Seven Helpful Travel Planning Tips

While planning a trip on your own can be hard and time consuming, it can be one of the most rewarding and accomplishing feelings once you’re at your destination and everything is in place. Below are seven travel planning tips that we abide by when planning our adventures.

1. Utilize points

I can’t stress enough how crucial it has been for us using credit card points while booking flights. There is no way we would be able to travel as much as we do without the help of credit card points.

We put almost every purchase we make on our credit cards to earn mileage for travel. Some cards have a greater advantage than others depending on your spending habits. For information on which card might be best for you, head on over to The Points Guy to take a look at what each credit card has to offer. Many cards also include a sign up bonus that can be worth up to 50,000 points (that is $500 worth of money to spend on flights with money you would already have spent anyways!)

We make sure to pay off our cards in full at the end of each month to ensure we’re spending within our limits and not building any unnecessary debt.

If you’re OK with the potential for annual fees, open more than one card to get multiple introductory offers.

I won’t go into detail all that these cards have to offer, but the main ones we use are:


2. Make sure you’re booking the cheapest flight

Scott’s Cheap Flights has been a complete game changer in finding cheap flights. I switched from the free version to the premium version last year and get daily deals in my inbox.

If you’re looking for a specific destination and time frame, set up flight alerts on Skyscanner or Google Flights and you will be notified when the price drops

If you are at all flexible with your dates, Google Flights will show you the prices for leaving on different dates (see below).

Leaving on Sunday the 7 instead of  Friday the 5 would save you $493!

3. Maximize any paid time off

You might be reading this thinking “these are all great tips but I can’t take that much time off of work”. You might be right – but if you are fortunate enough to work in a position with “paid time off” don’t be afraid to use those days. Some things are more important in life than being tied to your desk.

If you have limited/no PTO, try to combine your trip with a long holiday weekend to minimize days you’ll need to take off. Look into “comp time”, or compensatory time, which allows non-exempt employees the ability to swap overtime pay for PTO.

We are both lucky enough to have jobs that allow us to work from home when needed. If you’re able to work from home when your sick instead of taking the day off, do it. This has helped us save our paid time off days for traveling instead of laying in bed.

Plan your year out in advance and prioritize how you’d like to use your paid time off days. You may need to weigh your options between a two- week trip to Europe vs. multiple long weekends throughout the year.


4. A smarter way to pack

We’ve come a long way in packing since when we started traveling. When we first started to travel we would use full size checked suitcases along with a backpack, purse, camera bag, etc. I would bring a different outfit for every day and even 3-4 pairs of shoes.

Even if you prefer checking a bag, you will be much happier if you have a smaller piece of luggage with you. All we bring now are our back packs along with carry-on size rolling suitcases. Traveling lighter allows us to hop around easier from city to city. Here’s how we do it:

  • Plan your outfits out in advance so that you only bring what you know you’ll be wearing
  • Mix and match your outfits by switching up your layering and accessories so you don’t feel like you are repeating outfits as often. I like to bring neutral colored clothing so that I can mix and match easier
  • Utilize layers so you are prepared for any type of weather
  • Plan to do a load of laundry on a longer trip. Even when we don’t have access to a washer and dryer, we will buy some laundry detergent at a store and wash our clothes in a sink!
  • For many, packing cubes are a total game changer
  • If you think you may need a full extra bag on the way home for souvenirs, pack a smaller suitcase and put it inside a larger one to check on the way there and then you’ll have two suitcases to pack on the way home


5. Making friends on the road

One of the best parts of traveling is meeting people around the world. Aside from staying in hostiles, here are some of our favorite ways to meet people:

  • As tempting as private tours can be, going on group tours is a great way to meet people from all different parts of the world. Don’t be afraid to start a conversation, you may make a friend that you keep in touch with for years to come
  • Look to see if there is a free walking tour available. This gives you a chance to spend some time with a local, ask questions about the place you’re visiting and possibly keep in touch the rest of your stay. (Make sure to tip generously, even on a free tour!)
  • Don’t be afraid to strike up a conversation when you’re out and about no matter where you are
Grabbing coffee with our Vietnamese tour guide (and friend) we met in Hanoi


6. Using the save function on Google Maps

Do you find yourself getting overwhelmed with travel recommendations when doing research on a destination? Navigating a foreign place is admittedly difficult. So many bars, restaurants, shops and attractions can be overwhelming.

When doing your travel research, open the Google Maps app on your phone (if you don’t have it, I highly recommend downloading it). You can start a list for the city you’re saving locations in. Then each recommendation you get, or place you want to check out, save it to your list. When you’re at your destination you’ll be able to view where all these places are on the map and can plan your days out much easier!


7. Booking an affordable accommodation

Accommodations can be tricky. We make sure to do our research to find the cheapest hotels we can. One website that has been helpful in finding the best rates is Depending on the city, an Air BnB may even be cheaper than a hotel.

If your budget is tight, try house sitting with Trusted House Sitter. You pay a fee once a year and are able to stay for free, while the homeowner in turn receives a house sitter for free, how cool!


If you have any questions about our travel planning tips, please feel free to message us! We’d love to help you plan your next trip.

Emilie & Chris

Published by happilyaway

We are a married couple living in Chicago, and we are obsessed with traveling (probably like you). Unlike many travel bloggers, we have no intention on quitting our jobs and traveling full time because we actually love our jobs (shocker- I know) and we have a sweet puppy that we can't bear to leave for for than 3 weeks at a time. This hasn't stopped us from making all of our travel dreams come true. We are excited to share our adventures with you and help show you how you too, can travel the world- even while working full time. Emilie & Chris

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