Maximize Your Travel: How I’m Going to 3 States (including Hawaii!) & 5 Countries for Under $1,200

Maximize Your Travel: How I’m Going to 3 States (including Hawaii!) & 5 Countries for Under $1,200

The past 2.5 years in the “real world” have been the most pivotal years of my life. I graduated college, moved to Dallas from Kansas City, accepted my first corporate job, experienced a lay-off, took a six-week hiatus, found a new corporate job, reached a new level of health and wellness, and earned my first job promotion. Now, I’m three months away from turning 25 (crazy!) and finally have somewhat of a grip on life. With age, I’m realizing how important it is to create the life I want – to stop wishing and start doing. I refuse to let my 8-5 grind control me, and it sure as hell won’t stop me from continuing to do the things that fulfill me. Now that I have a few years of solid paychecks under my belt, some accrued PTO, and a laundry list of places I want to visit, I decided 25 was the perfect age to really experience the world. In January, I booked my first trip of 2019 – a 9-day vacation to Italy and Greece for my 25th birthday. Since then, without stressing too much about PTO, work, and “where I’m going to be in 5 years,” I’ve managed to book 5 more trips this year for under $1,200!

From when to start, where to go, when to commit, what to spend, and most importantly – how to save, this post will cover everything you need to know when planning your next adventure. 


Choose Your Destination + Route

First things first is deciding what cities/area/region you want to visit. If you’re looking for a domestic adventure, feel free to skip onto the next section, as this part pertains to international travel and discovering your route. Planning a European or Asian trip can be overwhelming with all of the airports, cities, and opportunities. If you’ve never been to a country, I suggest hitting the major, popular cities first. This will allow you to experience the culture and people, and then if you love it (or if time allows you to extend your trip), you can go back and visit smaller, less touristy places. The initial flight from the United States will be the biggest chunk of traveling, but once you’ve spent the money on the first flight, you’re just a short flight or train away from your next stop.

My European trip in June includes the Amalfi Coast of Italy and then catching a quick, two-hour flight to Mykonos, Greece. I chose these destinations because I’ve always dreamed about the colors, beaches, and views from the islands of Italy and the dreaminess of Greece. I’ve never had an urge to visit Rome so we completely nixed it and are flying straight to Naples.*

Greece was an easy extension to our Italy trip because it’s so close to Italy and both have very similar vibes – which means similar packing (major key!) Flights from Naples to the Greek Islands are between $70-100 on cheap airlines. We don’t mind flying cheaper airlines here because the flight is so short and nonstop.

Below, I’ve put together a list of European cities that are easy to pair if you’re looking to travel for around 8-12 days (with 2 days of travel at the beginning and end of your trip.)

  • Amalfi Coast of Italy (Naples, Sorrento, Capri, Positano), Greek islands of Mykonos and Santorini (My route!)
  • London, Manchester/Liverpool, Dublin, Belfast (Northern Ireland)
  • Paris, Brussels (Belgium), Amsterdam (Netherlands)
  • Lisbon (Portugal), Seville/Granada (Spain), Madrid, Barcelona
  • Rome, Florence, Venice, Geneva (Switzerland)
  • Florence, Venice, Pula (Croatia), Split (Croatia)

*Note – Naples is a little pricier to fly into than Rome but it’s a short, 20-minute drive to the Marina to catch a ferry to another Amalfi port, rather than a two-hour train ride from Rome. If you’re not sold on a city, or feel you can live without it, don’t feel obligated to spend time there! Time is money – especially when you have a certain amount of PTO days! 

Find Your Flights

I suggest looking  for flights 3-6 months prior to your departure date, especially if you’re looking to travel during peak season (April-September.) The biggest thing I’ve learned when booking international flights is to fly out of a major US city on the coast closest to your destination. For example, the 3 airports in New York offer much cheaper options for flying to the UK, France, Italy, Spain, Portugal, and Ireland. Other less-expensive airports for international travel include Orlando, Boston, Atlanta, and sometimes DFW. DFW can be cheap but you’re most likely flying American Airlines or United, which can be more expensive (for example, my one-way flight from NYC to Naples was $450, from Dallas it was well over $1,000!!) In addition, if you’re planning Asian travel, flights out of LAX, San Francisco, and DFW are better options. 

The best websites for finding cheap airfare on trust-worthy airlines include: 

  • Skyscanner
  • Hopper (App) 
  • Google Flights  – great for seeing all of your route options, leg room comparisons, and the map view is clutch to see other nearby-airports
  • Scott’s Cheap Flights 
  • Cheap DFW – perfect for someone who is flexible on days, ultimately just wants to save money, and doesn’t want to venture too far to surrounding cities. Most of the cheap deals require a 7-day stay and have to be booked as a round trip

The best airlines (routes, meals, bang for your bunk, comfort, and short layovers) for European travel include:

  • AirTap – Portugal’s airline. Flying this airline to Naples from NYC, with a 1.5 hour layover in Lisbon for $450
  • Aer Lingus  – Irish airline
  • Air France
  • Norwegian – UK’s cheaper airline (in comparison to British Airways), with comfortable economy seats. A great option for easy upgrading without the charges and a very user-friendly website. Flights connect through London which is a great hub
  • American Airlines/British Airways

Once you’ve booked your long-haul flight, which is most likely a one-way if you’re planning on returning from another city, you’ll need to book your flight to your destination airport. For me, this is where the Southwest Airlines credit card comes in.

As mentioned in my post about the southwest card, this is mainly how I “afford” to travel. I put everything on my southwest card, I mean EVERYTHING (including $3 coffee) and pay it off as quickly as possible to earn the points. Since Southwest has pretty cheap fairs in general, I try to purchase as many SW flights as I can, before using my points. I fly home to Kansas City a lot and tend to do weekend trips, so I always try to buy at least one way with money to earn the double points, in addition to the miles for the flight. It is important to note that if you use points on a flight, you don’t earn the additional miles**.

