May 12, 2020

Our Process for Planning Affordable Vacations

Posted in: Travel

It’s no secret that Weston and I love to travel.  We made a goal at the beginning of our marriage to take a trip at least once per year.  Seven years later and still going strong! 

We get a lot of questions about how to go about booking vacations.  I wanted to share our process for booking our annual trips! 

1. Save money in a sinking fund

The most important piece of the planning process is saving up for the trip so that it doesn’t follow you home (i.e. credit card payments).  If you have an idea of where you want to go, estimate how much it will cost and divide it by the number of paychecks you get per year.  That’s how much of your paycheck you need to save.  When you consistently add money to a fund to reach a certain amount, this is called a sinking fund.

We have our travel fund money automatically transferred to a separate online account each paycheck.  Out of sight, out of mind.  At least until it’s time to use it. 

I listed this as the first step because even if we know exactly where we want to go, we have to have money to be able to do it. 

2. Decide where we want to go

When we were still paying off student loan debt, our plan was to spend the least amount possible on vacations.  Our first 3 years of vacations were a road trip and two cruises.  We still aim to spend the least amount possible, but becoming debt-free gave us the freedom to spend a little more.  We have been to Hawaii, Europe, and an Alaskan cruise and we were under budget on all of them!

We don’t have a solid process for deciding where to travel.  I just wanted to travel for the first few years and we discovered that cruises were super affordable!  We said if we were debt-free we would go to Europe for our 5-year anniversary trip.  Alaska quickly became our next destination when we decided to travel with friends.  Now we’re just kind of winging it on deciding where to go!

3. Research flights on Skyscanner and Hopper

If our destination requires flights, I always start with Skyscanner to see which airport is the cheapest. After a little research, I play around with the dates to see if it’s cheaper to leave a day or two earlier or later than what we had in mind.  Once we nail down the dates, I look up the same flights on Hopper, which sends notifications when it’s cheapest to book.

If we are going to multiple destinations, I also check to see if it’s cheaper to do our trip backward. For example, our original plan was to fly Los Angeles, Honolulu, and then San Diego.  We ended up flying San Diego, Honolulu, and then Los Angeles because it was a few hundred dollars cheaper. 

4. Research Airbnbs and hotels

Airbnbs are consistently cheaper than hotels in all the cities we’ve used them.  The only exception is if we are only staying one night.  On our Europe trip, we stayed 3 nights in London, 3 nights in Paris, and one night in Baltimore.  We booked Airbnbs in London and Paris, but a hotel in Baltimore.  Rates are still more affordable even with the cleaning fees on multi-night stays, but not so much for a single night.  I always compare Airbnbs and hotels to make sure we’re getting the best deal and saving as much as possible.

Other than rates, Airbnb gives you views that most hotels don’t.  These two photos were taken in our Airbnbs from our balconies!

If you’ve never used Airbnb, I highly recommend trying it out! Here is a code for $40 off your stay! 

5. Book flights and lodging 

When Hopper sends the notification to go ahead and book, we book our flights and then immediately book our Airbnb.  We book flights and lodging at the same time to make sure the dates coincide and there are no gaps. 


Weston likes to print out every booking confirmation and information we need for our trip.  He keeps it in a folder that we refer to throughout the trip.  I tease him about his little folder, but it’s actually very helpful. 

I tried to answer questions that we receive most frequently, but if you have additional questions please feel free to leave them in the comments!  Also, please share if you have any helpful travel planning tips!

  1. Douglas N. Shelton says:

    Very insightful! Thank you!

  2. Jessica says:

    Love this! My husband and I have already discussed ideas for our 5 year anniversary next year. We just started a sinking fund last month. Thanks for all the other helpful ideas.

  3. Jan Hulsey says:

    Great information! Wish I had been a planner early in our marriage!

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