I don’t have any breathtaking insights. These questions are hard to answer definitively, and the best example is the latest weather forecast for Montreal:

• Today (Wednesday 12/16): snow and 15°F
• Tomorrow: clear and 8°F
• Fri: clear and 10°F
• Saturday: snow and 15°F
• Sunday: partly cloudy and 17°F

And here’s the norm: 26°F during the day and 12°F at night.

In 6 years of Christmastime vacations in Montreal, we’ve experienced a temperature range from -15° to 40° and heavy snow to rain to dry weather. If you’re planning a short trip of 2-4 days, you can tune your packing more closely to the weather forecast . But for longer trips like ours, we try to be prepared for a broad range of weather, with varying success from year to year.

Here’s the outerwear (and underwear) portion of my packing checklist:

• warm gloves, quality scarf, cap (think cold and wind).
• winter coat: rather than a heavy, long winter coat, I prefer a combo coat and hoodie sweatshirt. Most of the time, you’ll want and need both of them, but for unexpectedly warm days, remove one and wear the other.
• long underwear: your lower extremities will thank you for this.
• socks: we pack a mix of regular winter socks and heavy winter socks.
• shoes: we pack a pair of tennis shoes, and a boot of some kind. I have some Timberland boots that are fur-lined and quite warm. I can wear them every day if I need to (most restaurants are casual). Ideally, your shoes will be waterproof; melting snow can leave huge pools of standing water, especially in Old Montreal. It’s no fun being soaked to the skin.
• umbrella: we had rain briefly in 2007. The cap you packed will come in handy or you can toss a travel-size umbrella in the suitcase.
• sunglasses.

It’s often windy, and even if the forecast doesn’t indicate it, it can still be blustery in the wind tunnel of urban streets. Probably not as intense as a winter day in downtown Chicago, but even if it feels nice when you step out the door of your hotel, I’d still recommend hat, gloves, and scarf.

Layers is the standard recommendation, right? It’s a good idea, especially if your trek around the city includes periods of walking outdoors and walking in the Underground City or while you’re shopping. When you’re indoors, you’ll want to peel off some of your gear without removing all of it.

First, a reset: Each year, we spend the Christmas holiday in Montreal, with a trip of 6-8 days. We’ve done this since 2004. We do it because it’s relaxing, a nice time to reconnect with friends who join us, and it’s become, over time, its own holiday tradition.

We like to eat good food, and so a big part of our planning for the trip is actually planning where we’ll eat. Each year, we choose a mix of favorite restaurants, as well as a few new ones to try.

This year, with 8 nights to fill and perhaps a 9th, here’s the plan:

• Friday 12/18: Toqué
• Saturday 12/19: Newtown
• Sunday 12/20: Laloux
• Monday 12/21: Trois Petit Bouchons
• Tuesday 12/22: DNA
• Wednesday 12/23: Au Pied de Cochon
• Thursday 12/24: Bonaparte
• Friday 12/25: TBD

There are long-time favorites like Toqué and Au Pied de Cochon; restaurants we tried last year and enjoyed, like DNA and Laloux; new restaurants on the list, like Trois Petit Bouchons and Newtown; and the Christmas Eve tradition, Bonaparte. In the case of Newtown, we’re following the chefs, Marc-André Jetté and Patrice Demers, from Laloux to their new venue.

I’ve written about this before, but one of the factors Chuck considers when he’s working on the plans is the style and type of restaurants on the list. He likes a mix of “signature experiences” and homier fare. Naturally, he wants all of it to be good. Now, he’s figuring out whether we’re too heavy on a certain style of bistro cooking – expressed differently at each restaurant, but still similar in style and concept. If that’s the case, I expect we’ll see a replacement of the dinner for Monday night – jumping into one of the ethnic traditions, perhaps.

More to come.

