“How Do You Afford to Travel All The Time?” Tips from a Boujee Traveler

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If you follow a lot of travel influencers on social media, you’re probably wondering how TF some of these people afford to travel all the time. They’re living their lives in airports, boats, islands, crystal clear waters, 5 star resorts, and you’re left wondering HOW!? If we haven’t met already, I’m Gina, and I’m an aesthetic traveler whose iPhone location should be set to read “Probably Out of Town.” In this post, I break down my top travel tips and secrets for how I am able to be on the go, all the time.

Although much of what you see on social media is smoke-and-mirrors, there are indeed people who do travel often, and I happen to be one of them. Most of the time, I take a trip once a month or once every other month.

Traveling all the time is financially difficult, and it’s even harder when you’re a boujee, high maintenance traveler like I am. My life would be much easier if I could just backpack all over the world, but I’d rather be in a nice dress in the middle of Positano with my makeup done and a glass of wine. I’m just being honest with you.

Before I get into the good stuff, I do want to give you a little bit of background about me personally, and certain events in my life that have led up to me being able to travel so often:

I have another job outside of this one, and it pays well. In fact, I have been fortunate enough to have jobs that paid well for the past 10+ years. My current job is also remote, so it allows me to travel and work. The job I had before this one had a great PTO policy, and I was able to figure out how to use it to my advantage after I had accrued so much.

I also lived at home for 4-5 years in my 20s after college, and this allowed me to pay off my students loans and bank a lot of money. Lastly, I make income from this travel website that helps pay for my trips too (I talk more about having multiple streams of income here).

I don’t say any of this in an arrogant way, but rather, to be as transparent as I can. I always like to be honest with my readers. I think a lot of people today make travel and influencing “look easy” and imply it takes minimal effort to be able to revolve your life around globetrotting. I’m not saying this isn’t true for some people, but for the majority of us, we aren’t making hundreds of thousands of dollars each month off of our Instagram accounts.

Now, you’re probably thinking…”if I don’t have everything you mentioned above, how am I supposed to do this?!” While I admit I am very lucky, I also know people that make less than I do that travel often. Maybe you need to be very cognizant about saving money for a year in order to be able to be a boujee traveler. Maybe you need to downsize your house or apartment. Maybe you need to build up your side hustle. My point is, there are ways…and now, I’m going to give you my top tips that help me afford to travel all the time.

If you have any specific questions after reading this post, write me a message using the Contact Me! form at the bottom of this page, and I’d be happy to help you further!

How I Afford to Travel All the Time:

1. Invest in a Good Travel Credit Card

You’ve probably heard a ton of hype about the benefits of travel credit cards, and TBH, most of it is true. My travel cards have helped me save money on a lot of trips.

I could probably devote an entire blog post to travel credit cards, but there are other websites (Nerd Wallet, The Points Guy, etc) that have made travel credit cards their entire business. I’m not going to go as in-depth here as they do, but I can give you my personal advice/guidance surrounding travel cards.

• If your main objective for using your credit card points is to travel, I would suggest putting the majority of your purchases on a good travel card so you can rack up as many points as you can.
• There are airline specific travel cards and there are also “everyday” travel cards from Chase, AmEx, Capital One, etc. that give you a broader range of travel benefits. The card you choose will ultimately depend on how you want to use your points.
• There are different levels of top-tier travel cards, and the one you get should depend on how often you travel.
• Two of the best cards for people who travel often and require maximum travel perks are AmEx Platinum and Chase Sapphire Reserve. These come with a hefty annual fee ($695 and $550, respectively), but the perks quickly pay for themselves. Both of these companies also have travel cards with lower annual fees but less extensive travel benefits.
• Some people will tell you not to use airline specific cards. I would say if your life heavily revolves around travel (like mine does), you want to go with an “everyday” card with great travel perks. If you only travel a couple times a year, this may not matter as much.

I personally have 2 travel cards. One is an airline specific card, the other is a top-tier travel card. I use my airline specific card for everyday things and will book most of my domestic US flights through it using my points. I use my top-tier travel card for my travel blog expenses and all other travel-related purchases aside from the flights I book domestically using my other card.

I mainly do this because it makes it easier for me around tax time to have all my “business” expenses on one card. However, you could also do it this way if it makes sense for you and your lifestyle.

