The Best 3 Ways to Plan a Cheap Family Trip!

Yes, it is possible for a family of four to get cheap flights, score affordable hotel stay and complete their family trip for $961. Is it a knock-down, blowout of a trip? No. Does that include tickets to the Parks? No, but there’s probably a way to do that cheap, too. Does it get you to some warm weather and let you decompress from the grind of the normal work week? You betcha.

I was not born with the travel bug. I contracted it from a travel-holic, my wife. Jessica has always enjoyed the challenge of planning and executing a good trip.

Travel is ingrained in our relationship. This is partially due to the fact that we met on a plane and also because we are always up for a good challenge that we can all tackle as a family. Sometimes it feels like an escape room, except there’s no man behind the cameras to help you if you get stuck.

This is great and all, but we also have another view of travel. The cheaper we can make travel cost, the more trips we can go on. Additionally, I happen to be someone who values a good deal. So, if I feel like we are getting a good deal on a trip, then it is just an absolute slam dunk for our family.

With great pleasure, I tallied up the costs associated with our latest trip. 6 nights in Orlando cost us $961, and it was so nice to get away from home. The only caveat to that cost is I didn’t include groceries because we would have paid for those anyway if we were home.

The first three expense categories are cornerstones of our travel strategy. The remaining items are things we just had to pay.

Cheap Flights

The first part of the strategy is acquiring TWO Southwest Companion Passes. For our family of four, this means that we travel for the cost of two.

Additionally, the Rapid Rewards points that we accrue through earning the two passes ends up paying for almost all the cost of the roughly 5 round trip flights we take per year.

The remainder is paid for by credit card signup bonuses here and there as well as spending on the Southwest credit cards or other Chase credit cards (all Chase Ultimate Rewards points transfer 1:1 to Southwest Rapid Rewards points).

You do have to pay for the taxes and fees, though, for the companion.

For this roundtrip flight in October ’19, we paid a grand total of $44.80 for flights. We had to pay $11.20 for each of our flights. The two adults’ plane tickets were purchased for about 24,000 points each (aka $0). The kids were added as our companions, but we all had to pay $11.20 for each roundtrip ticket.

Ways to Travel for Cheap | Cheap Southwest Flights
We have years of pictures with the Southwest logo in the background. The Southwest Companion Pass was a game changer when we scored our first one in 2016.

Time Shares – Deal or Scam?

The short answer is that they can be a good deal IF you put the effort into understanding all the details.

I should also say that you have to want the additional expense of having to travel to take full advantage of it. If you buy the week but don’t use it, then it is certainly not a good deal.

We have a good deal in that Jess’ parents bought the original time share as well as still pay the annual dues. But, that will change over time as we use the time share more than they do. But, I will add up the total costs (excluding the purchase cost – I don’t know what that is) to see if this type of strategy would work for you.

They purchased the time share directly from a hotel. As long as they pay their dues, a particular week every year at that hotel is theirs.

What they do instead, though, is deposit that week into a pool of other time shares via a company called Interval International. That gives them the option to book a different week at a different hotel.

The annual dues are $99 to become a member. This includes being able to deposit your week into the pool. Because we are often the ones who use the timeshare even though it is owned by Jess’s parents, we have to pay $139 to upgrade our membership. In the end, Interval costs $238 per year.

Then, to book a week through their exchange program, that costs $209. The hotel then usually adds on some taxes and fees.

For our 7 nights (we only stayed 6 due to other commitments), the cost was a total of $336 for the whole week. $209 went to Interval International and the remainder to Marriott.

By the way, this was a two bedroom Marriott (Marriott Royal Palms)! The kitchen was fully loaded; the living room was spacious. It is an incredible luxury to have so much space! We almost exclusively choose Marriott when booking through Interval!

Snacks at the pool | Groceries are good for cheap travel
It was kind of nice there wasn’t even a restaurant at the pool to tempt us to order something. All snacks came from the grocery store which is awesome for the wallet and the body.

If we play our cards right, we can usually get almost three weeks of accommodations out of the original 1 week time share. I will divide the annual costs by 3 to try to get a weekly cost for this trip.

The annual dues divided by 3 are $79 added to the one-time purchase for the week’s accommodations come out to a grand total of $415 for the week of hotel lodging!

Marriott Royal Palms Playground | Luggage Cart Kids Love | How to travel cheap
If there are two things our kids love, it’s playgrounds and luggage carts.

There are full blogs and books written about time shares, so I know this can get complicated.

Of course, I didn’t consider the purchase price of the time share in this calculation. If you are considering buying a time share, you would obviously have to take that into consideration.

But, I’ll just tell you that it is nice having the ongoing expenses of a week of travel being so low.

