Dream Destination

I’m Off to My Dream Destination for My 40th. Guess and Win!

Derek Personal Stuff 182 Comments

Dream Destination
On March 31st, I shall turn 40 years old. And tomorrow I’m off to my dream destination.

When it comes to turning 40, I’m all good.

Of course, there’s always a chance that the clock will strike midnight on that day and I’ll have a breakdown, then head off to Ibiza, pluck the first few gray hairs from my head, rent a Harley and cruise up and down the main strip, trying to feel as carefree and invincible as I did when I was 18.

Is that how it works?

I highly doubt that will happen though.

In all honesty, what a 40 years it’s been. From growing up in a town outside of Boston, to three different universities scattered around two countries, to wanting a career as a sports agent and then to a post-school life that I could never have envisioned, and that certainly didn’t involve becoming a sports agent.

Visiting ten countries? Maybe I would have believed that to be possible.

A year or two of traveling? Absurd, but I guess it could happen somehow.

98 countries (with #99 and #100 coming up next month), 18 years of travel, working as a blogger, organizing tours, living in various destinations overseas? Absolutely unimaginable!

(Take that as a lesson – the most unimaginable goals in life really can be achieved. It’s no joke and as a result, there is little time to waste. Please take a step today, even a tiny one, towards some goal or dream that you want to reach in life but have yet to move towards. Again, just a tiny step. It’s the only way to build momentum and actually make that change happen.)

So, When’s the Birthday Party?

As I write this post, I can easily remember when my father turned 40 years old. We had a big party for him at our house. Dozens of friends and family attended, we had a BBQ, the adults drank a little and it was a grand occasion. I recall wondering at the time what my very own 40th birthday party would be like when the day arrives.

Well, the day has arrived.

But it turns out that my 40th birthday won’t quite be like that one. I don’t have a house to party in, my family and friends are quite scattered around the globe and oddly enough, I don’t travel with a BBQ grill.

Am I sad about that? Not at all.

Here’s why…

I Really Am Off to My Dream Destination!

Ever since I was about 13 years old, when I read a particular article in a travel magazine, there has been one country on this planet that I have labeled as my ‘dream destination’. It might seem odd that, despite my life of travel, I have yet to visit my one and only dream destination, but that’s how things turned out.

Maybe I was just waiting for the right time.

Recently it occurred to me. I’ll be damned. It’s now the right time!

Tomorrow, off to my dream destination I shall go. My girlfriend and I will spend almost two weeks in this location, which will include my 40th birthday celebration on March 31st.

For me, it is a dream come true, literally. And despite the places I’ve been in my life, I still can’t believe this is actually happening!

Where is this dream destination?

Well, I can’t tell you that, at least not right now. This is going to be a surprise trip that I’ll reveal once I’m there.

But to make things interesting…

Wandering Earl’s 40th Birthday Giveaway

If you want to guess my dream destination, please go for it!

Here’s how it will work:

1. Leave a comment on this post or on today’s FB post with your guess.

2. Only one guess per person.

3. Guesses are accepted until 11am EST on March 24th.

4. On March 25th I shall reveal my dream destination (I’ll already have arrived by then).

5. The first three people who guess the correct destination (based on day and time) will win a gift package containing:

  • cool local products from my three upcoming destinations
  • 50% discount voucher for a Wandering Earl Tour
  • $50 VISA gift card

** If I receive more than 500 comments on this post (on the blog and FB post combined), I’m then going to choose three more comments at random, regardless of whether it is the correct guess or not, and those people will receive the above prizes as well.

6. If you are a winner, you will be notified directly on March 25th.

*Close friends and family of both my girlfriend and I, who already know the destination, are not eligible!! Sorry 🙂

So, what’s your guess? Where is my dream destination?


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Comments 182

  1. Belated Happy Birthday, Derek!! That island was WOW. And those rocks at the back? It looked like someone had manually placed them on top of each other to look picture perfect. Thanks for taking us along with that video!

