How To Book an Awesome Travel Itinerary

You may have heard about JetBlue’s “All You Can Jet” promotion. You may have thought, “I could do that, but I don’t know where I’d go.” You are not thinking *strategically*! As you may know from reading Chris Guillebeau’s blog, Art of Nonconformity, the world is full of places to go (and he has been to most of them!).

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:

Aguadilla, Puerto Rico BQN
Aruba AUA
Austin, TX AUS
Bermuda BDA
Bogota, Colombia BOG
Burlington, VT BTV
Cancun, Mexico CUN
Chicago, IL ORD
Houston, TX HOU
Las Vegas, NV LAS
Montego Bay, Jamaica MBJ
Nantucket, MA ACK
Nassau, Bahamas NAS
New Orleans, LA MSY
Portland, OR PDX
Puerto Plata, Dominican Republic POP
Saint Maarten, Netherlands Antilles SXM
Salt Lake City, UT SLC
San Francisco, CA SFO
San Jose, Costa Rica SJO
San Juan, Puerto Rico SJU
Santiago, Dominican Republic STI
Santo Domingo, Dominican Republic SDQ
Seattle, WA SEA
Washington, DC IAD

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:

Destination Possible Origins
Aguadilla, Puerto Rico BQN JFK, MCO
Aruba AUA JFK , BOS
Austin, TX AUS BOS , FLL , LGB , JFK , MCO , SFO
Bermuda BDA BOS , JFK
Bogota, Colombia BOG MCO
Burlington, VT BTV JFK, MCO
Cancun, Mexico CUN BOS , FLL , JFK , MCO, TPA, IAD
Chicago, IL ORD BOS, LGB, JFK
Houston, TX HOU JFK
Las Vegas, NV LAS BOS, BUR, LGB, JFK
Montego Bay, Jamaica MBJ JFK
Nantucket, MA ACK JFK
Nassau, Bahamas NAS FLL, JFK, MCO
New Orleans MSY BOS, JFK
Portland, OR PDX LGB, JFK
Puerto Plata, Dominican Republic POP JFK
Saint Maarten, Netherlands Antilles SXM BOS, JFK
Salt Lake City, UT SLC JGB, JFK, SAN
San Francisco, CA SFO AUS, BOS, LGB, JFK
San Jose, Costa Rica SJO MCO
San Juan Puerto Rico SJU BOS, FLL, JFK, MCO, SDQ, IAD
Santiago, Dominican Republic STI JFK
Santo Domingo, Dominican Republic SDQ BOS, FLL, JFK, MCO, SJU
Seattle, WA SEA BOS, LGB, JFK, SAN
Washington, DC IAD BOS, CUN, FLL, LGB, JFK, OAK, MCO, SJU

 

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:

New York JFK
Portland PDX
Long Beach LGB
Seattle SEA
Long Beach LGB
Las Vegas LAS
New York JFK
Orlando, FL MCO
Bogota, Colombia BOG
Orlando, FL MCO
Orlando, FL MCO
Cancun, Mexico CUN
Orlando, FL MCO
Orlando, FL MCO
San Jose, Costa Rica SJO
Orlando, FL MCO
New York JFK
Houston HOU
New York JFK
New York or Boston JFK/BOS
Bermuda BDA
New York or Boston JFK/BOS
Boston or New York BOS/NYC
Saint Maarten, Netherlands Antilles SXM
Boston or New York BOS/NYC
Boston, New York, Washington DC BOS/NYC/IAD
San Juan SJU
Santo Domingo, Dominican Republic SDQ
Boston or New York JFK
Boston or New York BOS/NYC
New Orleans MSY
Boston or New York BOS/NYC

… 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:

