Episode #355 – Vacation 101: How We Took 5 People to 5 Cities in 3 Countries on 2 Continents in 14 Days

This is a vacation 2024 recap, otherwise known as that time that I took five people to five cities in three countries on two continents in 14 days.

Welcome back, my friends, to the Brilliant Balance show. I am happy to be back behind the microphone this week after a couple of weeks traveling with my family. As you can tell from the title of this episode, that’s what I’m going to talk about today. As I get ready to share this episode, I admit that I really worried it would be self-indulgent to record a podcast episode—maybe even two, as the case may be—about our family vacation. I was talking with my team about this, and I got a really important reminder from the women on my team.

Here’s what they reminded me: as I was talking to them about some of the things that had happened on the trip, they were asking questions that I wanted to share. This episode has the opportunity to do two things for you as a listener. One is, hopefully, if I do my job well here, to inspire you to take a big trip with your family—whatever the definition of “big” is for you, whatever maybe stretches your family in a way you haven’t done before. If I can provide the inspiration for you to do that for yourself, that will mean everything to me. The second thing is that I can help equip you to do that. Through what we’ve learned in this travel experience and several others, I can provide a thread of practical guidance—some ideas and tips that will be there for you when you start planning, dreaming about, and then ultimately executing a trip with your crew. So, that was kind of the permission slip that I needed to share this, and I hope that you love it.

If you’re not interested in hearing about our travels, how we made this trip possible, and some of the ways I think we really helped make it exceptional, you can skip this one, right? Permission granted. But I am really excited and genuinely delighted to share with you what this experience was like with my family over the last couple of weeks. I’m pretty fresh back. I’m back less than a week as I’m recording this, so the memories are still really fresh and new. They haven’t really fully faded into the background yet. I’m just going to let this surface. I have a couple of points written down that I want to make sure I share that are on the practical side of things, and then I’ll fill this in with some stories from the trip that hopefully will add some color commentary behind the whole thing.

Here is what I said is the headline, to set the stage for this particular vacation and trip that we took. The last time we did a really big trip as a family was in 2019. So, think about where that puts us in history, right? We are one year pre-COVID. At the time, we had been talking about doing a trip to Europe with my kids for years and years. I really thought that 2020 might be the right year to do it, and as 2019 was on the horizon, there were some reasons that made us think maybe this is the time to do it. I was going back and forth. Ultimately, my dad, a sweet man, is the one who pushed me over the edge and said, “Look, I think you should just do it. If you do it, you’ll never regret that you did it. If you wait, you never know what could happen.” Boy, were truer words never spoken, because one year later, of course, we were in the depths of COVID, in the middle of a global pandemic, everyone in quarantine. It would have been an impossibility, and I think it would have taken several more years before we would have even thought about venturing out of the country.

So, in 2019, we took our young family to three cities: Paris, Rome, and London. I called it the Highlights Tour of Europe because I felt like those were three places that my husband and I had already been. We were on familiar territory. We knew what the key highlights and sites were. We knew our way around a little bit. In at least one of those countries, we spoke the language, and I speak enough French to be dangerous. So, we were on solid ground. We had an exceptional experience with the kids during that trip. Our youngest, when we took the first trip to Europe, was, let me get this right, nine. The other two were 9, 12, and 14—maybe they were like 9, 11, and 14 at the time we traveled, but close enough. They were old enough to remember things, but also young enough to do whatever we said. They were along for the ride. We planned the whole thing on our own. My husband and I planned that trip ourselves. We booked the hotels ourselves. We figured out all the intra-country and inter-country transportation ourselves, and we had a fantastic trip, one that many times over the last five years I have said, “I am so glad we did that.”

But this time, as we started planning to go back, the kids are five years older. We’re five years older. We honestly hadn’t been anywhere really, really exciting since that trip. My husband and I both felt like we wanted to go to places we had never been before. We wanted this time to be a fresh experience for everyone. We spent some time thinking about where to go and ultimately decided to hit three different countries and then five cities within those countries in total. We were able to bridge two continents, Europe and Africa. Our three countries on this trip were Spain, where we went to Madrid, Portugal, where we went to three cities: Porto, Lisbon, and the Algarve, which is the beach and coastal region in the south of Portugal. Then we hopped on a plane to Africa, into Marrakech, Morocco. That’s where we went on this trip.

Everyone was very excited once the plans started getting made. This time, we really involved the kids a lot more in choosing where we were going to go. We gave them a couple of different options and also planned what we were going to do. Just as a backdrop, yes, we’ve done this once before. That was three cities and three countries all within Europe, all places we’d been before. This one was a bit more of a stretch, adding a couple more cities and a few extra days beyond the trip before. It was the first time that my husband or I had ever been on the African continent, so it was like adding a new element to our bucket list as well. Although I think we would probably need like five trips to Africa to hit all the different experiences that we could have there across the full continent, this was certainly a very unique and singular one in Morocco.

What I want to talk about today is some of the principles or headlines of lessons that were important as we planned this trip, which really allowed it to be one that I think we’ll always remember. I think it went very well. I may come back for Episode 2 and do a deeper dive into one particular thing that was the secret weapon behind the entire experience.

