A Little Musing… Where Do I Go from Here?

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“So, when do you head out again, where are you going next?”

And that is the ten million dollar question, my friends.

Truth? I don’t know.

I have a conundrum. I’m living at my parents’ house, readjust to life in the U.S., and plotting next steps. When I left a year ago, I was supposed to return to Los Angeles at the end of this trip. I feel in my heart that’s not the right next step—I’ve felt that way for a while. Even when I left, a part of me knew I wouldn’t return to LA right way.

los angeles palm trees
Missing those sunny LA days . . . kind of.

Two months ago, while backpacking Ireland, the last stop on my round the world trip, my plan was simple: come home, see family and friends, stay through Christmas, then backpack south through South America starting in January.

Other travelers invited me to hike Machu Picchu with them. But I have other options . . . confusing options.

I may visit Cuba next.

My dad’s best friend is a commercial fisherman in the Gulf of Mexico and he’s hoping to get approved for a permit to dock in Havana Harbor—if he does get it, then I have a ride to Cuba! If he doesn’t, then I will fly through Mexico en route to Cuba, since Americans can’t legally backpack Cuba for fun. And also, I have a South African travel friend who will meet me there no matter how I arrive, if I head that way.

The big fat reality check, however, is the fact that it’s a bit illegal for me to Cuba as an American. And by “a bit illegal,” I mean that it’s flat out against the law for me, as an American, to spend money in Cuba, though going there isn’t illegal per se . . . as long as I don’t spend money?!

Since the U.S. government still has an embargo against Cuba, gung-ho travelers like struggle to visit a country that lies just 90 miles off US soil.

And as my favorite Nepali phrase says, raamro chaina: not good.

Reading up about other Americans who have ventured to Cuba despite the embargo tells me it’s possible to fly to Mexico, forgo the exit stamp (possibly with a small bribe), and find myself wandering La Habana in no time.

Now I just have to decide if it’s worth it. I would have to bring all the cash that I would need because U.S. bank and credit cards don’t work in Cuba. But a small hiccup, it’s still possible. Is it the right next step though?

And then, as if I weren’t already feeling a bit confused as to what I want to do, I’m also considering heading back to Cambodia to volunteer at FLO. I spent time there earlier this year and enjoyed working with the teachers to implement lesson plans for the 200+ kids in the FLO program.

My truly crazy thought: Can I do all three? Head to Cuba, stay for a month or so, then fly back to Mexico, make my way to South America to meet my friends. I would then come home for the summer before heading out to Southeast Asia. Sounds doable right? Perhaps if I were independently wealthy—which I’m not, by the way! I still work remotely every single day. :)

I’m brainstorming here and would love to hear thoughts/experience/tips on Americans traveling to Cuba! Or just thoughts on where I should head next in general!  :-)

24 thoughts on “A Little Musing… Where Do I Go from Here?”

  1. Thanks for the feedback Lauren – I've heard that it's just amazingly neat to see a place that has been basically stripped of rampant US influence :-)

  2. Thanks for the tip – I am thinking of going through Mexico if I have to fly…but some people have recently emailed me some sentiments that it's not a positive place for Americans to visit and they had some negative experiences…thoughts?

  3. Go to Cuba! I went about 3 years–flew through Cancun, brought a ton of cash (due to the ATM situation), had no problems with the double entry stamp from Mexico. I even brought back some souvenirs. In terms of US Customs, just keep a low profile, be respectful and remember that tons of Americans fly to Mexico without going to Cuba, so there's nothing particularly suspicious about you. Customs agents are just doing their jobs, and probably won't want to dig through your dirty laundry and toiletries and write lengthy reports.

    That being said–boat ride to Cuba?! I wouldn't be able to resist. Arrest, fine or otherwise. Can I go? :)

    Cuba is super interesting, especially if you've traveled to other Latin American countries and have a kind of broader context to put it in. Probably the most different place I've been to, with the least influence of American culture (though there's definitely still a presence).

    Go! Take me with you!

    • Thanks for the feedback Lauren – I've heard that it's just amazingly neat to see a place that has been basically stripped of rampant US influence :-)

  4. Go to Cuba! I went about 3 years–flew through Cancun, brought a ton of cash (due to the ATM situation), had no problems with the double entry stamp from Mexico. I even brought back some souvenirs. In terms of US Customs, just keep a low profile, be respectful and remember that tons of Americans fly to Mexico without going to Cuba, so there's nothing particularly suspicious about you. Customs agents are just doing their jobs, and probably won't want to dig through your dirty laundry and toiletries and write lengthy reports.

