Travel in the off-season is a joy. Especially living in these gray Seattle winters, I’m jumping for joy when March arrives and I head out for the early tour season. I know that empty museums and crowd-free cities await, as well as great photography opportunities with the brilliant lighting of the low winter sun. Packing for off-season travel is not so delightful, however, it’s a little challenging. Challenging but not impossible.

What you take and what you will leave behind will depend on exactly where you go and how extreme the conditions are. If we are speaking of Europe, the off-season weather may surprise you. It can be cold in almost any part of Europe, even the southern Mediterranean areas like Sicily and Spain. Remember that Europe is much more northerly than many people expect. Although southern Europe seems to have a climate like southern California, it is more similar to Oregon in terms of latitude.

When I lived in Rome many years ago during university, I brought only summer clothing along because I assumed that “sunny Italy” would be warm and sunny all year. I mean, come on, you never see a postcard of Italy with clouds or snow, do you? Well, November rolled around and I found out that travel brochures are not exactly showing the whole picture, winter weather hits the Mediterranean too. All of the shorts and sundresses I’d were not going to cut it year-round. I learned my lesson well, always bring warm things and clothes you can layer.

Even in the colder weather, I firmly stand by my normal packing advice: you can live happily and comfortably with everything you could possibly need for a month in a carry-on sized bag that weighs less than 16 pounds. The main strategy still applies, weigh everything and make careful choices.

There will absolutely be some things that are heavier and bulkier that you will want to bring, such as a heavy coat or boots. My simple solution to keeping to the carry-on size and weight restrictions is to just wear the heavy stuff on the plane. Planes are notoriously freezer-like anyhow, you’ll be doing double duty by wearing your warmest and heaviest things to stay comfortable while keeping your bag minimal.

I still suggest choosing things that are lightweight, but lightweight doesn’t have to mean light on warmth. I bring clothes that are made of materials that deliver coziness without weight or bulk. Cashmere, lightweight fine wool (such as Merino), down and fleece will all keep you cozy without weight. Silk is super light and weirdly warm. Cotton and linen are not necessarily warm but are fine for layering underneath warmer things.

Let’s take a look at the things you might bring. Let’s assume you’re traveling like me, on a three week trip to Europe in March.

Pants and Shirts

I bring four pairs of pants. One pair of jeans that make me look and feel good, with a bit of stretch in case I’m eating any big dinners or too many cannoli. I like dark denim, it can pass as something nicer if you accessorize it right. Black pants are a must, especially for the sloppy traveler like myself. Goes with everything, shows no dirt or stain and can be worn again and again without a wash. I’d pick a chino-style pant for versatility.

Knit pants in a neutral color are my third pair. They aren’t light, but are comfy airplane wear. It’s easy these days to find “sweat pants” that are cute, stylish and warm. Before you become concerned that I’m suggesting sloppy sweats, I have a pair of knit pants from the Gap with an interesting texture and pockets which are technically sweats but pass as good-looking pants. I’ve gotten compliments on them, so I’m guessing I’ve gotten away with it.

My last pair are leggings. Leggings aren’t pants, in reality, and you probably shouldn’t wear them that way. Leggings are for keeping you extra warm, under a skirt or dress or under pants in chilly weather. I also use them for lounge clothes in my room in the evening. They are so light, you could even bring two pair of these if you wanted some color choices.

For tops, I’d probably stick close to my suggestions for summer season packing, keeping in mind that the trick to staying warm is by wearing lots of layers. I bring a couple of tank tops in neutral colors to layer beneath other tops. If you are staying mostly to the south, it’s not a bad idea to have a short sleeved top or two in case you get some warmer days, but you can also layer these under other things too. I’d bring 2-3 long sleeved shirts, maybe one soft long sleeved tshirt and one button up collared shirt. I recently found a long sleeved t-shirt at Costco made out of knit merino wool. It’s a tiny bit heavier than a cotton t-shirt, but looks almost the same and is much warmer.

The remainder of the space you have available in your shirt cube should go to sweaters. I would bring at least two, a black one and another in a color that matches your other clothes. I am always on the lookout for thin, airy sweaters that I can wear over other tops, that take no space and weigh little.

If you can manage the expense of it, bring something in cashmere. I know it’s a little trendy to wear cashmere but there’s a big reason for its popularity. I’m not one to fall for trends or spend recklessly on anything, but I’ve got a serious thing for cashmere sweaters. They are soft, light and surprisingly warm. They are made of natural fibers so don’t make you stinky like synthetic fleece can, but not itchy like wool. If you choose one thing to splash out on, I would make it a black cashmere cardigan, it’s always useful for layering and can look dressy as well. It’s something that will never go out of style and can be used on any sort of trip. You can find a good one here, I’ve also had luck finding good deals on cashmere at Nordstrom Rack and at Macy’s after Christmas.

Even in the cold season, I bring a dress and skirt. My favorite summer dresses can be worn with a sweater over the top and leggings underneath, along with knee-high leather boots. Add a scarf and jacket and you’ve got a sharp looking outfit.

Outerwear

I have tried many different combinations for outerwear through the years. I’m always looking for the perfect combo of warmth, comfort, style and packability. I can’t say I’ve ever gotten it exactly right but I’m getting closer. The way I choose what to bring depends on the destination and time of year. As a caveat, I’m very tall and live in Seattle, so most of the jackets I own are from local outerwear company Eddie Bauer, and I’ve linked to the exact jackets I own. It’s the only place I can find that sells coats with sleeves long enough for my monkey-like arms.

