Planning a big trip and need a little help? Excited but not sure where to start? We got you fam.
Of all the trips Allie and I have taken together, our favorites seem to be the ones where we did our research beforehand and had a solid plan of what we wanted to do when we hit the ground.
In this post, I’ll show you the exact way I go about planning our trips.
It’s super easy. All you need is 2-4 hours, the internet, and excel or a google sheet like this one.
But first, why? Why do this at all? Why not buy a plane ticket and figure it out when you get there?
Don’t get me wrong, spontaneity can be fun. A great itinerary will leave room for spontaneity. But many parts of your big trip don’t need to be spontaneous. They shouldn’t be.
Showing up without a plan is a great way to waste time and money. Following this method will help you maximize your time, and significantly reduce your expenses, all while leaving room for spontaneity where it makes sense!
Ready? Let’s Go.
Here’s the basic process:
- Decide where you’re going and when
- Book Flights
- Map out points of interest
- Sketch out a rough itinerary
- Point to point transportation
- Book Lodging
- Sights/Bites
- Refine and simplify
A couple of notes:
This is more art than science. There’s no secret formula to planning your big trip. These are just the basics you’ll want to cover. And in each area, I’ve provided a few tips and tricks we’ve picked up over time.
This is an iterative process. Starting out, you may only know that you’d like to take a cooking class in Italy. Now you’ve got to figure out where, when, and what else you may like to do there. As you delve deeper into research, you’ll find other things you want to do, and maybe other places you’d like to go. I find each new piece of information builds on the other. You don’t have to go exactly in the order listed above.
- Decide where you’re going and when
This can be a real chicken vs. egg decision. Maybe you know you can take off the week after Thanksgiving, but not sure where you want to go. Maybe you know you want to go to Germany but aren’t sure when.
For us, this is a balancing act of what makes most sense for our schedule, what destinations we could fly to cheaply, and whether that destination is in peak, shoulder, or off-season at the time.
Keep separate lists of potential dates and destinations. This will give you flexibility when booking flights.
**Tip: Make a shared travel calendar
Allie and I both work full-time, so at the beginning of every year we sit down together and make a list of dates we could potentially travel based on the amount of vacation time we have to use and our company’s paid holidays. This puts the two of us on the same page, gives us a range of possible options, and allows us to maximize our vacation days by leveraging time off our companies are already giving us.
**Tip: Keep a running list of potential destinations
We also keep a running list of places that interest us and that we mutually agree we would like to visit someday.
Having both of these things planned out in advance will make it EASY for you to jump on a great flight deal. Which brings us to step 2.
- Book Flights
Flights are typically the number one expense related to travel, and understandably, the cost of flying is often what keeps people from traveling more.
If you’re taking an international trip, I recommend you book your flights several months in advance. This isn’t a hard and fast rule, but in general, prices for your dates will probably start to rise 45-60 days out.
**Tip: Use Google Flights
Google Flights is a flight search engine by google. It’s not a booking service or travel agency. Simply, it’s a free tool for researching flight availability and pricing that shows you options based on your dates and other search criteria.
It’s also very easy to use. Just punch in your departing and arriving airports and dates. Clicking into one of the dates boxes will show you a calendar with prices on each day – allowing you to find the best deal. You can then choose your exact times and book direct with the airline.
You can also sign up for alerts about these specific flights and Google will email you when pricing for this itinerary changes.
**Tip: Sign up for Flight Alert Services
One way we’ve saved thousands of dollars on flights is by signing up for flight alert services like scottscheapflights and faredrop. Companies like these scour the internet looking for reductions in flight prices and then send you an email when they see a good deal. They work an awful lot like Google Flight Alerts, except you don’t have to go in and create all your individual itineraries. You just provide your email and home airport(s), and as deals are discovered they are delivered straight to your inbox.
In general, the drops are unpredictable and fares don’t last long. You need to be ready to pounce. Most deals seem to only last 24-48 hours. That’s why it’s important to know your dates and potential destinations.
We’ve booked 3 or 4 trips as a result of receiving killer flight deals via email and being ready to book.
If that kind of pressure is concerning to you, don’t worry. Airlines by law offer a 24-hour cancellation policy. So you can lock in your amazing deal and if for some reason you can’t go, you can cancel within 24 hours and get a full refund.
- Map out points of interest
From here, I do a lot of research on all the countries/cities/regions we might like to go while we’re gone.
Let’s say you’re planning a 10 day trip to Italy. You found a great flight deal and locked in your dates. Now you need to figure out where you plan to spend your time. Will you spend all 10 days in one place? Or would you like to hit a few different cities?
Avoid trying to do or see too much. 10 cities in 10 days would be exhausting. Conversely, some people may find 10 days in 1 city to be boring. You have to figure out what’s right for you.
