My husband and I just returned from Italy.

Italy. Was. Fabulous.

In this 3-part series, I’ll explain the tricks and strategies I used to stretch my dollars to the max on flights, hotels and meals for our anniversary vacation to Italy, and collect thousands of dollars in travel rewards and savings in the process!

In this first part, I’ll explain how I:

Booked a 7-night trip to Italy that included round-trip flights, hotel, daily breakfast and rental car for 60% off

Spent $187 and ended up with nearly $1000 in additional travel credits and savings before we even got to Italy!

Then Read Part 2, where I detail all the hotel perks and upgrades we enjoyed during our trip!

How to earn cheap or even free travel

I first mentioned this vacation to Italy in Travel Rewards: A 5-Star Life on a 3-Star Budget. I wrote that post months ago as my interest was first piqued by earning travel rewards. Since then, I’ve done some massive research and tested out several travel rewards programs.

If you’re new to the world of travel rewards (sometimes called travel hacking, but I learned that this term is frowned upon when I was at FinCon!), it is a hobby involving collecting and redeeming travel points, miles and maximizing freebies and perks with travel loyalty programs.

The goal of the travel rewards life is to collect hotel and airline points to pay for some or even all of your travel expenses, stretch those points as far as possible, get the most value from every dollar or point you spend on travel, and maximize your upgrades and perks.

When you first start collecting travel points and rewards, you’ll find that you earn the most rewards by actually paying for travel directly, especially if you’re combining loyalty programs with travel rewards credit cards. If you travel already anyway, you can start booking your travel more strategically and use some tools to start earning travel rewards, points and miles!

I’m still diligently and strategically collecting my miles. This trip to Italy was not free, but my next one will be, since I was able to collect tons of rewards to use for future travel.

Since I started in travel rewards earlier this year, my husband and I have collected nearly half a million travel points from various travel programs!

If you don’t travel yet, but want to start earning some free and heavily discounted trips, you can also earn lots of points with travel rewards credit cards all by themselves. In fact, using travel rewards credit cards is how we were able to spend the night in this $600 room at The St. Regis Rome for only $180!

You can apply for any card I mention that you think might be a good fit for you by clicking on the name of the card, highlighted in green throughout the posts. You can earn a big pile of travel points when you’re approved and meet the minimum spending requirement, and I might earn some extra points for sharing these strategies with you. For more information about how to maximize the travel rewards credit cards I have and love, read Choosing Your First Travel Rewards Credit Card: 3 Things to Consider.

Please note also that I carefully considered, planned and budgeted all expenses ahead of time, because we do not carry credit card debt. You shouldn’t carry or rack up credit card debt either! Yes, I am always looking out for your coins, my friend.

Travel Rewards Tip:

Always remember that travel rewards do not outweigh the cost of credit card interest!

The discount Italy vacation package

I found a cheap trip to Italy on Groupon Getaways that included round-trip airfare to Milan, hotels in 2 cities with free breakfast, and a rental car for only $649 per person (and actually was only $599 if you flew from New York City, but we needed to fly from Chicago.)

While you can usually earn the most hotel points and frequent flyer miles by booking your travel directly with the airline or hotel, the savings on this trip to Italy far outweighs the potential travel rewards. I was still able to earn some travel points when I booked though, which I will get to in the next section.

Being who I am, I just had to know exactly how much I saved on this trip. To compare what our trip cost vs what we paid, I did a search of this flight for the dates we traveled.

I’m sorry…whet?

I spent 1/2 of what they’re asking for these coach seats, for an entire vacation package!

If you’re on a budget (everyone should be!), you really cannot beat an opportunity like that to go overseas. I always check Groupon Getaways for super cheap travel packages.

Check out current discount travel deals from Groupon Getaways here!

When I spotted this Italy travel deal, my thoughts were: buy this package as the “base” of our trip, then customize it so we could have the experience we wanted to have on our vacation.

It worked out really well!

My husband and I have 3 boys, ages 9, 6 and 3. We booked this trip for just the two of us, a celebration of our 5 year wedding anniversary.

