How Do You Know When To Travel?

Dreaming of full-time travel but unsure when to start? Learn how to prepare for your big adventure with practical tips on budgeting, family alignment, destination planning, and overcoming fears. Discover why the best time to travel is now—and how to make it happen without regrets. Start living your dream life today!

You’ve been dreaming, planning, and thinking about a big trip for as long as you can remember, yet something has always held you back from taking the plunge to travel full-time. So, when is the right time? I’m here to share our insights and, hopefully, get you on your travels and living your dream life as soon as possible.

Step 1: Get Your Ducks in a Row

You don’t need to meticulously plan every detail, but there are a few non-negotiables to sort out before embarking on your big adventure:

  • Finances: Create a budget and understand how long it will last. Will you earn as you go? Can you transition your work online? Could you rent out your property for extra income? Research flights, accommodations, and other costs that fit your budget. If finances aren’t ready yet, make this your top priority.
  • Family: Align with your travel companions. Are everyone’s expectations and budgets in sync? If you have kids, can you take them out of school, and are they excited about travelling?
  • Must-Have Items: Start gathering essentials as early as possible. This builds momentum and ensures nothing is forgotten. Think passports, insurance, visas, medicines, and luggage. When buying new clothes, choose versatile, packable, and quick-drying options.
  • Home and Belongings: Decide what happens to your home. Will you rent it out? Sell it? Have someone look after it? Start decluttering and organising now—tackle one room or cupboard at a time to build momentum.
  • Destination Planning: This may seem fun (and it is!), but decision fatigue is real. Narrow your options based on your priorities, safety, and interests.

For more tips and detailed solutions, check out our other blogs.

Step 2: Overcome the Fear of Taking the Leap

Life is full of reasons not to pursue your dreams, even the ones you want most. But sometimes, you just have to go for it. When we booked a single flight and left home with our small children, I was terrified. Yet, the excitement was exhilarating, and I don’t regret a single moment of that trip. Now, we’re busy preparing for our next adventure.

Here’s what’s next:

  1. Choose a Destination: Research safety, activities, visa requirements, and how long you can stay.
  2. Book a Flight: Lock in your plans with a ticket.
  3. Find Accommodation: Coordinate this with booking your flight.
  4. Finalise Your Priorities List: Make sure your must-haves are ready to go.
  5. Go Have the Time of Your Life: You’ve earned it!

Biggest Regrets (and How to Avoid Them)

Many people wait for a major life event or scare to push them toward their travel dreams. Others wait until retirement. But why wait? Why not go when you’re healthy, young, and able to share these experiences with your children?

  • Starting Too Late: My biggest regret was waiting so long to begin.
  • Unfinished Priorities: Leaving without finalising our to-do list led to costly mistakes and time wasted fixing things remotely. Learn from us: get your priorities sorted before you leave.

Returning Home: What to Expect

Coming home can be one of the hardest parts of travelling. You’ll go from the excitement of constant movement to the stillness of one place. You may face unanswered bills, a space that no longer feels like home, and friends whose lives haven’t changed while yours has transformed.

But you’ll adjust—eventually. Here are some tips to make the transition easier:

  • Don’t sell your home if you can avoid it.
  • Keep ties with the people and communities you’re returning to.
  • Leave options open with jobs, clubs, schools, etc.

For us, returning home was a fleeting visit—just long enough to catch up with loved ones before planning our next trip.

The Right Time Is Now

Sometimes, you’ll know for sure when it’s time to travel. Other times, you’ll need to step far out of your comfort zone to find life’s joys. If long-term travel is something you dream about, don’t wait for the perfect moment—make it happen now. The only right time is as soon as possible.

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