the water!

Y’ALL” Elbow Patch Sweatshirt (Under $20!)| White 9″ Frayed Hem High-Waisted Shorts | Navy Allbirds Tennis Shoes (Similar Amazon alternative HERE) | Pearl Stud Earrings | Necklace (Similar less expensive HERE)

Tip #7: Communicate in Advance With the Group

Looking back, as I said earlier, it would have been helpful to know if there were activities and mindsets that group members had going into the trip. Instead, we let our previously distributed itinerary suffice. It wasn’t enough. Face-to-face (or virtual) communication would have been better.

We should have had a family Zoom meeting a week or so before leaving and asked everyone two questions:

  • Are there any activities you really want to do?
  • What are you most looking forward to?

If your group includes infants or small children, this is even more important! Be sure to check with parents in advance on things like naptimes, noise level requirements, eating schedules, etc. Then make everyone in the group aware of those things. The same goes if your group includes members with health issues that may affect the group at large.

woman wearing marley lilly pink fleece sweater posing in the woods

Monogrammed Tunic Sweatshirt (Also comes in gray.) | Jeans (Similar – 55% off) |Pink Allbirds Mesh Tennis Shoes (Sold out. Amazon Alternatives HERE and HERE.) |Sunglasses (Similar) | Faux Pearl Cluster Stud Earrings ($7.99!)

Tip #8: Adjust Your Expectations

When you go on a family vacation, being together as a family is the main point????????! The purpose of a multi-generational family trip is to grow in your relationships with one another. It’s important that everyone go into the trip with this understanding and expectation.

It’s also important to realize that it is inevitable that someone (or more than one someone) will be disappointed or frustrated at some point. Leading a trip like this is fun, but it can be stressful! As the famous saying goes,

“You can please some of the people all of the time, you can please all of the people some of the time, but you can’t please all of the people all of the time”.”

John Lydgate
woman wearing draper james navy and white gingham sweatshirt posing in the denver airport
Travel look – headed home! As you can see, there weren’t many people in the airport!

White Long Sleeve Crewneck Tee | Lightweight Gingham Sweatshirt (Amazon Alternative HERE.)| Jeans (50% off!) | Navy Allbirds Tennis Shoes (Similar Amazon alternative HERE) |Faux Pearl Cluster Stud Earrings ($7.99!) | Necklace (Similar less expensive HERE)

Tip #9: Be Flexible

On a multi-generational trip, everyone in the family will need to be flexible and compromise at some point. There will be times when the needs of the group may have to take precedence over individual preferences. This might include the type of accommodations, activities, meals, and more. On our multi-generational trip, for example, five people shared one bathroom! As one of two girls in that group of five, I’ll tell youby the end of our trip, things got very hairy in that bathroom ????!

Tip #10: Enjoy!

21 year old with cookie cake
My nephew celebrated his 21st birthday right before we left, so his mom picked up a (random!) cookie cake so we could celebrate!

Without a doubt, the best thing about a multi-generational trip is that everyone will get to know one another on a deeper level. Our family had conversations that might never have happened otherwise. We gained insight into one another’s lives and interpersonal relationships. We learned to understand each other better and appreciate each other more.

There were definitely things we’d do differently next time, but overall, we had so much fun. We came out the other end with sweet memories and a whole lot of gratitude for our family.

Have you ever taken a multi-generational trip? I’d love to hear your tips! Please leave me a comment, and share!

Blessings,

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Suzy Mighell

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12 Comments

  1. Suzy, I am so glad you enjoyed your trip to Idaho. We have friends whose son, Yale, was in the productions with your daughter. We love going up to Starlight. There is nothing else like it, the stage, the mountains, the air. Except for the Idaho Shakespeare Festival setting in Boise. Maybe one day your daughter will get a contract and perform there!

