This post is specific to JetBlue’s flight schedule, but it is applicable to any airline pass where you have a fixed amount of time, but an unlimited number of segments. You would want to modify this strategy somewhat if you purchase an around the world plane ticket that allows a fixed number of segments of the period of a year. Your goal in both cases, however, is to maximize the number of places that you want to go to that would normally be very expensive.

Step 1: Figure Out What Your Options Are

I first downloaded the PDF of JetBlue’s electronic timetable (see this page for all of the formats). I read all the destinations and thought about which might be interesting to go to. It is okay if this list is pretty long. For me this list was:

How did I come up with these options? If I either didn’t know anything about the city, or if I knew of a landmark in the city it made the list. It is better to be inclusive rather than exclusive at this point.

Step 2: List the Potential Origins

With your list of exciting destinations (okay, so Nantucket probably isn’t too exciting) you now need to figure out what cities get you there. List all of the airports that have connecting flights to your destination. You will find the information in the timetable:

Add this to another column in your list:

Step 3: Create Segments

You will notice that many of these destinations go back to the same city. This is because airlines use a hub and spoke model. Hub and spoke makes this step easier to figure out, but it means more flight segments since you cannot fly from one destination to another without going back to the hub.

For JetBlue, it appears that the primary hubs (where most flights originate) for the destinations I am interested in are: New York (JFK), Orlando (MCO) and Long Beach (LGB). This means I have to come back to these cities before moving on to the next destination. Because of JetBlue’s one day rule for the pass (one flight per city per day), you want to minimize the moves between the hub cities, otherwise you would lose an extra day.

So, to create segments, group the cities that have potentially the same hub city:

… and the list goes on. It is also helpful to note if the flights are daily (most on JetBlue are).

Several places where I am able to take advantage of connections, without going back to the hub city are Washington, DC (IAD) to San Juan (SJU) [Saturdays only] and San Juan (SJU) to Santo Domingo (SDQ). Also, I can fit Las Vegas in by adding it on the way back from Long Beach (a hub) to New York (another hub)

Step 4: Combine your segments into a list

Now that you have your list of connections, you need to put them in a logical order where the hubs match up. For me this was:

We hoped to come back to Houston to visit family and friends in the middle of the month, which is why you notice that unusual excursion.

This is a perfectly valid itinerary that you could accomplish with the All You Can Jet pass. It would mean 23 consecutive days of travel, but you could do it.

Step 5: Decide what you really want

If your goal is to make it to as many cities as possible, by all means stop here and book. However we decided that we wanted to spend some real time in some of our more exotic destinations. I am working on a video project for TheStrategyBlog, conducting video interviews entrepreneurs and business owners around the world to gain strategy insights, and this would allow me more time for interviews.

If we spend three to four non-travel days in some destinations, we go way over the 30 days of the pass, so some destinations have to go (no pun intended). The strategy here is to eliminate destinations that you would be able to affordably visit without the pass and other destinations that don’t interest you as much.

With that in mind, I eliminated the entire west coast portion of the itinerary, plus the side trip back to Houston and also Burlington and San Juan.

This leaves:

Finally, considering the pace of the trip I decided that Bermuda would be a better fit to provide some R&R at the end of the trip, so I just reversed the itinerary.

Step 6: Pick Your Flights

For this step I moved from the PDF timetable to the desktop application. I did this because you can put in the date of your travel and it shows exactly what flights are available, rather than having to translate numbers on the timetable.

This step is technically not necessary, but your booking agent will thank you and you will be sure to get the more desirable flight times.

Step 7: Book It

Call 1-800-JETBLUE (538-2583), prompt 4 and book your itinerary! Right now! Don’t hesitate!!