The Two Wonderers’ Flight Secrets: Travel 10X a Year with a Full-Time Job!

Hey everyone!

If you’ve been following our journey, you know we made the leap from the traditional 9-to-6 to a life with more freedom and flexibility. But it wasn’t always this way! There was a time, not too long ago, when we were both navigating the world of corporate jobs, complete with the standard 18 days of annual leave. Even with those constraints, we consistently managed to squeeze in around 10 overseas trips a year!

How did we do it? The answer lies largely in becoming absolute ninjas when it comes to finding amazing deals on flights. Living in a travel hub like Singapore certainly helped, but the principles we used can be applied no matter where you’re based.

So, whether you’re still dreaming of more getaways, or you’re simply looking to save money on your next trip, we’re here to share our top tips and tricks for snagging incredible flight deals. Get ready to unlock a whole new level of travel possibilities!


Our 2024 Flight Haul: More Trips, Less Spend!

Here’s a look at some of the trips we managed to take, even with limited leave, and what our flights actually cost us in 2024. This shows you just how much is possible when you know how to hunt for deals! (the flight costs below are per pax)

  • January: Tokyo (AirJapan) – S$493.62
  • February: Seoul (Scoot) – S$403.85
  • March: Kota Kinabalu (AirAsia) – S$164.00
  • April: Taipei (Scoot) – S$258.89
  • May: Osaka (Scoot) – S$360.64
  • June: Bali (Scoot) – S$244.70
  • August: Christchurch (Singapore Airlines) – S$1248.90
  • September: Penang (AirAsia) – S$77.50
  • October: Koh Samui (Scoot) – S$374.04
  • November: Haikou (Jetstar) – S$232.73

Our Go-To Tool: Mastering Google Flights

Our absolute secret weapon for finding cheap flights is Google Flights. It’s incredibly powerful if you know how to use its filters and features. Our strategy revolves around a few key principles:

  • Maximizing Weekends & Public Holidays (Our Core Strategy!): This is our #1 secret to squeezing in so many trips! We leverage every weekend and public holiday possible, whether it’s for:
    • Short Getaways (3-4 days): Quick trips to nearby countries, often just requiring a Friday off or spanning a long weekend.
    • Longer Adventures (Around 9 days): These involve flying out on a Friday night and returning the following Sunday night, utilizing two weekends and typically only requiring about 4 to 5 days of actual leave. We always strategically align these with public holidays whenever possible to stretch our time even further!
    • Our dates are usually semi-flexible, which is key to uncovering better deals than rigid dates.
  • The “Explore Anywhere” Strategy (Finding Your Next Destination!): Most of the time, we don’t have a fixed destination in mind. This is where Google Flights truly shines and is our starting point!
    • We simply search from our departure city to ‘Anywhere’ and input our tentative travel dates (often around the middle of the month, as Kelly is usually busier at the start/end due to her job nature). The results instantly show us the cheapest deals across various destinations on a map, giving us incredible options to consider.
  • Smart Filtering for Optimal Results: Once we have our initial results from the ‘Anywhere’ search, we refine them to match our specific needs:
    • Outbound and Inbound Flight Time Filters: We adjust these to find times that work best for our schedules, especially for those desired Friday night departures or Sunday night returns.
    • Non-stop only Filter: While we’re open to layovers for really great deals, starting with non-stop helps us see the most direct (and often most efficient) options first.
  • Price Alert Perfection: Once we’ve shortlisted some flights or routes that look promising, we always set up a price alert notification. Google Flights will then send an email whenever the price changes, allowing us to pounce when it drops!

