How to Plan a Big Trip

March 16, 2017

Planning a trip for anything longer than a week can seem pretty daunting! When Dave and I decided to do Europe for a month, I definitely didn’t know what I was in for. I knew I was pretty good at planning weekend trips, but a whole month?! In 10 different cities?! Daunting to say the least. Even though we definitely could have been more prepared (remember the whole Italian driving nightmare?), I feel like we did pretty well. For the most part, we knew what we wanted to do, where we wanted to go, how much we could spend, and only had a couple of meltdowns along the way (mostly on my end). If we can plan a trip this long, anyone can! Here are a few of my tips for planning a long trip, whether you’re going for 2 weeks or 2 months.

1 // Figure out where you want to go

Picking out a destination seems like the easiest part, but it definitely takes some time to think about, especially for a long trip. We originally wanted to add Switzerland to our trip, but after some research we learned that November is pretty much the worst month in the whole year to go, so we decided against it. Once you decide what countries, narrow down which cities you’d like to see, and make sure it seems actually doable (aka the cities aren’t on the opposite ends of the country).

2 // Decide on dates

Once you’ve decided where you want to go, pick your dates. As I mentioned above, make sure you’re going to your destination at an appropriate time! Fall in Europe was absolutely perfect. We decided against Switzerland in the fall because we were envisioning green hills and blue skies, which is NOT what it would have been in November! So make sure you’re picking dates that make sense for your destination.

3 // Assess your costs

Once you’ve roughly decided on your dates, figure out roughly how much the trip is going to cost. Factor in approximate airfare, accommodations, food, and extra activities for the duration of your trip and go from there. If you think you can make it work for a month, do it! If you’d rather spend more on hotels and do 3 weeks instead of 4, do that instead. Figure out what works best for your needs!

4 // Make a budget

Once you’ve figured out roughly what you’ll be spending, budget accordingly. If you’re cutting it close budget wise, make sure to start saving ASAP. Cut back on eating out and shopping sprees before your trip. I mean, you would rather be spending your money eating out in your fabulous destination, right?! Saving little by little beforehand means you’ll have a nice chunk saved just for your trip, so it’s not like you’re yanking hundreds and hundreds of dollars out all at once and not being able to pay rent.

5 // Book main flights

I like booking my flights as soon as my dates are figured out. I just can’t stand waiting and I like to have a set plan to base everything off of. So if you’re able to, I suggest booking your main flights as soon as you can. As I mentioned before, we flew with Norwegian and couldn’t recommend it more. They have one way flights (nonstop I might add) from LAX to London for $384. I MEAN. You’re just not going to get a better deal than that. It makes me want to book another flight!!

6 // Research, research, research

This is where the bulk of your trip planning will be. Buy books on where you’re going (I still love going through actual books. And they usually have maps which sometimes come in handy!), and scour the internet. If I know a blogger who’s been to a certain city, I’ll start there and see their recommendations, and I always love checking geotags of certain places on Instagram to find great local restaurants and cool spots. Research as much as you possibly can, so you’re prepared when you get to your destination and can hit the ground running!

7 // Make a rough itinerary

Once you’ve done your research, map out a rough itinerary. It might seem a little intense, but having it written down is really helpful! You probably won’t end up doing each thing on the specific day you have planned, but at least you’ll have an idea of which things you want to do and what you can realistically fit into your trip.

8 // Book accommodations

After nailing down the cities you’ll be in, start booking your accommodations. Dave and I lucked out and stayed with family friends for half of our trip (which really helped keep costs down!), and did Airbnb for the rest. If you know anyone where you’ll be going, reach out and see if you can stay with them! And if not, I really couldn’t recommend Airbnb more. There’s an Airbnb for any budget, and in Europe they are pretty darn cheap! Plus, you really get to know the culture of the city!

9 // Book shorter flights, trains, etc

Now that you know pretty much all the cities you want to go to, book as many of your shorter flights and trains if at all possible. Especially if you’re doing the Eurostar– it books up fast and you want to make sure you get a seat! Booking things beforehand just means one less worry when you’re on your trip.

10 // Finalize details

Talk everything through with whoever you’re going with. Talking through it all helps a ton to make sure you’re on the same page! Make sure you’ve got all the details planned like how you’re getting to the airport, how are you getting to your hotel when you arrive, and all the little nitty gritty things that are actually super important. It’s all in the details! 😉

The last step is to go and ENJOY!!!



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  • Lots of great tips! I’m heading to London in the Fall and I’m already in full planning mode. Planning is half the fun, isn’t it?