The “How” Part 1: Flights

I recently posted a video explaining why I travel so often, and although it touched upon how I do it, I wanted to try to really describe it in detail. There are a few different methods to this madness and it’s somewhat complex (hence the verbal explanation), but if you get nothing else from this post, I want to be sure you remember that the key is to just book it. There’s a 24-hour window during which you can cancel without penalty and deals don’t last; I’ve had friends get back to me within an hour and the price was already gone.

Helpful Links:

Method 1: Pop-up sales and mistake fares

Method 2: Research

Method 3: Points

I hope this helps! Please feel free to email me with any questions. 🙂

MileagePlus Program (iLOVEYOU)

After doing some mileage program research, I decided to go with the Chase United MileagePlus Explorer card a few years ago. There is an annual fee, but it’s minimal and you more than make up for it if you use the card wisely and take advantage of its benefits!


Generally, the way it works is that you build “miles” according to how much you’re spending and what you’re buying. Every dollar is equivalent to at least one mile, though shopping at certain places earns you more. For instance, Nordstrom is typically at least 4 miles to the dollar. FTD is another favorite of mine – a $100 bouquet of flowers can earn you thousands of miles! I send flowers to everyone for the most random occasions (it’s a win-win)! 😉 is another huge one; a magazine subscription can earn you ridiculous amounts of miles, and I’m an avid Cosmo reader so this one’s huge for me; I get the US, Italy, and UK versions delivered to my apartment.


When you actually travel, you earn not only on the ticket price but also on the distance flown. It’s great!


Once you’ve accumulated points and are ready to book, it’s important to keep in mind that “miles earned” is not equivalent to “miles you want to fly.” In other words, if you’re trying to go from NYC to Rome, you’ll unfortunately need more than ~4,300 miles (which makes sense considering you can accumulate that many from one bouquet of flowers alone!). Instead, a one-way ticket from NYC to Rome is 30,000 miles (round-trip is 60,000). Domestic flights are way less!


Using the United MileagePlus card, I’ve managed to have almost every other flight completely paid for in miles. In other words, zero dollars. When I do spend on flights, I spend hours looking for deals – I try different combinations of airports (out of Newark but back into JFK, for instance) and dates. I credit my psych background for these incredibly valuable research skills B), and I spend on average $600 for round-trip flights to Europe when I pay out of pocket.


It’s safe to say that miles are more valuable than money for me at this point in my life, and I’m not even ashamed to admit it. ❤


Any time I talk to someone new about my “galavanting” as my grandma puts it (she’s the one who’s so lovingly called me a gypsy my whole life, too), they’re convinced that either a) my dad pays my rent (HAHA!), b) I have a rich boyfriend in Italy (another joke.. I’m Miss “Don’t Even Say the R Word in My Presence”), or c) I’m in insane debt and spend beyond my means.


Obviously, none of these are true (& thank GOD c isn’t). Truthfully, I’m just careful. When I get paid each week (or got paid, since I’m now solely volunteering), my direct-deposit check was automatically split into three accounts:

  • Rent Checking: $300
    • This amounts to $1,200/month, which is enough to cover both my rent and utilities
    • I don’t even see this money, so I never have to worry about being tempted to spend it or about scrambling at the end of the month to come up with rent
  • Savings: $100
    • It’s probably not a lot, but for me this is huge
    • I started my automatic savings deposits small ($20) and had them gradually increase to where they are now
    • Up until embarrassingly recently, a “savings account” to me was one I drained when I wanted to buy something big or go somewhere extra far.. I definitely wasn’t saving to save (& would’ve been screwed in the event of a full-blown emergency for sure)
  • Regular Checking: the rest
    • It’s from this account that I pay my credit card and other bills (lease, insurance, etc.)

BIG checks from real estate deals are split in a similar manner, though only between savings and regular checking. The majority goes to savings and to pay a chunk of my school loans.


Automatic payments are lifesavers for me! As I’ve said, I’m constantly going in 73 different directions at once – between work and school alone I’m swamped, and if something isn’t in my iPhone calendar, it’s not happening. Automatic, recurring payments save me from having to remember certain bills (& spare me from ever being late!).

  • Car: my lease payment is automatically taken out of my checking account at the end of the month
  • Student Loans: these payments break my heart when I see them constantly withdrawn L but it has to be done
    • I didn’t defer my loans/put off payments until after graduation, so I’ve always paid as I’ve attended classes
    • I make these a devastating once a week (even now while I’m unemployed.. posso vomitare)
      • I think the minimum is like $40/month, but I end up paying about $300/month because I’m neurotic


I’m sure you could make automatic payments for credit card bills, but I don’t. As neurotic as I am about school loan payments, I’m way worse with my card! I only have one: the Chase United MileagePlus Explorer Card. I am obsessed. I use Chase for my checking/savings/rent accounts, as well, and I can’t say enough good things about them or their app. I’ve heard it’s good to keep a small balance on a credit card, but I literally would lose sleep at night – I immediately pay off any charges I make directly on my iPhone through the Chase app. I always saw my parents pay early and in full, and I guess I’ve picked it up from them!


Budgeting aside, the MileagePlus program associated with my card has allowed me to travel like the gypsy I am and then some. It changed my life! It even has its own separate post, that’s how f’ing valuable it is to me! 😉 Check that out for more info.