    That being said–boat ride to Cuba?! I wouldn't be able to resist. Arrest, fine or otherwise. Can I go? :)

    Cuba is super interesting, especially if you've traveled to other Latin American countries and have a kind of broader context to put it in. Probably the most different place I've been to, with the least influence of American culture (though there's definitely still a presence).

    Go! Take me with you!

  5. It is so great that you have a proper 'location independent' income. (That is an aim of mine too!) Cuba sounds really interesting….
    Good luck.

  6. Hm. While Cuba won't stamp your passport – be warned that if you travel via Jamaica (an otherwise great thing to do!) you will have the ink stains 'in transit to Havana' for all to see…

    But then, most of the joy of visiting Cuba is that it is SO different to so many places – and that is likely to change if (when?) the US changes policy…

    Tricky…Buen viaje!

  7. I'm in the same boat. My plans shift like that too and I want to do everything. For me personally I take a look at the map and my budget to make sure I don't rush things or overspend. Seeing my route on a map makes me realize what's realistic and what would just be too much ground to cover. I've also got my 'bunker' spots along the way where I set aside time to live in a certain city and work overtime. During that time I travel locally in the area and once I've got enough saved I can hop somewhere else. Not sure if that helps any, I'm a terrible planner.

    As far as Cuba goes I've heard of many who've gotten away with it. Not sure the exact process although I think almostfearless.com (if I remember correctly) has a good post on it.

    • Thanks for the tip Anil, I will make sure search Christine's site for it! I think our travel is right along the same lines – slow and local with long stops!

      • Hm. While Cuba won't stamp your passport – be warned that if you travel via Jamaica (an otherwise great thing to do!) you will have the ink stains 'in transit to Havana' for all to see…

        But then, most of the joy of visiting Cuba is that it is SO different to so many places – and that is likely to change if (when?) the US changes policy…

        Tricky…Buen viaje!

        • Thanks for the tip – I am thinking of going through Mexico if I have to fly…but some people have recently emailed me some sentiments that it's not a positive place for Americans to visit and they had some negative experiences…thoughts?

  8. Thanks for the tip Anil, I will make sure search Christine's site for it! I think our travel is right along the same lines – slow and local with long stops!

  9. I pretty much agree with you – for all of the talk, I don't see the embargo getting lifted within the next year, but once it does, it's going to be a very different place to visit. I really think I'm leaning toward going there in Cuba so that I can make it before the embargo's lifted…but you didn't hear me say that! ;-)

  10. I am actively working (I worked all through my RTW trip on some SEO stuff via the internet!), so I just need to save up a bit of a nest egg again…and then it's deciding where to go?! Ack :-) The blog is also something I'm working on too, so many choices!!

  11. I'm in the same boat. My plans shift like that too and I want to do everything. For me personally I take a look at the map and my budget to make sure I don't rush things or overspend. Seeing my route on a map makes me realize what's realistic and what would just be too much ground to cover. I've also got my 'bunker' spots along the way where I set aside time to live in a certain city and work overtime. During that time I travel locally in the area and once I've got enough saved I can hop somewhere else. Not sure if that helps any, I'm a terrible planner.

    As far as Cuba goes I've heard of many who've gotten away with it. Not sure the exact process although I think almostfearless.com (if I remember correctly) has a good post on it.

  12. Unless the administration surprises everyone, that embargo is not getting lifted any time soon. I think it is fascinating. If at all possible I would get there before the embargo falls. It's going to be vastly different once that happens.

    But you didn't hear me say that….

    • I pretty much agree with you – for all of the talk, I don't see the embargo getting lifted within the next year, but once it does, it's going to be a very different place to visit. I really think I'm leaning toward going there in Cuba so that I can make it before the embargo's lifted…but you didn't hear me say that! ;-)

  13. Unless the administration surprises everyone, that embargo is not getting lifted any time soon. I think it is fascinating. If at all possible I would get there before the embargo falls. It's going to be vastly different once that happens.

    But you didn't hear me say that….

  14. Decisions decisions…. You are definitely at a crossroads! I can't tell you where to go, I have a hard enough time deciding that for myself and would want to do all 3 anyway!! Can you get a job for a while and save? or better stll launch a new product from your blog?

    • I am actively working (I worked all through my RTW trip on some SEO stuff via the internet!), so I just need to save up a bit of a nest egg again…and then it's deciding where to go?! Ack :-) The blog is also something I'm working on too, so many choices!!

      • It is so great that you have a proper 'location independent' income. (That is an aim of mine too!) Cuba sounds really interesting….
        Good luck.

  15. Decisions decisions…. You are definitely at a crossroads! I can't tell you where to go, I have a hard enough time deciding that for myself and would want to do all 3 anyway!! Can you get a job for a while and save? or better stll launch a new product from your blog?

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