Walter’s Legacy Continues and Other Travel Wisdom

by James Lange, CPA/Attorney

Most of my longtime clients and newsletter readers know that my wife’s father, Walter Weinstein, sponsored an annual vacation for his children, grandchildren, and even great-grandchildren. For the last 30 years, he brought the entire family together to gather in the Poconos for five days of family time — all meals shared together and everyone recreating in the resort’s many activities.

Walter always paid for the following year’s vacation at the end of the trip, so we all knew the tradition was continuing at least through the year following Walter’s death. He passed in December 2025 at age 101, so the expectation was that we would all gather one last time and either stop the tradition or perhaps continue it in a reduced-expense capacity.

Cindy and her brother, Barry, decided to keep the tradition going and split the cost 50/50. My wife tends toward the frugal side and always worries about our daughter’s financial security after we are gone. I think part of her reasoning — which I support 100% — is that keeping the family closer by continuing this tradition will be a great thing for our daughter, not only now but long after we are gone.

But interestingly, the biggest objection I get when recommending family vacations to clients is not necessarily the money. It’s that kids and grandkids have busy schedules and it’s very hard to pick a time when everyone is available. My slightly sarcastic answer to that problem: tell your kids and grandkids that you’re updating your will, and that their attendance — or rejection — of the family gathering is something you take seriously.

For both me and most of the clients I serve, our biggest problem is that we will run out of life before we run out of money. For years, I have been practically begging my clients to spend more money. I have never really advocated buying more stuff — though I confess I’ve bought a lot of stuff lately, and I’ve enjoyed it. That said, it’s been an easier and typically more successful effort to get clients and readers to spend more money on family vacations than any other way of spending money.

Now I want to shift the travel discussion from large, sponsored family vacations to travel for you and perhaps your spouse and/or very close friends.

A recommendation I received from a friend, who received it from a fellow luxury traveler, has always stuck with me. He recommends making a list of all the vacations you would like to take for the rest of your life and rating them in terms of physical difficulty. An example of a more rigorous vacation might be hiking in the mountains in New Zealand — physically demanding just to get there and a serious hiking trip once you arrive. An example of a less physically taxing vacation might be a theater trip or a museum trip to New York City. The recommendation is to start with the more physically demanding trips you can still handle now and reserve the less demanding ones for later. This makes a lot of sense to me.

Of course, a lot of people like to travel with an organized group — whether it’s a physically active trip with outfits like Backroads, or educational and cultural trips through Road Scholars, formerly Elderhostel, or you might prefer a high-end touring company like Tauck, which this same friend highly recommends. The alternative is to pick somewhere interesting and do all the planning yourself.

I’m going to take the liberty of talking about the way I personally like to travel. I want to be the opposite of the old movie joke — if it’s Tuesday, it must be Belgium. My idea of a great trip is picking very few places, or even one place, and going there for an extended period. For example, I’m currently looking at spending a month in Spain or Portugal and staying in perhaps only two places or possibly even just one.

I tend to enjoy active trips right now. That means bike rides in the mountains and hikes in the range of six or seven miles with around 1,000 feet of elevation gain — which is pretty much Cindy’s upper limit for a comfortable hike.

Why not go somewhere, rent a house, maybe have friends join for part of the time, and actually get to know a place? In that way, you’re not spending all your time packing, unpacking, moving, and traveling. It’s a much more relaxing experience than a vacation where you’re moving every day or every couple of days.

One option that I’ve heard nothing but good things about — anecdotally, at least — is river cruising. You sleep in the same place every night but wake up to different scenery and different ports every day.

Usually, since I do prefer longer stays with fewer stops, I tend to prefer Airbnb or Vrbo vacation rentals over staying in hotels. I can also personally recommend the benefits of a home exchange. When our daughter, Erica, was young, we had a professor friend who knew a professor in the Bordeaux region of France who was going to spend a month on a research project at the University of Pittsburgh. He was married with two young children and wanted to stay in a nice house close to the university. Like us, he had a well-appointed house, working cars, and working bicycles. So, we arranged a swap. No money was exchanged, but it was a great experience for both families.

Instead of spending all our time at tourist attractions, we spent a lot of time at the local playground where our daughter, Erica, interacted with young French kids. We used their car and their bicycles, and it was a wonderful experience. The French professor, meanwhile, bicycled to work at the University of Pittsburgh.

The other bonus was that we both had a circle of friends we introduced to each other. When we went to France, we had built-in friends who invited us to dinner. When he came to Pittsburgh, he had built-in friends here. That’s something you don’t get from a hotel.

There are organizations that act as matchmakers for people looking for home exchanges. Pittsburgh, which you might not immediately think of as a great tourist destination, is actually an excellent destination for home exchanges because there are a lot of professors and physicians who have reason to be here for an extended period. They typically want to bring their families. Staying in a hotel for a month is neither as comfortable nor as affordable as staying in a nice house close to where you’re going to work.

As you know, my articles often have an ulterior motive. But, in full disclosure, one of the purposes of this article is to get you to travel more and have a better travel experience.

Photos: Cindy, Walter and Barry in 2017; Walter Weinstein in 2008; Woodloch 2023 Family Reunion. Walter passed in 2025 at the age of 101.