Where in the World Would You Go With $25,000?

Tanzania - Ngorongoro Crater

Tanzania - Ngorongoro Crater

I never enter contests. The cynic in me says you never get something for nothing. Supermarkets want access to your buying history. Timeshares just want to sell you something you don’t need that you can’t afford. I never fill out any of those silly entry forms to be stuffed in a big box wrapped with gaudy paper. So I don’t know what possessed me to enter the $25,000 Dream Trip from Conde Nast a few months ago. Maybe it was just the millisecond of fantasy — where would I go if I could go anywhere in the world and spend $25,000 doing it? Maybe I was bored at work and was trawling through travel websites and daydreaming. Maybe my evil twin entered those photos.

Rome - Da Vinci Museum - Hall of Mirrors

Which one of my evil twins broke into my computer WHILE I WAS AT WORK and entered me into this contest?

I’ve always been a scrimp-and-save type person. A planner. Ultimately practical yet tenuously repressing a frivolous streak. I’ve gotten to about 60 countries so far and most of the time, it’s been by taking advantage of credit card promotions to rack up miles (while barely spending anything), signing up for annoying weekly newsletters for the chance to snag a once-a-year cheap flight somewhere or staying in barely habitable hotel rooms where sleeping on top of the covers is often preferable to under them. All of this while living on a meager salary in Cambodia for the last 10 years. I haven’t done too shabbily.

Kuala Lumpur - Tune Hotel - AC Credit

Literally a countdown clock of how much a/c I had left. So very sad.

So imagine my surprise when I came home to an email tonight saying that I was one of 25 finalists in Conde Nast’s Dream Trip thanks to this photo that I took in the Ngorongoro Crater, Tanzania. I checked the number of entries, and there were more than 21,000. Yeah, so some of them look like they were taken with an iPhone 3 after a drunken night out. But some of them look like the second coming of Ansel Adams. Seriously.

Conde Nast past winner

A past winner. A frozen lake in Mongolia. Really? I'm supposed to compete with this?

I barely even remember entering and certainly haven’t given it a second thought in the past three months. But right at this moment, I can’t breathe. I’m one 300 word essay away from a $25,000 customized trip of a lifetime, put together by the travel experts of the biggest travel magazine of them all. They come out with yearly Gold Lists. I always peruse and always come away acutely aware of the fact that I have never stayed in any of the properties listed. In my world, Holiday Inn is fancy.

Tune Hotel - Kuala Lumpur

My Kuala Lumpur hotel room. Literally the size of a bed. Toiletries cost extra. I stood outside the room to take this picture.

My last big trip at the end of 2011 was 3 months of traveling around the world, traipsing through Asia, New Zealand, Western and Eastern Europe, a transatlantic cruise followed by a Caribbean cruise and then a week in Hawaii and even with all that, I barely spent USD 10,000. I told you, I’m a bargain hunter. The around-the-world airfare was done through frequent flyer miles. I snagged a promotional round-trip flight to New Zealand for a little over USD 400, booked 11 months in advance. The 14 night transatlantic cruise was a last minute repositioning insanely priced at USD 499 + tax. If there was a coupon code, shared airport shuttle or intercity bus, you’d better believe that I took it.

Now that I have a whiff of a chance to spend $25,000 (or as my sister, always the pragmatist [aka Dream Killer], reminded me when I told her I was a finalist, “I wouldn’t get too excited. You haven’t won yet.”), I don’t know what to do with it. Splurge on a ridiculous Six Senses over-the-water villa somewhere where I could literally step off my balcony and dive straight into the water? Travel to some far-flung corner of the globe that would otherwise be impossible to get to? Trek to some swathe of Borneo jungle a la Birute Galdikas, searching for some elusive animal? Cruise around the Tahitian islands like 5 times in a row?

Maldives - Overwater Villas

In the words of Liz Lemon, "I want to go to there"

Now that I have to actually think about it, I honestly don’t know what I’d do or where I’d go. All I know is that I have 10 days to come up with the answer and will be pretty much useless to the outside world, trapped in an endless loop of my very own daydreams. Not that that’s a bad thing. After all, I think that’s what got me here in the first place. At least I’m pretty sure it was daydreaming. Or it could’ve been my evil twin.

Photo of Maldives villas by Pondspider, all others courtesy of the author and may not be used without permission.

