How I Plan My Trips

For someone who loves to write, it’s been a long time since I’ve written anything on here. Eh. Lots been going on the past several months that have made casual writing harder than it used to be. But today is not a time to get into that! Today I’m talking about traveling. ✈️

If you’re reading this you probably follow me on some form of social media, and you’ve probably seen that I’ve been traveling a lot lately. It’s become a big part of my life and I’m really grateful I’ve been able to see so much of the world in the last few years.

I just have to do a couple of disclaimers so we’re all on the same page: 

1: I do have a job, and I usually work during my trips. I do digital marketing remotely, which means as long as I have a decent internet connection and can work around time zones I can work pretty much wherever I want. I do have to schedule my traveling around meetings and time-sensitive work, but again, most work can get done on my own time, which is awesome. It does mean I’m subject to 5:00 am meetings and middle of the night alarms to post something online before trying to go back to bed, but it’s definitely worth it for me in the end. (Obviously.) 

2: So going along with my last point, I pay for almost all of my travel expenses on my own. (I am lucky enough to have parents who love traveling as well, and I have done some traveling with them in the past. But other than that I pay for basically everything on my own.) Traveling can be expensive, but I do my best to save as much money as possible. I use credit card travel hacks, get email alerts for flight deals, put in hours of research for the best deals, etc. I could definitely travel for less money if I wanted to stay in hostels or do something like WOOFing, but for various reasons I’ve found my comfort level where I’m at. 

I also have very few expenses right now – I’ve been living at my parent’s house since graduating college last April (so almost a year ago! Wow.) and honestly it’s been super frustrating at times. I love my family, but I’ve been dying to get on my own for a long time, and my job just wasn’t providing enough hours for me to do so until very recently. The plus side of that is I don’t pay for rent, food, or pretty much anything except my phone and gas. So, for example, living in Hawaii right now I’m only paying rent for one place and not stacking expenses on each other. 

OKAY. Now that we have that out of the way.

After I got back from my last trip to New Zealand & Australia (my first solo trip, by the way! I should do a post on that) I had quite a few people ask if I could write a post on how I plan my trips. 
Not to “toot my own horn” as the kids say, but I’m pretty good at planning trips. The determining factor is that I have anxiety and obsessively planning every detail of a trip helps calm it a little, but I also just really enjoy researching where I’m going and what I’m going to do. There are a few situations where I’m a fan of winging it, but if there’s a lot you wanna get done in a short amount of time you gotta plan!

I don’t really follow a step system, but for the sake of this article I’ll try to break my planning process down the best I can.

Step 1: Pick Your Location(s)

This seems pretty obvious, but a lot of people have maybe one or two things in mind that they want to do/see and that’s it. I’ve had a lot of people tell me they’re amazed at everything I got to see on my trips, and it’s almost always because I did stuff outside of the normal well-known places. 
You have to have some starting point, so if you have say, a 1-week vacation, pick the main place you want to go or thing you want to see. Maybe you want to go to the beach over Spring Break, see the Eiffel Tower in Paris, eat your way through Japan, etc. You don’t have to figure out the whole trip right off the bat – start with one thing you’ve always wanted to go/see/go to. 

If you have a general idea of what to do but not a specific location in mind (i.e. a beach vacation), getting ideas is as easy as a Google search. It does help to be specific based on your availability – instead of searching “where to go on a beach vacation” search “best beaches in the U.S.” or whatever you can realistically do or the type of vacation you want.

I would also be careful about basing your entire trip around a single place unless you know it’s great. For example, basing a trip around seeing Westminster Abbey in London is probably fine because it’s very established and you know what you’re getting into. Basing your trip around one picture of a beach you saw on Pinterest is risky because that beach could be photoshopped, hard to get to, or even on private property. This can be avoided by some extra research as well. 

Another thing to keep in mind is how much you want to do. There are two ways to approach trips:

1. Do and see as much as possible
2. Take it slow and relax

For most of my life, my family trips were #1. I used to joke to my friends that I got in better shape on my vacations than I did any other time of the year. My parents are what you’d call “go-getters” and every vacation had a “leave no stone unturned” mentality. Our trips together are absolutely exhausting, but we really do see a lot – I always have people ask how I was able to do so much on trips, and part of it is definitely planning but the main part is that we are basically sightseeing from sunrise to as far past sunset as we can.

It’s a lot, but looking back I’ve always been glad we did it this way. Last summer I took a trip to Europe and we visited five countries in two weeks. It was a total whirlwind, but I still felt like I got to experience every country and I checked off so many things from my bucket list!

The first time in my life I took a trip at a slow and relaxed pace is actually right now as I’m writing this article. I’ve been in Hawaii for the past three weeks, and the trip has been relaxed because I’ve been working while traveling so I can’t go out every day or I won’t make any money. 🙂 And I do have more time, but I love the relaxed pace as well! There’s definitely a lot less pressure to constantly be doing something.

