Trip Planning 101: Planning without the Stress

Trip Planning
Stress Free Planning

Even though the trip planning phase one of my favorite parts, for a lot of people it can be overwhelming. There is a lot to think about,  decisions to be made, and a ton to keep track of. Many people begin trip planning a year in advance due to all the preparations (and of course deals for booking early.) Some people just go the “Expedia” or “Travelocity” route and book a vacation package to lessen the burden. While Expedia and Travelocity can have some great deals, depending on your destination it can be a lot cheaper to do the work yourself. If you’re not sure where to start, this post is for you. I’m going to go over how you can have a stress free planning experience when you start planning your next trip.

Fair warning: This is a long post. There’s a lot of information here. If you know how to plan but are just interested in a more organized way to go about it, check out Need Help With Organization? The Most Detailed Trip Planner Ever.

I planned my first international trip for myself and three friends, before I graduated High School, and I’m glad to report the trip was successful, smooth, and convenient. Since that trip, my planning style has changed a lot – but one thing has remained constant. The thing that allows all of my trips to go as smoothly as possible. So what’s the secret?


Staying organized right down to the smallest detail is what makes my trips successful. You can plan anything if you stay organized. If someone asks me where I am staying, what dates, what the checkout time is, and the address of the hotel – I should be able to pull out my phone and tell them.

Some people might disagree with me, and prefer to “wing it”, claiming better deals and more flexibility. For me though, not knowing where I might sleep next week while in a foreign country is what stresses me out. I don’t like to go into situations unprepared. That’s not to say that if I were walking down the street and saw a hotel I was much more interested in, I wouldn’t switch my plans around – I’m flexible, but it’s more about always having a safe option to fall back on.

When I planned that first international trip at barely 18 years old, I used a binder, divider tabs, and envelopes. I had a detailed itinerary and receipts for each person who had given me their money to pay for their shares. Now-a-days the tools I use are much different, but the techniques I use are the same. The most important thing to remember about this trip planning process, is to document everything you find, as you find it

During your research, you will likely come across plenty of things that you want to come back to later. I use a Google Spreadsheet that I created for trip planning. You can find the template here: Trip Planning Template

I keep this spreadsheet in google drive, so that I can access it no matter where I am, as long as I have the internet. For a more detailed description of how to use this spreadsheet, take a look at my post,  The Most Detailed Trip Planner Ever for Superior Organization

Elusive Traveler’s Trip Planning Process:

The Destination:

For me the most difficult part of trip planning is deciding on my next destination. I always try to visit as many places as I can in the time that I have, while also not feeling rushed. I do actually want to enjoy my trip. So organizing my itinerary often involves a lot of changes the more research I do and it’s never really final until my airfare is booked. Don’t make the mistake of getting too attached to your itinerary and refusing to change it, even though you find another schedule might work better for you.

To start, I figure out how much vacation time I am able to use. (Those who have jobs with designated vacation time know it can be hard to get away.) The amount of time I have available will determine the destination. This is because there are a lot of places that are not practical to visit from the United States, with only a week free. (Australia, Asia, etc.) Traveling to that part of the world will often eat up 4 days of just travel time. If you only have 9 days for a drip, that obviously won’t work. You will want to go somewhere that only requires 1-2 days travel time (one on the way there, one on the way back.) Once I know how much time I have, I decide what time of year I want to take my trip. If I’m going in February, then I would probably choose somewhere like the Caribbean over London. Also keep in mind that countries on the other side of the world have different seasons. For example, December in Australia is summer. Start with a range of months. (“I’d like to go in either July or August.”)

Detailed Destination – Cities:

Now that you know which country you want to visit, and have a general idea of the time of year you’d like to go, you want to do two things. The first thing, is type that information into Google for the months you’re thinking about and see how much a general flight is, to the most popular airport wherever you will be visiting. This is just to make sure your expectations are realistic about how much it will cost you, when it comes time to do the budget. You don’t want to plan an entire trip and then realize airfare is going to be 2,000.00 when you thought it’d be 800.

The second thing, is to decide which cities in that country you would like to visit. If the country you are visiting has a short commute to another place you’d like to visit, are you going to try and do both? (A good example of this is Paris and London. You can get to one from the other with a simple 2 hour train ride under the channel.) If so, how much will the transportation cost, and what is the travel time?

