The Art of the Free Upgrade: My Guide to 3 Years of Comfort Without Paying For It

I'm finally back in Southeast Asia, and after a half-around-the-world flight, my head is still spinning a little. But it got me thinking: 3 years of full-time travel is also 3 years of perfecting how to travel not just cheaply, but comfortably.

Let’s be honest: the whole "digital nomad" thing looks glamorous, but when you're on a real budget, you have to fight for every inch of comfort and every dollar saved. You deserve a little bit of luxury on a backpacker's budget, right?

Here are my favorite tips for scoring premium experiences without paying premium prices. It all comes down to a little patience, a good smile, and knowing how to ask.

Tip 1: The Window Seat Free Upgrade

You know the deal on a long-haul flight: a window seat is essential! Having that wall to lean against makes sleeping so much easier than in the middle seat (hell on earth) or the aisle (too close to the foot traffic). Airlines know this, so they charge a ridiculous amount for it.

Here’s the thing: I never pay. My success rate is about 9 out of 10 times.

My Method:

1. Check-in Online (But Don't Pay): When you do your online check-in, just confirm whatever awful seat the system assigns you. Don't pay for a change.

   
   

2. Arrive Early & Smile: Get to the airport early (three hours is ideal). After they check your bags, look the agent right in the eye, smile genuinely, and ask politely: "Hi, I was wondering if I could get a window seat, please?"

   
   

3. The Pro Move (Emergency Exit Row): The ultimate win is the emergency exit row. That extra legroom feels like first class for your knees! I swear, after three years of doing this, I almost know the safety procedures by heart 😉. They often release these seats for free at the counter, so it's always worth asking about those, too.

   
   

   The Secret? Airline staff don't get a bonus whether you pay or not. Just be nice, maybe crack a small joke. You'd be surprised how many people are willing to help someone friendly.

My usual seat :)

Tip 2: The Art of Negotiation for Long Stays

When you travel full-time, the euros and dollars saved on accommodation really add up. I've learned that almost every price is negotiable, especially for longer stays (a month or more). If you prefer Airbnb over hotels, here’s how to try and snag that stylish loft or rooftop apartment at a discount:

1. Do Your Homework: Make a shortlist of Airbnbs that meet your criteria (full kitchen, good neighborhood, etc.).

   
   

2. Pitch Yourself, Not Just the Price: Prepare a short, polite message template, but focus on why you are the ideal guest. Mention that a long stay means less cleaning and hassle for them. Frame yourself as a stable, respectful guest (quiet remote worker, not a party tourist).

   
   

3. Leverage Offers: Send your message to multiple hosts simultaneously. If Host A gives you a discount, you can use that offer as leverage with Host B (the one you actually prefer) to try and get a similar price.

   
   

4. Honesty Moment: I've tried this negotiation tip several times, and honestly, it doesn't always work. Sometimes hosts just aren't flexible for month-long bookings. Maybe I still need to work on my pitch to sound more convincing! 😉

My $15 p/n hotel room in Ho Chi Minh City, Vietnam

Tip 3: The Secret to Finding the Actual Lowest Price

Even with negotiation, sometimes Airbnb prices are just crazy high. That’s why I always compare across multiple platforms. There are two great ways to do this:

• Option A: The Chrome Extension (The Quick Win): I love this because it's fast. You can download a free Chrome extension called TripChipper. While you're browsing hotel sites (I use Booking.com a lot), the extension automatically flags when the same room is cheaper on another site like Agoda or Expedia. It saves me SO much time! Instead of opening 50 tabs to compare, you get the answer at a glance. Just remember to check the fine print – sometimes the "cheaper" price doesn't include free cancellation or breakfast.

  
  

• Option B: The Google Maps Deep Dive (My Favorite Way): This is the most reliable way to compare everything and get the real truth. When I find a hotel I like on one platform, I just search for the hotel's name on Google Maps. Google Maps pulls in the prices from all the different booking platforms in one convenient spot. But here’s the real value: you get to see all the unfiltered reviews right there. Knowing the truth about the plumbing or the noise level before you commit to a month-long stay is priceless.

Tip 4: Sleep for Free (And Make Furry Friends)

If you're flexible, want to save serious money, and love animals—this tip is a game changer.

The method I use to live in some of the most expensive cities in the world (like London or Sydney) without paying a dime in rent is called House Sitting.

