Seeking Your Advice

flight flying plane air travel

Photo by Josh Sorenson on

Readers, from far and wide, I appeal to you for some wisdom. I have a choice to make, but I am struggling to come up with the best solution.  I would love to hear what you think.

I am planning my winter vacation and what I thought was a simple decision seems much harder. I am genuinely feeling confused and I need some help putting it into perspective.  Now I realize that this is very much a first world problem, but still…..

I have narrowed down my choices to three places. They are all cycling trips.  Here are my choices in alphabetical order and my perceived pros and cons.  Granted, I have not done a lot of research.



  • It is beautiful looking.
  • I have never been to South America before.
  • I could probably add on a few days in Santiago, which would be awesome.
  • There is a slight discount as this is an Exodus Travels trip


  • It is the most expensive of the choices for the tour itself, not to mention my stay in Santiago.
  • I believe the airfare is similar to choice 3 owing to the need to fly domestically to the starting point.



  • There are one week and two week options.
  • The price is quite reasonable.
  • The cycling would be relatively easy.
  • I could maybe do a week before in Costa Rica or Panama.
  • Airfare is cheap.


  • Most people have told me that one week in Cuba is enough.
  • I am not sure about the viability of the other country option (which also might be really hot).
  • Serious vaccinations needed.
  • There’s no cache in traveling to Cuba for a Canadian.  Thousands of us do it all the time.
  • There is no discount as this is an Intrepid trip.

Sri Lanka


  • The price is quite reasonable.
  • The cycling route seems challenging.
  • I have heard that the hotels are beautiful.
  • It looks beautiful.
  • There is a slight discount as this is an Exodus Travels trip.


  • It seems so far away (the older I get the less appealing long flights to Asia seem).
  • I have not heard back about the flight cost or transfer city.

These thoughts are mostly preliminary, but based on how these things book up quickly, I do really need make some definitive plans fairly quickly and need your help.  If you’ve been to these places or have any wisdom, I would love to here it.

About Anthony

I am: equal parts rebel, romantic and shockingly average Joe. a writer trapped inside of an ESL teacher's body. an introverted attention seeker. a teacher who hopes one day to be called "Captain, my Captain." an intellectual who can do some very dumb things. a person whose Japan experience, despite being so long ago, still exerts a strong influence upon him. a lover of books, music, beer, hockey and Pizza.
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17 Responses to Seeking Your Advice

  1. My immediate response was Cuba. (I have it on my list) Yes, as Canadians it is easy for us to travel there. However, if you want to visit a country still partially in the past I say do it sooner rather than later. I have never met anyone who did not enjoy their time there. Vaccinations? Really?
    I would save Sri Lanka for another trip that could include hopping to nearby countries. Which would mean needing more than two weeks.

  2. rootchopper says:

    A Chilean friend has been urging me to go there for several years. My former co-worker Jessica is living there as an ESL teacher. She is in the Altacama which seems stark and beautiful. Another friend Adam went all over the country. Loved it. There is so much to see.

    All I know about Sri Lanka is that it is amazingly beautiful.

    As for Cuba, it strikes me as a time capsule that will eventually become more like its neighbors. It may not be as beautiful as the other places but it the Cuba you see now may be gone in 10 years.

    The Handsomest Man in Cuba by Lynette Chiang is a very good bike touring book about cycling there. (She’s Australian. I think the book is at least 15 years old.)

  3. Andrew Vance says:

    I’ve heard Chile, including Santiago, is amazing. Been to Cuba. Aside from nice beaches and a day in Havana, there’s not much to see. The food was so-so (I mean, it was fine for me, but if you were a foodie, you’d probably be disappointed) Not been to Sri Lanka, but apparently the scenery/beaches are amazing and the people are very friendly.

  4. Sarah Warsi says:

    My first thought was no to Cuba since the food is arguably pretty bad from what I have consistently heard from others. I would say Chile should be your first pick. 🙂

  5. Sarah Warsi says:

    Sri Lanka would be beautiful as well. Very Exotic.

  6. Hunida says:

    I’ve never been out of the country but based off your pros & cons list, I’d choose Cuba!

  7. Heide says:

    Chile is gorgeous, but alas I’ve never been to Cuba or Sri Lanka so I can’t make an informed recommendation. If it were me I would choose Cuba, though, because as others have said its culture is changing quickly, and may be much more commercialized in 10 years.

  8. John says:

    Cuba would be my choice. I was at the Moscow Olympics in 1980 and on the plane home we saw our first western newspapers in 10 days.
    Two things caught my eye. The death of Peter Sellers the actor and disturbances in a shipyard in Poland. Although I did not know it then i was witnessing the last decade of soviet rule. I have never forgotten the experience of being at the very edge of History.
    So for much the same reason my choice would be Cuba.

  9. windswept007 says:

    Reading between the lines, it seems like you favour Chile. I would go with your gut feeling.

    • Anthony says:

      You’re right, Chile had been my choice. Sadly, I dithered too long (worrying about finances and wondering if I could swing a trip to Rapa Nui along with it) and didn’t reserve the trip in time. It is now full.

      • windswept007 says:

        It’s full for now, not forever. Start planning now for a time when it is available and you have time. Then you can also go to Rapa Nui. Just take a cheaper trip for now and start a chile fund with what you save.

      • Anthony says:

        That is very wise advice. Thank you.

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