How I Booked Our Fancy Flights to Italy for Just $416

After sharing a few highlights from our trip to Italy on Instagram, my inbox was full of questions about how we planned and booked everything – especially how we were able to fly business class for a fraction of the cost. So, I’m pulling back the curtain and breaking down exactly how we booked two incredible trips (Destin, Florida and Italy) using points and miles, plus a peek into how I plan our travel.

Destin, Florida: 4 Flights for $44.80

Let’s start small. For a quick weekend trip to Destin, the cash price for four roundtrip flights plus two nights of lodging usually runs around $1,268. Our out-of-pocket cost? Just $44.80.

Here’s how we did it:

• I booked two Southwest flights for Adam and me using Rapid Rewards points.
• We used our Companion Passes for the kids, which allows them to fly free with us. We only paid the taxes and fees, which came to $22.40 per pass.
• We stayed with family, so we didn’t pay anything for lodging.

We used 14,530 Southwest points and paid a total of $44.80 for all four tickets. If we’d paid cash, the flights would’ve cost us $868. The Companion Pass alone saved us hundreds.

Want to learn more about how the Companion Pass works?
Check out How to Earn the Southwest Companion Pass for a step-by-step guide on earning and using it.

How We Earned the Companion Pass

To earn the Companion Pass, you need to accumulate 135,000 Rapid Rewards points in a single calendar year. Adam and I each opened one personal and one business Southwest credit card. The welcome bonuses and minimum spend requirements gave us just over 135,000 points each.

Since we now each have a Companion Pass, we can each fly someone with us for nearly free through December 2024. There are no blackout dates, no limits on how often we use it, and we can change our designated companion up to three times per year.

If you’re applying for both cards, I recommend starting with the Performance Business card, then applying for the personal card. Be sure to space your applications out by at least 30 days.

How We Booked 4 Business Class Flights to Italy for $416

This is where it gets good.

We flew from New York to Milan in lie-flat business class seats on Emirates for just $104 per person. We returned two weeks later on Air France in business class for about $300 per person.

The cash price for these same flights? Nearly $24,000. That was never going to happen for us. Points and miles made this dream trip possible. If you’re curious how I decide which cards to open and when, here’s a deep dive into how the 5/24 rule works and why Chase cards are often the best place to start.

Where We Went

Over two weeks, we visited Milan, Venice, Bologna, Rome, Naples, and the Amalfi Coast. Then we circled back to Rome for a few more days before flying home.

We stayed in:

• Milan for 1 night
• Venice for 2 nights
• Praiano (Amalfi Coast) for 3 nights
• Rome for a total of 6 nights

Total cost for lodging: $1,300.83. Our entire trip, including flights and lodging, came to $2,980.03. If you want to see another detailed trip breakdown, check out our Trip Report: Two Weeks in Italy.

My Flight Planning Process

Here’s a quick breakdown of how I plan our trips:

1. I look at what airports we can fly in and out of.
2. I compare different weeks and routes to find the lowest rates.
3. I run a variety of searches to figure out what fits best for our schedule and preferences.

My Flight Search Spreadsheet is what keeps me organized. It helps me compare options side-by-side so I can make the best choice without losing track of everything I’ve researched.

When flying internationally, I always prefer nonstop flights if they’re available. They make the travel day much easier, especially with kids. That helped me narrow down the options quickly.

Why We Chose Emirates

Even though Emirates had slightly higher taxes, the number of points required was much lower than other airlines. And once I looked into the airline more, I was completely sold. The experience felt luxurious from start to finish.

To book the flights, I transferred points from a credit card to Emirates Skywards and booked directly through them. It was seamless, and I’d absolutely do it again.

We booked our outbound and return flights separately using one-way awards. This gave us more flexibility with routing, dates, and airlines. It also makes it easier to mix and match award availability without getting locked into one roundtrip itinerary.

A Quick Note on Perspective

Sometimes it helps to visualize how manageable a destination really is. Did you know Italy is about the same length as Georgia and Florida stacked together? That shifted my thinking. It made the idea of visiting five or six cities feel a lot more realistic, especially with Europe’s fast and efficient train system.

Want a Personalized Credit Card Strategy?

Every trip we’ve taken this year has been funded using points and miles, and it all started with the right card strategy. If you’re not sure where to begin, I’d love to help.

I offer free personalized credit card consultations based on your travel goals. Just fill out a quick form, and I’ll walk you through what cards to open, in what order, and how to start building your own points-powered travel strategy.