We work a lot, we don’t live near family (no baby sitters!) and while our Groupon Getaway travel deal came with hotel, we really wanted to see as much of Italy as possible while we were there, which meant booking additional hotels in the Italian cities we wanted to visit.

To maximize the value of these extra expenses, I used some tools: airline and hotel loyalty programs, and specific travel rewards credit cards.

Travel Rewards Credit Card Winners

I will get into hotel loyalty programs in Part 3. The travel rewards credit cards that really came through for us on our trip to Italy were:

Chase Sapphire Preferred

The Starwood Preferred Guest Card from American Express

The Platinum Card from American Express

Of those 3 travel rewards cards, the real MVP was probably The Platinum Card from American Express. This leveled-up rewards credit card comes with an intimidating annual fee of $550, but some massive travel perks! The Platinum Amex card has more than paid for itself for us, and we’ve only had it for 2 months! 

I booked the Groupon Getaway travel deal with our Chase Sapphire Preferred card. Generally you can earn 2x points on travel with this card, but I purchased the deal via the Shop Through Chase portal.

In the Shop Through Chase portal, you can earn extra points with certain retailers, and Groupon was one of them at the time. I earned 4x points on this discount vacation package to Italy that totaled $1398 for both my husband and myself.

This is a savings of 60%, which comes to over $2000. Yasss!

I was telling someone that they’d have to mess this trip up really badly for me to feel like it was a rip off, since the flight itself was worth way more than the cost of the full vacation package.

I’m happy to report that the accommodations included in the Italy vacation package exceeded my expectations. Even should you not upgrade anything and simply take the vacation package as it comes, I can honestly tell you that this cheap Italy trip is worth far more than you pay.

Travel upgrade #1: First class flights (attempted)

For $649, including round-trip flights from Chicago to Milan, hotel, meals and rental car, obviously our package came with the lowest level economy class seats on KLM Airlines.

My husband really wanted to experience a first class seat on this trip. He’s a big guy at 6’3, with a large frame. The thought of a cramped economy seat for an 11 hour flight sent him into a sort of panic!

We called the airline ahead of the trip to see about an upgrade to first class seats on the flight, and were quickly snatched back to reality when we were quoted the $3000+ cost to sit in business class for just one leg of the 4-segment journey.

That’s…gonna be a no for me. Sorry, husband.

I did, however, tuck the idea away and wait patiently until flight check-in came around, because I thought maybe a first class seat upgrade would be offered for less.

Sure enough, we were offered business class seats for a few hundred dollars. We were all over it!

Sometimes it pays to spend a little extra. To me, as an investor, it’s all about cost vs value.

Since the trip was a special one, I did not want to be stressed out with messy airlines or rude customer service as we headed out. Also, since first class seats come with extras like food, drinks and free checked bags, if you can snag a first or business class airline ticket for the low, you could even come out ahead!

For my husband, it was all about the value of our time on our trip together. He wanted the first class seats so he could get some rest on the overnight flight, and be refreshed by the time we got there so we could maximize our time (which, by the way, is why it’s called “business class”. Companies will pay for their employees to fly in comfort so they can be fresh by the time they reach their meetings, or so they have the resources needed to get some work done on the plane. It saves them in payroll and productivity. It’s all about the value, not the cost!)

Travel Rewards Tip:

If you have your sights on buying a first class flight ticket and are willing to take a chance of not getting one, you can save big by waiting until you check-in on your phone or get to the airport.

Chances are the ticket upgrade will be a fraction of the cost, if a seat is still available!

Unfortunately, when we got to the airport, there were changed flights, switched itineraries, whole new airlines we had never heard of, checked bag mix ups, mass confusion, and suddenly no space for us in business class.

Luckily, KLM Airlines took great care of us and offered us lots of perks for our troubles, including $30 in meal vouchers, $200 in flight credit for a future flight, and even blocked off an entire row of seats for us so we could be comfortable! I have nothing but positive things to say about how the error was handled.

As I mentioned in the video above, we ended up with the exact same seats we started with, except we got a bunch of freebies thrown in for the temporary inconvenience. I will totally take it. Thank you, Nathan from KLM!

