How To Plan Your Next Vacation

Here is a guide for those of you planning any upcoming trips this year courtesy of Diana, one of our readers.

I am type A when it comes to planning trips.

Ok, who am I kidding? I’m type A when it comes to most things. Luckily, my husband is really laid back and lets me go crazy with trip planning. I like to do my research well in advance of the visit. When we arrive in a new city, I want to know that I’m staying in a good hotel/rental located in a great part of town.  Once we’re there I want to make sure we’re not wasting precious time wondering what to do – we already know.

So let me walk you through the method of my madness.

First, I create a new spreadsheet on Google Drive so it is easy share with whoever else is travelling with us. Label it with where you’re going and the month and year.

On the first tab, I create my overall itinerary. I add the following columns to the spreadsheet:

  • Day
  • Date
  • Location
  • Travel
  • What
  • Hotel
  • Confirmation
  1. Day

I like to know what day of the week it is, whether it is a Monday or a Thursday. It is usually cheaper and more convenient to move around cities during the weekdays since bus/trains/trams have more frequent stops on the weekdays versus the weekends.

  1. Date

Plug in the date, it makes it easier to look up flights when you already know what the correct date is.

  1. Location

When we’re travelling, we’re usually going to 2-3 different cities so I like to have a visual of what city we’re going to be in on which day. It also makes it a lot easier to book hotels when you can quickly see how many nights you need in each city. Obviously if you’re only going to 1 city, take this column off.

  1. Travel

This is where I take notes on if we have to travel anywhere, whether by air, train or bus. I include what time the plane/train/bus departs. I usually like to be able to settle into 1 city for at least a few days before having to move around.


There are a bunch of different theories of what days are the best days to book flights. For a long time, I followed the Tuesday and Wednesday is the cheapest day to book a flight theory, then started paying attention to the Saturday and Sunday is the best day to book a flight theory. The bottom line is – once you know your destination, spend a few weeks checking out prices. There is this great article that talks about timing as well: .

My go to site for booking flights is . On Kayak, I input the departing and arriving city, then scroll down to Best Fares and input the month of travel to select the cheapest days to travel.

For short flights, always do your research to see if you should fly or take the train. Often times, if the flight is about 1 hour, and you can take the train for a few hours, you may be better off just taking the train. Trains usually run on time and you don’t have to arrive to an airport 1 hour in advance or deal with flight delays. Also, often times, the train stations are right in the middle of the city, whereas, you have to travel out of the city a bit to head to the airport.

  1. Hotel:

This is where I keep track on which hotel or rental I’m staying at. I book my accommodations after I book my travel.

I first read blogs on Lonely Planet and reviews on to find out where the best part of town to stay is (safe, close to public transportation, close to sites and attractions).

Once I narrow down which part of town, I take a look at the pricing for hotels (checking Tripadvisor for the top ranked hotels – by users, not by stars).  We have also booked many places off of . When you are booking on Air B&B, make sure you always book from a user that has reviews, with no cancellations (it will be posted as a review), and ALWAYS make sure they have a picture of themselves on the page – not of scenery. There are scams so be careful. All the places we booked in the past are with users with great reviews and have been a wonderful experience

If you would like to book a rental, you can also check out .

  1. Confirmation

Here is where I’ll include all hotel, flight, train confirmation numbers.

  1. What

I usually plug this section in last after I book my flights and hotels. This is the fun part – looking up what to do and planning activities for the day. I always make sure that my activities are around the same geographic region so you’re not hopping all around the city in one day.

I will also create separate tabs for each city based on various research that I do on Google to find out where I want to go. I’ll Google “Itinerary for Paris in 3 days” to see what the top sites are. I’ll also check out TripAdvisor to see the top attractions for the city as well.

Then I narrow it down so we’re only doing 2 things per day with a list of extra things to do if we end up having extra time. I will then map out all of the attractions and lump the attractions that are geographically closer together. This is the part that gets me excited for the trip – looking at the finished product.

The process is not complicated when you go about it in an organized way. Remember to also look up how you’re going to get from the airport to your hotel. TripAdvisor will have reviews from users on the best way to do that and if you book a rental off of Air B&B or VRBO, the owners will let you know as well.  In addition hotels can help accommodate travel to airports if you need.

Happy Travels and have fun!

Ethan Lieber

Ethan Lieber is a founder at ZeroToComplete where he focuses on leadership and entrepreneurial productivity.

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