How I Plan and Organize a Trip: A Step-By-Step Guide

I have a big announcement today regarding my 2018 travel plans! It is so exciting, and I can't believe how spoiled I am. My husband and I have almost finalized all of our travel plans, and now I can share the news with you: in October of 2018, we get to visit England, Austria, and Italy! We are headed for a couple days to the English countryside to stay with some friends, then will be off to Vienna for a week and Venice for another week. I am so ecstatic; I've been aching for a big trip like this for awhile, and here it is!

To keep myself sane, I've been trying to funnel all of this excited energy into trip planning - because if you are a regular reader of this blog, you already know that planning trips is my number one hobby. Even when there are no trips on the horizon, I like to sit and make pretend and extremely detailed itineraries for future trips that may or may not happen. Since I know this particular trip is indeed happening, I've been having a blast planning it all out.

We are traveling with another couple to Venice from Vienna, and my friend Jess was asking how I go about doing all of my planning. She came over one evening, and we sat down together to determine our dates of travel, flights and accommodations. While we were muddling through it all, Jess was asking about the things I do to get trips planned and how I keep it all organized. I was more than happy to share my tips and tricks to avoid feeling overwhelmed!

Excited to be touring around this beautiful city in October! Image via.

My husband was feeling the same way: with this trip, we have multiple flights, train rides, hotels and rentals to take care of. Plus, he didn't know anything about the city of Vienna and what we should focus on seeing while there. He decided to just leave it all up to me, because this is what I love to do. But he did toss out one suggestion: "Lots of people have no idea how plan a trip of this size. Why don't you write a post about it to help people like me, who hate trip planning but need to learn to do it?"

Excellent suggestion, husband dearest. So I set aside my list-making for a moment and thought about how I plan trips; my process, the sites I use, and how I keep all of my information together. I know not everyone likes to be as Type-A organized as me when it comes to travel, and plenty of people like to just 'let it ride'. But for others, organization is key to a successful vacation, and getting organized can be overwhelming.

So here is how I plan a big trip, from start to finish. Even if you can take away a few things from this post, I hope it helps!

CONCEPTION

Let's start with the conception of the trip itself. You are thinking of traveling somewhere, or know that the opportunity to travel is on the horizon, so now is the time to get inspired! We knew Joey had this conference in Vienna in October for awhile now, but it wasn't until about two months ago that we decided to add on a jaunt to England and a small stay in Venice. It was all just a swirl of 'what ifs' until then.

Trying to determine which activities I need to organize, and which my husband's company will organize.

To begin, I like to make lists of the places I want to visit and experiences I want to participate in while touring around a city or country. In this way, I can see the amount of activities available, which will help me determine how long or short our stay in the area should be.

For example, Venice has a lot of architectural features to see, but a lot of them are not very time-consuming, and there's only so many 80 Euro gondola rides you are willing to pay for. Three full days in Venice was deemed 'enough time' for us, considering the list I had made of things for us to do.  On the other hand, Vienna has a lot of things to see in the city as well as around the countryside, so staying for five or six days made more sense. Three days would definitely not be enough for me to feel like I had fully explored the city.

So the conception time period is what I consider my 'brain-storming phase'. Just go crazy doing research on the area, writing lists or idea webs or jam sticky notes onto a piece of poster board (whatever your style is) filled with ideas on things to see and do. I like lists, but also like to use sticky notes because as ideas come and go, you can add and remove stickies without having to scribble all over your page. (Yes, I am THAT Type-A. Don't judge!)

Trying to determine what points-of-interest are closest to one another.

Helpful websites: I love to use www.pinterest.com to find ideas for things to see and do. Make a board for the city you are visiting, and pin everything and anything that interests you. Later on you can revisit each pin and click on the linked website to do further research. You might find that a spa you were interested in visiting is too expensive or too far away, and can then remove that item from you list of ideas. But pin away while you get inspired!

Another helpful website is www.atlasobscura.com which searches for the strange and more unusual attractions in the city you are visiting. These places are off the beaten track and might not be for everyone, but if you are looking for a unique experience, this site is a great help!