This is where it pays to do your research. Watch some youtube videos. Search for things like “10 Days in Italy” or “What to do in Italy”.
**Tip: Don’t exhaust yourself trying to fit an entire country into a week or just a few days. Going deep in a few cities is much more rewarding. Assume you may come back someday.
- Sketch out a rough itinerary
Now that you know where you want to go, it’s time to decide what route you’ll take and how long you’ll spend in each place.
Take your points of interest and do your best to determine how long it would take to “do them justice”. For example, you will find that a place like Rome needs 3-4 days minimum, whereas you could probably enjoy Milan in about 24 hours.
Open a map and lay out your itinerary logically to minimize travel time from point to point. This can help you determine what order you’ll visit your points of interest.
With the template provided, start plugging cities into the ‘Day’ and ‘Night’ columns. This doesn’t have to be perfect right away. You may end up going through a couple of iterations once you’ve completed steps 5 and 6.
- Point to point transportation
What’s the best way to get from A to B?
Are the cities you are interested in car-friendly? How good is the rail system? Are buses available?
Google is your friend.
I almost always start this process with a simple google search like “Rome to Florence”. This brings up a google maps result showing me travel time from Rome to Florence via car (which is approx. 3 hours). If I switch the mode of transportation to train, it takes 1.5 hours. Now I may do a more specific search like “Rome to Florence Train” and get results from train booking sites.
Allie and I have become big fans of public transportation and generally don’t want to mess with renting a car. However different situations call for different modes of transportation. Like an epic national parks road trip. You’ve got to do your research and decide what’s right for you.
When you’ve made decisions, start booking your train tickets, rental cars, bus tickets, etc. and plug those into the ‘Tickets’ column on the sheet provided.
**Tip: If the transportation mode isn’t available to be booked in advance, you should make a note in your sheet of what your plan is. Even something like “get an uber” or “buy commuter train ticket day of” can reduce your stress in the moment.
- Book Lodging
Lodging is another major expense related to travel and it’s often something I see people overpay for.
We have stayed in all kinds of accommodations and what we decide to do varies based on our goals. You will have to decide what’s right for you.
If you’re traveling to a new country, the best way to experience that culture is usually through local-run bed and breakfasts, airbnbs, or hostels in the center of town.
Our favorite method is almost always airbnb or local bed and breakfasts.
**Tip: Many local bed and breakfasts and mom and pop hotels list their accommodations on airbnb or booking.com. You can almost always save money by calling them and booking direct. It doesn’t hurt to ask for a better rate!
Once you book, plug a link to your check in details in the ‘Lodging’ column of your Itinerary.
- Sights/Bites
This is the fun part! Deciding what you are going to do and eat!
Keep a list of activities and sights that interest you for each of the places you plan to visit. You probably won’t be able to hit them all, but this ensures you can make a plan to hit the ones that are most important to you.
When it comes to museums or major sights like castles, the colosseum, the eiffel tower, etc. you can almost always reserve your entry time. Some places require it!
Do your research and weigh the cost, but it almost always pays to get the ‘skip the line’ pass for major cultural landmarks. For me, it’s an easy cost benefit analysis. Would I rather stand in line for 2 hours or pay $10 and get in now? I’m a frugal guy by nature so this may seem counterintuitive, but think about how much you paid to be here. Your time counts! It could make sense to skip the line.
**Tip: Buy a ‘skip the line’ pass where it makes sense
When it comes to food, look into the ‘must try’ food and drink for the region you’re visiting. Maybe you never knew Belgium was famous for french fries, or the part of Spain you’re headed to is known for Sangria.
Once you know what you’re looking for, you could do a search like “Best fries in Brussels” and see what comes up. You can also generally search for things like “top places to eat Brussels”. These types of searches are just to help you show up prepared, and it never hurts to have a list of names of places you’ve heard are good.
**Tip: If you are traveling with your significant other or spouse and want to do one to two nice meals, consider reserving those in advance.
On the flip side, don’t reserve all of your meals in advance, and in general, don’t overplan your meals. This is where it’s fun to be spontaneous. Some of our favorite travel memories are popping into a random pizzeria in Florence or getting a Sausage and Beer from one of the thousands of stalls all around Munich.
Talk to your airbnb host, or the person running the desk at your hotel, hostel, or bed and breakfast and ask them where they like to go. Tell them you don’t want a touristy recommendation.
Plug all of these details into the ‘Notes’ column of your Itinerary. I like to give simple reminders to myself like ‘Neuschwanstein Castle Tour – Book at the window – $13’ or ‘Augusteiner – Beer Hall for Locals in Munich’.
- Refine and Simplify
All of this planning is meant to make your trip more fun and less expensive! So as you go through this process, look for ways to make your life easier once you’re there. Your future self will thank you!
