A financial planning lesson from Notre Dame

If I were superstitious, I’d say I bring destruction when I travel. Back in 2000, I’d left Paris only a few days before the Concorde crashed. In 2008, I spent a lovely day roaming Athens’ Syntagma square, the scene of riots only a few weeks later. On that same trip, I spent quite a bit of time wandering around Cairo’s Tahrir Square and the Cairo Museum—it took until 2011 for Egypt to feel the “effects” of my visit. But I swear I had nothing to do with the fire at Notre Dame—I’ve been there about half a dozen times and until now it’s escaped my curse.

Nevertheless, it’s an unqualified disaster, and I can’t find any humor or irony in it at all. But it did get me thinking about places I’ve always wanted to visit, and goals as yet unachieved.  How sorry I feel for people who never saw it, and may never see it intact again in this lifetime. I remember well the feelings I’ve had for other places and opportunities that suddenly seemed to disappear: after 9/11, how many of us wondered if the whole world had changed and if we’d ever be able to travel again? In 2013, dear daughter and I were in London; would we go now? I’ve always wanted to travel in Israel, but never been able to wrap my mind around the dangers. And I have a long-standing aim to go to India, and to take a cruise to Alaska, both completely unplanned as of now.

How can we change that? Actually accomplishing travel (or any dream that costs money) has a better chance of becoming reality by working through some clear steps.

What do you actually want to do?

I’m happy schlepping through Europe, and don’t worry about languages (where I can scrape by in a few), managing train travel, or finding a hotel. I’d be pretty content with an inexpensive, weeklong cruise to Alaska with an interior cabin. But an India trip is a different story—I want everything taken care of, a guide, transportation arranged and probably first class, hotels all pre-booked. I’ve also considered a language immersion trip. Some people gravitate to cooking schools, or ukulele camps, or fiber festivals, or following the route of Joan of Arc. A theme can be quite an organizing principles, and you should decide just how exactly you want to travel.

What are the obstacles?

Money is the most common. Turns out, time available also can be difficult. Then there are the mental quirks that only live in my (or your) head: although I’ve wanted to see the Palio in Sienna, I’ve actually never made the slightest effort to think it through because it’s run in July and August, probably the two worst months for seeing the rest of Italy. Consequently, while I’ve been to just about every other Western European country, I’ve missed Italy entirely. Unless you can identify what’s stopping you, you can’t investigate and make a plan.

When do you want to go?

This can be both what season and what month or year. You need to give yourself enough lead time to come up with the money and find the time. But having a specific calendar timetable can move the dream from someday to (exact date). Someday will never happen.

What do you enjoy once you get someplace?

For me, it’s all restaurants, museums, and historical sights (some with significant admissions costs). As long as it’s clean and close-in, I don’t care much about hotels. My toleration for shopping is about 2 hours max (unless it’s the Marché aux Puces or a museum shop). You’ll never find me at a sporting event, and only once in about a million miles of travel have I ever taken a nature hike. YMMV. Preferences definitely influence cost and destination selection.

What does it actually cost?

It’s a lot cheaper, of course, to go to St. Louis for a weekend than to spend three weeks touring India. But what’s the actual possible dollar figure? Have you looked up airfare, packaged tours, hotel costs in Amsterdam? Do hotels at your destination customarily include breakfast? What level of luxury are you after? Will you rent a car or buy a rail pass? Researching the trip has been shown to extend the pleasure—the anticipation and choosing possibilities is a huge part of the fun.

Can I get it cheaper?

Here’s where the whole world of travel hacking comes in. Based on my own experience, it’s easier to get it cheap if the destination is popular, close, or more familiar. Our 10 day London trip (including Bath and Oxford) cost about $1,000 total for the two of us. Key West was only the cost of food and a not inconsiderable amount of tropical booze. A western Caribbean cruise we took cost the price of the shore excursions (I could do better now). But so far I haven’t had similar luck trying to snag a low cost way to India. I’ve had the best reductions using travel points of all kinds, leaving at the last minute, and not caring too much where I was heading or precisely where I was staying (Hyatt Regency St. Louis for $49/night—mystery selection on Priceline).

Once you know where and when, you can set up all kinds of alerts, figure out when the cheapest days and times are, and concentrate your points spending. Make a plan for yourself and make those dreams real before they turn to smoke.

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