Had we not held the business class ticket, we may have lost our luggage, or missed our flight completely. We actually got first class service without having to pay for it. Win.

Travel Rewards Tip:

People working at the airport are generally awful, in my experience…unless you’re holding a first or business class ticket!

Travel Upgrade #2: First class flights (successful!)

Despite the four seat section we got to ourselves on the overnight flight from Chicago to Amsterdam, my husband didn’t sleep a wink. We were concerned we’d lose a whole day of sightseeing, trying to sleep off our jet lag! When we got our connecting flight in Amsterdam, we upgraded our seats so he could sleep. Opportunity cost.

Our Platinum Card from American Express offers a whopping 5x points on every dollar spent on flights, which made the upgrade even more appealing. The Platinum Card from American Express also offers a $200 per year airline fee credit for checked bags or other airline fees, and sometimes upgraded seats on certain airlines (but we already used ours up when we went to FinCon in Dallas.)

We were served lunch in the KLM Airlines first class seats, which meant savings on airport food when we landed (and we were in the Milan airport for quite some time, unfortunately!) Speaking of meals though…

Travel upgrade #2: Airport lounges

One of the best perks of the Platinum Card from American Express is the airport lounge access.

I joked when I visited my first airport lounge that I felt like a hillbilly. I did! I had never even been in an airport lounge until I started exploring this world of travel rewards.

Airport lounges provide a comfortable and quiet(er) place to relax or work before your flight. There are snacks and beverages, wine and beer, and the better ones provide hot meals.

Not only are airport lounges a much more enjoyable way to spend your time waiting for your flight, but if you find yourself in an airport frequently, lounges can actually save you quite a bit of money because you don’t have to drop a fortune on overpriced and under-tasty airport food!

The Platinum Card from American Express comes with Priority Pass, which gives you access to thousands of airport lounges worldwide. I’ve been in four Priority Pass lounges, and while the amenities vary, they’re always much more comfortable than waiting at the gate.

If you have a Chase Sapphire Reserve card, you also get Priority Pass. However, The Platinum Card from American Express does one better: with this card you get access to the holy grail of airport lounges: The Centurion Lounge. There are only 10 or so of these, so we did not experience the Centurion lounge on this particular trip. We were able to visit the one at Dallas/Fort Worth recently and let me tell you: gourmet food, top-shelf drinks, massages, attentive service…it was fabulous, and it was all free because we hold The Platinum Card from American Express!

The video earlier in this post about KLM was taken in the Swissport Lounge at Chicago O’Hare, available with Priority Pass. We met some great people and shared some drinks and laughs before we all hopped our flights to different corners of the world. It was a fun experience, and we even took some snacks and drinks for the road (because we’re hillbillies. Don’t tell on us).

Travel Rewards Tip:

Most people budget for flights and hotels for their vacation, but be sure you don’t overlook incidental costs: things like meals and transport to and from the airport.

While the annual fee on The Platinum Card from American Express looks fairly ridiculous, I know we’ve saved at far more than $550 during our travels, just by all the free food and drinks we’ve consumed alone! This card also comes with $200 a year in Uber credits, which have also made a huge dent in these incidental costs for us.

Here are the totals so far for what I spent, and what I got:

And we’re not even “officially” on vacation yet!

Certainly, the values of the here can vary widely. The meal savings are totally dependent upon what you eat, whether you drink alcohol, etc. Also, the value of points earned depend on how you end up using them later on when you redeem them. I base the value of travel upgrades and freebies on what they would have otherwise cost me personally, and I calculated the value of travel points and miles based on The Points Guy’s valuations. His site is an excellent resource for maximizing travel rewards.

In the next sections, I’ll dig deeper into how you can stretch a “cheap” vacation deal into a 5-star, luxury getaway with the right tools and some research, planning, budgeting ahead of time…at least for part of it, the way we did!

Part 2 is where it gets really interesting and we reaped some serious travel benefits. Find out how I got over $1000 in upgraded rooms and freebies in gorgeous, high-end hotels during our tour of Italy!

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