The Perfect Trip Planning Checklist

Travel planning is hard! But that doesn’t mean you can’t plan the perfect getaway! The trick is to keep it simple – and this fun itinerary template will help!

You want to plan the perfect trip – filled with adventure, relaxation, and plenty of stories to tell after – but before we start, you’ll need a checklist – complete with everything you need to remember for the perfect vacation, including a vacation activity planner.

By using this exact template, we’ve been able to plan over 20 vacations and maximize our paid time off! Including some of the trips listed below!

Trekking though the Sahara Desert by moonlight on camel
Road tripping through Italy
Dogsledding in Norway
Oktoberfest in Munich

But I get it. Travel planning is hard. Believe me, I know.

So in this post you’ll get the exact steps we take to plan every trip.

Grab your free copy of the Travel Planning Template from our resource library and let’s get started!

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Travel Destination and Flights

Ok so step one obviously has to be where are you going?

Maybe you have a destination in mind. That’s great! If not you can browse for ideas on our Destinations page to get started.

*And if you’re open to trying someplace new, just do what we do – go to Skyscanner and search from your nearest airport to “everywhere.” Then filter by “cheapest month. It will automatically give you a list of the cheapest places to fly to!*

Now ask yourself the following questions as you look up flights and hotels:

Is it the off season for that destination?
Is there a cheaper time to go there?
Are flight more or less expensive the weeks before/after?
Are there any major events in this place at that time?

These questions are super important because I’ll bet that you don’t want to pay any more than you absolutely have to. So let me give you an example:

We recently started planning our trip to Amsterdam. Immediately we realized that it was going to be super expensive even though it was the off season. All the hotels were booked – and what was left was insanely overpriced. We even started to reconsider our travel plans.

But before we gave up, I decided to see what else what going on in the city at that time. Turns out there was a super high-profile technology conference that week that brings in 67,000 visitors to the city. Needless to say we rescheduled for the week after and ended up paying half the price for our hotel!

Moral of the story: timing is super important.

Try to be flexible with your dates – even if it means rescheduling because it will help you have a good time in the long run!

Travel more with a full time job!

Travel planning is hard. But it doesn’t have to be. Get access to our free travel resource library to start crossing things off your bucket list!

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Things to do on vacation

So now you have an idea of where you’re going – and when. Kudos if you even have some flight information written down.

Now let’s look for things to keep you entertained – Pinterest is great for this.

Look up things to do, photo diaries for inspiration, and travel tips for your destination. TripAdvisor is also an awesome place to look since they have activities with reviews and can show you new ideas!

During this phase it’s important to get an idea of how much these activities cost! Unlike the flights and hotels (which are usually prepaid), you will have to put aside money to pay for the things you want to do while you’re there – AND what you’re going to eat.

Julien and I are major foodies so we always look up a few restaurants we want to go to and jot them down as well. Sometimes we rely on that list, and sometimes something smells really good and we just throw the list out the window 😛

But it’s better to have a go-to list when you’re starving than to get hangry and eat at some random not-so-great place.

Hotel and Extras

After everything else is taken care of, it’s time for the final touches. If you’ve been paying attention so far, you know that we haven’t covered hotels yet.

That’s because to us, the hotel is one of the final details.

You want to stay close to the majority of activities you want to do, but also somewhere that’s easily accessible. And you don’t know where that is until you actually do some research.

Here’s a few things to keep in mind:

Try to stay outside of the main tourist area, but not completely out of the city. Especially if you’re going to use public transportation. You don’t want to find out that the bus to the outskirts of town stop running at 9 pm and you need to get back later than that. That’s how you end up blowing your budget on taxis. Trust me.
Most major cities have multiple neighborhoods with different vibes. Look up your destination + neighborhoods and get an idea of where you want to be.
Try to use the same booking platform for the majority of your travel to cash in on rewards points. We love the free nights we get with hotels.com and always check there first.

The last details are the extra things you’ll need.

For example, we always need a dog sitter for Milo since no one will take care of a 100 lb dog for 1-2 weeks.

You may need a baby sitter, new luggage or new passports before you go. Jot those down so you won’t forget!

If that seems super simple it’s because it is! Travel planning doesn’t have to be complicated. By breaking it up into small sections, it’s easy to plan an entire trip from start to finish.

Just follow these simple steps: