As anyone who follows my tweets knows, I'm going to be doing the JetBlue All-You-Can-Jet promotion. Because I'm flexible, I saved $200 and bought the five day pass for $500, which means that I can't fly on Friday or Sunday. The pass entitles me to fly from September 7th until October 6th for free on all JetBlue flights. This includes all taxes in the US, but not outside the US. I've been thinking about the best way to use this pass, and I'm going to share my strategy with you, in case you bought one as well.

Mostly International

There aren't all that many places in the US I want to go. Within a month or two of the promotion I will have been to NY, Boston, Austin and LA, which covers most of my bases. So I'm mostly seeing this as a ticket to get HUGE discounts on international travel for a month.

There are two types of international travel: the type where you blow through and do the best you can to check somewhere out for future extended visits, and then there are the extended visits. Obviously, these trips will be the former. Here's where I'll be going:

Colombia

I've never been to South America. I've been to Aruba, right off the coast, and I've been into the jungles of the Darien Gap between Panama and Colombia, but no farther. So it's time. Taxes for this are $267, which is about 45% of what I'd normally pay to go there from San Francisco. It's the worst deal of all the trips, but I'm excited about Colombia and South America, so I'm doing it.

Jamaica

Jamaica is only about $100 in taxes. I have a friend who is obsessed with Jamaica, so I'm hoping to get some tips from her and check it out. I know it's super touristy, but I really want to climb up that waterfall that all the tourists climb. Hey... I'm into that kind of stuff.

Dominican Republic

I'm not 100% sure I'm going to go here, mainly because I got robbed last time and I think that soured the experience a bit, but it's a good place to practice some Spanish and I'm already familiar with it so I won't need time to acclimate. I never got a chance to see Tres Ojos, some cool caves, so I'll do that.

Costa Rica

I didn't love Costa Rica when I was there, but I was only around for a couple days and did pretty touristy stuff. There's a lot of awesome nature there, though, so I'll go check it out for a bit. Maybe I'll find some couchsurfers to go camping with or something like that.

Saint Lucia and Barbados

I don't know the first thing about either of these countries, but they're the two remaining countries that JetBlue flies to that I've never visited. May as well get them checked off the list and see what they're all about! That's four new countries total that I will hit within the month.

Less and Better Gear

I'm going to use this month as the final test for some new gear I have. Gear post coming afterwards (or maybe during), guaranteed!

Buy All Tickets Up Front

The pass stipulates that I can cancel any ticket as long as I give them three days notice. As soon as I'm allowed to book flights on August 27, I'll book every flight I intend to take, so that I don't get stuck somewhere I don't want to be. If plans change, I'll just cancel the tickets and rebook.

No Round Trips in The US

Round trips in the US are a waste of time and travel days, so I'm going to try to string all of my US cities along. For example, I'll probably go to Las Vegas first, then Seattle, then New York or Boston.

The Skateboard is Coming With Me

JetBlue has free checked baggage, which means that I'm taking my 30 pound electric board with me, at least in the US. I may stash it with a friend in NY when I head out of the country, and come get it later.

Cheap Extension

I haven't planned my full route yet, but I may try to end up somewhere near SF at the end and buy my own ticket for a week later. Then I could get an extra week, if I'm not totally burnt out. You could also do this in the beginning... buy a cheap one way from Boston to NY, for example, and then start flying from there.

Mostly Couchsurfing

Two reasons: first, I'm going to be spending another $500 or so in taxes on top of the $500 pass, so I want to keep my costs down. Second, short trips are WAY better with a local to show you around. I only spend three days in Haiti and I really got a solid feel for the country. I spent the same in Singapore solo and can barely tell you anything meaningful about it. If you want to host me in one of those countries (I think I'm covered in every US city), let me know!

Tynan.net meetup?

If you want to meet up, send me an email. If there are a few readers doing this promo, I'll organize something for us somewhere. Let me know in the comments or by email.

###

I'm in Boston right now visiting family. My family from Texas thinks it's refreshingly cool here. I think it's refreshingly warm.

If you still have the Sprint SERO plan, hang in there -- they're about to allow you to pay $10/mo more and get any of the new devices. If only they'd make an Android world phone!