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The Beginner's Guide to Overseas Trip Planning

Julia R

A guide for how to plan an international trip for the first time

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How to Plan a Trip

Planning a trip overseas can be overwhelming. There are so many things to think about! Will they speak the same language as you, where is the best place to exchange money, and are ANY stores open on Sundays??

If you’ve never planned an overseas trip before, I’ve put together some ideas, tips and things to know to help you get started. So here is your guide on how to plan an international trip

Let’s go!

Start the Planning Process

This is my favorite part of trip planning; the door is absolutely wide open and anything is possible!

Pick a Destination

The very first thing to do when planning a trip is to pick a destination (or two!). You most likely already have a destination in mind, like you want to go to New Zealand to visit the hobbit holes or Canada to see Niagara Falls.

The destination is pretty broad, not just a specific city. I usually start with a country I know I want to visit, like Germany at Christmastime. I will narrow down what specific parts of Germany to visit later.

If you don’t already have a destination, do some research on Pinterest or Instagram to see what places stand out to you.

Research Things to Do

Now that you have a country picked out, it’s time to do some more in depth (but still broad) research.

I search for “things to do in …” to see what that country has to offer, other than what I already know about. For example, I knew that I wanted to visit Hobbiton in New Zealand, but I had to find other things to do in New Zealand.

You do not have to plan your whole trip out minute for minute via the iternet. We’ll leave room for change and spontaneity. But this step gives us an idea of what there is to do, and gives us the outline for our trip.

Here are some places to search for things to do:

  • Pinterest

  • Instagram

  • Google

  • Travel blogs

Schedule Your Trip

Decide How Long Your Trip Will Be

Everyone has a different timeline they’re able to take for their trip. Some people can travel long term, and some people only have a week, or even a few days.

If I’m traveling internationally, I like to see as much as possible while I’m there. Most of my international trips are planned for 2 weeks. I would suggest your trip be around 10-14 days.

Be sure to account for travel time. Most international trips lose a day in travel.

Decide When You Want to Go

Do you want to go during a certain season or for a specific event? Like visiting Germany for Christmas markets, Hobbiton for International Hobbit Day, or Niagara Falls in summer?

Decide if you want to be there when the weather is warm, or if you want to avoid crowds and get the best prices during the off-season. Do you have to travel around a school break or your work schedule, or can you go whenever you get the cheapest price?

Decide on Your Travel Style

I like to see as many places as possible, but I also like to stay in the same place every night.

For your trip you will have to decide how often you want to move around between places. Do you want to stay in London for a week, exploring the city and also day tripping to nearby places, but always coming back to the same place every night? Or do you want to rent a car and road trip through Scotland and wake up somewhere new every day?

I personally like a mix of the two. I try to day trip as much as possible to the places I want to see, so I have some consistency every night. But I’m not opposed to picking up and moving around to see everywhere.

You also should consider if you want to be somewhere at night or in the early morning. As a photographer, I love being places at sunrise and sunset. I rented a car in Scotland specifically so I could be at certain places on my own time to take pictures, instead of coming with a tour during the day.

Make a Schedule

This is the fun part (at least for me—I’m obsessed with planning)!

Make a list of your “Must-dos” from all your research. Map out where they are in relation to each other. Are a few of them near a major city that would be easy to day trip from? Are you going to need a car to get to them?

Plan out a route that can get you to all of your must-dos and fit them in your time frame (remember to account for travel time!).

I usually make up a million different iterations of what my route could be (I love to plan…). It’s ok if you have to try a few different plans to get everything in. If you can’t fit everything in your time frame or budget, you might have to consider cutting a few of your must-dos.

This isn’t the final version of our trip, but basically an outline of all the major stops. Figure out in what city or town you’re going to stay every night.

Here is an example from our trip to England:

I didn’t have everything specifically planned out for each day, but I knew the major things I wanted to do. We can fill in all the little details later.

Book Your Trip

Once you have a rough schedule figured out, with all the main things you want to do and the places you want to stay, you can start to book things like your flight and your hotels.

Where/When to Book Airline Tickets

There are a million places to book airline tickets out there. A lot of travel bloggers suggest Skyscanner for comparing flights.

I usually look at flights in Google Flights. If you want to book directly from the airline, search for a flight on Google Flights to find the one that you want, and then look up that specific flight on the airline’s website.