TIME-LINING

Now that you have a working list of what you'd like to do while on your trip, you can determine how long your vacation needs to be. You may be working with an already tight schedule or pre-determined amount of days off, so that will obviously help you in creating a timeline for your stay.

Try to think realistically about what you can achieve in one day. Are you the type of traveler who likes to linger, eating long lunches, stopping for drinks, preferring to visit only one or two attractions per day? Or are you a go-go-go travel fanatic who can't sit still from sun-up to sun-down while you are in a foreign city? Know your style so you don't under- or over-estimate the time you'll need, or the amount of things you'll get to see.

I need a visual plan to keep myself organized - and I love presentations!!

Here's where I get really dorky! I build a PowerPoint presentation and make each slide represent one day of our trip. Then I add activities and points-of-interest to each slide, based on what I think I'd realistically be able to see in one day. This gives me an idea of how long our trip needs to be.

At this point, my husband usually steps in and reels me in, or we'd be booked for a 56 day trip. Together we whittle the list down and agree on the amount of days to take off. But by this point in my planning routine, I have a very good idea of what we will be seeing, what we might see if we have time, and what we will probably leave out.

This website is da bomb when it comes to trip planning!

Helpful websites: If you want to check walking, driving, bus, or train distances to really make sure you can fit everything in in one day, my favourite website to use is www.rome2rio.com which lays out best routes on a map and tells you how long each route will take. It is a fantastic website that helps me plan things out super efficiently!

BOOKING FLIGHTS 

Now that you know how many days you will need to make your trip successful, it is time to book flights. I don't think many people need instructions on how to do this - you can book online through several different sites, book directly through the airline either online or through the phone, or call a travel agent and have a professional take care of the flight details. Totally up to you and your style!

Helpful websites: My usual go-to website for booking flights is www.expedia.ca, just because I earn travel points with them for each flight I book. I also really like www.redtag.ca which works a lot like Expedia, but sometimes surprises me with cheaper flights. So I usually search through both sites before finding a flight I like.

BOOKING ACCOMODATIONS

Once the flights have been decided and you know when you'll be cruising into town, you can book where you'll be staying. Some people prefer good old-fashioned hotels, while others prefer the cheaper, more social experience of a hostel. For our stay in Venice, we opted to rent an apartment in conjunction with the couple we are traveling with to save money. It turned out to be much cheaper than the cheapest hotel option (within reason).

A snapshot of our AirBnB location - it looks very promising! 

Helpful websites: I'm a big fan of using www.hotels.com to book my international accommodations. This time around though, we used www.airbnb.com to find a really great apartment in Venice. You need to have an account for AirBnB but not necessarily for Hotels.com.

NAILING DOWN THE DETAILS

Once all of the major reservations are in place (flight, accommodation, days off from work), you can take your time doing the final planning, which I call "nailing down the details". This includes a plethora of things all specific to your trip and your personal preferences. Things you might need to remember to do in advance include (but are certainly not limited to):

- train tickets
- performance tickets (opera, Broadway, etc.)
- registration for local classes such as cooking classes or language classes
- entrance tickets for busy sightseeing locations that sell by date and time slot (i.e.: London Eye tickets, Eiffel Tower tickets)
- tour tickets (i.e.: salt mine excursion, rafting excursion)
- spa reservations
- games (baseball, NHL, etc.)

A lot of places don't require you to plan this far in advance, and you can purchase tickets upon arrival at the attraction, or even a day in advance. But for some of the events listed above, you might want to ensure your place on the day you've planned for, or risk missing out entirely.

After all of this, you can rest assured that your trip is going to be awesome and, pending unforeseen disasters, relatively smooth. As always, be ready for bumps in the road and try to stay flexible. Even though I have my days mapped out via PowerPoint, down to walking distances between attractions, I am always open to change and ready to explore, list or not! Some of the best times I've ever had while traveling was when I took the advice of locals and ventured out into the unknown.

This guide, however, should get you started and feeling confident about your upcoming adventure. If there is anything you do differently that works for you, for sure let me know in the comments below! We can all learn from each other!