I don’t tend to like waterproof Gore-Tex type jackets. I have brought a few different ones but they are a little too telling of my casual Seattle origins and are not soft and cozy. True, they can be easily layered with sweaters or a down vest, but with that many layers on I just feel like that kid in A Christmas Story that can’t put his arms by his sides. Am I going somewhere wet and cool like the Netherlands? Ok, then the waterproof rain jacket like this one is the only choice.

I have a black fur-fleece jacket that is cute and cuddly warm. It’s a little velvety and can pass as a bit more dressy, although it’s so soft and furry that total strangers may pet you spontaneously. Only downside is that it has little rain protection and is not for extreme cold. Am I going to cities before it’s gotten really cold. Then I’ll take one like this.

Really cold and potentially rainy, like Turkey in November? Down coat. Actually, my mom talked me into bringing the down coat to Turkey last winter, she owns the same one and thought I’d be happier on the plane with it. I was skeptical because it’s pretty bulky, and you know how conscious I am of not bringing more than I can handle. However, bringing this coat saved my trip as I would have been miserable without it, it was much colder than I expected.

I always bring a down vest with me for an instant shot of warmth. It’s super light and packs into it’s own little bag that is attached on the inside. All year round, this vest is scrunched up at the bottom of my day bag, just in case. I showed this vest in the Rick Steves Packing Light video and the office got tons of queries about where to find it, so for the record I bought it at Costco, but you can also get it here.

Accessories

You may have noted my passion for scarves. Bring a warm one if you have one, otherwise you can wait and buy one when you arrive. A scarf around your neck is magically warm, and you can wrap it over your head in a pinch to cover your ears during high winds. Cashmere is always best, but even the cheap-o “Cashmerino” knock-off scarves that sell for $5 are just fine.

I never bring gloves but I will from now on. I am cold pretty much all of the time. It occurred to me while hiking in the snow in the Dolomites last September that I really need an ultralight pair of gloves for emergency situations. I have my eyes on these gloves made of silk, they look pretty light and easy to pack.

If you like hats, toss a warm knit one in the bag, I suggest that especially for men that are…challenged in the hair department. As camping enthusiasts will tell you, a warm head means a warm body. I don’t love hats, it’s a personal thing. I think they look weird on me. I would wear one that I bought in a cool place, though, so this might be another souvenir opportunity.

Shoes 

My typical suggestion for mid-year travel is three pairs of shoes- walking/athletic shoes, sandals, and flats or flip-flops. Obviously that will not work in the winter. In the off-season you will probably encounter more cold, wet and muddy terrain, so plan accordingly.

I’d still suggest a good lightweight walking or running shoe, and I have brought my current favorite Asics Metrolytes in March, they were great with a pair of wool socks. Any black walking or athletic shoe with a decent, gripping rubber tread will work. These should be your main pair.

I bring a comfort slip-on as my second pair. I’ve got several pairs of Tom’s shoes, and they certainly fit the bill for lightweight and packable. This pair of Tom’s were my absolute favorites, warm gray wool on the outside and fleece on the inside, almost like slippers. I speak about them in past tense because I wore them to death. The Skechers that I suggested in an earlier post come in a variety of styles, for winter I might buy a similar pair that covers my foot more, sort of like these ones I found on Amazon.

The third pair I’ve brought the past few winters are my black leather boots. I had brought them for the first time a few years ago, sheerly out of vanity. I think they are kind of sexy and look great with skinny jeans. It just happened to be a strangely cold winter and I found those knee-high boots were the best way to keep me warm. They aren’t so bad weight-wise, but even so, I wear them on the plane to avoid packing them.

If you are looking to buy boots for travel, just make sure they are made of actual leather and will be durable, with good tread. I will admit that I kind of love Ugg boots, even if they are a little clunky. They are so very warm and soft, it’s like wearing bedroom slippers all day. They aren’t too heavy either, so you may consider bringing them if you own them.

As far as socks go, I’d suggest at least 3 pair of wool socks, I like the Merino wool ones from Costco. I still bring a couple pairs of lightweight ankle socks, they take up very little space and are a good alternate if the weather warms or my wool socks are drying.

Other Things to Consider

Hotels can be a little chilly in the off-season, so bring things to make yourself a bit more comfortable. Put warmer pajamas in your bag, even leggings and a long sleeved t-shirt will do. I don’t typically bring slippers with me, I usually hope that some of those free ones will turn up in one of my hotel rooms, but I’ve been known to bring ones like these to keep warm.

I’ve been enjoying my titanium travel mug and coil water heater during the colder months. Having a warm cup of tea upon return to my hotel room is such a delight. That is something to bring as your luxury item though, only if you have available space and weight.

You can splash out and buy a fancy travel umbrella, ricksteves.com also sells a nice one. I’m bad with umbrellas, I forget them constantly. When I leave one behind (yet again), I think about the happy umbrella-less person that will find it by serendipity and stay dry thanks to me. Because of my forgetfulness, I keep 5 Euro in a pocket of my bag for emergency umbrella purchases. When it starts to rain, there is always someone who magically appears out of thin air, offering you a 5 Euro umbrella.

If you are going somewhere really cold or plan to be outdoors often, you may consider bringing long underwear, such as Cuddly Duds. I use my leggings and wool t-shirt for this purpose.

Remember to check if bringing a swimsuit is a good idea. Some of our tour hotels have saunas and pools that are available in the winter, so I usually bring one just in case.

Overall, the lesson I have learned in off-season travel is that it’s better to err on the side of packing too many warm things. When we travel, we tend to spend more time outside than we do at home, so things that I would wear on a typical day at home in the winter will not be warm enough while traveling. If you’re having a hard time sticking to your weight limit, bring fewer things and remember that you can always buy things at your destination.