Things to pay attention to:

  • Is there a charge for bags (including carry-ons)?

  • Is there a long layover (look out for overnight layovers!)

  • Does it require a change of airports?

  • Consider the cost of the flight vs. the time of the flight

How far ahead to book:

There really is no one answer to this question. Costs of flights vary greatly. If you’re able to be flexible, look for a good deal, and just fly out whenever you can get that deal.

What is the best day to book flights:

Also look at the prices for different days of the week. They vary greatly amongst flights, so the best way is to start searching for flights to your destination and see what days have the cheapest flights (usually week days are cheaper than weekends, but not always).

You might not have much flexibility with your dates, so just go for the best that’s available on your dates. I like to travel Saturday to Sunday to maximize my time in a destination. But if you’re able to be flexible, you can get the best prices on random days of the week!

What to Book Ahead of Time

There are so many things to book for your trip! Your flights, your hotels, dining, transportation, activities!

It’s good to have some things booked ahead of time, but also to have free time for things to not go as planned.

Things to book ahead of time:

  • Your flight!

  • Hotels

  • Rental cars

  • Popular attractions

  • Anything you absolutely MUST do

  • Literally EVERYTHING at Disney World

Anything else you are probably good purchasing on the go. Something like train tickets for day trips or moving between cities are really up to you. There are perks to booking ahead of time, and perks to buying them as you go, so that will be based on your travel style.

Again, if there is anything that you absolutely MUST do, book that, and all the transportation required for it, because you don’t want to risk not being able to do it.

Tips for Booking

  • Pay attention to what day of the week their calendar starts! A lot of countries start their calendar week on Monday, NOT Sunday.

  • Try to keep your first day pretty open, so you can adjust to the time difference or in case your transportation gets delayed.

Travel Documents

Make sure you have your passport for any international trip! But there are a lot of other things to consider. Do you need a visa or any immunizations to get into the country? Make sure you have all of the required documents well before you plan to leave.

Research Your Destination

Of course you’ve already researched your destination, but now it’s time to get into the nitty gritty of it.

Find Potential Things to Do

You already have your must-dos, but now it’s time to fill up all the rest of your trip.

Now that you have specific destinations for each day, you can research that specific city more in-depth. For example, if you’re staying in London to go to the Harry Potter Studio Tour, this is the time to start finding other things to do in London (and there are a lot!).

These are not things that you absolutely have to do, but rather possibilities to fill up your free time. That way you are not stuck in the middle of downtown Boston wondering what you should do, and ending up paying $25 a person to go to the aquarium because it’s the only thing you can think of to do.

You also have room to be spontaneous here, if you find something in the city, like the Cadbury Chocolate Factory you didn’t know was there! Since not every minute of your trip is accounted for, you have time to visit said chocolate factory, but you’ll also have back up things to do that you researched ahead of time.

You might even find some more “must-dos” here, so don’t be afraid to go ahead and book some more things after you research your destination.

Look Up Places to Eat

It’s good to have an idea of where the restaurants are in a city. In some places, it’s easy to walk out the door of your hotel, head down the street, and find somewhere local to eat. In other places, things are so far spread out it can be very hard to be spontaneous.

Research popular areas for food, like Borough Market in London. Also research popular foods to try in that city or country, so you know things to be on the look-out for.

  • Pro-Tip: Research whether or not it is common to leave a tip at restaurants. While this is common in the US, it is not always typical around the world.

Research Common Scams

It’s a good idea to Google “common scams in …” Tourists are an easy target for scams, so even though you hopefully won’t have to worry about it, it’s good to be aware of common scams so you won’t fall for them.

One common scam in Europe I discovered (since it happened to us…) is to be charged for damage to your rental car after you’ve already returned it and passed inspection. Always take your own pictures of your rental car (before and after), so you can dispute any false claims.

Figure out Transportation

The first step to figuring out transportation is to research how people usually travel around that country. Is it somewhere that is well-connected by trains, or is it somewhere more spread out, where people commonly drive themselves everywhere?

Then you have to decide for yourself what your style of travel is. Do you want more freedom? Book a rental car. Do you want less responsibility? Book a tour. Or maybe… a bit of both?

Rental Car

The most convenient way to get around is to drive yourself with a rental car. Of course, this means having to drive in a foreign country, where they might drive on the opposite side of the road or have road signs in different languages.