This is the question that vexes the traveler who isn’t planning to spend the holidays with family or friends. And the holidays are a great leveler because whether you’re new to a city or a frequent visitor, you can still be frustrated when you start to feel hunger pangs and you face the prospect of block after block of closed restaurants.

We’ve been spending the holiday in Montreal for 6 years now, and every year, we subject our long-considered list of desired restaurants to the reality of holiday hours. Most of the time we can make it all work out. We arrive about a week before Christmas and leave shortly thereafter, so we can manage our reservations around what’s open on a particular night.

But it’s not easy. Not only do most restaurants close for a few days (or longer) but others close capriciously – and here’s what I mean by that: last year, we reserved at Bronte about 3 weeks before our trip – it had been on our list for a couple years and we wanted to check it out. A week before our trip, Bronte called. They wouldn’t be able to fulfill our reservation on Open Table because they were actually closed that night. Why they’d not communicated that with Open Table? I’m not sure, but during the phone conversation they told us they’d be open on Boxing Day and they could accommodate us. So, we reserved for 12/26. On the afternoon of 12/26, Bronte called again: “We’re sorry but we won’t be open tonight.” It’s likely they looked at the number of reservations for the evening and decided it wasn’t worth bringing in the staff. Understandable, but frustrating, and Bronte is now off our list.

Christmas Eve is usually workable. A number of reputable restaurants are open because families and large parties often eat out before Midnight Mass or other celebrations. Christmas night is another matter. With the exception of hotel restaurants or Chinese restaurants, most everything is closed. Our Christmas dining record? Four Christmas night meals at Otto (W Hotel) and one dinner at Koko (Opus Hotel).

Whenever I mention Otto as the Christmas Night meal, it seems, a Chowhound or foodie will write to say something like, “I hardly think Otto is a great choice for someone interested in food.” To which I always respond with a sanitized version of, “Duh, but please suggest a better restaurant that’s open on Christmas Night.” I’ve never received a suggestion.

Chinese restaurants are a well-known option for Christmas Night because many of them are open. That’s something we’ve considered, except that our other Christmas Day tradition, dim sum for lunch, provides us with enough Chinese food for the day.

Locals can’t often provide much help with this question because most of them are at home with family and friends, recovering from a huge Christmas dinner.

But surely someone – tourist or local – has gone to a restaurant on Christmas Night in Montreal. If you’ve done so, where have you gone? What can you recommend?

photo: Christmas Day dim sum consumption at Ruby Rouge

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.

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.

We made one change – this year we’ll fly to Toronto and go by train to Montreal, but we’ll fly from Montreal all the way home. The train ride is enjoyable and relaxing, but after nearly a week away, we find we’re anxious to get home and the train ride back to Toronto extends the trip a bit too much. Nevertheless, I expect we’ll have a good time, despite the shuttling from plane to train.

When we first discovered this list, we were pleased to find all of our favorite restaurants on it. Now, we consult this list first when we’re planning our trips.

A few of the returning favorites:

1) Les Passants du Sans Soucy – I love this little auberge, situated along the oldest street of the Old City. During the day, it bustles with tourists; at night, there’s the clip-clop of hooves, carriages transporting people down the narrow streets after dinner. And late night, there’s quiet. The rooms are wonderful, the staff delightful and accomodating, the omelettes what one would expect from a fine French kitchen.

2) Bonaparte – this is a fine hotel, too. We have dinner there on Christmas Eve. Our eating is broadly ethnic and weighs heavily toward The New, so a traditional, perfectly prepared French meal (with Canadian influences) on the night before Christmas is a treat.

3) Mont Royal – We walk from the Old City to Mont Royal on Christmas Day, usually leaving around 10am, generally arriving back home around 2pm. If the weather is too cold, we “cheat” by walking through the Underground City for much of the way there. Let’s face it, there’s not much else to do when you’re on vacation on Christmas, and the walk is a good way to get a little exercise outdoors.

Those are what I would call the mainstays. We’ll piece the rest of the trip together as we go.