2. If You’re Going to Multiple Destinations, Space Out Your Hotel (and Airfare) Payments

If you are familiar with this website, you know that I often travel solo. Traveling solo has its perks (doing what I want, when I want, where I want, for example!), but there are also downsides…such as having to pay for everything by yourself. One of the best ways I afford to do this is by spacing out my hotel (and possibly airfare) payments. Let me give you an example.

Let’s say I’m going to Europe and I want to visit Amsterdam, Paris, and Barcelona. It is currently March, and my trip is in August. Let’s pretend I find a hotel in each of the cities I’m visiting, and they each cost $500. I will book my Amsterdam hotel and pay for it now, and then I will book my Paris hotel and choose the “pay at the property” or “pay later” option, so I am charged for it closer to the date of my trip. I will then favorite some Barcelona hotels to book the following month (aka on my next credit card statement).

• For my day-by-day itineraries for Amsterdam, Paris, and Barcelona, click the links above!

I pay very close attention to when I will get billed for things based on the closing date of my credit card statement. If my statement closes on the 15th of each month and today is the 13th, I can book one hotel now and another hotel in a few days, because it will go on the next credit card statement.

This way, I am not paying $1500 at once.

I also never choose the “pay later” option for all 3 hotels, because then I will have to pay for all 3 accommodations on top of paying for everything else during my trip…food, activities, etc. When I’m on my trip, I want to feel like I can “treat myself” to the fullest extent…because isn’t that what we do on vacation?!

For my top hotel tips, check out The Best Apps to Find Cheap Hotel Deals and How I Use Google Maps to Find Cheap Hotel Deals

As you can imagine, this gets especially important when you’re booking flights on top of hotels. I talk about booking flights with points below, but if you can’t do that (don’t have enough points, etc), I would follow the same principle of spacing out payments.

3. Explore All Accommodation Types

Although I prefer staying in hotels, I have also been known to stay in AirBNBs or even hostels if I have to in order to save money. I try to limit my hostel experiences to one or two days if I’m going to be somewhere fast, because I’m in my 30’s and can’t run off of no sleep like I used to. But I’ve actually come across some hostels where you have a room all to yourself – in fact, THIS HOSTEL in Amsterdam (yes, it is actually named THIS HOSTEL) is one of the coolest and most unique places I’ve stayed.

4. Know How to Find Cheap Flights

I’ll admit, I’ve become a bit of a hustler on the airline apps when it comes to finding a good deal. I’ll also admit that sometimes, I have better luck than others. Regardless, these are the things I do when I want to find a cheap flight:

• I book flights as far in advance as I can. Flight prices tend to increase as the date of the trip gets closer.
• I take advantage of the “Anywhere” feature in Google Flights to search for cheap flights around the world. This is how I “let my destination choose me.”
• If I know where I want to go, I use Skyscanner to compare flight prices worldwide. Google Flights has this feature too, but Skyscanner pulls in more airlines. Try it below!

• Many travel apps will color-code days green, yellow/orange, or red based on how expensive the flight prices are. I always try to fly out on “green” days if I can.
• If flight prices seem high, I go on Hopper and add the flight to my Watch List. Hopper has an algorithm that predicts if you should “wait” or “book now,” and can send you notifications when the price drops.
• I search one-way flights if a round-trip flight is too expensive. Sometimes it’s cheaper to fly to a destination on one airline and home on another.

Like I said…I’m a hustler. But it’s worth it when I find a cheap flight.

While we’re here, I also want to say that I don’t discriminate about airlines that I book through. In other words, I will fly economy class on Spirit just as fast as I will fly first class on Emirates. I look at my flight as something that will get me from A to B. The 3 biggest factors I look at when booking flights are the prices, the departure/arrival times, and the amount of layovers.

5. Use Points to Book Flights

Remember how I said earlier to invest in a good travel credit card? I almost always use my credit card points on flights. This is because I can transfer them to different airlines or hotels to get an even better deal instead of booking directly through the card’s travel portal.