A good way to decide on the cities you’d like to visit is researching the things you’d like to do. If you decide you want to go to Italy, and you know you want to take a Gondola ride – then you know you need to go to Venice, not Florence.I know. I know. Most people don’t like to research. Luckily for you – I do. Check out my “Destinations” tab to see if I’ve already put together some research for a place you are interested in. If I haven’t don’t hesitate to comment and ask for suggestions. I may have visited that place, even if I don’t have a blog post about it. (I’ve been traveling a lot longer than I’ve been blogging.)

While you are picking out the cities you want to visit and researching the things you want to do, you will need to decide how many days you will stay in each city. I recommend at least 3-4 days in each place to not feel rushed and like you’re constantly unpacking, re-packing, and moving. Stay longer, if you have longer. So for a one week (Saturday to the next Sunday) you shouldn’t try to overload yourself by visiting more than two places.  A good way to gauge how long you should spend in each city is by having a rough idea of what you want to do there.


Now that you’ve chosen a destination, some cities, some general things you want to do, and have looked up a ballpark price for your airfare (so you don’t die of sticker shock after planning a whole trip), it’s time to start looking up your accommodations and comparing their available dates to your flight costs. Look up different dates and times for your airfare and determine which specific dates and prices suit you best, then use those dates for your hotel search.

I typically use, hostelworld,, AirBnB, or Reddit to find hotel suggestions. I like because you can enter a specific landmark or neighborhood that you want to be close to, and sort it by distance from that location. Know where you are staying. Look at maps and determine where you will be doing most of your activities. You will probably want to stay somewhere close to the city center so you can walk to most things.

Once you have a couple of places in mind that you’d be interested in staying – look those places up on trip advisor and read reviews to make sure that place has been accurately represented. You don’t want to see a beautiful picture and arrive to find roaches in your bed. On Trip Advisor you can see photos from guests who have stayed before, not just the professional hotel photography you see on the hotel website.


While you should have a general idea of the things you want to do so you can choose your exact cities/locations, you will eventually need to research these activities in more depth. Since you should have been writing down everything you’ve been finding that interests you so far, you should have some ideas already. Start googling those specific items. If you want to see elephants in Thailand, then type “See Elephants in Thailand” into Google. Worry about one activity at a time. A lot of activities will involve paid tours, while some will just involve you walking around exploring for free. For each paid activity, you should be looking up and recording 5 things:

  1. The company offering the activity
  2. The price of this activity
  3. The website linking the activity description and price
  4. The hours of operation and the duration time of your activity (if your tour is 9 hours long then that is probably the only thing you will be able to do that day.)
  5. The location and transportation information to get to and from this activity. (Sometimes tours will pick you up at your hotel, sometimes you will need to take a cab or public transportation, sometimes you can walk.)


Now that you have an idea of what you’re working with as far as activities, accommodations and transportation goes. You can star formulating your budget. For more information about this, read  Budgeting 101: Organization is Only Half the Battle.


Once you have a pretty good handle on most of the vital pieces of your trip, you should put it together in a comprehensive itinerary that allows you to look at it in one organized page (ie: The Trip Planning Spreadsheet I have linked. It should be mostly filled out already if you have been recording this whole time, as recommended.) Include your top choices for airfare and hotels here before you book them, so you can see if the trip works for you as a whole before confirming anything. This is where you can start making adjustments and changes based on prices, dates, availability, ease of travel, etc. Always look into all forms of travel between your destinations so you can choose the route that is most convenient in terms of both travel time and method, and price. Maybe you realized there’s a huge festival you want to go to that you are currently missing by two days. This is the time for changes.


Once you have decided that everything on your trip planning spreadsheet is exactly the way you want it. Start booking! Things may have changed a little bit depending on how long you’ve taken to fill out your spreadsheet and review it, before pulling the trigger – So it’s important to remember throughout the entire travel process (From planning to arriving) to BE FLEXIBLE. Maybe your flight has adjusted in price or maybe the hotel you wanted is no longer available for your dates and you have to pick a new one. Don’t stress about it. You’re going to have an amazing time either way.  Another option is if you see a hotel that you really love while you’re in the research phase, see if it offers free cancellation. That way you can book it to hold on to it, and if you need to make a change it’s no big deal. Once you have booked, confirmed, and paid for your trip – mark this in your spreadsheet.

There you have it folks! My entire trip planning process. I know it’s a lot of information, but I promise if you stay organized and record this information as you go – it is SO much easier and faster to finalize everything. Your trip will only be as smooth, as you are prepared.

How do you plan your trips? Do you use a trip planning spreadsheet? Any hard and fast rules you always follow?

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