How to Optimize Your Travel Planning (While Working a Full Time Job) – Net Worth: $79.7K (CoffeeForTheBuzz)

Net Worth Update – $79.7K

Another day, another dollar. I have saved up a bit since my last post due to having a received a paycheck. The most pressing update I have is that I have finally committed to making my side hustles a reality. I am compiling an informational product on how to purchase a multi-family investment property for first time buyers and have been continuing to design websites for a few clients. The level of effort that it takes to make your side hustles successful is no joke – it’s hard work. But I am excited to keep grinding on these things so that someday I will not have to work a 9 to 5 job. That’s the dream that I’m working to make a reality.

How to Optimize Your Travel Planning (While Working a Full Time Job)

If you ever studied abroad in college or have been on a backpacking trip at any point in your life, you probably know how it feels to catch the travel bug. The first time I ever flew overseas to study abroad in London, I knew the experience had me hooked for life. Seeing the way others lived their lives and having the realization that there is so much more to the world than the things that occupy our daily lives was a life-changing experience. I enjoyed those few months so much that I knew I had to keep exploring the world whenever I had the chance: Japan, Southeast Asia, and Colombia are just a few of the places that I have had the pleasure to experience over the past few years and I have no plan to quit exploring until the day I die. My ultimate goal (insert link) is to visit 100 different countries before I die.

Someday, I’ll be able to take my dream tour of the world where I am able to travel for several months with nothing but a backpack of clothes and my laptop, but for now I’m constrained to making trips that allow me to stay within my company’s guidelines. I know many of you are in the same position so I wanted to share with you how I maximize the vacations I take when holding a full time job.

Step 1: What is the most amount of time you can possibly take off?

This is probably the most critical boundary of what kind of trip you can take. Some companies only give their employees 10 paid vacation days, while some (like mine) have an “Open PTO” policy which essentially sets no limit on the amount of PTO you can take. In my case, it is usually expected that you will take no more than 25 days in a given year, but there is some wiggle room. Generally speaking, the longest trip you can get away with taking is two full weeks of time off. So that is how I am going to base my trip (10 days of PTO to work with).

The max number of days you can take off is obviously a very company-specific number, but a couple good ways to benchmark your trip include monitoring how long other co-workers have taken off for a single trip as well as how long your manager(s) would generally go away for. Once you have determined how long is the “longest” you can take off, I say why not push the button and ask for a little bit longer? The worst thing they can say is no right? 

Key Takeaway: Figure out how many vacation days you can possibly take consecutively so that you have a baseline to frame your trip around.

Step 2: What is the best possible time of year you can take that trip?

 Once you know the maximum amount of vacation days you can take away from work, it’s time to find the time of year that is best for you to optimize the trip. A big key in this step for me is to look for times that I’m already getting days off due to holidays or special company events. For example, the 4th of July, Thanksgiving, and Christmas/New Year’s are always a great time to consider taking your trip because sometimes you can squeeze in up to a whole extra week of travel without having to take any additional vacation days.

This year, I’m likely going to get promoted in November in the days just before Thanksgiving and likely won’t be expected to come into the office on that Wednesday. So that right there will give me 3 days off that week for free, the weekend, and then two full weeks of vacation days and weekends to travel. So by taking 10 PTO days at the right time of year, I am now going to have 18 days to travel and explore – not a bad trade off. I should mention that my family often celebrates Thanksgiving the weekend before the actual holiday which makes this plan possible because many of you would not want to miss holiday time with the family. So now I know how many days I can take off, and have determined that late November/early December will be the best time for me to go travel.

Key Takeaway: Figure out what time of year is best for you to go as far as getting extra travel days due to holidays when the office is closed, special company events, or slow season for your industry. 

Step 3: Based on the combination of amount of time you can take off and time of year you can go, where is the best place in the world to go?

 Now you have determined the length of your trip and the dates that you’re going to go. But the biggest question now is “Where should I go?”. Let’s look at the key considerations that you should look into when determining the best place to go. Every time I plan a big trip like this, I’ll print out a map and start making a list of the places I’m going to consider going to.

What Will the Weather Be Where You Are Going?

 If you live in Chicago like me and can’t stand winter, you really have no option but to go somewhere where the weather will be at least above 60 degrees in December (unless you’re going skiing). That cuts out a lot of options right away. So, I start listing warm weather places that I haven’t been: Dubai, Hong Kong, Southeast Asia (Vietnam/Cambodia), Australia, New Zealand, South Africa. Just typing out the names of these places makes me excited for December.

What Types of Things Do You Want to Do?

