How to Plan a Trip When You Hate Planning and Love Spontaneity

You know how I said I really wanted to limit my international trips this year? Yeah I’m not sure how well I’m going to do with that little New Year’s resolution. And don’t even ask about my resolution to only eat chocolate once a week.

I’ve been trying to focus all those wanderlustful feelings on planning a trip (or like ten) around Norway this year, but then for some mysterious reason my browser keeps getting filled with Wikitravel tabs of South American cities. What’s going on?

I even caught myself researching national parks in the US, and it’s been ages since I’ve traveled through the United States. Maybe too many ages?  

Which is all to say, I’m totally on trip planning mode over here. Maybe you’re feeling the same?

The funny thing is, I’m not actually much of a planner. I don’t know how to work a spreadsheet, and I am all about straying off the beaten path on my travels. And I mean, it’s not like you can plan your detours from the beaten path, right?

Actually, in some ways you can.

I always want flexibility in my travel plans, but at the same time, I do carefully plan my trips in a way that allows for spontaneity when I’m traveling.

Seeing how impressively organized some people are with their travel itineraries, lists, calendars, Google docs, etc. used to make me feel super overwhelmed, and like the least organized traveler ever. But I’ve come to learn that a lot of that prep work is unnecessary for me, and in fact can tie me too firmly to a plan I made about a place I haven’t even visited yet.

Instead I’ve developed a system that involves minimal planning, while at the same time taking care of all the necessities so I don’t waste time on my trips looking up things to do or stressing because I broke my leg but totally forgot to get travel insurance and now my bank account is empty (okay, luckily that one never happened to me).

So if you’re like me and the thought of planning out every little detail of a trip stresses you out, here’s what you can do instead:

Choose your destination and travel dates

Pretty much every trip starts with either a destination or a travel date.

If I have travel dates, I’ll take a look at the fifty page travel bucket list taped to my wall and see which destination fits the travel time frame and season.

Okay, I don’t actually have a list taped to my wall, but you know what I mean.

I always have a bunch of places I’m dying to visit, as well as a general idea of how long I would need for the trip. I generally choose cities for shorter getaways, and wilderness or a mix of cities + nature for longer trips.

But if you don’t have a bucket list of your own, check out my travel map for some inspiration.

And then maybe check out the destination pages of some other travel blogs. I always find it so interesting to see where other people have traveled, and how many of us tend to focus on particular areas of the world (if you look at my map you’ll see I really need to work on my Spanish!).

Another key step in choosing my destination and travel dates is of course researching flights! This is usually when my initial plans will totally change because I’ll realize different dates would be cheaper, or that it’s peak season for flying to that destination so I should go somewhere instead.

I’ve recently been using Kiwi.com for finding flights, and I love that the search results will also tell you how much money you could save if you flew on a different date or into a different airport. It saves so much time over having to search the same route on a bunch of different dates and compare. You can also set price alerts for specific flights so you’ll get an email when a fare drops.

Research visas and vaccinations

Before I get any further into travel planning I’ll check to see if I need a visa and how long it will take to get one. Because I definitely don’t want to waste time planning a trip only to find out later that I won’t be able to get a visa there anyway!

This is also a good time to figure out if you’ll need vaccinations, as it can take a while to set up appointments for those.

Set your budget

Obviously this is going to vary depending on how you handle your finances, but I always like to set aside a rough amount that I’m happy to spend on the trip.

I do this before booking any flights because I want to make sure that my budget will allow for the type of vacation I’m looking for in the place I’m planning on visiting.

Basically I’ll check how much flights will cost and then I’ll have a quick look at transport costs (how much a car rental will cost, train prices, etc.) and accommodation prices on Booking.com and/or Airbnb to get a rough idea of how much this sort of trip will cost, because of course travel expenses can vary wildly from country to country.

Flight search engines often also include hotels and car bookings, so you can usually search for flight, transport, and accommodation prices all in one place.

Map out an itinerary

How do you decide on an itinerary that will be detailed enough to include all the best experiences, but flexible enough to allow you to get off the beaten path a bit once you arrive and get a feel for the destination?

This is going to sound super biased since I’m a travel blogger, but I do pretty much all of my travel research through travel blogs. I might take a quick look at Wikitravel to get a very general feel for the place I’m visiting, and then I’ll Google “[destination name] travel blog” to see how other travelers like me chose to see the place.

This is also a reason that I’ve been writing so many itineraries lately – personally I find them so helpful when I’m planning a trip.

Guidebooks will usually focus on all of the main tourist spots, while blogs often highlight less visited spots. Of course this isn’t always the case, so I always try to find bloggers with similar travel styles to me – if it sounds like they didn’t talk to any locals or experience anything beyond the hotel and main tourist spots I’ll probably skip over their advice.

And unless I’m just going on a city break, I will always, always check out the local national parks. I love beautiful views, and national parks tend to have the best views.

I don’t over plan my itinerary, largely out of laziness, but also to allow myself flexibility. I make note of all the options available to me, but I let myself decide things like where to eat and places to visit on the actual day based on how I’m feeling, the weather, and what I’m actually finding most interesting about the place I’m visiting.

Book flights

There are a lot of theories about the best time to book flights, but generally I just try to book as early as possible. Or if I’ve set a price alert through Kiwi.com I might wait a few weeks to see if the flight I’m looking at goes down in price (though of course that’s a bit of a gamble, as the price could go up instead).