    1. Sheri,
      How fun that your friend Yale performed with Becca! She has had such a wonderful experience with Starlight! We feel so blessed to have been there, and I know she does too!
      Thanks for reading and leaving a comment!
      xoxo Suzy

  2. Great post! This is my favorite type of content that you do,
    I am the planner in my family for these kinds of trips and it is STRESSFUL! I always feel responsible if things don’t go as planned, or if places, events, restaurants, etc are a disappointment.
    We took a multi-generational cruise to Alaska last summer. (Thanks for all your great tips, of which I used a TON!)
    Cruises (before The Covid) are great for trips like that because there is something for everyone. We planned a couple of dinners as a big group but everyone planned there own excursions, etc. There were hurt feelings when an aunt and uncle didn’t realize we would be taking a family photo and felt like they did not bring appropriate attire. I apologized profusely and felt terrible that I had assumed everyone would bring at least one “dressy” outfit. Communication!! Oh well!
    The only other pickle is deciding how to handle finances when your grown kids are at different stages of their career and have different financial situations. I would love to hear some 20 somethings take on that. You want to be fair and equitable, you don’t want to make them feel as if they are being disrespected as adults, and yet, sometimes, if you want to do things as a big family, you may need to gift some part of the trip in order for it to happen. Tricky!

    1. Kellie,
      Thank you for your insightful comment! I love doing really in-depth posts like this too, but there are also people who beg for more fashion and beauty content! I do try to spread it around, and I’m so grateful for your feedback!
      I loved your comments and I so agree that cruises might just be the ideal multi-gen trip – everyone has some privacy with separate cabins, there are a variety of excursions to choose from, and there’s always something to talk about at dinner! Here’s hoping they’ll be back sooner rather than later, right?
      I loved your point about finances, and have never really thought about that aspect! I’m going to think on that and ask a few of the smart 20-somethings I know what they think about that!
      Thanks so much for reading and commenting!
      xoxo Suzy

    2. Great comments and yes the finance situation is a tricky one esp when like you say grown children all in different situations. We are away for 8 nights with our children and their spouses and two grandchildren. We decided to pay for all the accommodation and the kids have to take care of activity expenses and cafe visits and their own fuel costs. Holidays are expensive and it’s so nice when kids want to holiday with us and their siblings. We are all traveling in our own cars which gives everyone some space and own time but have a big house booked. I’ve booked separate motel units for our one night stays

      1. Elizabeth,
        That’s similar to what we did! We paid for accommodations and picked up the tab for meals out, but everyone else had to pay to get themselves there and also buy their food, drinks, etc. That was a good way to do it, I think!
        xoxo
        Suzy

  3. I’d love to know what you packed for the trip. Was luggage a problem with that many people?

    1. Gina,
      Great question! You can see from the photos in this post pretty much what I took! It was A LOT, because we wore layers and added/stripped things off as needed throughout the day! Add to that – my Becca had things she wanted us to bring her and things she wanted to send home! I’m embarrassed to tell you that Bob and I had FOUR suitcases! (To be fair, he also had to pack his waders and other fly-fishing gear!)
      Thanks for reading and leaving a comment!
      xoxo Suzy

  4. Great post, Suzy! Even though there were a few bumps, it sounds like a wonderful family trip! And thanks for sharing ways that it could have been better. Good advice!

    1. Shannon,
      Thanks so much for your kind words! It really was good, but as always, I wanted to share what I learned! We’re thinking our next multi-gen trip might need to be a Disney Cruise! What do you think?
      xoxo Suzy

  5. Some great tips! We are about to head away for six nights with ten of us – our children and their spouses and Two grandchildren aged 5 and 2. It will be fun but I know having two little ones along can add stress especially with sleep times and long car drives. But we also think how cool is it that our kids and their spouses want to do a holiday with us .

    1. Elizabeth,
      That sounds fun, but yes! There will be some stress in that for sure! We felt so blessed that everyone wanted to go as well! So cool! Have a wonderful trip and thanks for your comment!
      xoxo
      Suzy

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