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8 Reasons to Book Your Winter Vacation NOW

I know what you’re thinking, “I’m currently sweating buckets trying to survive the hottest summer in history… How on earth am I supposed to think about winter vacation?” I get it, the last thing on my mind are icy roads, heavy coats, and snow boots! However, if you can manage to take your mind off these record high temperatures and think ahead six months, I promise it’ll be worth it in the end. After all, as everyone knows, the best time to buy is in the opposite season. This means right now is actually the best time to start planning and booking your winter vacation, and here’s why.

Why You Need to Book Your Winter Vacation Right Now

1. Get ahead of everyone’s busy schedules.

Here’s the thing – we all know that right now everyone is in a bit of a lull. It’s the dog days of summer, and most people are as relaxed as they’ll be all year. We’re coming off family trips, taking advantage of the longer days, and generally doing the minimum at work so we can enjoy life. As soon as fall hits and there’s a coolness in the morning air, everyone is off to the races. Kids are back in school and that means endless carpools, homework assignments, and school activities. You often have bigger projects and meetings at work, and there are seemingly a million events filling up the calendar. 

Trying to plan a winter vacation when everything is in the midst of the fall rush can be excruciating. Just imagine trying to get date confirmations and budget limits when everyone is suddenly in “active mode.” Nope, get ahead of all of this by locking in all your travel companions now rather than later. Plus, if someone’s coming off a great vacation, they’re much more likely to commit to another one in a few months!


2. You’ll be able to pick the absolute best flight with the best prices.

Here’s the deal – airplanes can only hold so many people. And there are only so many routes you can take to get to your chosen destination. If you want to not only get the best route possible but also the best deal possible, you want to book those flights right now. Some airlines or booking sites even run early bird offers. Experts say the best deals are often found in July and August, so time really is ticking!

To a lesser extent, this goes for hotels and tours as well. Just be sure to check early bird specials anywhere you look. I would also check to see if your airline or booking site has a best price guarantee option. I know for sure Google Flights just introduced this option.

3. Popular destinations book up quickly.

People often tout winter as a great time to travel because it’s low season in many countries. Keyword – many – not all. Any resort, whether for skiing or the beach, will fill up quickly during winter, especially during key holiday and vacation weeks. If you have your heart set on going somewhere particularly popular, the longer you wait, the less likely you’ll be able to find a room. I forget where I read it, but I once saw that Disney World can be fully booked as early as mid-August!

4. Have all sorts of options and choices.

Furthermore, the longer you wait, the more slim the pickings get. Restaurants, especially ones with a lot of buzz, can book up months in advance. Hotel-wise, if you want a specific room with a specific view, chances are a lot of other people do too. Trust me when I say, booking a trip for December or January in August is going to give you the best chance to stay, do, and eat exactly where you want.

5. It’s something to look forward to.

One of the best parts of booking a winter vacation now? Looking forward to it! If you’re planning a cold winter trip, just imagining snowy landscapes and ruddy cheeks will help you get through the last bit of this summer heatwave. If you’re planning a hot weather vacation, it’ll be something to look forward to as the weather gets cooler, the trees lose their leaves, and there are more gray, cloudy days than hot, sunny days. 

Scientists have done many, many studies that have proven how beneficial travel is for mental health. The act of planning and getting ready for a trip alone can improve your happiness even more than buying material goods. 

6. Gives you and your loved ones something else to bond over.

One of the reasons they say travel makes us happier is that it gives us something to talk about with other people. Think about how fun it’ll be to chat about plans and anticipate your winter vacation with your loved ones? Whether you’re planning a family trip, a multigenerational trip, a friends’ trip, or a romantic getaway – being able to talk about it for the next few months offers another way to strengthen bonds. Going somewhere popular? It’ll be fun to get advice from friends who have been there before!

7. There’s plenty of time for any extra planning.

Planning your trip and getting into a travel mindset now means you’ll have plenty of time to consider all sorts of logistics that may have fallen to the wayside. Consider this my reminder to you: check your passport if you’re going somewhere international! Wait times for renewals are pretty long and getting a new passport altogether is even longer. August is a very good time to make sure you have enough blank pages and months left to get through TSA and customs.

8. If you go somewhere warm, good time to buy clothes at a discount.

For anyone planning a hot weather vacation, August is a fantastic time to pick up some outfit necessities at a discount. We all know retail is about 3-4 months ahead of the season, so right now store floors are full of back to school styles and autumn staples. You know what’s stuffed in the clearance section all the way at the back? Bathing suits, cover-ups, shorts, and all sorts of summery goods!

Fantastic Winter Destinations…

Now that I’ve convinced you to start planning and booking your winter vacation now, here are some ideas.

If you want to go somewhere warm…

  • St. Augustine, FL – Great if you want some historic sightseeing mixed in with your beach vacation. Take advantage of the food scene.
  • Hong KongReady to fly halfway across the world? I can guarantee Hong Kong will be well worth the jet lag. Meander through the many alleys and take in the beautiful chaos of this major metropolis.
  • Savannah, GA – This is a destination where the aim is to slow down and just take in your surroundings. Between the beautiful nature and elegant architecture, Savannah is the perfect antidote to a busy life.
  • British Virgin IslandsMost destinations in the Caribbean are actually best visited during the winter as it’s their dry season. Why not try sailing around the BVI for a truly once-in-a-lifetime experience?
  • SoCal Road TripThe best way to see California is by car. With this route, you can take in the coast as well as the desert and even squeeze in some skiing if you want some snow mixed in with your warm vacation.
  • San Antonio, TXA popular destination for good reason. Be sure to enjoy the river and get out of downtown to really enjoy its charm.
  • The Florida KeysAlways a classic vacation spot with one of the most beautiful highways in the country. It’s like getting a taste of the Caribbean without needing a passport!

If you want to go somewhere cold…

  • Madison, WIThis is a city that really knows how to embrace winter! Cozy up at a supper club, explore Madison’s rich history, and learn the art of curling all in one place.
  • Big Sky, MTBig Sky is underrated gem of a ski destination where there’s just as much to do in town as there is on the slopes.
  • Quebec City, CanadaFor those of you who want to feel like you’ve stepped inside a Christmas fairytale, Quebec City is the place you want to visit.
  • Seoul, South KoreaWinter in Seoul can be brutally cold but it also can be magical on its own. Fewer crowds and easy shuttle access to ski resorts a few hours away can make it a fun trip. Plus, if you’re lucky, you’ll get to see one of the palaces during a snowfall.
  • Lake Geneva, SwitzerlandWhile I experienced Lake Geneva and the Valais region in summer, I imagine it’s equally as stunning in the winter. Valais is especially great for winter hikers, and Geneva is, of course, a gateway city for the Alps. 

Are you planning a winter vacation this year? Let me know where below!

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