I have 40 flights before the end of fall, so unsurprisingly, I’m now traveling. I left on Wednesday; I had 2 events (at the beginning and at the end), and I’m taking advantage of the time between the 2 to tackle the JetBlue challenge that gives 350,000 points (value of 5950 CAD to UNLIMITED). I’m doing this mostly as a mileage run, which means a lot of flights again.
You can follow my daily stories on my personal Instagram account, like for all my many trips. But I’m trying hard to create more content about my travels here on the site, too.
Here’s the introduction to my North American trip with 13 flights in 13 days, specifically the context and the itinerary. The logistics, the reviews, the experiences, and all the details will follow soon.
Context of my trip in North America
I love free travel, so I love points. So I decided to do the Turkish Airlines challenge that gave 1 million points, AND also the JetBlue challenge. It’s getting excessive, but I really love it. And I have FOMO (fear of missing out); maybe there won’t be more!
I couldn’t say no to 1M Turkish points, and it didn’t make sense not to do a few more flights to reach the 20 JetBlue destinations required, since I already had enough trips planned this fall to integrate several JetBlue flights organically.
This JetBlue challenge is less interesting, of course, but it’s still very interesting.
My last trip was precisely my trip to the 6 continents for Turkish Airlines in August (with a weekend in Toronto with my girlfriend right after). I had started it by flying New York-London on JetBlue, but I was still at just 1 flight done out of 20!
So this current trip started with a marketing industry conference in Toronto, where I go each year to meet representatives from several banks (a different one from the one where I’m speaking in October). I took a JetBlue flight (#2!!!) to get there, with a huge detour that also involved 16 hours by train/bus.
And this trip ends with the entrepreneurship event that I host each year at the awesome LSU (Louisiana State University). I go through New Orleans because Baton Rouge is too small for JetBlue, so I have 3 other JetBlue flights there (1 for my outbound and 2 for my return, thanks to a stopover).
I was supposed to be a speaker at a travel rewards event in Vancouver right after Toronto, but it was cancelled because it was too small.
(That’s precisely why I told you that the other travel rewards event where I’m a speaker is really the one I recommend you attend. That one is in its 15th edition and won’t be cancelled; it’s one of the biggest!)
In between my events, I had planned to do 5 other JetBlue destinations in 3 days. With the cancellation, I was finally able to fit 6 by changing everything at the last minute!
(Flights on U.S. airlines are all modifiable for free, which is very useful. That excludes the Basic Economy fare class that I normally always book; but for the JetBlue promo, you have to book Standard Economy or higher!)
So I’m doing 7 flights in 6 days between the 2 events, so it’s obviously a business trip where the business is to get JetBlue points. I won’t have much time to visit, but I didn’t really have a choice, considering the little time I had to visit more places this fall.
So after this trip, I’m going to be at 11 JetBlue destinations out of 20. More than halfway there.
I’m going to do 6 in October, between the When We Were Young festival in Las Vegas and the Chicago Seminars, where I’m a speaker the weekend after. I’ll then complete by doing 1 each to start my already planned trips to Orlando (Vans Warped Tour music festival), to Miami (Art Basel/Art Week festivities), and to Mexico (reviews of nice Marriott hotels).
Itinerary of my trip in North America
It’s another very atypical trip, obviously, with an itinerary that makes even less sense than the round-the-world trip and the trip to the 6 continents for the other challenges.
Here’s my overall itinerary.
I did NOT optimize for efficiency at all. I optimized for price only. As always, my goal is to get the most rewards for the least amount of spend.
(As you should always do for everything; it’s SO easy… just use all your spending to unlock huge welcome bonuses!!! Simple!)
The lowest prices are to leisure destinations, as always. Because flight prices have nothing to do with the cost of operating a flight or the distance, unlike what so many who are not knowledgeable about flight prices think.
So I’m flying between the Northeast and South a lot. It’s also more efficient, because I can fly back to a different Northeast airport to have 2 destinations per roundtrip (there are many short and cheap flights in the Northeast, but they’re only served by BOS and JFK so the return is wasted).
I’m quite satisfied with my itinerary, because I managed to keep costs very low. While keeping the risks of IRROPS (flight disruptions) relatively low with a bit of buffer, and while protecting my nights of sleep.
I paid a bit more to add Santo Domingo in the Dominican Republic, because otherwise it would have all been in the United States and less interesting. I could have saved so much more if I had more flexibility on the dates, obviously, but I had to do them exactly on those dates.
It’s 18,145 kilometers (11,275 miles) in the air, so about 1/3 of the round-the-world trip and 1/4 of the trip to the 6 continents. It’s a lot of flights, but they’re relatively short.
Here are the many cities on this itinerary:
- New York, New York
- 1 night
- To position for a JetBlue flight
- Buffalo/Niagara Falls, New York
- A few hours
- To get JetBlue destination #2 to get to my conference
- Toronto, Ontario
- 1 night
- To attend a conference
- Orlando, Florida
- 1 night
- To rescue the Vancouver cancellation
- Worcester, Massachusetts
- A few hours
- To get JetBlue destination #3
- Boston, Massachusetts
- 1 night
- To position for a JetBlue flight
- San Juan, Puerto Rico
- A few hours (airport only)
- To get JetBlue destination #4
- Santo Domingo, Dominican Republic
- 2 nights (arrive late, leave early)
- To get JetBlue destination #5
- Newark, New Jersey
- Arrival and train to change airports
- To get JetBlue destination #6
- Fort Myers, Florida
- 1 night
- To get JetBlue destination #7
- Westchester, New York
- 1 night (in New York by train)
- To get JetBlue destination #8
- New Orleans, Louisiana
- 1 night
- To get JetBlue destination #8
- Baton Rouge, Louisiana
- 3 nights
- To host my event
- Washington, DC
- 1 night
- To get JetBlue destinations #9 and #10 (layover in JFK)
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Summary
I just started my trip in North America. I wanted to share the context and the itinerary for the trip overall for those who often ask for more content on our own trips.
What would you like to know about my trip in North America? Tell us in the comments below.
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Featured image: New York and Niagara Falls, New York (image credit: Andrew D’Amours/Flytrippers)
