An investor from Indonesia will be visiting for two days and wants to see five locations across three states. The Augusta National Golf Club calls with an open foursome tomorrow morning, just before the U.S. Open tees off. The perfect house out east overlaps with Camp Faraway for the kids, a nine-hour drive into Pennsylvania, and there’s only one day to visit. The decision to fly privately is often clear and memorable, but the timing of when to upgrade can be less obvious.
For many, the first experience is a simple charter flight: someone has a connection, and options arrive quickly in your inbox. After a few flights, preferences take shape: newer aircraft, a flat floor, a more reputable operator. Mix in some great trips, a few challenging ones, maybe a different broker, and before long, a 25-hour jet card seems like the natural next step.
What comes after a 25-hour card? Often, a 50-hour card or a fractional share. These typically bring lower hourly costs, better response times, and fewer restrictions. Over time, though, limitations emerge: 10 to 30 days a year with blackout periods, extra fees, or constrained service. Travel needs continue to grow, and soon usage climbs to 150 to 200 hours per year.
At that point, the question arises: Does it get better? It often does. Whole aircraft ownership joins the conversation at 100 hours of annual travel and makes more sense for those who fly 150 hours or more and want a higher degree of control and customization.
Here are some things to consider:
Bonus depreciation. The return of 100% bonus depreciation for new and preowned aircraft will motivate some purchasers. Some will pursue bonus depreciation and settle on straight line, and others will buy their aircraft personally. Tax benefits are meaningful, but not always the deciding factor.
High-demand days. Frequent travel on peak days often pushes flyers to upgrade sooner. Programs may impose stricter notice periods or departure flexibility, substitute smaller or third-party aircraft, or apply surcharges to manage demand. By contrast, aircraft owners get their aircraft, their crew, and their departure time even on the busiest days. When not flying, many owners also rent their aircraft back to hours programs at favorable terms. Just be sure to work with a good advisor so you meet program standards and can maximize your return.
The 80/20 rule. Another consideration: will one aircraft meet 80% of annual needs, and how do you address the other 20% of your flights? For some, an occasional fuel stop on a cross-country trip is no issue. For others, booking a large-cabin aircraft—or borrowing a friend’s—works well when it’s an annual summer trip to Europe.
Hours anxiety. High hourly costs can create hesitation and anxiety. Six hours at $12,000 per hour adds up quickly, and even well-resourced travelers notice it. For some, this “hours anxiety” is what drives the move to full aircraft ownership, where a larger upfront cost lowers the ongoing hourly rate and provides flexibility when travel exceeds expectations.
Flying privately—whether it is charter, fractional, or full ownership—should be one of life’s great joys. The timing of an upgrade varies, but it usually comes down to usage and one simple question: Are you happy? Happy with the service, the terms, and the aircraft?
If so, stay the course. If not, it may be time to explore other options with a trusted, independent advisor. After all, upgrading isn’t always about flying more; it’s about flying smarter and flying better.