Origin Destination
Houston, TX HOU New York, NY JFK
New York, NY JFK Bermuda BDA
Bermuda BDA New York, NY NYC
New York, NY NYC San Juan, Costa Rica SJU
San Juan, Costa Rica SJU Santo Domingo, Dominican Republic SDQ
Santo Domingo, Dominican Republic SDQ New York, NY NYC
New York, NY NYC St Maarten, Netherland Antilles SXM
St Maarten, Netherland Antilles SXM New York, NY JFK
New York, NY JFK Portland, OR PDX
Portland, OR PDX Long Beach, CA LGB
Long Beach, CA LGB Las Vegas, NV LAS
Las Vegas, NV LAS New York, NV JFK
New York JFK Houston, TX HOU
Houston, TX HOU New York, NY JFK
New York, NY JFK Orlando, FL MCO
Orlando, FL MCO Bogota, Colombia BOG
Bogota, Colombia BOG Orlando, FL BOG
Orlando, FL BOG Cancun, Mexico MCO
Cancun, Mexico MCO Orlando, FL MCO
Orlando, FL MCO San Jose, Costa Rica SJO
San Jose, Costa Rica SJO Burlington, VT BTV
Burlington, VT BTV New York, NY JFK
New York, NY JFK Houston HOU

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:

Origin Destination Days
Houston HOU New York JFK 1
New York JFK Bermuda BDA 4
Bermuda BDA New York NYC 1
New York NYC Santo Domingo, Dominican Republic SDQ 4
Santo Domingo, Dominican Republic SDQ Orlando, FL MCO 1
Orlando, FL MCO Bogota, Colombia BOG 4
Bogota, Colombia BOG Orlando, FL MCO 1
Orlando, FL MCO Cancun, Mexico CUN 4
Cancun, Mexico CUN Orlando, FL MCO 1
Orlando, FL MCO San Jose, Costa Rica SJO 4
San Jose, Costa Rica SJO New York JFK 1
New York JFK Houston HOU 1
Total 27 days

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.

Origin Destination Flight Start End
9/8/2009 Tuesday
9/9/2009 Wednesday
9/10/2009 Thursday Houston HOU New York JFK 626 2:35PM 7:17PM
9/11/2009 Friday New York JFK San Jose, Costa Rica SJO 1695 6:30AM 11:25AM
9/12/2009 Saturday
9/13/2009 Sunday
9/14/2009 Monday
9/15/2009 Tuesday San Jose, Costa Rica SJO Orlando, FL MCO 1696 12:20PM 5:37PM
9/16/2009 Wednesday Orlando, FL MCO Cancun, Mexico CUN 1715 1:55PM 2:52PM
9/17/2009 Thursday
9/18/2009 Friday
9/19/2009 Saturday
9/20/2009 Sunday
9/21/2009 Monday Cancun, Mexico CUN Orlando, FL MCO 1710 3:52PM 6:45PM
9/22/2009 Tuesday Orlando, FL MCO Bogota, Colombia BOG 1783 5:35PM 8:29PM
9/23/2009 Wednesday
9/24/2009 Thursday
9/25/2009 Friday
9/26/2009 Saturday Bogota, Colombia BOG Orlando, FL MCO 1784 9:00AM 2:02PM
9/27/2009 Sunday Orlando, FL MCO Santo Domingo, Dominican Republic SDQ 1717 8:50AM 11:23PM
9/28/2009 Monday
9/29/2009 Tuesday
9/30/2009 Wednesday
10/1/2009 Thursday Santo Domingo, Dominican Republic SDQ New York JFK 822 10:55AM 2:39PM
10/2/2009 Friday New York JFK Bermuda BDA 1731 9:15AM 12:29PM
10/3/2009 Saturday
10/4/2009 Sunday
10/5/2009 Monday
10/6/2009 Tuesday
10/7/2009 Wednesday Bermuda BDA New York JFK 1732 1:35PM 2:47PM
10/8/2009 Thursday New York JFK Houston HOU 625 10:00AM 1:53PM

Step 7: Book It

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

 

Photo by Capturing the human heart. on Unsplash