What about you? Where in the world would you go if you had $25,000 and a travel expert to help you plan it? (And I promise I won’t steal your ideas… Well, most probably won’t.)

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14 thoughts on “Where in the World Would You Go With $25,000?

  1. Gwen Healy

    Where would I go, to the place where the Euphrates river becomes three, the Hiddekel,the Gihon, and the Pishon. The place where beauty is surpassing and peaceful. A place of wonder and imagination. I want to go home to the place where it all began for man and see what has become of it. is paradise lost or can it be found?

    1. James Post author

      Wow. Great choice. In search of the Garden of Eden, eh? And what would you do once there? A bit of archaeology, perhaps?

  2. The Pragmatist

    I would recommend going somewhere that you could never go in a million years if you had to pay for it. Maybe various countries in South America, Galapagos Island, Seychelles, or string together a series of exotic places like swimming in a lagoon at night where the things in the water light up like in a sci-fi movie? Or pick some of the most interesting landmarks in the world that you’ve never seen balanced with the best beaches you would like to go back or never been …

    1. James Post author

      I was kind of thinking of a best beaches in the world tour – Fiji, Bora Bora, Tahiti, Seychelles… But that seems a bit shallow. Although something my shallow self would definitely enjoy!

  3. Dyanne@TravelnLass

    “Travel to some far-flung corner of the globe that would otherwise be impossible to get to?”
    That gets my vote (with skipping ’round Borneo a close second.)

    “…Six Senses over-the-water villa”? Don’t be silly. Stepping off that balcony could get you a chunk of sea coral stuck in your head (or worse). But seriously, were it me at Six Senses, I’d be (and I’ll wager so would you) bored out of my skull in 5 minutes, no?

    Just tuned into FIF (as a direct result of your spelling lesson kindly left in the comments of my TravelnLass blog), and I’m loving it! You truly sound like my kind of traveler (shoestring penny-pinching, but has the good sense to know when to splurge on that flight over Everest.)

    Am I right? Or am I wrong? 😉

    O.k. now… where’d you hide the RSS feed button? Honestly, I don’t understand why more folks don’t offer/use RSS. I’d be lost w/o my Google Reader. I mean, they don’t call it “RSS – Real Simple Syndication” for nothing! So where IS it???

    Better yet, perhaps you can TELL me over an icy “Cha Da” here in Saigon sometime. Though it will have to wait til I return from Cambodia – hmmm… seems like you and I are playing musical (country) chairs here, yes? 😉

    1. James Post author

      Hey Dyanne!

      Yeah, I’m getting a lot of Antarctica suggestions via Facebook… Borneo. Hmmmm. I don’t know if that would cost $25,000. I’ve been already, but perhaps to see the orangutans would be nice.

      LOL re: Six Senses. But I’m surprisingly good at doing absolutely nothing. Plunk me in front of a gorgeous beach and come get me at nightfall. I’ll still be there, albeit a few shades browner.

      Sorry about the feed. It’s up now. This site just went live three days ago, and as you can see, there are lots of teething problems. Bear with me, I’ll get there…

      I’d love to chat over a drink. Let me know when you get back from Siem Reap and we’ll go out for an iced coffee. My treat!


      1. Olivia

        Simple. A luxury private charter sailboat with a gourmet chef and staff so well trained as to be virtually invisible. If the $25,000 lasted longer than a week or 5 days I would have to say that it wasn’t luxe enough.

        1. James Post author

          Hmmm. I think I saw that in an ill-advised Madonna movie once. It didn’t end up well for her. It’s the eternal question, isn’t it? Stretch it out and make it last or blow it in one hedonistic affair? And where would my private yacht be sailing to?

  4. Manjari Bhatnagar

    I will definitely travel all over India… This country is so diverse that every state differs from the others when it comes to languages, customs, rituals, lifestyle and traditional dresses. Moreover, there is no dearth of luxury… India rocks !!!

    1. James Post author

      Thanks, Manjari! I did consider India for its diversity. Every province could be a trip in and of itself. I just wasn’t sure how to spend $25,000 there! Maybe if I traveled for an entire year… But it’s on my list of places to go, for sure. Check back in 2 days to see where I chose. Now I just need to actually WIN. haha. Thanks for reading!


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