The concept is simple: I take care of someone's home and pets while they go on vacation, and in return, I get a whole house to myself.

I use the Trusted House Sitters app, and it works like magic: I get accepted to 99% of the sits I apply for.

The win here is double:

1. Massive Savings: Weeks or months of rent money stay in my pocket.

2. Authentic Local Experience: I don't stay in a touristy hotel; I live in a real neighborhood. I get to know the neighbors, the local grocery store, and the dog park. The owners always leave me a list of their absolute best local recommendations (restaurants, cafes)—hidden gems that tourists never find.

If you're an animal lover, this is the ultimate Win-Win.

👉 Join Trusted House Sitters Here

The most handsome cat I sitted, Phnom Penh, Cambodia

Tip 5: The Carry-On Shuffle (and the Pillow Trick)

If you're flying budget airlines (which I try to avoid, but sometimes you gotta do what you gotta do), paying for a checked bag feels like throwing your money away. It completely defeats the purpose of the cheap ticket.

My Method:

1. The Layer Up: If your carry-on is slightly overweight, don't pay! Instead, wear your heaviest items – the boots, the bulky sweater, the jacket – even if you're flying to 30°C Bangkok. Yes, you'll be hot for 15 minutes boarding, but your bag is instantly lighter, and you save $70. Totally worth it.

   
   

2. The Power of the "Personal Item": Know the airline's rules for the "personal item" – that smaller bag you keep by your feet. I always use a large-ish, soft backpack that technically might be slightly over the dimensions, but looks small and squishable. If it fits under the seat in front of you, they rarely check it. If you can fit two days' worth of clothes in your personal item, you've won. There's also a cool trick with a travel neck pillow cover you can stuff with clothes.

   
   

   I bought one online and managed to stuff an extra kilo or two of small items inside. Honestly, the pillow itself wasn't comfortable for me at all, but if weight is your main issue, it's a creative solution. I've since switched to a different pillow that is an absolute dream – this is the travel pillow I use now.

   
   

   I sleep through entire long-haul flights (yes, even 10+ hours!) and wake up with zero neck pain. Worth every penny! It's a bit of a game, honestly. I've perfected the look of someone completely unaware that their backpack might be slightly too big 😉.

My Travel Pillow 😍

Tip 6: When To Book Your Flight (Timing is Everything)

Everyone talks about when to fly, but the real money-saver is knowing when to book. Flight prices are insane, changing every few hours, and it’s exhausting trying to catch the lowest fare.

My Method:

After years of tracking this, while it's not a written rule, it's a very reliable pattern: Never book flights on a Tuesday or Wednesday. 

Airlines tend to raise prices over the weekend (when people are home planning), and they release their best new deals on Thursdays and Fridays.

Booking early in the week almost guarantees you're catching a price that's still inflated from the weekend push. I always aim to actually hit "book" on a Thursday evening or Friday morning. That way, you catch the deals, and you still have the weekend to finalize the rest of your trip plans.

Tip 6: Zero Tolerance for Foreign Transaction Fees (A Nomad Must)

This is less of a clever trick and more of a mandatory budget discipline. When you're traveling full-time, those little bank fees – the "foreign transaction fees" – add up to hundreds, even thousands, of dollars per year. It's literally paying your bank just to spend your own money. No thanks.

My Method:

Before you leave your home country for any extended period, it's essential to get a bank account or credit card that offers zero foreign transaction fees and zero ATM withdrawal fees (or at least reimburses them). I've personally used Wise for years. It's a multi-currency account that allows me to hold money in different currencies, convert between them at competitive rates, and withdraw cash almost anywhere in the world with minimal fees.

When I'm moving countries constantly, I need a solution I can trust everywhere. This is non-negotiable. It gives you the freedom to use your money anywhere, anytime, without doing that mental calculation of "Do I really want that street food, or will they charge me $5 just to withdraw the cash?" It's a fundamental step towards true financial freedom on the road.

My Wise travel stamps

It’s these tiny habits – being kind, showing your value, doing your research – that allow you to build a life where you feel comfortable and confident, even when you're constantly moving. They're the small hinges that swing open big doors to experiences you might have thought were out of reach.

Some of the links in this post include affiliate links — if you choose to purchase through my link, it won’t cost you anything extra, but it helps me keep writing and sharing this journey with you.

Which of these tips are you going to try on your next trip? Let me know in the comments below! 👇