How I Got Almost $2,000 of my Vacation Paid For

I’m all for a good deal on travel- and I used to get them much more frequently. But now, my
boyfriend is a teacher and it really limits when we can travel together. We’re headed to Greece
next week to celebrate my 30th birthday with friends. Traveling with friends presented another
wrinkle: the only dates that made sense for all of us coincided with the 4th of July- $$$$.
After procrastinating until less than three months before (because I’m human and was so
paralyzed by the thoughts of ALL the expenses associated with a 9-day trip for two to the Greek
Islands during high season), I managed to get creative to bring in just under $2,000 to help pay
for the trip. And no, I didn’t get another client or otherwise increase my business revenue.
Here’s exactly how I did it:

1) Leveraging Credit Card Points

I have several credit cards all with different point systems and values and it’s really hard to
remember which is which. All of them could likely be used in some way, shape or form to help
with travel expenses, but I treat credit card points like money and try to get maximum value so I
won’t use them unless I do the math and it’s a great deal. A quick Google search usually tells
you what is and isn’t a good value once you know what you’re looking for, but I really had no
idea and didn’t want to Google all my business and personal cards. So, having a 15 minute
commute every morning to my office and to and from the gym, I called about each of my cards
in transit. In was very straightforward with the service reps and told them I was trying to figure
out what the best value was for my points with each card and made mental notes. Through one
of these conversations I was reminded that the points for one of my cards – the Amex Blue Sky-
can be cashed in for a statement credit if you have travel charges to apply against. I didn’t have
a ton of points on that card, but it was enough for $300 worth of hotel or flights as long as I
booked at least $300 on that card. Score!

2) Leveraging the Sharing Economy

Since we knew we’d be gone with the dogs out for those 9 days, I figured this was a prime time
to try out Air BnB. I listed our place for a competitive price, and less than a week later we had
the apartment booked for a $388 payout. We already have a cleaning service come once per
week for a reasonable price so there were no accommodations that needed to be made before
or after the stay- and we actually had the ability to pass off the cleaning fee for that week to our
renters.

Next up was sharing my car. I recently leased a gorgeous Alfa Romeo Stelvio, which is an
Italian-made SUV. It’s brand new, super fun to drive… and usually sitting in the driveway. A few
friends of mine have been renting out their cars on Turo and on Getaround with no complaints
recently so I figured it couldn’t hurt. I signed up and posted a listing for mine. The first two weeks had
no activity. Turo suggested the price for my car- about $150 per day- and I just figured most
people aren’t looking to spend that much on a rental for the day to run errands. I’d heard from a
friend with a much cheaper car that he’d get bookings all the time and was a bit bummed that I
didn’t have any luck right off the bat. Another week went by and I got a Saturday rental request
that was extended to Monday- that was $315 for the two hours plus a late fee since he didn’t
return it on time. Then, the next weekend I got another one-day rental with a request for me to
deliver it. I was heading into the city to spend the day with a friend anyway so I agreed to deliver and scooped up an additional fee. Three days without my car amounted to a $447.25 payout.

Not bad.

3) Leveraging Relationships

Having dogs can get expensive, especially when you need to travel without them. In the past,
I’ve had family who could help feed and let them out when I’ve been away, but life’s changed
and we just don’t have that luxury anymore. Unfortunately, many boarding facilities charge more
for bigger breeds and on the cheap end it can cost around $100 per day to have both of my 65lb
Pitbull mixes taken care of while I’m away. This time, being gone for 9 days it would have been
$936 plus taxes and fees to be exact, AND my dogs (who are spoiled and used to laying on the
couch all day and sleeping in our bed at night) would have been miserable dying to leave when I
picked them up and out of sorts for the week after. Not good.

So, instead of immediately looking for options and knowing I’d likely be able to board them last
minute if needed I started letting friends know we were looking for someone to watch them
when we were away. Lucky enough, a friend told me she had a friend who was thinking about
adopting a dog but was on the fence. She thought she might be up for a test run, introduced us,
and the friend loved our puppy. She and her husband offered to watch her for the 9 days for free
as a way to test run dog ownership!

I have another friend whose kids LOVE my other dog and would have taken him in a heartbeat,
but she had a conflict the holiday week. Because we’d already committed to an Air Bnb guest
we couldn’t have someone watch him in our home which ruled out a bunch of options so we
were getting a bit nervous. Fortunately, we learned from another friend that Rover (another
sharing economy-type app for dog-sitting) had sitters who would take your dog into their homes.
That night, we logged in and found a very close sitter with a good setup for a super cheap price
and ended up booking the 9 days for $288.

Having a friend watch one dog and having the Rover sitter commit to the other saved us
$647.10 plus tax AND saved us a ton of bad pet-parent guilt.

So that’s how I got over $1,782.35 of our vacation costs paid for.

I actually got great deals on out flights as well, but I’ll save those resources for another post
because flight prices change ALL THE TIME and in my opinion, flight prices are like stock
prices- hindsight is 20/20 and you don’t know you’ve won until after you’ve booked.