Flight Search Engines Compared

While Google Flights is our primary tool, no single search engine catches every deal, and we believe in checking multiple sources to ensure we’re getting the best value. All three of these platforms are excellent, each with its own strengths:

  • Google Flights stands out for its incredibly fast and user-friendly interface. Its “Explore” map is unparalleled for discovering new destinations when your dates are flexible, and its price tracking and prediction features are invaluable for timing your booking perfectly.
  • Skyscanner is a powerhouse for casting a wide net. It searches a vast number of airlines and online travel agencies (OTAs), often unearthing deals that might not appear elsewhere. Its “Everywhere” search is also fantastic for destination flexibility, similar to Google Flight’s “Anywhere” search.
  • Trip.com is a convenient one-stop shop, not just for flights but also hotels and other travel needs. We often find competitive fares here, and a major bonus for us is the regular ShopBack cashback available through their platform, especially during those big monthly sale dates.

Our Verdict: We start with Google Flights to get a broad overview and find initial options. Then, we cross-reference with Skyscanner for its extensive search capabilities, and always check Trip.com to compare prices and capitalize on those sweet cashback opportunities. This multi-platform approach ensures we’re consistently snagging the best deals out there!

Pro Tip: If you’re not already using ShopBack, it’s a game-changer for getting cashback on your online purchases, including flights via Trip.com. It’s essentially free money back on spending you’d do anyway!

  • Keep an eye out for their special promotions:
    • The 21st of every month often brings bonus cashback deals for Trip.com on ShopBack.
    • Major online sale dates like 6.6, 7.7, 8.8, 9.9, 10.10, 11.11, 12.12 are also prime times for boosted cashback rates.

If you don’t already have ShopBack, you’re in for a treat! Sign up using this link and get $5 Cashback when you shop online with ShopBack!


Maximizing Your Returns: Cashback Cards vs. Travel Currency Cards

We’re big advocates for being “cashback chasers,” making every dollar count. However, when it comes to flights, there aren’t as many dedicated high-cashback credit cards specifically for airline spend.

For our flight bookings, we typically rely on cards that offer general online spend cashback:

  • SC Spree Credit Card: This card offers a decent 2% cashback on online spend.
  • HSBC Advance Credit Card: We also use this, which provides 2.5% cashback on online spend, provided we meet the minimum spend requirement of S$2,000 in a month.

Important Note on Cashback Caps: Most online spend credit cards come with monthly cashback caps. Always check your card’s terms and conditions to understand these limits and ensure you’re maximizing your returns without hitting the cap on larger purchases like flights.

Beyond Cashback: The Power of Travel Currency Cards

While a good cashback card is useful, sometimes the best savings come from avoiding foreign currency conversion fees altogether. When booking flights, especially for international routes, it can be more cost-effective to pay in the local currency of the flight’s origin.

This is where travel currency cards shine! Instead of your regular credit card’s foreign transaction fees (typically 2-3% on top of the exchange rate), these cards offer competitive real-time exchange rates and no transaction fees on overseas spending. You can load funds and convert them when rates are favorable, or simply let the card convert on the spot.

  • How it Works: When booking online, check if you can select the currency of the country where the airline is based, or the currency of your destination if it’s an option. Then use your travel currency card to pay.
  • Popular Options:
    • Cards like YouTrip are designed for seamless multi-currency payments, offering excellent real-time exchange rates.
    • The Trust Bank Cashback Card (different from the usual Trust Bank NTUC Linkcard) is another strong contender. While its exchange rates might be slightly less competitive than YouTrip’s for direct currency conversion, the added 1% cashback on foreign currency transactions can often make it the overall better choice for your total savings. Both make excellent choices for flight bookings and spending abroad.

If you don’t already have the YouTrip or Trust Bank Cashback Card, do consider signing up with our referral codes below!


Want Us to Plan Your Next Adventure?

Mastering flight deals and crafting itineraries takes time and practice. If you’re keen to maximize your limited leave or simply want someone to help you find those incredible flight deals and build a custom itinerary, we can help!

Kelly, with her knack for detailed planning and finding hidden gems, offers customized travel planning and booking services. Do check out her Fiverr profile!

Or, feel free to Contact Us Directly with your travel dreams and we’ll get back to you!


We hope these insights into our flight-finding strategy empower you to start planning your own incredible, affordable adventures! With a little patience and these tools, you’ll be amazed at how much you can save on flights, leaving you with more budget to truly enjoy and experience your destination. Happy hunting!