How to Plan a Vacation That Works for You

Vacations are fun, but vacation planning can be tedious. Researching, booking, timing, and budgeting for a trip can take away all the fun of daydreaming about it. Oftentimes, because planning a trip seems like such a monumental task, people tend to over-plan and structure their trips so rigorously that a vacation sometimes doesn’t feel like a vacation at all. You book the flight, get ready to enjoy, and wind up turning an easy and relaxing getaway into a frantic game of catch-up where you scramble to see everything, go everywhere, and stay everywhere you planned to. Enter the “loosely structured itinerary” method of trip planning. This lesser-known and easy-to-follow technique consists of doing some research, booking the bare minimum, and letting the rest happen in real time.

What Is a Loosely Structured Itinerary?

In short, a loosely structured travel itinerary is a trip planning method that provides all the comforts of a trip structure, but leaves out a bulk of the specifics. There are no hour-by-hour or minute-by-minute plans. There are no museum tours you have to see or group excursions you have to wake up early for. With the loosely structured itinerary, you get to flexibly choose exactly what you want to do, all while having the blueprint of your trip in your back pocket. It’s a way to plan a vacation that allows you to wake up every morning and decide what you want to do rather than abide by what you have to do. This not only takes the pressure off individual days of your trip, but more importantly, it allows you to take into consideration recommendations and information from other travelers and locals when you actually land in the country, rather than basing your entire vacation off a Yelp review.

How Do You Create a Loosely Structured Itinerary?

Define Your Non-Negotiables

Every trip starts and ends with a few inflexible limitations, and they’re usually time-frame, budget, and destination. Whether it’s how many vacation days you’ve accumulated or how much money you have to spend, these are the fixed restrictions that you’ll have to work within, mostly because they’re out of your control.

So, before delving into the fun part, start here. Ask yourself:

How long can I be away?
How much money am I willing to spend?
How far can I go within the confines of this weekend, this week, or however long I have?

Once you establish these boundaries, you’ll have plenty of room to plan the fun bit.

And when picking a destination, consider currency, climate, and expectation.

How far does your dollar get you in the local currency?
Does this country have dry and wet seasons?
Are you looking for a relaxing beachside vacation or an adventurous trek up a mountain?

Thinking these factors through will make it much easier to narrow down a long bucket list of countries you’d like to see to a much more manageable and realistic size.

Get to Googling

Once you’ve nailed down the constraints of your trip, you can get to the fun bit. Spend a few days researching your destination so you can familiarize yourself with what you’d like to see, do, or try while there. Whether it’s hiking, exploring a city, eating local cuisine, or taking museum tours, doing your research will get you acquainted with your destination and give you options, ensuring that you always have an activity and sidestepping the dreaded day of nothing to do.

And other than the obvious activity research, be sure to look into the more practical stuff as well:

What’s the daily cost of living where you’re going?
Do you need any vaccines?
Do you need a special visa?
Are there any significant cultural norms you should know ahead of time?

Looking these up well before your trip will cut out any unexpected obstacles when you arrive at your destination.

Map Out Your Route

Depending on how long your trip is, mapping out your route can be as simple as flying into and out of the same city. For more extended trips where you may fly into one city and out another, this step is paramount to getting a sense of orientation and planning the direction of your trip.

Think of it like connecting the dots: if you fly into City A and fly out of City B, all that’s left to do is connect the two with sights you’d like to see along the way. Let’s say, for example, that you’re booking flights to Peru and would like to fly into Lima and fly out of Cusco. Then, you’d have to take a look at a map of the country and find cities along that route that you’d like to visit, like Ica, Paracas, and Arequipa. Now you know vaguely in which direction you’ll be traveling and can plan accordingly. The reason this step is so important is that having planned a route like this will ensure you won’t spend precious hours or days of your trip winding around detours and circling back to your point of origin. You’ll have an easy-to-follow and straightforward line to follow from Point A to Point B. You can even plot it on a map and bring it with you.

Divide Your Time

Now that you know where you’re going, you can divvy out your days based on how long you’d like to stay in each city. Keep in mind, this is tentative and will likely change. The whole point of a loosely structured itinerary is to allow for flexibility, so think of this step as formulating a skeleton of a trip so you have a sense of timing, but with wiggle room in case you want to deviate from it.

Say you arrive in Rome and find it too loud and boisterous. Your itinerary may say that you have four days there, but you hear that Florence is nice and quiet. There’s no reason why you should force yourself to stick around Rome if you don’t want to. Go ahead and move on! But having this sort of backbone to your trip can be really helpful in figuring out how many cities you’ll have time for, and how long you can realistically be in each one.

Book the Bare Minimum

The final step in planning a trip is always booking flights and accommodations. It’s tempting to want to book everything ahead of time so you don’t have to think about planning on the fly. However, when you do book everything ahead of time, you leave yourself no flexibility at all. Maybe you liked the last hotel a lot; maybe you weren’t finished exploring a city; maybe you heard that the hostel you booked ahead of time has bed bugs. Book the flights in and out of your destination and your first hotel, with ideas for the next few in mind. That way, you’ll have your major expenses covered, but also leave room for changes that will inevitably happen along the way.

There are obviously a few exceptions to this rule, notably in places where there’s a busy season. Japan during the cherry blossom bloom, for example, or New York at Christmas time. There are also some cities that are notoriously tourist-heavy where you may want to check availability ahead of time so you don’t show up with nowhere to sleep.

Now that you know how to plan a vacation, just follow these 5 simple steps and you’ll set yourself up for success! Worries about getting lost or bored will fly out the window with the structure you plan, but nothing will be fully set in stone. Leave room for recommendations, let life happen, and spend your precious vacation days … well, enjoying your vacation!