How to Plan a BIG Trip

I will be the first to admit it… I’m not a good traveler. I know some people live to travel and can pack up a backpack and spontaneously live life to the fullest in new countries. I’m not one of those people. I’m a serious homebody. Even the thought of travel can make my heart rate pound– and not the excited fun type of pounding!
I used to confuse my anxiety about traveling with thinking that I didn’t know how to plan a trip. I found the opposite to be true. Planning a trip actually reduces my anxiety about traveling in general, and I’m not that bad at planning either.
Now, again, I’m not a very go with the flow person, in really any element of my life. I prefer to plan, to stick to timelines, to research as much as possible. I like to know what I’m getting into. I realize that not everyone is like me (and I totally wish I was able to be even a little bit more flexible), but this is my reality. 
When we planned the trip to Alaska, Thomas did a lot of heavy lifting and then I just would answer the easy questions. “Should we do X or Y?” “X.” For Ireland, I helped a lot more, and it made me more confident in my abilities to plan a longer trip. I’ve been planning short trips and find them pretty simple since there are only a couple of days and, therefore, fewer logistics!

My process:
ONE // Set dates
This seems easy enough, of course. But I think it can be challenging. My work schedule is a little bit more flexible, although there are still things I have to take into account. Gar had a stricter schedule and needed ample time to request time and days off. Regardless of where you’re going, unless you’re 100% open, it’s a good idea to start with the dates.
While you’re setting the dates, also double check on the location of where you’re going to see if you need tons of time to plan or not. I don’t mind traveling in the off-seasons, but that might be a deal breaker for you. 
And while you’re looking at your calendar for dates, cross-reference with average weather, flight prices, and hotel availability. You don’t need to finalize anything just yet, but you may find it helpful for budgeting and planning purposes to know what you’re working with.
We were originally going to go to Ireland at the end of April to meet up with T&J as they would still be in Europe from other trips. But Garrett couldn’t get those days off; we decided we’d have better weather in June, and T&J would be better rested for a separate trip.

TWO // Build a Google Spreadsheet
While I tend to also keep a messy list in a notebook, I recommend keeping everything organized within a Google spreadsheet. The best part about this is that you can share with anyone else going on your trip, and you can access it wherever you are, including your phone.
I love that you can create different sheets within the spreadsheet. You can see in the images above that I have notes from readers, itinerary, hotel list, packing list, and worksheet pages. Having everything in one spot makes things a whole lot easier!!
In addition to the spreadsheet, I also think creating a Google Map is also helpful, especially when you have a lot of distance to cover. (But I think I’ll be using it every time we travel to map out where things are, even within one city. It’s amazing.) I found it confusing at first, but I got the hang of it after watching a few Youtube videos.

As we planned out the trip, I would create different points of interest to get a general idea of where everything was and then finalized it as we made more concrete plans.
THREE // Research, research, and research
I think one of my biggest points of anxiety around traveling is not knowing something or missing out on an opportunity. Because we were going to Ireland and we were only going to be there for a week, we wanted to cover as much ground as possible and see as much as we could. I didn’t want to leave one stone uncovered when planning the trip! I knew we’d eventually have to make some difficult decisions around what we had time for, but I wanted to know everything that was possible first.
Four ways I recommend researching:
– Start with friends. Chances are, someone that you know has been. And they’ll be able to give you great, non-generic, super personalized tips. I found that some of the best advice I got for the trip came from you guys! THANK YOU!!!