If you want to travel to a lot of off the beaten track places, or have the freedom to be somewhere at a certain time of day, or just at your own pace, renting a car is a good idea. Just read up on the travel rules of the country you’re visiting, and common scams as well.

Renting a car in a foreign country always feels very intimidating, but just relax and go for it, and you’ll probably find it starts to feel natural after a little while.

Book a Tour

The easiest way to get around is to book a tour. Just book the tour, show up to the meeting spot, and you won’t have to worry about anything else. This is especially good if you’re worried about driving in a foreign country or are prone to getting lost (me…).

Unfortunately, this is also the most expensive method, and you will be stuck with a bunch of other tourists (you can also book private or smaller tours, that will help with that).

I, personally, prefer to go somewhere using public transportation, but if it is challenging to get to, I would rather book a tour. That way I get some experience of really “traveling,” but also can relax and just enjoy myself.

Public Transportation

My favorite way to get around is public transportation. It is often the cheapest way to get places, but it can sometimes be a real hassle (like when the London Overground line we needed was shut down).

Much of Europe is connected by train, so using public transportation is fairly simple and common. Other places, like New Zealand, are not so well connected, so your best bet is to book a tour or drive yourself.

Learn the Language

What language do they speak in the country where you are traveling? Even if they speak the same language as you, do they have different words/phrases for common things like “where is the bathroom???”

Here are some common phrases to look up how to say:

  • Hello/Good Day

  • Thank you/You’re Welcome

  • Excuse me

  • Could you help me please?

  • Where is the bathroom?

  • How do I get…/How do I find…?

  • How much does this cost?

It’s a good idea to download the Google Translate app to your phone before you travel, although you might not always be able to access it.

What to Pack

What Will the Weather be Like?

Research what the average weather is like in your destination for the time of year that you are going. You can also Google “What to pack for…” Google is the answer to everything!

  • Pro-Tip: Bring some plastic bags, in case you need to transport wet clothes. Like if you went swimming in the pool the night before you leave, or you can’t figure out the washer/dryer combo and end up washing your clothes three times before you have to leave to catch your train… Stuff like that.

What Kind of Outlets do They Have?

Make sure you check what kind of outlets your destination has, and get an outlet converter if you need one. You can get a universal outlet converter, and then you’ll be able to travel anywhere!

Consider Luggage Size

Are you going to be traveling around a lot? Will you have to roll your luggage from city to city and across train stations? Do you have to pay for checked bags, and do you even want to check a bag, or do you just want to stuff everything in your carry-on? Is there a weight limit for luggage on ANY of your flights, OR any of your trains?

These are all things to consider when packing.

  • Pro-Tip: If you’re starting out at a smaller airport, a lot of times the flights get full and they need volunteers at the gate to check their bags for FREE! So as much as I like to keep all my stuff with me, I also like not to have to drag it around everywhere (if it’s not gonna cost me!).

Easy Foods to Pack:

  • Raisins (or other dried fruit)

  • fruit leather

  • Granola bars

  • Fruit snacks

  • Nuts (if you’re not allergic…)

  • Gum (to stop your ears from popping!)

  • Microwave popcorn

  • Microwavable meals (like mac n cheese)

  • Little cereal boxes

  • Jerky sticks

  • Applesauce pouches (like…the kind my two-year-old niece eats… Super great for traveling!) Or just regular cups of applesauce and a spoon.

If you’re unsure if anything is allowed in your carry-on bag, just Google “Is … allowed on a plane.” Google is the answer to everything.

Watch Movies!

I love watching movies or TV shows that take place somewhere before I go. Or reading books that were written there.

I find it makes the experience more full. Plus it just gets me excited to go (I also love watching movies when I come back, and dramatically pointing from my couch and shouting “I’ve been there!”).

So Google “movies to watch before going…” and “books to read before going…” and make yourself a list.

I like to include a few suggestions at the bottom of all my articles. Unless I have SO many suggestions, that they need their own article! Here are the destinations I have specific read/watch lists for:

Any more questions?

If you have any questions about how to plan a trip overseas, don’t hesitate to email me, or ask them in the comments below!

Any tips or advice from your own trip planning? Share those in the comments below as well!

Planning a trip?

Save one of the pins below for future trip planning:

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The Beginner’s Guide to London

The Beginner’s Guide to New Zealand

The Beginner’s Guide to the Dominican Republic

This article was written by: Julia Rexford