Reflections on the longest vacation of my life

It’s been just over a month since my last post – the longest writing break I’ve taken in the year that this blog has existed! Why did that happen? No, I’m not just being lazy. It was primarily because I was traveling with my family for five weeks. Yep, you read that correctly. Like most people, our vacations have historically been one week, with a few 10 to 12-day trips in recent years. This means that this trip was the longest we’ve ever taken, by more than double! What was that like and what lessons did we learn from the experience? Read on to find out all the details!

Wow, five weeks? How we spent all that time

As for many people, COVID-19 lockdowns and precautions meant that it had been about a year and a half since we’d last seen extended family and friends. Since we live in California and my wife and I are originally from the Northeast US, plane travel is effectively required to visit our parents along with other relatives and friends. By late spring we finally felt sufficiently comfortable to plan this trip. We had several family events on either end of a five-week period in June and July, and that ended up defining the duration of our travel.

In total we traveled to five states (CT, FL, MA, ME, and NY), took six flights, and drove an awful lot of miles. About half of our stays were in the homes of relatives or friends, with the remainder in vacation rentals and hotels. We had a rental car for about half of the trip and a relative graciously lent us a car for the other portion. Besides our travel and lodging, very little of our trip was planned in advance – more on that later. Most of our time was spent visiting with people, and my wife, Lorri and I spent six days properly vacationing in the Florida Keys and Miami area.

In short, our trip went really well! It was wonderful to see our family and out-of-state friends after such a long time apart. We really enjoyed the time we spent with everyone and made some nice memories. In terms of logistics – honestly, the air travel went better than expected and we felt pretty comfortable with how all of that was handled. While we needed to move around a lot to make all our visits, I think we struck the best balance we could between traveling and downtime. It was a lot of driving, but having such a long vacation meant we could spread things out to make it more manageable. Taking our longest vacation ever also taught us a lot of things.

Lessons learned from a long post-FIRE trip

I thought it would be useful to summarize our learnings in a list of short snippets, which is what I’ve done below. Recently we recorded a Two Sides of FI episode on this topic that will go into more detail on these points. I’ll update this article with a link to the video once it’s live!

Longer duration trips = less planned time, lower stress, and more relaxation

In a 1-2 week trip (or especially a three-day weekend!) I, like many, tend to feel pressure to schedule the majority of our time in order to maximize our time away. In other words, try to see/do as much as possible to get the most value out of the trip. I found that this pressure is greatly reduced in a >1 month vacation. We planned fewer things in advance and just organized our time as we went based on how we felt. We even had days where we simply took it easy. One day in Key West we just walked around and took in the sights. Not having pressure to “do stuff” was really great, and much more relaxing.

No interference from work is an obvious but amazing reality for me now

As I left my career behind more than a year ago, there are naturally no more work-related interruptions to vacations. Of course I knew this would be true but on reflection I realize how big of a deal this is. In the past, I spent my early mornings (while the family was still sleeping) on vacations catching up on work email, phone calls, etc. Occasionally trips were briefly interrupted to deal with the latest crisis back at the office; an hour-long work call while at Disneyworld comes to mind. That pressure and inconvenience is now gone! That means a more relaxing trip overall and a quicker ability to get into a vacation mindset. That’s not just better for me, it’s better for my family!

I pay even more attention to spending and being thoughtful about choices now

I’ve always considered myself a thoughtful spender, even on vacation. And this is certainly essential when you are saving and investing on a path to early retirement. It’s also true that on this first big post-FIRE trip, I found myself even more conscientious about spending. I wouldn’t say I felt limited, as budgeting for vacation is very much part of our plan. But I did think more about the merit of individual choices and trying to maximize the benefit of the expenditures. Lorri and I did have one really nice dinner out in Miami, which was wonderful. But I opted to skip the wine pairing as I wasn’t excited about it vs. having that money available to spend on something else for our trip. That’s just a simple example but it makes the point. When you are drawing down vs. accumulating assets, this mindset makes sense.

The flexibility afforded by removing work constraints is really valuable

In the past, we always had to plan family vacations around my work schedule. That didn’t always coincide with school breaks either. There were even times when my wife and daughter traveled somewhere without me because I just couldn’t get away from the office – or I had business travel that conflicted. That’s no longer an issue. This has a lot of benefits, including reducing travel expenses. Now we can plan flights or hotel stays on less expensive / less busy days or times of year. Even while my daughter is still in school and longer trips are limited to her summers off, we can leverage this. Just like going grocery shopping mid-morning on a Tuesday, post-FIRE schedules afford a lot of benefits.

This trip was a great way to test the waters of future long-term travel

My wife and I have always dreamed of longer term travel, living abroad for part of the year, etc. But it’s just a romantic notion until you’ve done it, right? While the format of this trip wasn’t exactly what we have in mind for future vacations, the duration let us test how we’d feel being away from our home so long. As we discussed at several intervals on the trip, we both felt really good about it. Five weeks never felt “too long” to us. We did agree that moving around weekly was probably about the shortest frequency we’d want to relocate on a longer trip. That was a good lesson, was the overall finding that we are now ready to try longer trips! Once our daughter is out of high school I’m sure we will do that – and now with a much higher degree of confidence. I can’t wait!

Wrapping up

Everyone has their own version of what they want retirement – early or otherwise, to look like. For Lorri and I, that vision has always included longer term travel and short term relocation. We know that this first long trip is only the first chapter in that book, but we’re happy to now have it written! There are many things that can define a successful retirement, and for us, fulfilling and fun travel is a big part of that. Irrespective of your own goals and preferences, I hope you find utility in our learnings. I’m grateful to have the opportunity to share them with you.

What questions do you have that I didn’t answer here? I’d love to hear from you. Best wishes to you all! Mahalo. ?