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        Hey Esther – As I had stated in the post, the winners would be the first 3 people who guessed correctly. There were about 5 or 6 people who had guessed Seychelles before you. Sorry!

  3. Here’s my guess: Brazil ! If I’m right and you need any help navigating the country, let me know! And my wife and I wish you a happy 40th! (I’m getting there soon…)

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  4. Hi Earl! Well, since you say you haven’t been there and you recently arrived in Africa I will go with Madagascar ??

  5. For your 40th Birthday, I imagine it has to be something that was very intriguing that you have still been thinking about this place since you were 13 years old. My guess is that you are going to Peru to hike the Inca Trail and finally visit Machu Picchu. While the four day hike is doable, the second day is definitely challenging and a great way to test your strength – both mental and physical – as you look forward to your 40th year on this planet. If I am right, then I really hope you enjoy the trek. It is certainly worth it!

  6. Wow! turning 40… that’s kinda like a BIG deal!! I will be turning 40 this year as well but on December 1st. I will also be taking a dream trip. My trip will be to Bali, Indonesia. Since you love Asia… I’ll say you will be traveling to Bali as well. Have a Fantastic and Fruitful 40th Birthday!! Be Blessed….

  7. Figi

    Happy Birthday hoping it’s great! Enjoy your special day.
    I enjoy reading your blog and I like the pictures too.

    Hope you have an wonderful time celebrating a life well lived with your girlfriend.
    My guess is that such celebrating will be done in..


  9. Hey Earl, I just realised we have birthdays a day apart. I know you have already been to a lot of your dream destinations, so this is a tough one. I notice you haven’t been to Russia yet (I think) so I plump for Russia as it’s got so much diversity. Have a safe trip!

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      Hey Jonny – A big Happy Birthday to you as well! And while my destination is not Russia, it is a country I need to visit one of these days! Safe travels as well my friend!

  10. Japan, because my birthday is March 31st and as a fellow life-long traveler, its been my one dream destination that I’ve yet to conquer!

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      Hey Rory – Happy upcoming birthday to you! Japan is very high on my list and while it’s not where I am now, I do hope to get there later this year!

  11. Happy Birthday Earl!
    When I was 10, my dream destination was Japan, so I’ll go with that. A close second would be Georgia.
    Have a fabulous time!

  12. I will say Seychelles. If I am right, let me know if she sells sea shells by the Seychelles seashore. Yes this is an excuse to tell that lame joke. Happy birthday.

  13. I’m on a flight myself to Japan on the 24th so that will be my guess… although I suspect you will be off to a more adventurous destination. Wherever you end up happy 40th and enjoy your trip!

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      Thanks Mike and enjoy Japan! I hope to get there later in the year. I’m currently in the Seychelles, that’s my dream destination…not so adventurous though, more of the sit at the beach all day kind of place!

  14. Wow! 40! My guess is Southern Chile. The desert area.
    Wherever you go it will be fantastic!!
    Happy Birth Day Earl!!!!

  15. A very happy birthday to you, Derek!!

    My guess is….. Somewhere in Africa.. more specifically South Africa?

    Have loads of fun!

  16. Congratulations! Thanks for all the great posts this year and well, for all the years really. You were the blog that pushed me over the edge and got me to try solo travel (which I love!!!)

    I’m going to say Spain. It is one of my favorite places and I didn’t see it on your list…if that is your place I don’t blame you! Don’t miss Seville!

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      Hey Ada – Thanks for that kind comment and I’m really happy to hear that you took that step to try solo travel and you now love it!! I wish you many more wonderful travels ahead! And while my destination right now is not Spain (I have been there before), that is certainly a great country to explore.

  17. TONGA!

    Wherever it is, enjoy every single moment, every day. 40 is a great milestone, it is an advanced beginning of this amazing journey through life. And remember: you are getting more experience being young!