The first thing that was absolutely critical to getting a trip like this done was setting expectations. We sat down as a family several times. My husband and I had conversations with each other, individually with the kids, and collectively about what it really means to travel with five people for that long. What was important to everyone? What were the things that were table stakes in the experience? From our recollection of having done this before and from the way the kids were anticipating it, what did we think might be some of the challenges we would face and how were we going to handle those? I call this the five people, five experiences rule. It really comes from my godfather, who, during one of the earlier times we were traveling as a family of five, said to me, “The thing you have to remember is no one is going to be having a peak experience at the same time. When you look across the table at people or maybe you’re out having an experience somewhere at a particular site or you’re on an airplane, someone is going to be having one of their best moments of the whole trip. Someone might be having one of their worst moments of the whole trip, and the other people are going to be somewhere in between.” If you can get clear about that upfront, that you are taking five people who are going to have five unique experiences and do not attempt to synchronize those, you’re going to come back a lot more stable. He was 100% right about that.

When we’re dealing with kids of these ages—my kids are now one and have just turned 14, I have one who’s about to turn 17, and one who’s 19, soon to be 20—they have such different interests. There were very different things that were going to be their favorites. There were different things that were going to be their least favorite, that they would just have to tolerate. They have different mood cycles around what makes them anxious or what calms them down, their own highs and lows. I think it’s such an exercise in the art of compromise, of getting some of what you want, but not all of what you want, and also in turn-taking. In learning as a family, when is it our time to get exactly what we want, and when do we need to be pleasant to everyone, even when we’re not getting exactly what we want at that moment?

That was a really important thing. There are some nuances to traveling with teens. Teenagers are, in some ways, like mini-adults. The level of autonomy they are accustomed to having at home gets compromised when they’re traveling as a crew, at least it did for ours. For example, my kids all have their own rooms. One of them is at college most of the year. Even when they’re living in our house, they have their own spaces. They have a lot of their own autonomy to decide when they wake up, when they go to bed, what they’re going to do for certain aspects of their day. When you travel together, especially for an intensive period, there are more constraints and boundaries around what you can do. You have to be really clear upfront about how you’re going to navigate that. We really thought a lot about it and talked about it in the trip planning process, and that helped quite a bit. When you are clear about expectations going into a trip like this, it can really make a huge difference.

The second thing that I think made a big difference is that we had a balance of activities. As we were planning the days, what we really thought about was how to get a nice mix between activity time, downtime, and some time to rest. In each place, we stayed somewhere that had a pool or some area to cool off, relax, and not have to be in motion for a period of time. We had a nice balance of scheduled activities and unscheduled downtime. In some of the places, we planned and booked things like guides and drivers. In others, we were really on our own. We got the kids involved in choosing what things they wanted to do. As we went into each city, we asked them, “What are the things you are most excited about doing?” We would sort of order the day around those things.

We learned that traveling to Europe in July can be quite hot, even hotter than I remembered. Most of the time, it was about 100 degrees. We planned a lot of our activities in the morning or later in the day. In the middle of the day, we had siesta time, just like the Europeans do. So, the balance of activities made a big difference, and having some really active things, some really chill things, some scheduled things, and some unscheduled things all made a difference in the outcome of the trip.

The next thing that made a big difference for us was having great guides. We worked with a phenomenal travel planner named Marla. Marla has a company called Across the Pond Vacations. It really was a delight to work with her on planning the trip. She took a lot of input from us about the kinds of things we were interested in, the kinds of things that we had loved on past trips, and the things we wanted to try this time. She put together a proposed itinerary for us to review and then kept iterating on it until we had the perfect combination of things for us.

Marla had phenomenal guides and drivers available in several of the cities, which made a huge difference. These were people who were so knowledgeable about the cities, in many cases about the specific subject matter that they were showing us, and who really knew how to get us into places, past lines, and knew all the best stops for gelato and places for us to get water. They made it very easy for us to get around. One of the benefits of this is that the guides take a lot of the stress off the parents. You’re not constantly responsible for everyone’s good time. You’re able to delegate some of the hard work of travel to this very expert resource, which really allowed my husband and me to enjoy this trip a lot more. I think that was one of the key lessons learned, that if you can invest a bit in getting some support for travel like this, it really makes a difference in the experience. That’s the headline of what I want to share with you today. I am going to come back for a second episode to share some more details about a key part of the trip and go a little deeper into some of the stories from this experience.

But the bottom line is this: traveling with your family is just as important now as it ever was. I was honestly surprised at how similar it felt. If I had not known it was the post-COVID travel era, I would not have had any inclination that the world had just been through such a crisis. The world is open again. People are out exploring, discovering, having adventures, learning about history, and learning about culture. It was remarkable to see. I’m so grateful for this opportunity.

If this episode has inspired you to think about planning a big trip with your family, don’t hesitate. You really won’t regret the investment of time and money in creating these experiences. Your future self will be so grateful for the memories and the opportunity to be together on this kind of adventure.