By BRENDA The holidays carry a special kind of energy.
There’s excitement in the air—reunions, celebrations, endings, and new beginnings—but there’s also pressure.
Pressure to show up, to move fast, to be everywhere at once.
A get away during this season can either amplify that stress or soften it, depending on how intentionally it’s planned.
In my experience, holiday travel is not just about the destination.
Factors like timing, people, weather, energy and purpose do matter.
Over the years, I’ve learned that the most fulfilling trips are not the most packed or expensive ones, but the ones that respect the season of life you’re in.
Whether you’re traveling to see family, exploring somewhere new, or carving out quiet time for yourself, here are the 6 most important things to consider when traveling for the holidays.
1. Weather: Let the Climate Guide Your Travel Style
Weather is one of the most underestimated factors in holiday travel—and one of the most powerful.
Before booking flights or accommodations, you want to know your comfort when it comes to extreme temperatures and be prepared for once weather changes wherever you will be traveling to.
One Christmas holiday, I remember traveling to Florida, the sunshine state in America known for its warm weather and frequented by people from Northern parts of the country during winter.
I didn’t bother carrying any warm clothes because duhhh it’s Florida.
On Christmas day that year, a cold front swept through the parts of Florida I happened to be in during my stay.
Not a beautiful experience for someone like me that is not comfortable with the cold.
Plus, plans had to change to cater for the drastic change in weather.
This is not something you want to experience on a trip meant to be filled with good memories.
Some questions you want to ask yourself before travel include:
- Am I comfortable navigating extreme cold or unpredictable weather?
- Will winter conditions limit movement, sightseeing, or spontaneity?
- Am I craving warmth, sunshine, or cozy indoor moments?
If you can answer these questions, then yes, go ahead and book the ticket.
Remember that cold and brittle winters—especially in regions prone to snowstorms or freezing temperatures—tend to work best for:
- Shorter trips
- Structured itineraries
- Cities with reliable public transport
- Travel centered around staying indoors (family gatherings, holidays at home, museums)
On the other hand, milder or warmer climates allow for:
- Longer stays
- Slow travel
- Walking, cycling, and outdoor exploration
- Solo travel that feels safer and more enjoyable
If you’re traveling alone, choosing a destination with stable weather can dramatically improve your experience.
You’re less likely to feel stranded, fatigued, or overwhelmed, and more likely to enjoy quiet exploration and unplanned moments.
2. Who You Travel With Shapes Everything
The people you travel with matter just as much as the destination—sometimes even more.
Holiday travel magnifies personalities, habits, and expectations.
Understanding group dynamics ahead of time can save you stress and disappointment.
When traveling with family or large groups, short trips of about 2–5 days tend to work best.
Having clear schedules help reduce tension and fewer accommodation changes mean smoother logistics.
It is also important to have shared expectations to cater for everyone’s needs during the trip.
Large groups thrive on structure and making the trip shorter limit decision fatigue, budgeting conflicts, and emotional overload—especially during an already busy season.
On the other hand, traveling with a partner calls for a more intimate experience.
It calls for alignment on priorities early on before the trip(rest vs adventure, sightseeing vs relaxation) and discussing budgets openly.
While it’s a trip of two, it’s also important to account for personal time.
And solo travel—my favourite, longer trips are often more fulfilling.
I first explored this concept during my trip to Mallorca and never turned back.
When I’m in need of me-time, and a break from routine, solo trips do the trick.
They allow flexible itineraries which cater for movement at one’s own pace.
During the holidays, solo travel can be deeply nourishing.
Especially when you give yourself enough time to settle into the destination rather than rushing through it.
3. Timing: When You Travel, Can Make or Break the Experience
I think it’s international law that traveling during the holidays comes with inflated prices, among other things.
So choosing when to travel can dramatically affect how the trip feels.
In case you’re planning to do holiday travel, it’s better to do so just before or after major holidays and avoid peak travel days when possible.
For your own sanity, consider flying mid-week instead of weekends and choose early-morning or late-night flights for calmer airports.
Sometimes arriving a few days earlier—or staying a little longer—turns a stressful trip into a peaceful one.
Meanwhile, the goal isn’t to beat the crowds completely, but to reduce friction wherever you can.
Timing also affects energy.
Traveling during peak chaos can leave you exhausted before the trip even begins.
So you want to avoid that by traveling slightly off-peak to give youself space to arrive fully present.
4. Your Purpose for Traveling
One of the most important—and often overlooked—questions to ask yourself is:
Why am I traveling this holiday season?
I’ve found myself traveling during the festivities for both adventure and rest simultaneously, especially when I needed downtime abroad.
Whatever your needs are, let that inspire the why and where you want to travel to.
Whether it’s to rest and reset, to reconnect with loved ones, to explore somewhere new, to create space away from routine or to celebrate or to grieve.
Your purpose should guide the destination you choose, how packed your itinerary is and whether you prioritize comfort or adventure.
While a trip meant for rest doesn’t need a full schedule, a trip meant for exploration needs flexibility, not rigidity.
When your travel plans match your intention, the experience feels grounded rather than forced.
5. Budget With Kindness, Not Comparison
Holiday travel can be expensive, and it’s easy to feel pressure to “do more” or “upgrade everything.”
Instead, before you set out for your journey, set a comfort budget factoring in the essentials like food, transport, and downtime costs while leaving room for unexpected expenses.
In my opinion, while it might feel nice to do what everyone else is doing in the destination you chose, you want something that satiates you.
Not luxury, but presence.
A simple stay in a place that allows you to rest, walk, and breathe can be more fulfilling than an expensive itinerary that leaves you exhausted.
Let your budget support peace, not pressure.
6. Plan for Rest—Not Just Activities
Going to a new place for the first time makes you feel like you must do everything and anything recommended by Google or your favourite influencer.
I’ve been there.
At the end of the day, you’ll tick off stuff on your bucket list but at what cost?
It’s the holidays for crying out loud.
So you want to factor in some rest in all your sightseeing plans.
To easily add rest to your schedule, find out days with no major plans and get you accommodation that supports comfort.
Another way is to plan a visit to a quiet space or a natural space.
This will help you reach home feeling full rather than depleted.
Closing Reflection
Holiday travel doesn’t have to be perfect to be meaningful.
It just needs to be intentional.
When you consider the weather, the people you’re traveling with, the timing, the duration, and your deeper purpose, travel becomes less about escape and more about alignment.
If you plan to travel this holiday season, travel in a way that allows you to arrive home softer, clearer, and more connected to yourself than when you left.
That, to me, is the true gift of holiday travel.
Otherwise, happy holidays!