 Are you a skier? Golfer? Interested in adventure sports like bungee jumping or skydiving? Or do you just want to hang out on the beach for a while (not a bad option either)? This one is totally up to you, but you’ll have to do your research on the places that can accommodate your desired activities.

How Much Time Do You Need for the Places You’re Looking At?

Depending on how many days you have laid out for your trip, there may be some places where it just doesn’t make sense to go if you don’t have enough time. For example, to go somewhere like Australia or New Zealand you should probably have two full weeks at the very minimum if you’re traveling from the U.S. On the other hand, 7 to 10 days in Europe is a very doable period of time due to its relative proximity. This one is pretty much common sense, but just don’t make the mistake of traveling across the world without enough time to do all the things you’d like to do. 

Set Google Flights Alerts to Be Notified of the Opportune Time to Buy Flights (Also see Hopper, Skyscanner, StudentUniverse, Contiki, etc.)

Once you do decide on a place (or a few options for places) to travel to, start setting Google Flights alerts so that you will be able to keep an eye on the prices for flights to your desired destinations. Google will then email you with tips on the best times to purchase flights for given trips and will give you a good sense for whether or not you can get a lower fare if you wait until a certain time to buy your flights.

Other great sites to check out for purchasing flights for big trips include Hopper (just an app), Skyscanner, StudentUniverse, and Contiki. They all have their pros and cons so I highly recommend checking out all of them.

Key Takeaway: Come up with a list of the places you would consider going based on weather, activities, and projected flight prices, and then set Google Flight Alerts for all potential destinations so you can get a better idea of which trip makes the most sense to take.

Step 4: How to Maximize Your Budget Regardless of Where You Decide to Go

Traveling doesn’t have to be expensive if you do it right and are willing to take the time and effort to plan ahead. With AirBnb gaining popularity and constant hostel availability, it likely won’t be that tough for you to find lodging for quite cheap no matter where you go in the world. The four considerations below will make a world of difference for the overall cost of your trip.

Hostels ( and AirBnbs

This day in age, unless you have a ton of hotel points racked up, it doesn’t make sense for the 20-something traveler to stay in hotels. The comfortable lodging options that are available to you through Hostelworld and AirBnb are plentiful, affordable, and fun to stay in. With hostels you can expect to pay less than $10 a night in many parts of the world and you will have a built-in community of people to socialize with which is great if you plan to travel alone. AirBnbs offer the unique experience of being able to live like a local in the cities you are visiting which adds a great element to any trip. If you have been skeptical on AirBnb in the past, I highly recommend you give it a shot this time to see what the hype is all about.

Take advantage of free breakfasts

Many hostels will provide free breakfast and this can be a great way to save money on your travels. If you stock up on breakfast in the morning, you’ll be set for the better part of the day and can get away with a light lunch and have more money to spend on nicer dinners. Most places you’ll go make dinner their featured meal so I think this is one of the best ways to approach your eating schedule while on a trip.

Research in-trip flights and public transportation before you go.

Public transportation is a huge asset if you’re going to a large city. You will save a ton of money by using public transit rather than Uber or Taxis. You’ll just want to make sure you do your research ahead of time especially in the event that you’ll be traveling to a place where you don’t speak the language. Additionally, do your homework on in-trip flights between cities in a country or continent. Some airlines have special passes that are made specifically for people who will be taking a few short flights over the course of a vacation and this can be a great way to save money.

Plan tours/activities ahead of time to lock in any potential deals

 You can save money on any tours and activities, almost without exception, if you purchase tickets ahead of time. For example, the price of visiting Machu Picchu is a minimum of 20% higher if you try to buy the ticket the day or two before the tour and sometimes they will sell out. Putting in the extra leg work up front will ensure you get the best possible deal and have a guaranteed spot to be able to do what you want to do.

Key Takeaway: Stay in hostels/AirBnbs and do your homework when it comes to transportation and activities that you’ll be doing on your trip in order to find the best possible deals.

Budgeting Tip: Take Off 1 Night Per Week of Going Out With Friends and Put That Money Into Travel Fund Account

 You might be asking yourself, how am I going to afford this? One strategy I frequently use for going on big trips like this is to take off one night per week of going out with friends (I usually will go out both weekend nights, but I cut back on Fridays in this situation). You should take the money you would have spent (say $50-$100) and put it in a special bank account just for saving up for your trip. In a few months, you will have built up a sizable nest egg that can be used to supplement the money you’ll need to spend for your travels (and you’ll probably feel healthier for it too).


What travel tips do you have for planning a big trip? Have an exciting vacation lined up? Share some details in the comments below!

Posted by CoffeeForTheBuzz


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