Transferring to a partner airline or hotel will always get you better value for your points. For example, if I had 100,000 Chase Sapphire Reserve points and wanted to use them to book a flight, this would equate to a value of $1,500 if I booked through Chase’s travel portal directly. But if I booked through an affiliate partner, I could get up to $2,200 in value for my points.¹

TBH, points transfer to airlines can get complicated, and I am by no means an expert (yet). When I am, I will teach you my ways. This is what I’ve learned so far:

• There are 3 different airline alliances: Star Alliance, SkyTeam, and oneworld. You can use points from one airline’s loyalty program to book flights on partner airlines in the same alliance.
• Different credit cards have different “partner” airlines that you can transfer to in order to get the most bang for your buck…I mean, points. For example, Chase is a partner with United.
• Once you transfer credit card points to an airline, you cannot transfer them back. If the airline’s website doesn’t tell me how many points I need to transfer in order to book my flight, I will call them and ask.
• Every so often, certain credit cards will have “bonus transfer” periods that allow you redeem even less points for epic flights.
• You get a MUCH better value if you transfer points to a “reward flight” vs. doing a “cash flight redemption” using points.

Just as I like to be honest with my readers, I also like to give credit where credit is due. NerdWallet.com is a great resource to teach you about booking travel with points. This post about using Chase travel reward points is a great example, but there are many others.

¹ – according to NerdWallet.com; Keep in mind, points/prices can fluctuate over time

6. Rent New Clothes

All my Aesthetic Travelers out there know that having new outfits for trips is more of a “need” than a “want.” However, the price of clothes in today’s economy doesn’t exactly help you budget for your trip.

One of my favorite life hacks is to rent clothes for trips and mail them back when I’m done. My favorite website to do this is FashionPass.com because the clothes are cute, trendy, and versatile. You can find outfits for all seasons, destinations, and events. I rented the dresses in the photos below for my trip to the Amalfi Coast, and they were among my favorite Fashion Pass finds.

7. Be Cognizant About Saving (and Making!) Money

One of the best things a past mentor in college taught me was to create a savings account and have a set amount of money deposited from my paycheck into it each week. I did this as soon as I got my first job, and it has been instrumental in my ability to travel. If I am planning to go on a trip that will be more expensive (i.e., most international trips), I will often use money from this account if I need to in order to pay for some things. That way, I am not constantly depleting my bank account.

I realize this is not always feasible for some people, and some people need their savings for things like childcare, home improvements, etc. I am not married and do not have children, so for me, this savings account is used for travel and the occasional “oh shit!” moment if I happen to need extra money.

Another great way to afford to travel more often is to create multiple steams of income. There’s been a lot of hype around this recently. Anything that you can do…bartending once a week, dog walking, freelancing a specific talent…can help. For me, I have income from my everyday job along with my travel blog. I also sell things on Poshmark and LTK (@ginaonaplane). All of these things contribute to how I am able to travel.

Lastly, I am also cognizant about saving money at home if I know that I have a big trip coming up. I won’t get my nails done as often, I won’t buy things that I want but don’t need, and I will figure out ways to make my groceries go further so I am not eating out as much.

8. Balance Weekend Trips vs. Longer Vacations

One of the ways I am able to take a trip once a month or every other month is because many of my trips are weekend trips. Weekend trips are obviously much less expensive than if I’m going overseas for a week or more, which is why I can afford to take them more often. I will often save my credit card points for my longer vacations and save/budget my regular income for smaller ones.

I have also been blessed with friends that live in New York, Nashville, and other cities that I like to visit. Often times, I will stay with them during my weekend trips, which saves me money on hotels. Getting to see your friends AND save money is a win-win!

9. Use the Go City Pass to Save on Attractions

Let’s face it: Exploring a new city is SO fun, but it’s also SO expensive. If I’m visiting somewhere and there are a lot of buildings, museums, tours, etc. I want to check off, I’ll look and see if my destination has a Go City Pass. Sometimes, I can save money this way if a lot of the things I want to do are included.

Go City has different passes for various cities that allow you to explore a bunch of top attractions for a fixed price. I especially liked it for Paris – in fact, you can read about it in my post, Free Champagne(!)…And Other Reasons You Need the Paris Pass.

To see passes they offer in other cities around the world, click here to view all Go City Destinations.

A Word About Working Overseas

Another way I know some people travel often is by finding jobs overseas and living there for an extended period of time. Many of these jobs revolve around teaching English, pursuing an internship or volunteer program, etc. I do not have any experience with this whatsoever, and therefore do not feel qualified to write in detail about it. But it IS possible to do.

As you can imagine, a lot of these jobs do not pay overly well, or we’d all be out here getting our visas. Keep in mind, some countries are also more affordable to live in than others. Regardless, I wanted to put this on your radar as something to look into if you’re feeling daring, or maybe just having a midlife crisis and want to get out of here. 😉