Ultimately it depends on your style, so just make sure you pick a destination that allows you to vacation or travel the way you want.

Step 2: Plan Your Itinerary

I like to plan a basic itinerary before I book flights and hotels so I can then try to book a hotel close to either certain attractions or public transportation to get me to those spots. A good accomodation location can mean the whole world on a trip, so keep this in mind.

What you do on a trip is obviously totally based on what you want, so here are a few ways I get ideas for what to do:

  • Google “Things to do in ________”. This will give you a ton of search results, but what I want you to look at is Google will compile a list of its highest-rated attractions/destinations automatically. I like looking through these because 1) You’ll get a good idea of what’s popular in the area, and 2) Everything shows reviews, which are a huge part of my planning process.

  • Search for your destination in TripAdvisor. Similar to the Google search, but lots reviews are from frequent travelers so you can see what experienced travelers liked and didn’t like. 
  • A lot of people like to search on Pinterest, which isn’t a bad idea, but it’s not my favorite place because everything is very curated to look nice, so a lot of photos you’ll see have been heavily edited. It’s fine to get inspo here, but make sure you look at some photos of that beautiful hidden lake on Google to make sure you know what you’re getting into. 🙂 

You should be able to get plenty of ideas from these sites. I generally stick to Google Trips/Maps and TripAdvisor to get a basic itinerary. From here you can narrow your search if you’d like. I always like to search for local thrift shops, places to get locally made souvenirs, local restaurants & bakeries, and at least one thing to do that isn’t very popular with tourists. 

It’s a good idea to create a very basic daily itinerary to get an idea of how much you can do. Both Google Trips and TripAdvisor give estimates on how long people usually spend at each place, so you can use that to plan as well. 

Step 3: Book Your Accommodation & Flights 

As soon as I have a general itinerary, I like to get my accommodation and flights figured out ASAP. You’ll get the best selection and prices the earlier you book for accommodation, and to some extent flights (flights aren’t necessarily cheaper the earlier you book them, but they will get more expensive the later you book them).


I’ve really liked Airbnbs lately, because you definitely feel more like a local and get a better idea of the culture than if you’re in a standard hotel. However, ultimately you’ll have to decide what works best for you on your trip. If you want a beach vacation and can’t find any Airbnbs walking distance to the beach, you’ll have a better experience in a hotel. Note that I have nothing against hotels, I just really like Airbnbs! My family stayed in an actual castle in Ireland last year. But depending on your trip, a hotel can definitely be a better option.

My favorite sites for booking accommodation:

  • (book 10 nights and get one free)
  • Google Maps (search “hotels near ________”)
  • Travelocity

If you’re booking a hotel, I highly recommend comparing prices across several websites. Prices vary all over the place, and you can save a significant amount of money by looking at 3-4 booking sites instead of just one. 


Flights tend to be the thing people focus on the most as the priciest part of a trip. And depending on where you’re going and how long your trip is, they can definitely take a chunk out of your budget. Unfortunately, there aren’t a ton of “tried and true” methods to save on flights, but here are my best tips:

Know your booking window. You tend to see the best ticket prices about 6 weeks in advance for domestic flights and 2-3 months in advance for international flights. As I mentioned earlier, booking a flight six months in advance is not going to get you a cheaper flight – it might actually be more expensive because you’ll then lose out on any price drops in the future. I would wait until the booking window I just mentioned, but not go too much later than that.

Some people swear by booking last-minute flights, but this is risky and doesn’t really work anymore.

Compare prices. Just like with hotels, never book a flight without checking a few different websites.

Compare airports. For cities with multiple airports or cities that are very close to each other, some airports are cheaper to fly into than others. For example, Gatwick Airport in London hosts mostly budget airlines and tends to be cheaper than Heathrow.  

Sign up for flight alerts. There are lots of websites out there to help people find the best flight deals. Hopper tracks specific flights and alerts you when it’s the best time to buy. Scott’s Cheap Flights is a free email service that emails you flight sales and mistake fares, and you should definitely sign up because they are AMAZING. Pomelo Travel is a similar service. 

Come to terms with the price. I know, terrible advice. But unless you get lucky and find an amazing deal on a flight, you’re going to hit a point where the price won’t go down and you just have to be okay with that. I’ve had multiple people ask me to find them a better flight, but a little research showed me they had already found the best price. There are no magic tricks out there – flights are just expensive sometimes. 

Step 4: Make a Detailed Itinerary

Once you know where you’re staying and when you’re arriving & departing, you can make a more detailed itinerary. How detailed you want to go is up to you – I prefer an hourly schedule (not joking) but once again, depending on what kind of trip you’re taking you may not need to plan that much. Trying to fit five countries into two weeks takes a meticulously planned itinerary, while a casual weekend in the mountains could definitely be less planned.