  18. Hey Earl, Happy 40th to you!

    Thank you for all the articles you’ve given us throughout the years. You’ve definitely been inspiration for me to get out in the world and experience different cultures. I can still remember first finding your blog when I was planning my first trip to Central America 4 years ago now. I’ve been following along ever since.

    My guess for your dream destination is Brazil! Either way, happy birthday!

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      Hey George – I really appreciate that comment and I’m really just thrilled to know that the blog helped inspire you in some way. Here’s to many more brilliant adventures ahead! My current destination is not Brazil but I haven’t been there yet so I should get there at some point!

  19. My best wishes to you Derek!
    No matter where you going, be safe and have wonderful time!
    Happy Birthday to you!
    I guess it’s ITALY !

  20. Happy 40th!!!! I think I’m going to say Ireland, but that might be because I’m completely biased and it was my first living abroad experience.

  21. Holy Shit 40!!!! All the best my friend!

    Best guess……… Denmark

    So how I’m not very confident in my guess as I know how you love the warmer climates, but I’m excited to hear where you are going

  22. I haven’t followed your blog long enough to have a good sense of all the countries you’ve already visited, so I doubt I have much hope of guessing correctly. You’ve worked on cruise ships a lot, so it must be off the usual cruise ship itineraries.

    I’m going to say Fiji.

    And, having myself had a huge midlife crisis when I turned 40 (way back when….) I can confidently say you won’t have one. A mid-life crisis is the result of living a life where your dreams are on hold. If you are loving the life you’re living and living each day fully–as you seem to do–then there is no reason for a crisis. Enjoy your birthday! I toast you for living your dreams and encouraging others to do the same!

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      Hey Scott – Good guess but I was actually there a few years back. Still ranks as one of the most unbelievable destinations I have ever experienced!

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  23. I’ve been reading your post for a while,, I don’t remember you going to china,, and since its my dream destination – I’m going with that answer.. the orient express,, the terracotta soldiers, and the great wall…… have fun……

  24. Happy 40th WOW what a milestone. You are well preserved. My guess is mauritius,
    Wherever you are dont forget to enjoy your special day and the people you are with. MAKE memories and please lots of photos for us that are not in your dream destination.
    Regards llisa

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  25. I have no idea where but I do wish you a dream like 40th Birthday. Costa Rica? I really enjoy hearing from you about your travels and your story of following your heart inspires me to follow mine, thank you very much. You’d be an inspiring dad to have!

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  26. I’m going to Madagascar in Sept and Oct- with a wildlife photographer and my world traveling nephew who has been to more counties than I have and Madagascar will be my 155th. _ remember there are different ways of counting countries and I count the UK as four!

    So I shall add Madagascar as my guess.

    My perverse side wants me to suggest Cancun, Acapulco or Las Vegas. Disney World?

    Congrats and have a happy birthday.

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      1. Hi Derek, I’m going to North Korea in about three weeks so naturally it’s on my mind. The only way to really get a sense of life there is to go. I want to hear the voices and see the faces. My experience will be very limited but as my love Mimmy said about me “better than nothing”

  27. Using context clues and seeing posts from other fellow travelers bloggers. As well as your current location. I would have to say it is easily MADAGASCAR!! Can’take believe you’re 40 years old..travel does wonders for not showing age I suppose. Anyways, Happy Birthday and have a great time!!

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  28. BAHRAIN!!!!
    Happy birthday Earl in advance. here is hoping you don’t wake up one day and decide to quit traveling.
    may the rest of your life, be better than the previous….
    i would guess BAHRAIN is your dream destination.

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  29. Hey bro,

    Wherever you go, the fact you turn 40 is the milestone by itself. I wish you all the very best. When I turned 40 I celebrated it on Green Island, Cairns, Australia. However I believe your destination is Mauritius?

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  30. Iceland is my guess.

    Cingratulagions in your achievements as you reminisce your history! Happiest Birthday where ever you are!! Keep Wandering Earl !!

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