I’m much better than I used to be about packing, but I still pack way too much stuff. I’ve discovered that the way to solve this problem is to get at the assumptions that drive it:

*My leisure travel experience is going to be so different from my leisure time at home.

If I liked to ski or was into climbing, the assumption might be correct. But, in fact, my leisure travel experiences boil down to lounging around, walking around, eating, sleeping, sitting in a cafe, walking through a museum… in other words, despite the change in location, my activities are not that different from when I’m at home. The clothes that I wear when I travel don’t need to be anything special.

*Packing is worst-case scenario planning.

Yes, but what if the Prime Minister invites us to dinner? A bit carried away, but I find that one of the biggest traps I fall into is trying to plan for all kinds of possibilities. The result is usually an array of different outfits stuffed into the suitcase – many of them “just in case” I need them. Usually I don’t.

*I’m going to wear lots of clothes while I travel.

Actually, I won’t. At home, over the course of a week – 5 weeknights and 2 weekend days – I probably wear 3 different shirts and one pair of jeans. But if I’m traveling for a week, I pack 7 shirts and 3 pairs of jeans. Why? The truth of the matter is that when I’m traveling for pleasure, I wear the clothes that I like more than once, just as I do at home.

For me, those three assumptions get at much of what is wrong with my packing. So, taking the 7 day trip to Montreal as my example, here’s my plan for the next trip in December 2008:

* Choose one core color
I have lots of black shirts, sweaters, shoes, etc. If I put one brown thing in the suitcase, it’s all over because I have to pack the brown coat, the brown shoes, the brown belt. So I can choose one or the other, but not both.

* Realistically assess how you’ll wear what you pack
Over seven days, I can easily get by with 3-4 t-shirts for casual wear during the day, maybe less if I’m going to be wearing sweaters or sweatshirts, too. Two pairs of jeans is plenty. You want to think about what happens if something gets dirty, but don’t think about it too much. For evening wear, again be realistic. This year I took two dress shirts and a pair of dress pants, just in case I wanted to wear them to dinner. They never left the hotel room. If your dinners are going to be at casual restaurants, don’t bother with that stuff. If you want to turn up the knob just a bit at dinner, you can put on a nice sweater without having the ditch the jeans. That sweater will probably do you just fine for any number of dinners where you want to look a bit nicer. And if you’re like me, most of the time you’ll be happy enough to stay in casual mode when you know the restaurant allows it.

Those two steps will cut the volume of clothes I pack by at least a third. Now, to the cords and shit that our connected generation requires.

* Pack a powerstrip
No hotel has enough outlets for all the stuff we cart along with us. A small powerstrip makes life so much easier.

* Portable speakers
There are times when I like having music on in the hotel room and I don’t want to be enclosed in headphones. Chuck bought me a small JBL speaker system with an iPod dock a couple years ago. This is a perfect solution, especially in hotel rooms that don’t feature the newer clock radios with aux jacks. It’s a one piece solution for soothing sounds in your room. It also charges the iPod.

* Cable management
“Management” is the best you can do – most devices have nothing in common when it comes to cords. Those travel chargers with all the various connectors are a big help, but I’ve also had success without them. I focus on charging and syncing, gather the cables that I need, and stow them neatly in the suitcase.

* Backup protection
You’d be crazy to backup your computer before a trip and then take both the computer and the backup drive with you – but I think you should have some kind of backup media along for the ride, especially if you’re going to be taking lots of pictures and uploading them to your laptop, or doing some writing while you’re away. I back my stuff up to 4 different places, two of them off-site, so I don’t feel like I’m living dangerously if I take my Time Machine portable backup drive with me. If both get stolen or destroyed, I might lose all my photos from that trip, but everything else is safe. And as off-site backup solutions improve, and quality (in other words, true high speed) wireless internet becomes more common at hotels and cafes, I can upload even large numbers of photos easily to off-site backup locations.

That’s the current state of my education in packing. I’ll apply my new rules to upcoming trips and adjust them as I need to. I’m sure there’s much more to learn.

Why no posting during the trip this year? Well, we were busy. It was interesting – this was one of the most relaxing of the Montreal trips, even though we did more things, and we had four friends along for the ride. Here’s why:

We didn’t go shopping. In years past, we’ve spent at least a few hours on St. Catherine, scoping out things to buy. It’s fun, but everyone in Montreal is there, doing the same thing. The result is an experience, that – even at its best – is stressful. We didn’t have to drop all shopping from the itinerary, it’s just the way it worked out. But it meant we didn’t have to brave the crowds.

Fewer activities. We’ve never stuck to a firm schedule for anything in Montreal, except dinner. But we’ve had a stable of activities, some of which have been “traditional” or considered obligatory, and for this trip, we cleared the schedule of those activities, too, primarily because we had others along for the ride. This, combined with the general ethic do what you feel like doing, led to an enjoyable vacation.

Our friends. They were so much fun, that the prospect of spending next year in Montreal without them seems kind of boring.

More specific posts are on the way, but in general, this was a great trip.

We wish we could make 5 trips there a year – or, better yet, move there – but this is all we can cram into our schedule at this point. And so, these 7 days in the city take on great importance.

I’ve been watching the weather forecasts across four different cities for the past week, looking for any signs of approaching storms which might delay our travel. Frankly, I’m more concerned about US airports than I am with Toronto (where we’ll land); Pearson has a pretty good record when it comes to staying in operation through major storms – witness this past weekend. In fact, many travelers found they were able to land at Pearson in the snowstorm, but they couldn’t get out of the airport by car or bus.

Well, I’ll fret (minimally) about potential delays to The Plan until we arrive on the Via Rail platform in Montreal on Friday afternoon.

In the meantime, off we go!

It’s a different trip this year, in a couple ways. First, we’ll have two great friends joining us for the days leading up to Christmas Eve. I wouldn’t say we’ve tried to over-script those 3 days, but we have rearranged our plans somewhat to give them what we hope will be an enjoyable snapshot of the city. This means plenty of downtime, but also a few focus destinations – probably Musee d’art contemporain and the Montreal Museum of Fine Arts; perhaps a visit to Notre Dame Basilica. Up to now, we’ve avoided Schwartz’s, but we might make our first visit this year, using our friends as a good excuse.

Because Chuck and I are foodies, we’ve also started rearranging our restaurant plans to highlight particular favorite restaurants while they’re with us. The leading candidates for “Dinners for Four” are Au Pied de Cochon, BAZaAR Anise, Brunoise, and Bonaparte.

I would hesitate to portray these choices as quintessential. I think that’s a mistake a lot of people make when they visit a place – they either have a list set in stone that “represents” a city, or they become overwhelmed trying to create that kind of list. We won’t play that game, but we do have a rationale for our choices, which takes into account the menu, the chef, the reviews, the patron buzz (Chowhound and elsewhere), proximity to our hotel or accessibility via Metro, previous experience, etc.

“Cochon” isn’t a restaurant that “represents all of Montreal” but it certainly represents the vision of Chef Martin Picard, and there’s something about that place that makes you think it would be hard to locate elsewhere. Bonaparte very nicely executes the French/Quebec theme and the ambience is quiet and restrained. As neighborhood bistros, Brunoise and BAZaAR Anise might offer an experience no different than you’d find in any other bistro, but again, it’s the menu, flavors and execution that make these restaurants shine.

Then there’s lunch! Frankly, I could have lunch every day at Olive et Gourmando and never be unhappy, but I expect Chuck will expand the lunch choices.

So that’s where we are now. This list will change, I’m certain.