10 Winter Travel Tips for Baby Boomers

I’ve been on several winter travel trips to Spain, Poland, and a Christmas Market tour on the Danube from Budapest to Prague, and Italy for 3 weeks that included a cruise on the Mediterranean and London. 

Being a Southern Californian gal from Los Angeles, I wasn’t used to dealing with cold weather and had to find warm clothes to wear and pack them so I wouldn’t break my back in the process. I made silly mistakes each time I went abroad and that’s why I wanted to offer these 10 winter travel tips so you won’t do the same.

The best way to travel during winter

1. Don’t be afraid of traveling when it’s cold

One of the best parts of winter travel is that there are fewer people on the streets to deal with and shorter lines at popular attractions. Traveling during the holidays is also gorgeously festive. When I read the itinerary of our Christmas Market cruise, I planned to skip the markets and sign up for other excursions because I’m not a huge shopper, Jewish, and thought it would be cheesy.

Was I ever wrong! The Christmas markets are stunning with amazing holiday foods, drinks, decorations, arts and crafts, music, and fun. Now, I want to see more. Luckily, I eat pork because there were yummy sausages everywhere and OH, were they delicious!

2. You get better rates and service during the offseason

You can often find affordable flights if you travel during winter because there isn’t as much demand. Our driver in Italy told us that we were there at the best time because in the summer it’s so crowded that waiters, hotel staff, and shop owners get cranky and customer service is bad. Traveling during the winter months is more relaxed. You can carry on meaningful conversations and get to know the locals. Prices overall are usually lower too.

Popular tourist spots like Saint Tropez and Positano are empty in the winter. Even though it’s nice to be there when more stores are open and be out in the sun, there’s a certain kind of magic in the quietness of busy summer towns.

3. Pack as light as possible even though it’s cold

In Spain, we hauled huge suitcasess that weighed a ton. Mine was stuffed with bulky sweaters, a big wool coat, and knitted hats.

We also carried formal wear because we had been invited to attend the Opera and a party afterward. Lugging our bags from one train to the other and to each hotel was a bitch and we swore we’d never carry that much again.

We were determined to travel light on our next trip. Before I left for Poland I bought a  down parka that easily squished into a small bag. It had a metallic lining that regulates heat and cold. Underneath, I wore a black thin cotton shirt, black leggings, and a sturdy pair of boots that were comfortable and had good treads for walking on cobblestones.

It became my basic uniform. I also packed a couple of infinity scarves, gloves, silk thermal tee shirts, and a flattering and easy-to-pack travel dress for special occasions. If you travel from city to city, no one will know if you’ve worn anything more than once so you don’t need multiple outfits. Shop for basic items you can mix and match.

4. Only bring a carry-on

As I learned in Spain, carrying too much luggage is hard, especially if you’re over 50.  I also hate the thought of losing my luggage in transit. Now I only bring a carry-on no matter where I travel or for how long.  A 21-inch carry-on bag, with a large pocket to slip my computer in, is all I need.  

If I weren’t a writer, I’d leave my computer at home because it adds to the weight. If you can, bring a tablet instead or just use your smartphone.

I always carry my coat on to the plane and put it in on my seat because it’s smooshy and comfy for long flights. Boots take up space in my suitcase, so I wear them to board the plane, but take them off once we’re in the air and replace them with socks and light slippers so my feet don’t get cold and to use in the restroom.  

The only hard part is getting the carry-on up into the overhead. I’ve found that younger men are willing to help if you give them a look like “Hey, I could be your mother. (or Grandmother) Be a good Boy Scout and help me out.” They usually oblige because they know you’ll accidentally whack them on the head with your suitcase if they don’t.

A good rule of thumb for knowing how much to bring on a trip is to take your bags downtown before you leave and walk around with them to see how hard it will be. There aren’t always elevators or help available in train stations and small airports.

When we arrived late at the Port in Rome to board The Queen Elizabeth for our Mediterranean cruise, we saw two “over 50” women trying to drag HUGE bags from the train to the ship’s Embarkation station. There was no one there to help because most of the passengers had already boarded.

5. Shop in countries that offer discounts

Because winter travel is considered to be the off-season, there are more discounts available. And you can get great shopping deals in countries like Poland, Hungary, and the Czech Republic because they’re not on the Euro. Also, if you live in a warm climate as I do, you may not have the best selection of stylish winter clothes to choose from. Shopping in countries where the dollar has more value is a good opportunity to find unique items you won’t find where you live at affordable prices.