– The internet is obviously a great place too. I always, always start with the tourism board websites. They can seem stale, but they always have great broad suggestions that can help you get a sense of what you’re trip will look like. (For example, has great itineraries to get you started with your planning.) I like Conde Nast Traveler’s website as well. I used their list roundups for hotels a lot!
– Books can be helpful as well. I’d be selective about what books you use and cross-reference with the internet to make sure everything is up to date!
– Finally… social media. There are so many ways social media can be helpful when you’re planning the trip. I always check the geotags of locations, cities, hotels, attractions, etc. on Instagram. Pretty obsessively in fact. I also look for other bloggers, especially local ones, to see where they’ve gone and what looked like a great experience or delicious restaurant.
As you research, make notes in your Google Doc of places that stand out to you. Note the type of point (attraction, restaurant, activity, etc.) and maybe bold the line if it’s something you’re for sure interested in.
FOUR // Roughly Map Things Out
Once you have a timeline (your dates), your planning infrastructure (your Google spreadsheet and map), and research (all your great notes!), it’s time to start mapping things out. Start with your must haves. Whether it’s a city you absolutely can’t miss, a day excursion you’re dying to take, a restaurant that you can’t get out of your head, or a hotel that you’re dreaming of… plot it on your map. Fill in all your must haves and look for a pattern. Depending on the type of place you’re heading, you may find that staying in one central location or bopping around to get the most of the place would be best. Even though Ireland is small, we knew traveling in a big loop was going to make the most sense for us and it was perfect.
As I mapped out the places we wanted to go, I was essentially mapping out our travel route too. It helped to know where we’d be spending more time (like the Ring of Kerry) and less time (like Belfast) based on the number of things and places we wanted to see and go.
You may find that you have a cluster of activities in one spot and then not a lot going on somewhere else. You’ll also want to round out your map, so you’re not traveling in one direction for just one spot. Either fill in the gaps with more stuff (aka research) or knock it off your list for now.
FIVE // Book Everything
My general rule of thumb when booking is to do a walk through beforehand, and double (and then triple) check the dates. We started with the flights, which is an excellent way to commit to the trip and set some good anchor points on when your start and stop will be. Thomas and I divided some of the hotels so he would book a couple for the four of us and I would book a couple for the four of us, and then we did a few on our own. We filled in confirmation numbers into the Google Doc and marked off everything we booked with green.
SIX // Finalize Details
Leading up to the trip and with the big things booked, it’s time to start finalizing details. I kept a running list, alongside my packing list of all the to-dos that I’d need to do beforehand. Setting travel dates for my credit cards, setting up a travel data plan for my phone*, getting travel insurance, double check on Global Entry, and so on. I literally make a list as I come up with things and check them off as we lead up to the trip.
SEVEN // Talk Through the Itinerary
This is something that I can’t recommend highly enough. Even with everything planned and squared away on paper (online?), it’s still a good idea to walk through the itinerary with your group out loud. We used to do this kind of visualization before crew races, and I think it’s applicable in various real life scenarios. Thomas and I hopped on FaceTime and walked through the entire trip. It helped us make sure everything felt even, figure out which days were going to be the most travel-heavy, which nights we could relax a bit, and to re-confirm that everything was booked for all the right dates! It helped ease my mind about the trip a lot as well. I knew we had the major things taken care of, and there we go!

*Verizon’s TravelPass is the best. Can’t recommend it enough. It’s only $2 extra per day in Canada and Mexico. And $10/day in most places (like Ireland). It’s so worth it as it uses your regular data plan.

The last step is to go and enjoy!!

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Great tips. I traveled around Europe wearing a backpack last summer, but unlike some other travelers I know I had my trip planned out almost to a T! I don't like surprises when traveling!


Leda Olia

I'm definitely similar to you in that I'm not much of a "go with the flow" kind of girl. But I don't think that makes you a "bad" traveler per se! I mean as long as you don't let it get in the way of your enjoyment. I think you should totally be proud of your planning abilities- that's what makes you a good traveler! I definitely went through a lot of these steps when planning a trip to Venice and then more recently a trip to Martha's Vineyard (on a student budget no less! I actually just wrote about that here

Also you definitely should look into travel books more! I know they may seem obsolete and you always do need to keep how updated it is in mind, but my moms a travel writer and updates hers every 2 years! Just a thought 🙂

Leda x

Audrey Lin

WOW I have never planned my trips like this before! I usually travel with family, and we take it day by day 😛 Sometimes we'll have an unofficial list at the beginning of the trip of places we want to hit, but only sometimes. -Audrey | Brunch at Audrey's


You are SO organized!! We recently booked our Airbnb and hotels for a trip to London and Paris with our mom in September & it took WAY longer than we thought to find a place we liked, figure out if it was the right fit, and then book. So happy to be done with that!

Now we need to plan what to see & do, so I'm going to start a Google spreadsheet right now! Thank you!!

xo, B&K


Tip #5 is very important, in my opinion. A lot of people say to just wing it when you get to your destination, but that’s just not possible everywhere. In Italy, for example, I had to book certain things as far as 5 months in advance. We wouldn’t have been able to see quite a few things if I hadn’t booked in advance.


This Looks like a full time job. I would plan the main things and let the rest be a part of an adventure.


Hi! I really need to thank you. This will be very useful and helpful when I plan my dream trip for the next year! 😀
I found your blog right now and I love it.

I will love to stay in touch with you talk and, who know? Maybe start a friendship, if you want it of course. I will love that.

Please visit my blog and tell me if you want to stay in touch, talk by e-mail or by any other way.

xx, Edna
Mercury Rose


Any way I can get you to make your google spread sheet available? I’m studying abroad and am planning on spending a week in Ireland.

Shane Diesal

I need to travel from Reno, NV to Las Vegas, NV for an event and then come back. My options that i can think of are to drive (my car gets 20-25mpg), take a gray hound bus, take an Amtrak or fly. Which one of these options do you think would be the cheapest and how much would it cost,,


I’ve referred to this post several times but never commented! I found your tip about Google Maps to be SO HELPFUL. We’re doing a roadtrip out west in a few months to do the national parks and absolutely loved messing around with the map so far.