3 Tips From Savvy Travelers Who Take Cheap Winter Vacations

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You don’t have to be a frequent flyer to take cheap winter vacations when affordable winter trips are easy to find. See how to stay curious and flexible. 

Finding cheap winter vacations doesn’t have to be complicated. With a little planning, and a willingness to be open-minded about dates and destinations, you can find affordable winter trips that deliver happy memories for years to come. The spirit of cheap winter travel is all about staying curious, being flexible, and having fun along the way.

The good news is that unlike Santa Claus, great deals on cheap winter vacations really do exist. If you want fun in the sun, on the slopes, or in a faraway city, your next affordable winter trip is out there waiting for you.

Let’s look at a few expert tips on how to take cheap winter vacations.

1. Be flexible on destinations

Where do you want to go on your winter trip? If you don’t have a specific place in mind, you can often find surprisingly cheap flights and affordable winter vacation lodging deals. Popular travel search tools, like Google Flights, Skyscanner, and Kayak.com, let you search airfare prices anywhere in the world, without even asking for your credit card.

I recently ran a search on Google Flights for a week in mid-January 2024 from my home city of Des Moines to a destination of “Anywhere.” By zooming out or in on the results map, or scrolling through a results list, I was able to find some surprisingly cheap flights to faraway places and nearby cities. I found great prices on January flights from my chilly home base to warm-weather cities like San Diego ($296), New Orleans ($329), Nashville ($257), and Miami ($310).

Airbnb also offers flexible search options to search for lodging in any location and across entire weekends, weeks, or months. This can help spark new ideas for places to visit, and lets you plan your cheap winter vacation based on price, not just available travel dates.

2. Compromise on “must haves”

When planning cheap winter vacations, you need to make a list of “must haves” and “nice to haves.” What are the experiences and amenities you absolutely want to have on this trip?

Your first list of “must haves” might include:

We want to go swimming in the oceanWe want to eat amazing seafoodWe want a big enough hotel or Airbnb for the kids to have a separate bedroomWe want to be close to museums and shoppingWe want a direct flight — no layoversWe want to be within walking distance of the beach

But as you start to look for cheap flights and hotels, you might discover that your “must haves” need to turn into “nice to haves.” What if you could compromise on some of these priority items and save hundreds (or thousands) of dollars? Here’s what a new list might look like:

We want to go swimming in the oceanWe want to eat amazing seafoodWe will share a small Airbnb, and the kids can sleep on a pullout sofa bed and an affordable air mattress that we’ll buy once we arriveWe want to be a short drive from museums, and we’ll skip shopping so we can save moneyWe will take a cheap flight, even if it has a connecting flight with a long layoverWe want to be a short drive from the beach

If you look at that list, the most important parts of your winter vacation plan didn’t change — you’re going to the beach, you’re going swimming in the ocean, and you’re going to eat amazing seafood. You’re just deciding to save money on a few other things.

3. Learn to love a less-than-perfect flight itinerary

To take cheap winter vacations, sometimes you need to embrace the adventure of unconventional flight plans. Especially if you’re traveling as a family, you might need to accept long layovers, multiple connecting flights, flying out of different cities or multiple airports, and even staying overnight in a different city (a “stopover”) along the way.

For example, in 2017, I took an international vacation with my family for the first time. We wanted to go to Germany, and we found cheap flights on Iberia Airlines, the national airline of Spain. We couldn’t fly on Iberia out of our home city of Des Moines — the flight was out of Chicago O’Hare, about a six-hour drive from our home. So we drove to Chicago, parked our car at a nearby airport hotel parking ramp (which was cheaper than long-term economy parking at O’Hare), and flew to Germany with a layover in Madrid.

On the return trip, we had a stopover in Madrid. So we flew from Germany to Madrid, arrived in Madrid at 11 p.m., slept for a few hours at an Airbnb, and then caught our flight back to Chicago the next morning. It was a whirlwind visit to Spain, but it saved us thousands of dollars compared to what we would’ve paid on a more “convenient” flight.

Most elite status frequent flyers would be horrified by all the hoops I jumped through. But back in those days, I didn’t know about the wonders of airline credit cards, frequent flyer miles, and reward points. And that vacation was some of the best money I’ve ever spent. Getting to explore Europe with my children was the experience of a lifetime.

Sometimes the best way to take cheap winter vacations is to embrace a spirit of curiosity and enjoy the journey. Go to a less-fashionable destination. Go during the off-season. Go to a cold-weather city in winter. Book a goofy-looking itinerary with multiple connections and an overnight layover. If the price is right, you can make it work!

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