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7 Easy Tips on How to Plan a Vacation So You Travel More and Stress Less!

This blog post was updated on August 4, 2021.

Not so pleased with how you’ve traveled in the past or feel as though you spent your vacation time unwisely in previous years? If you’re wondering where you’ll end up going over the coming months or worry that you’ll find yourself stuck in a travel rut, in the doldrums of getaways and adventures… we’re here to tell you not to worry! There are some simple things you can do now to make the most of your next 12 months of travel opportunity.

Here are some broad-stroke ideas to help you plan effectively and actually get to the places you most want to see this year. From pre-trip prep to strategic planning or even as specific as building out the perfect itinerary, these suggestions on how to plan a vacation will help you turn your travel dreams from abandoned adventures to exciting escapades this year!

Envision Your Trip

how to plan a vacation - envision your trip

First and foremost allow yourself a chance to fantasize about where you would like to visit, what you would like to see and do when you get there, and the kind of experiences and memories you want to have/make when you’re there. Put down your phone, close your laptop, shelve your guidebooks. Sit down in a comfy chair with a cup of coffee or tea and maybe a notepad and pen – and then envision your future trip. Where would you go if money, time, the job, family and other obligations weren’t an issue? Allow your mind drift where it wants to without inhibitions or thinking an idea is too expensive or farfetched. Ahhh!…see, wasn’t that nice? Almost like a mini-vacation in itself, right?

This is one of the most important steps in the process because this is where your very first “draft” of your potential travel itinerary takes form. The where and the what are the two most difficult aspects of planning a trip, especially considering external factors and obstacles that may get in the way of your picture-perfect vacation. Once you’ve envisaged your trip, you can set some parameters around how to plan (ie: if your dream trip is a pricey one you can start a savings plan to afford it).

Be Ahead of the Game

how to plan a vacation - look ahead

Now ease back into reality by taking a look at your calendar for the year ahead. What kind of weather did you imagine in your ideal vacation? What holidays do you definitely have off from work? If you have school-aged children when are their vacation days? What dates do you know you’ll need to visit with family or attend special occasions? Also, ask yourself when do you usually feel the strongest need to getaway. Height of summer? Depths of winter? Once you have a good sense of both when you can and most want to travel, make a note of the dates that match up (maybe give them a star on the calendar or block them off as travel days so you’ll know not to schedule other things). This will also help you in keeping an eye out for airline tickets and request time off well-ahead of your vacation to ensure you get those specific days off from work.

Make a Plan for Budgeting


If you’re wondering how to plan a vacation that leads to stress-free travel, obviously, budgeting is key. If you’re akin to the ways of start-of-the-year budgeting (if you’re not, here’s your wake up call!) you know that planning out your big expenses as early as possible will give you the best look what your potential savings for the year can look like. So, while you’re crunching the numbers for the year be sure to include how much you think you’ll need for travel.

Not only is starting your year by considering your expenses is always a good idea, but also, when it comes time for your trip, you’ll be ready to go without having to take extreme measures or pinch pennies at the last-minute to make it happen. How much you set aside for the next several months for your travel costs is really up to how much you can spare and how important going away is to you. Do you need to save up for a big trip at the end of the year or are you able to get away now – or can you do both? As the weeks pass, return to your budget to see how you’re doing with saving and spending.

Evaluate Your Past Experiences


An activity that might help with everything from deciding whom to travel with and for how long to budgeting and planning your trip itinerary is to remember past travel experiences. Have a think about the trips of your past that went really well and those that could have turned out far better. Do you want to repeat your travel style or do you feel like you could have more fun doing things differently? This will help you plan out your trip according to your preferences and will also allow you a chance to broaden your horizons on future trips.

Consider Your Priorities


Need to catch up with a friend or family member on the other side of the country? Would a surprise weekend city break be the perfect gift for your anniversary or partner’s birthday? Already know you’ll be traveling for work or family at some point this year? Maybe you can make travel a means to another end and achieve more than one goal at once. Planning out your trip length, location, and even your accommodation will be much easier if you have an idea of what your priorities are. Whether you’re a die-hard museum lover who needs to see all the ones in the destination you’re going to, or you’re all about seeing and spending time with loved ones, and itinerary becomes much clearer once you’ve noted your must-do’s for a trip.

Don’t Forget to Be a Little Spontaneous

how to plan a trip - be spontaneous

Be adaptable to your planning. You never know what’s around the corner. Besides, adding some slack to your calendar enables you to take those last-minute getaways and make some unforgettable memories! Don’t be so strict in your plans that you miss out on anything amazing that comes up on your next trip. Striking the right balance can be tough but not impossible. Maybe even save some spare vacation days or personal days for a “rainy day” or spontaneous excursion.

Trust Your Gut, Take the Plunge!

how to plan a vacation - take the plunge

So, are any of those dream destinations actually places you could visit? Once you’ve got down your free dates and funds for the year, see how feasible traveling is going to be while keeping in mind your travel style and relevant priorities. If those dream destinations are out of reach for this year, is there somewhere similar where you could go? When you decide on a trip you want to take, don’t hesitate to start making concrete plans. Book flights and accommodations as soon as it’s possible. Don’t let the inspiration die and don’t wait so long that you miss out!

How do you plan for your trips? Do you have long term destination goals or are you more a spur of the moment sort of traveler? We’d love to hear your suggestions to help others see more of the world and enjoy themselves to the fullest when they do.

About the author

Chris Osburn

Chris Osburn is a freelance writer, photographer, consultant, and curator and the driving force behind the long running and award winning blog, Originally from the American Deep South, Chris has lived and worked all over the world and has called London home since 2001.

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