Travel Shopping Tip – If you’re ever in Gibraltar, everything you purchase is duty-free.

6. Enjoy winter travel in hotels that reflects the culture of the country you are visiting

Small boutique hotels run by locals, as opposed to major chains, are a much better way to immerse yourself in the culture and lifestyle of the country you are in.  And during the winter, these little places can be charming during the holidays.

Before we left for Poland, we learned that our travel agent had booked us into an American chain hotel in Warsaw that was 30 minutes away from the old town center. I wasn’t thrilled with that because I love being within walking distance of historical sites and medieval towns.

I went online and found a Polish-run hotel with glowing reviews called The Castle Inn.  It’s located across from the Royal Castle in Old Town Warsaw and has a quirky, bohemian feel. Each room has a different theme. Our travel agent immediately protested, but I insisted that he change our reservations.

And, I’m so glad because we adored our room. The hotel staff was friendly, helpful and they had a fabulous free “Polish” breakfast. It made our winter travel experience much more fun.

Our room had a psychedelic theme.

I loved that we could walk outside of our hotel and immediately see Old Warsaw dressed up for Christmas. What a treat!

7. Dress so you won’t be tempted to delete your selfies

Bulky winter clothes make you look even bulkier, especially in pictures. If you’re not happy with your over-50 body, you may feel tempted to trash all your selfies before they make it to Facebook. No one wants to look 20 pounds heavier if you can help it.

Shoot wide shots instead of close-ups to show off the scenery and de-emphasize parts of your body you aren’t happy with. Warm, sleek leggings are not only comfortable but slimming when coupled with a long shirt of the same color. It’s a good way to disguise an over 50 muffin top.

8. Be careful with your money and stay safe

Even though there are less crowds in winter you still have to be aware of pickpockets, especially at a busy Christmas Market.

I like to carry a small backpack to keep my hands free and use it to store small purchases, food, my water bottle, and other paraphernalia I pick up while traveling.  But, I never use it to store valuables like my phone, camera, important documents, or money.  I wear those around my neck underneath my coat.

There are all sorts of small organizer bags available on Ebags that include passport holders, money belts, and RFID protected wallets, and purses.

It’s confusing when you travel to countries with different currencies, especially if you’re unfamiliar with them or the language. Poland has Zlotys, Hungary HUFs, Prague – Crowns, etc. Converting them can be hard to figure out if you’re not a math genius. There are currency converter apps you can use on your phone to help you with this.

Tipping in some countries is also confusing. If you put a tip on your credit card, the waiter may not receive it because the restaurant takes it all. It’s usually better to tip with cash. In many countries outside the United States, 10% is more than enough. Tipping may not be required in some countries and may, instead, be thought of as an insult.

As much as I hate to mention this, we all have to be careful about the possibility of terrorist attacks. I don’t believe it should prevent us from traveling but always keep a lookout and know what to do in the event something horrible happens.  The attack at the Berlin Christmas Market and so many other iconic places in the world is abhorrent and maddening.

9. Make rinsing out winter clothes easy

On extended winter travel vacations or any time of year, there will come a time when your clothes need to be rinsed out and the easier you can do this the better. Who wants to wait for a bulky sweater stained with hot cider to dry out when you can pack easy dry garments instead?

The same goes for underwear. Leave your cotton undies at home and pack 3 – 4 pairs of quick-drying underwear instead That way they won’t take up extra space and can be rinsed and dry by the time you wake up in the morning.

Most hotels offer shampoo samples. Instead of bringing detergent, rinse out your clothes with shampoo. Synthetic down winter jackets dry quickly but if you put them in a dryer use low heat so they don’t melt.

10. Be prepared for an emergency when you travel

While we were in Vienna, I received the sad news that my 90-year-old father had passed away. It wasn’t what I wanted to hear on my trip of a lifetime. I didn’t return right away because my sister was handling the arrangements and we were in the middle of a Christmas Market river cruise on the Danube.

On the last day of our trip, our hotel concierge in Prague was able to arrange a re-routed trip to rural Colorado so I could be there for the funeral. To qualify for a bereavement discount, I had to track down the funeral home to receive a copy of his death certificate.

During winter travel streets may be frozen or slippery so bring shoes with treads to avoid falls and injury. A bad fall can seriously screw up your vacation.  

Winter travel may also mean you have to cancel or reroute your trip due to weather or airport closures. Always purchase travel insurance whenever you travel in case of an emergency.

Do you have winter travel tips you’d like to share?  Please leave a comment below.