On longer trips I also try to roughly map out my itinerary before booking flights, because I might want to fly out of a different airport than I flew into (especially when visiting big countries like the US).

Book accommodation

Ideally I would love to only ever book my first couple of nights of accommodation and then wing the rest so that I can have ultimate flexibility, but depending on where I’m going this could actually really limit my options once I arrive. For example in Norway accommodation in off the beaten path areas is quite limited, so if you don’t book well in advance you’re going to have to either wild camp or stick to the main tourist hubs.

This also happened to Rachel and me when we were in Panama. We waited until the last minute to book accommodation on Bocas del Toro because we wanted to get local advice, but by the time we were ready to book all of the lovely boutique spots were taken so we ended up on a huge resort.

So these days I usually do try to book all (or most) of my accommodation in advance.

I really, really love hotels, but I also love the local feeling of staying in an apartment, so usually I try to go for a mix of accommodation styles, depending on the length of my trip.

Combining accommodation styles also adds variety to my trip and lets me experience a place from a bunch of different angles. So while some people might think it’s strange that I’ll go from a luxury hotel to a basic apartment in a local neighborhood to a lively hostel, I actually am doing this on purpose!

Book transport

Okay, this will depend on where you’re going and how you want to get around, but if you’ll be renting a car or taking public transport, it can be good to book well in advance.

Car rentals are almost always cheaper when booked early, and at least in Norway you can buy train tickets for a fraction of the standard price if you book early.

And even if you’re planning on hitchhiking it can be good to hop on Hitchwiki and check out the best spots to catch rides and which places are reported to be more difficult.

When deciding on transport I try to copy what the locals do. So in the US I’d want a car, in Thailand I’d rent a motorbike, and in Copenhagen I’d use a bicycle.

Book activities

To be honest, my itinerary usually consists solely of my accommodation for each night of a trip. I’m not one to decide on specific restaurants, shops, or museums (lol) I want to visit beforehand, as I like having as much flexibility as possible.

In fact I’d say the key part of planning a great trip somewhere is to talk to locals when you arrive. You can research as much as you want before a trip, but the best advice you’ll get is from locals when you’re there! Plus personally I think there’s no better way to get to know a new place and have a memorable experience than getting to know the people who live there.

So I try not to stress over gaps in my itinerary or how I’m going to fill my days, because I know that once I’m there I’m going to find more than enough things to do simply by asking. Or maybe I’ll meet someone and end up spending the day chatting to them over coffee, and that’s fine too. Not all great travel experiences have to involve visiting a bunch of new places – in fact my favorite travel memories tend to be about the people I met, not the sights I saw.

But if I’m going somewhere with a particular experience or activity in mind (like husky sledding, whale watching, or Northern Lights chasing in Norway), then I’ll make sure to book that in advance.

I also like taking a quick look at activity options on GetYourGuide, Viator, or Manawa, as sometimes I’ll find something fun to do that I wouldn’t even have thought of on my own. Manawa especially tend to have a lot of really unique options (and not all of them are super intense adventure activities like the name suggests).

Buy travel insurance

I used to only get travel insurance for longer trips or places where I think I might need it, but these days I book it for every single trip. So many unexpected things can happen on a trip that I personally think it’s worth paying a little extra for the peace of mind travel insurance gives me.

I always book through World Nomads because I’ve had good experiences with them when I’ve had to file in the past, but there are lots of other options out there as well. Just make sure to go with a reputable company with good reviews, because some companies will have so many rules and fine print that it’s almost impossible to get your claim approved.

Plan your packing list

Once I know where I’m heading I start to plan out my packing list. I usually do this fairly early, because I want to have time to buy any special clothing or gear for my trip.

These days I travel with either my Kosan backpack or my Lojel suitcase. So first I’ll pick which luggage I want to use (I way prefer a suitcase when I can, but sometimes it’s just not as practical), and then I’ll start thinking about what I want to bring!

Before leaving

Before leaving I’ll decide whether or not I’ll be getting a local sim card when I arrive, as having Internet will make a difference to how I plan. If I don’t plan on having mobile data on my travels then I’ll download local maps so that I can still use my phone to navigate while offline.

Maps.me is really great for offline maps that include shops, restaurants and custom bookmarks you can add to the map before leaving. Sometimes I’ll also check the app store for local apps that might be helpful. For example if you simply search “Norway” in your app store you’ll see a bunch of useful apps ranging from hiking routes to supermarket deals to Northern Lights alerts.

And if I do want to buy a local sim card, I’ll research which plan is best for tourists and where I can buy the card. Usually it’s easiest to do this at the airport, which is what I almost always do unless it’s considerably more expensive.

Right before leaving I’ll also figure out how I’m going to get from the airport to my accommodation. And if I’ll be taking a taxi, I’ll research what the taxi situation is like at the airport, as in some countries you have to be really wary of scams, whereas in other places everything is super easy and regulated. I like to know what to expect in advance!

And if I’ll be taking public transport to my accommodation I’ll research exactly where I need to go to find the bus/train/etc, especially if I’m coming from a long flight, as I know I’ll be too out of it when I land to want to figure it all out then. I like to make the process of getting off the plan to my accommodation as easy as possible.

This isn’t an issue with Norwegian banks, but depending on your card company’s policies you might also need to let them know that you’ll be traveling so that they don’t block your card when it’s used in a new country. This used to happen to me all the time when I used American cards and it was such a pain!

At the airport

Once I land in a new country I’ll get local currency at an ATM, and I might also buy a local sim card for my phone.

And then I’ll be off!