At the very least you should have an idea of what you’re doing each day, how long each activity/destination is going to take, and how long it will take to get between places. (A lot of people underestimate transportation time.) Google Maps is great for figuring out travel time, and Rome2Rio is another cool site that shows you multiple ways to get from Point A to Point B.

Once I’ve created a daily schedule I also like to look for places to eat near where I’ll be at meal times. Some places guarantee good food all the time (looking at you Japan) but it’s a bummer to be in a country known for great food and happen to pick a mediocre place. I’ve noticed meals and mealtimes change a lot while traveling, so I like to bookmark some good options all over the place so no matter where I am I can find a decent place to eat.

This is also the time you should book all tours and things you can pay ahead of time for. I recommend buying your ticket in advance almost always – unless you know you’ll get a ticket for the place you want at the time you want, there really isn’t a downside to booking in advance. It does constrain you to a time, but there’s nothing more disappointing than showing up to a place you’ve been dying to see and being told there are no more available tickets.

Booking in advance also keeps you caught up on schedules. Many places in Europe are close one or two days a week during the week, and it can be hard to keep track of when things are open.

My dad is a firm believer in printing all your bookings out before you go on your trip. Usually unnecessary, but we did run into a hotel issue once where the only proof we had was a printed copy of our booking. No downsides, just an extra precaution.

Step 5: Create a Packing List

I always make a packing list a couple weeks in advance so I have plenty of time to get everything I need and don’t have that last-minute stress.

If you’re not sure what to pack, just Google “packing list for _______” and you’ll find plenty of bloggers who have spelled it out for you. 🙂 Just keep in mind you NEVER need as much as you think you do. I’ve gotten better over the years, but as I write this I’m sitting in Hawaii next to two pairs of long pants and a bulky pair of Vans I have yet to wear after three weeks.

For trips 2 weeks or shorter, I only pack a carry on. It saves a lot of time and stress in airports and transportation. For longer trips (or trips with only one airport involved) a checked bag is fine. 

Step 6: Read Up on Your Destination, Double Check Everything, and Get Excited

Being the travel nerd I am, I love reading up at least a little on where I’m going, especially if it has some historical significance. It definitely makes the place a lot more interesting, and I get to feel cool telling my family/friends facts about the Great Wall of China.

Extra research on places can also get you information you wouldn’t have come across otherwise. For example, when I was planning a visit to Neuschwanstein Castle, everything I initially read indicated it was easy to stay in a nearby town and take a bus to the castle. But there were no bus schedules on Google Maps and the hotels felt very pricey and touristy. I did some research and finally came across a blog post that outlined the bus system, and I learned you could book hotels walking distance from the castle. Some of those hotels were expensive, but I was able to find a cute little bed-and-breakfast-type place with views of the actual castle for cheaper than a hotel in the neighboring town would have been! The buses also don’t start running for a while in the morning and they get crowded extremely quickly, so we would have wasted a lot of time and energy if we hadn’t been able to walk. Plus, walking got us there early enough that we had as much time as we wanted on the bridge with the castle’s iconic view without anyone else there. 🙂

A few days before your trip I would double check all reservations and tickets, and make sure you have confirmations for everything. You can also call to confirm reservations if you want.

Finally, get excited! You’re going on a super cool trip! It’s going to be awesome!

Things to Keep in Mind on Your Trip

If you’re going to a new place, especially somewhere foreign, a lot can happen. Here are some things to keep in mind:

  • Culture shock is a real thing, so be prepared when you’re visiting a new country. The heaviest (is that the right term?) culture shock I ever had was in China. Europe, not so much.
  • Things won’t always go according to plan. If something goes wrong, just accept it, do your best to fix it, and don’t let it ruin the rest of your trip.
  • The “travel” part of traveling is the WORST. Early or late flights, delayed flights, lost luggage, long bus rides…it sucks. Just try to have a good attitude about it because I promise you, being grumpy does NOT help at all. J
  • Be kind to people and they will be kind to you. I’ve visited a lot of countries where before going I was told “Oh, they’re so mean in _____” or “They hate Americans over there.” Uh, no. Locals hate Americans who waltz into a country demanding everyone speak English and cater to their culture, and honestly, who wouldn’t hate that? Try to learn a little bit of the local language, and the locals will notice and help you the best they can. And just be a decent human being.
  • Keep an open mind, be flexible, and take time to appreciate what’s around you.

There ya have it, how I plan my trips! I actually left out a decent amount (lucky for you) of all the nitpicky stuff I do along with all this, but if you ever want to chat about it just let me know. Happy travels!

Published by Anne Taylor

Anne Taylor is a freelance writer who loves talking about mental health, wellness, and all things Disney. She resides in Spokane, WA with her dog Pepper and spends as much time in the sunshine as possible.

2 thoughts on “How I Plan My Trips

  1. We love the fact that you made your anxiety convert into something that boosts your planning skills. It really is inspirational ❤️


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