How We Fund Our Travels

Introduction

One of the most common questions we receive from readers of Our Travel Journey is straightforward yet complex: “How do you afford to travel so frequently?” While careful budgeting and prioritization certainly play roles, a significant component of our travel strategy involves leveraging credit card points, loyalty programs, and airline miles. This approach has allowed us to experience premium accommodations and business-class flights that would otherwise be financially prohibitive.

This post outlines our systematic approach to accumulating and utilizing travel rewards, which has subsidized approximately 60% of our total travel expenses over the past three years.

The Foundation: Strategic Credit Card Selection

Our points strategy begins with a carefully curated portfolio of credit cards. Rather than applying indiscriminately for every available offer, we select cards based on three primary criteria:

1. Substantial welcome bonuses that provide immediate value
2. Earning structures that align with our spending patterns
3. Transfer partnerships with our preferred airlines and hotel groups

As Canadians, we face a more limited selection of credit card options compared to the U.S. market. Nevertheless, we’ve found valuable opportunities with several financial institutions. Our core portfolio currently includes cards from:

• American Express Canada – Offering some of the most valuable transferable points in the Canadian market
• TD Bank – Particularly for their Aeroplan co-branded cards
• Bank of Nova Scotia (Scotiabank) – For their Scene+ program with travel redemption options
• CIBC – For additional Aeroplan earning opportunities and unique benefits

This combination allows us to maximize point accumulation across spending categories while maintaining a manageable annual fee structure with benefits that offset most costs.

Point Accumulation: Systematic Approaches

Beyond ordinary spending, we employ several methodical strategies to accelerate point accumulation:

Strategic Welcome Bonus Timing

We time new card applications to coincide with major anticipated expenses, ensuring we can meet minimum spending requirements organically. For instance, when planning our kitchen renovation last year, we applied for a new card with a substantial welcome bonus, which ultimately funded our accommodations in Southeast Asia.

Category Optimization

Each purchase is made with careful consideration of which card will maximize returns. This practice becomes second nature over time and significantly impacts annual point accumulation. We maintain a simple reference document with category optimizations for quick decision-making.

Periodic Spending Analysis

Quarterly, we analyze our spending patterns and adjust our card usage strategy accordingly. This ensures we capitalize on changing bonus categories and identify any opportunities for improved optimization.

Business Expenses

For entrepreneurs or those with business expenses, business credit cards often provide enhanced earning opportunities. We have strategically channeled appropriate business expenses through dedicated business cards, substantially increasing our point accumulation.

Airline Miles: Beyond Credit Card Transfers

While credit card points form the foundation of our strategy, we also focus on airline-specific opportunities:

Strategic Airline Selection

We concentrate our flights with airline alliances rather than booking the absolute cheapest fare across different carriers. This approach, while occasionally resulting in slightly higher immediate costs, produces substantial long-term savings through status benefits and mileage accumulation.

Mileage Earning Optimization

Not all fare classes earn miles equally. We carefully evaluate the mileage earning potential of different fare options, sometimes selecting a moderately priced ticket with superior mileage earning over the absolute lowest fare.

Promotional Opportunities

Airlines frequently offer bonus mile promotions, particularly on new or underperforming routes. We actively monitor these opportunities and have occasionally adjusted travel plans to capitalize on exceptional mileage offers.

Hotel Strategies: Maximizing Value

Our approach to hotel loyalty programs focuses primarily on Marriott Bonvoy, which has become our preferred hotel group due to its:

• Extensive global footprint with properties across various price points and styles
• Robust earning opportunities through both stays and credit card spending
• Valuable transfer partnerships allowing points transfer to numerous airlines
• Status benefits that meaningfully enhance our stays

We’ve found that concentrating our hotel stays within the Marriott ecosystem allows us to accumulate points more rapidly and achieve elite status levels that provide substantial benefits like room upgrades, late checkout, and complimentary breakfast. In the Canadian context, where point-earning opportunities can be more limited than in the U.S., this focused approach has proven particularly effective.

Status Matching and Challenges

When changing preferred hotel chains, we utilize status match programs to immediately secure elite benefits rather than starting from zero. This approach has provided us with suite upgrades, complimentary breakfasts, and late checkouts that significantly enhance value.

Fourth Night Free Benefits

Select credit cards offer fourth-night-free benefits on hotel stays. For longer stays, we strategically book through these programs, effectively receiving a 25% discount on four-night reservations.

Point Redemption Optimization

Hotel points often deliver maximum value during peak periods when cash rates are inflated. We reserve our hotel points for high-demand locations and seasons, while using cash for more affordable destinations and off-peak travel.

Case Study: Our Japan Trip

To illustrate the practical application of these strategies, consider our recent two-week trip to Japan:

• Business-class flights: Secured through a combination of credit card point transfers and airline miles.
• Luxury hotel accommodations in Kyoto: Was able to use a free night certificate at Hotel The Mitsui Kyoto
• Ryokan experience in Beppu: This was paid for by using TD Points to offset the cost 

Potential Pitfalls and How to Avoid Them

This strategy delivers substantial benefits but requires discipline and organization:

Interest Avoidance

The fundamental rule of travel rewards maximization is avoiding interest charges, which rapidly erode any benefits gained through points. We pay all balances in full monthly without exception.

Annual Fee Evaluation

Each card in our portfolio undergoes an annual assessment to determine if its benefits justify the fee. Cards that no longer provide adequate value are either downgraded to no-annual-fee versions or closed.

Credit Score Management

Multiple credit cards, when managed properly, can positively impact credit scores through increased available credit and payment history. We monitor our credit scores monthly and maintain excellent credit profiles despite having multiple accounts.

Organizational Systems

Tracking multiple cards, payment dates, and bonus categories requires organization. We use a digital spreadsheet to monitor payment due dates, annual fee renewal dates, and current promotion categories.

Canadian Market Limitations

It’s important to acknowledge that the Canadian credit card market offers fewer options than the U.S. market, with generally lower sign-up bonuses and fewer category multipliers. This means Canadian travelers often need to be more strategic and patient in their points accumulation journey. Despite these limitations, we’ve found the effort worthwhile for the travel experiences it enables.

Getting Started: Recommendations for Beginners

For readers interested in implementing similar strategies, we recommend a gradual approach:

1. Begin with a single well-rounded travel card offering transferable points
2. Master the fundamentals of point redemption for maximum value
3. Ensure absolute comfort with consistently paying balances in full
4. Create appropriate tracking systems before expanding your portfolio
5. Gradually add specialized cards aligned with your spending patterns and travel preferences

Conclusion

Strategic credit card and loyalty program management has transformed our travel experiences, enabling us to visit more destinations in greater comfort than would otherwise be possible. While this approach requires some initial learning and ongoing management, the return on investment has been substantial.

We view points and miles not as free travel, but as a significantly discounted mechanism for expanding and enhancing our travel opportunities. With disciplined implementation of these strategies, we’ve been able to experience destinations and accommodations that would otherwise remain aspirational.

The Canadian rewards landscape presents unique challenges, with fewer card options and generally lower bonuses compared to the U.S. market. However, by focusing on high-value opportunities, particularly with American Express, TD, Scotia, and CIBC products, and concentrating our hotel stays primarily within the Marriott ecosystem, we’ve developed a system that works effectively within these constraints.

For those willing to invest the effort in understanding reward programs and maintaining organizational discipline, the travel subsidy potential is considerable. We encourage you to begin with modest implementations of these strategies and gradually expand as you become comfortable with the systems and processes involved.