Pool Time Is Great Family Time
The majority of the pictures from the trip are from the different pools at the hotel complex. The expectations of kid friendliness are exceedingly high!

Food and Drink on a Budget

The kitchen afforded us the perfect opportunity to cook nearly 100% of our meals in the room. This is just easier with young kids and makes it so that I don’t have to have ANY concerns about the cost of food.

Grocery delivery and/or pickup is a traveler’s best friend.

We ordered a day ahead of time from Walmart and picked up the groceries as we headed from the airport to the hotel. If you haven’t used grocery pickup from Walmart, it makes you feel like a rockstar.

When you are on your way to the Walmart, indicate in the app that you are doing such. Upon arriving in the marked parking spots, punch the number of the parking spot into the app. Then wait about 4 minutes, and a Walmart employee will show up with a roller cart of your groceries!

That was the bulk of the groceries ($247). Then, as we were running low near the end of the week I topped us up with Whole Foods Delivery as well as Amazon Prime Now. Amazon splits out Whole Foods and Amazon as two different stores in the app. The reason I did that was to save $4 on a 12 pack of Truly. I don’t recommend that as I paid about that much more on tips.

Snacks at the Pool | All Snacks Came from the Grocery Store
My favorite pool snack hack is to freeze the juice and apple sauce pouches so they have to spend a little extra time trying to thaw them.

For your reference, delivery is free (as long as you meet the minimum order of $35), but the app recommends a tip that comes out to be about 10%. Of course, you can always change the tip amount.

We spent $107 on those two orders ($69 and $38) that would keep us stocked through the end of the trip.

Total for the week, we spent $354 on groceries. This includes alcohol. We tend to drink a bit more while traveling. We cut costs by buying box wine (Bota Box), vodka (instead of buying more hard seltzers), and light beer (Miller Lite is low in carbs, relatively 😉 ). But, we had some more “full-priced” beverages as well.

This is money we would have spent if we were at home, so I’m not going to include this in the total number.

Groceries for Snacks by the Pool - Best Way To Keep Food and Drinks Costs Down on a Trip
This is what happens when we let our kids pick their snacks/treats – apple juice, apples and apple sauce. I see a trend 😉

Car Rental

No tricks here. We just had to rent one because Jess was commuting to a conference most days or at least partial days. The cost was $272, but you can probably avoid this cost with properly located lodging and appropriate car seats for an Uber/Lyft.

Airport Parking

Again, no tricks here, and you can definitely do better with asking for a ride from a friend. We paid $49 for our car to stay at the airport.

Dog Sitting

Sadly, again, no tricks here. We alternate between having our nanny take care of Buddy and using someone on Rover. Regardless, we pay about $30 per night. This time it was our nanny.

Rover is great, by the way. If you haven’t heard of it, it is the Uber of dog sitting. You search for service providers in your area (aka people who will watch your dog at their house) and book them through the app.

The cost came out to be $180.


The costs definitely add up even when we do things on the cheap. But, I am very pleased with the grand total coming to $961. Also to note, you don’t see any restaurant costs here because we literally did not eat anything that wasn’t prepared by us. That helps the wallet as well as the waist line.

I’m sure you also noticed that there were no trips to the Parks mentioned here. We were pressed for time as Jess was working most days. We were there for her conference, so that was the priority.

We did price out partial-day tickets to one of the parks, and it was going to be about $400 for the four of us. This alone would have become our highest expense for the whole week, so I was not that sad to miss out.

Minnie Ears | Cheap Travel | Ready for Disney World or the Pool
We bought Ellie’s Minnie Ears (at Target, not Disney) just in case we could go to Disney’s Halloween events.

We are lucky that our kids don’t beg to go; they really don’t show any enthusiasm at all for it. We went for the first time in Feb with our then 3 and 4 year olds. We did 3 days total in Animal Kingdom, Magic Kingdom and Epcot. They enjoyed it, but about as much as they would a trip to our free St Louis Zoo or a local kids’ attraction (costs hover in the $50 range for a family of 4).

While I personally love digging through these numbers, what I really hope as the result from this post is that I can share the mindset that travel doesn’t have to be expensive.

When comparing travel to home, in both cases you are paying for food, so that’s why I didn’t include food. Additionally, you could take out the rental car (and add in a little more for Uber/Lyft) and the cost goes even lower.

We hung out at multiple pools in great weather, explored elevators, and most importantly spent amazing quality time together with very little distraction from the real world.

Water Slide in Orlando World Center
We didn’t make it to any of the Parks, but the hotel still had some great attractions!

You’ll see that there’s a lot of travel focused content on our website and our social media pages, but the whole reason why we do this is to bond as a family and enjoy each other.

If travel is a way that your family becomes closer, I would love to hear from you over on our Instagram page.

Best 3 Ways To Plan a Cheap Family Trip