Everyone dreams of taking multiple vacations a year, right? No one wants to be stuck at home or work for weeks on end. This is a quick way to burnout. In fact, even those who do take time off admit to working. Breathe reported that 74% of 18 to 24-year-olds confessed to working “sometimes or often on holiday.”
But planning more than one trip in the same year is a quick way to become overwhelmed, especially if you are not organized. Unfortunately, not all people are planning professionals After all, there are reasons why one person in each group is the planner. Being sufficiently prepared is more important than ever with travel demand rising again and prices changing frequently.
If you would rather that 2026 be a year full of exciting adventures, begin planning early on. This post outlines some of the best aspects to keep in mind when preparing multiple trips in one year.
Set Clear Travel Goals
Before you book, take time to think about what you want from your travels. Setting goals helps you to avoid overspending or rushing. Start by writing down the main reasons you want to travel. Maybe you want to explore a new country, visit family, or just relax on a beach. After deciding the purpose, choosing destinations and length of vacation is easier.
Next, consider the type of experience you want for each trip. Do you want something budget-friendly or luxury? Are you looking for adventure or calm? For example, you might plan a short weekend trip for rest, then book a long international vacation for a cultural experience.
Being honest about your energy levels is important, too. Too many trips in a year will get tiring. Try to spread any vacations out, as this will enable you to recover between journeys. Keep balance in mind when planning to ensure each trip feels enjoyable instead of stressful.
Maximize Annual Leave
Annual leave is a very valuable tool, particularly for those working full-time jobs. If you want to take several trips during one year, strategic planning is a must. There is no way to succeed with spontaneity here. With good prep ahead of time, your holidays will last longer without using extra leave days.
To begin planning, look at your 2026 holiday calendar. Take a note of all public holidays, long weekends, and company shutdowns. Public holidays are especially useful. These dates give you extra days off without using your leave. An example of this would be if a public holiday fell on a Tuesday or Thursday. You could take Monday or Friday off as leave to turn it into a long weekend.
As small trips are often just as refreshing as long ones, divide your leave into sections. One main vacation will use most of your annual leave, but a few days should be saved for shorter getaways. Again, try to plan around the weekends; this offers the most value.
Of course, speaking to your manager early helps. Leave requests that are put in early are more likely to be secured. If your annual leave requests are rejected, then you will need to amend your plans. Doing this step before finalizing your vacations will prevent trip cancellations.
Purchase Travel Insurance
No matter what, travel insurance is vital. Even more so when planning multiple trips. It protects you from unexpected problems, from flight cancellations and lost luggage to medical emergencies to sudden changes in your plans. No one can plan for these surprises completely.
But travel insurance can help. If you know you will be travelling more than once in 2026, purchase an annual multi-trip insurance plan. Annual trip insurance usually costs less than buying separate insurance for each trip. All of your travels within the year could be covered. There will be a time limit set by the policy, though, so be aware of this.
Read the policy thoroughly when shopping around for travel insurance. Not all plans are the same; not all plans cover the same things. Consider what you need most:
- Baggage protection
- Medical coverage
- Trip cancellation protection
Travel insurance provides peace of mind. Instead of stressing about things that could go wrong, you will enjoyyour trips. Even if you want to participate in adventure sports, some insurance policies do provide relevant coverage. Just make sure activities like hiking, skiing, and more are included in your selected plan.
To conclude, stress doesn’t need to be part of vacationing. Multiple trips in 2026 are definitely a possibility; it doesn’t need to be a dream anymore. Whether you need a break from work or just want to tick countries off your bucket list, travel should be enjoyed.
But it is easy to become overwhelmed, though, so start early, stay organized, and make 2026 a year to remember. This way, you are almost guaranteed to see more of the world.
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