A Little Contemplation…Where Do I Go from Here?

“So, when do you head out again, where are you going next?”Havana, Cuba, Musicians in La Habana

And that is the ten million dollar question my friends.

And the truth?

I don’t know.

I have a conundrum. I’m living at my parents’ house right now as I readjust to the US and plot out my future travels and drag out the last of my Ireland posts for you. A month ago my plan was simple, come home, see family and friends, stay through Christmas and head out to South America in January.

And this is still, perhaps, the leading plan. Actually, I’m likely meeting up at Machu Picchu with a few fellow travelers I met on my trip all goes according to plan.

But I have this tiny confession to make…I think I want to go to 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 – and if he does get it, then I have a ride to Cuba! If he doesn’t, then I will be flying through Mexico to get to Cuba.Cuban man with cigar

But the big fat reality check is the fact that it’s just a bit illegal for me to go there…and by “just a bit” I do mean 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?!

Well, since my lovely US government continues to support the Cuban embargo that keeps gung-ho travelers like yours-truly from venturing to the shores of a country that lies just 90 miles off US soil…I’m at a loss.

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

Reading up about other Americans who have ventured to Cuba despite the embargo tells me it’s possible to fly to Mexico, pay a little bribe money to forgo the exit stamp, and be poking around La Habana in no time.

Now I just have to decide if it’s worth it. Because another issue is the fact that I would likely have to take aaaall of the money that I’d need with me (I want to stay for a least a month, so that’s a lot) because US bank and credit cards don’t work in Cuba.

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 Future Light Orphanage, I spent some time at earlier this year and had the most amazing, love-filled Valentines Day with the 200+ kids at the orphanage.

My truly crazy thought…can I do all three? Head to Cuba, stay for a month or so, then fly back to Mexico and make my way to South America to meet my friends. 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’m doing some brainstorming hereand would love to hear thoughts/experience/tips on Americans traveling to Cuba! Or just thoughts on where I should head next in general!!  :-)

Many thanks for photos on Flickr: Man smoking cigar photo thanks to alschim . Musicians in Havana taken by deVos


24 Responses to A Little Contemplation…Where Do I Go from Here?

  1. ShannonOD November 25, 2009 at 10:10 am #

    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. ShannonOD November 25, 2009 at 10:02 am #

    Thanks Emma, I'm pretty grateful for having it ;-) As for Cuba, well, still pondering…

  3. ShannonOD November 25, 2009 at 10:00 am #

    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?

  4. Lauren Quinn November 24, 2009 at 7:00 pm #

    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!

    • ShannonOD November 25, 2009 at 5:10 pm #

      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 :-)

  5. Lauren Quinn November 24, 2009 at 12:00 pm #

    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!

  6. EmmaOconnor November 22, 2009 at 2:35 pm #

    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.

  7. Abi November 22, 2009 at 12:46 pm #

    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!

  8. Anil November 21, 2009 at 6:10 pm #

    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.

    • ShannonOD November 21, 2009 at 11:57 pm #

      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!

      • Abi November 22, 2009 at 7:46 pm #

        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!

        • ShannonOD November 25, 2009 at 5:00 pm #

          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?

  9. ShannonOD November 21, 2009 at 4:57 pm #

    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!

  10. ShannonOD November 21, 2009 at 4:52 pm #

    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! ;-)

  11. ShannonOD November 21, 2009 at 4:51 pm #

    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!!

  12. Brian November 20, 2009 at 8:23 pm #

    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….

    • ShannonOD November 21, 2009 at 11:52 pm #

      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. EmmaOconnor November 19, 2009 at 10:40 pm #

    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?

    • ShannonOD November 21, 2009 at 11:51 pm #

      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!!

      • EmmaOconnor November 22, 2009 at 9:35 pm #

        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.

        • ShannonOD November 25, 2009 at 5:02 pm #

          Thanks Emma, I'm pretty grateful for having it ;-) As for Cuba, well, still pondering…

  14. EmmaOconnor November 19, 2009 at 3:40 pm #

    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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