How I Plan My Trips

There is nothing in this world I love more than planning a trip, especially to a new destination. My friends compliment me all the time on my ability to plan a trip, and even ask me to help plan theirs! So in honor of me taking my first trip of 2020 later this week, I’m going to share my process for planning a trip, along with some tips and tricks that I have learned along the way!

Research where and when you want to go

This is usually my first step, especially when I’m looking for new places to go. For new places, I pull from my arsenal of places on my bucket list and start there. But, if I already know where I want to go, I start jump right into researching. Another factor is deciding when you want to go. Fortunately enough, I have unlimited PTO so I can pretty much go whenever I want. However, I choose to utilize long weekends to avoid taking a lot of time off of work. If you have limited PTO, I highly suggest trying to work around when you might have a three-day weekend. That way, you can maximize the time off your company is already giving you. If you are going international, make sure you have a passport and your passport is up to date for what the country requires. Some won’t allow you admittance if your passport is less than 6 months from expiring.

Purchase your airfare

For me personally, this is a huge factor as to when I want to go. If I’m flexible, I usually go with the least expensive dates or fly during the week if possible. I like using Google Flights because it gives you all of the options across all airlines. Other services such as Kayak or Expedia are good too, but they are filtered to show sponsored airlines so you’re not getting the full picture. Another thing to beware of is bag charges. Usually if you are going international, they allow you one checked, one carry on, and a personal item in the fare, but most domestic airlines nowadays charge you additional for bags. I also prefer nonstop routes as opposed to those with stops. For one, they reduce your carbon footprint when it comes to flying, and for another, it gives you peace of mind, especially if you are afraid of losing your bags. If you are thinking about flying into one city and out of another, use the multi-city option when booking your flight! I can’t tell you how much of a godsend it is (and how much less expensive then two one ways!).


While you might be able to get your airfare for pretty inexpensive, the lodging is going to be your second largest expense. I’ve done both hotels and Airbnb so I have pros and cons for both. A few things you might want to consider:

  • How close is it to what you want to do while you’re there?
  • What kind of amenities does it have?
  • How much does it cost in total?
  • What area of town is it in?
  • Is it close to transportation?

This is usually my checklist when I go about booking a place to stay. The biggest things for me is the proximity to what I want to do and how close it is to transportation. If I can, I like to stay a little bit outside the main part of the city and take public transportation to where I want to go. This saves you on cost, while still getting to where you want to be. The reason amenities made the list is a lot of Airbnb’s don’t come with a lot of toiletries, so take that into consideration as you pack for your trip. I prefer Airbnb over hotels, but in smaller cities, hotels definitely surpass Airbnb, mostly from a safety factor. If you feel daring, you can also consider a capsule hotel if it is offered.


When planning, you need to think about how you are going to get from point A to point B. This might require more planning because of the logistics involved. You need to think about how you are going to get from the airport to your hotel, your hotel to the attractions you want to see, and back. This is where the mode of transportation comes into play. You can either take public transportation like a metro, a ride share, walk, or get a rental car. I opt for public transportation, especially in large cities where it’s superb. It usually takes you to all the stops and there are stations everywhere, so no matter where you’re staying, it’s accessible. This is why I mention choosing where you are going to stay carefully. If you are planning on taking public transportation, you might want to consider staying near a stop. If you are planning on going to larger destinations that require more than just a metro, do some research on the location. Chances are, it will tell you how you can get there.

Travel insurance

This is a must, especially for an international trip. With all of the money you spend upfront to plan the trip, you want to be reassured you can get it back in case of an emergency. Insurance can cover lost luggage, a trip interruption, and healthcare in case you really need it. And, it’s not that expensive either, so in the grand scheme of things, it’s totally worth having it in your back pocket in case you need anything.

Planning your itinerary

Your itinerary is probably the best part of the trip planning process. While the rest of the planning is about the logistics, this is an opportunity for you to create a “wish list” for what you want to do while you’re there. If you are looking to go to museums or other attractions, make sure you look up the dates and times they are opened and see if you need to purchase tickets in advance. This will help you structure the time while you’re there to know if you need to go see a specific attraction on a specific day. As much of a planner I am, I make a list and then just go with the flow each day to see what I feel like doing. You don’t need to have every minute of every day planned. If you do, you won’t enjoy yourself very much by the end of the trip.

Last minute considerations

Between when you do your initial planning and when you get on the plane, do some research and consider the following:

  • Do you need to register with the American embassy in the country you are visiting (I do this as a precaution in case something happens in that country so they know I’m there)?
  • Do you need any vaccines?
  • How do you to buy anything specific to bring?
  • Do you want to get Global Entry for customs (I highly recommend this one especially if you plan on doing a lot of international travel)?
  • Are there any customs you need to be aware of?
  • How are going going to access the internet? Sim card or a phone plan?
  • How are you going to organize your travel docs?

These are just a few things I always make sure to add to my travel planning check list. You’ll feel a lot more prepared when you get on the plane and ready to enjoy your trip.

Stay tuned for more posts on my tips and tricks for traveling!

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