The southwest card is crucial to me is because I can use points (or at least purchase the airfare and earn double points) on my flights to my departure airport.  I bought a one-way, Southwest flight to NYC to catch my flight to Italy*. I could’ve easily used points on this flight but it was less than $130, so I opted to earn the points so I could put them towards my Hawaii flights – which allowed me to book round-trip flights to Hawaii for zero dollars. This method was proven to be exponentially cheaper than flying straight out of DFW to Europe (which was more than $1,100 for one way!

*I also plan to use southwest points to book my one-way flight to LAX in order to catch my flight to Phuket, Thailand. 

**Miles and points are the same in Southwest, but I like to refer to the ones I receive from credit card expenses “points,” and those I receive from the actual flights as “miles.” However, they all accumulate in the same account. 

Commit & Start Booking

Now that you have your route and an idea on flight costs, it’s time to commit. Back in December, I took the lead on planning our European trip and spent multiple days researching flight departures, arrivals, costs, and exactly how many days we would need to take off from work. I then created an entire word doc, complete with links to the flights and all the days and times, and sent it to everyone included on the trip. I’ve found that if people know the plan ahead of time and are given all the details, from money to days, they are more likely to commit with you. My sister, friend, and I all agreed to only take off about 6-8 days, so when I told them the dates (Wednesday, June 26th – Saturday July 7th, with the Fourth of July as a paid holiday), they were thrilled and we were booked by January! 

It’s important to remember that the earlier you book flights, the cheaper they’ll be. Our trip is 6 months away, and no one is 100-percent sure what their schedule will look like and that’s perfectly ok! However, now that we’re booked and committed, we can plan around it. We have already all talked with our bosses to ensure our responsibilities are handled while we’re gone, we’ve respectfully declined wedding invites, and now we are able to confidentially say no to other major events, concerts, and trips prior to ours.

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Manage Your PTO & Don’t Be Afraid to Use It

In regards to this post’s title, I’m also traveling to Vegas, Cancun, Hawaii, Thailand, and Singapore this year, in addition to Europe, for a total of about $1,200 and 18 vacation days. When I posted my itinerary on Instagram, sooo many people reached out with questions regarding how I can “afford” this, whether in terms of money or PTO. To keep it simple and honest, I don’t have the exact amount of PTO for these travels.

Let’s talk PTO. Every company is different in terms of how you earn it and spend it, so if this doesn’t apply directly to you, I hope it helps you be more confident in your plans. My PTO hours are separated into vacation and sick. I accrue 8 hours of vacation and 4 hours of sick days each month. Since I usually book flights for late afternoon Friday and return Sunday night, I’ve managed to accrue 33 hours of vacation since September (I made a point to not take off extra days during Thanksgiving and Christmas because 1. It’s already FREE time off, and 2. I knew I wanted to go on a big trip this year.) By the time I leave for Europe (I’ll need 7 days), I’ll have only accrued about 6 days of vacation, since I am using one for Vegas in April.

My boss and I agreed I will work overtime hours a few weeks before my Europe trip to comp a few hours that I won’t technically have. This is hard and might suck during the time, but I am so thankful she is giving me this option! I let it be her decision by explaining how excited I was for the trip and how Italy and Greece have always been a dream of mine. I reiterated the fact that I didn’t take off extra days during the holidays and how I am willing to do anything to make this work. I’ve found if you just be honest with your coworkers, and demonstrate how committed you are to finishing your work in a timely manner, they will be more willing to work with you during your travels. Also, don’t be afraid to take leave-without-pay days. If comp hours aren’t a thing in your company, or you don’t have the exact PTO, mention to your boss that you would be willing to take LWP. I did this for my trip to Portugal last April, and trust me when I say the experience was far greater than the 2 paydays I missed on my paycheck. In fact, I hardly even noticed.

The thing I’ve realized with bosses and work in general, is that it NEVER hurts to ask, as long as you’re confident, honest, and mature about the situation. I’m going to a wedding in Cancun 2 weeks after I return from Europe, which I paid for one way with my Southwest credit card and used points for my return flight, so I may have to take LWP. In the big scheme of things, it doesn’t affect me too much. I will commit to finding some extra babysitting shifts and freelance a little more. There’s always a way to make money, just be willing to put the time and effort in! 

The Bottom Line

In summary, traveling in your twenties doesn’t have to be impossible and it surely doesn’t need to blow your savings. If there’s anything to take from this post (or if you skipped all of it and just want the major points), here you go:

  • Start researching flights 3-6 months in advance and create your route
  • Look for flights out of a major airport on the coast closest to your destination
  • Open a travel credit card to earn + use points for the flights to your departure airport (save money here and you can splurge a little more on the long-haul flight)
  • Create a detailed itinerary to outline times and prices to show your travel buddies
  • COMMIT to your vacation and don’t be afraid to talk to your boss/coworkers ASAP to show maturity, time management, and trust worthiness
  • Weigh all of your options when it comes to PTO – whether it be combining sick hours, taking a few LWP days, or working overtime
  • DON’T STRESS! If traveling is important to you, make it happen. Don’t spend time overthinking it or wondering if it’ll work out. The quicker you commit, the quicker you can plan your life around it!
  • Save and earn extra money when you can, be smart in your other spending choices, do your research, and create the life you want! 

I’m sorry for the lengthy post, I felt like I needed to cover all the bases while I had you here! Don’t forget to check out my post about the Southwest credit card to maximize  your travel and start flying for free!

Have any other tips for planning, budgeting, and committing to a big trip? Drop them below! 




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