Travel Memories: First Trips to Canada, Washington DC, Winning a Trip to Cancun

Note: This article is a compilation of several “travel memory” blog posts that have been combined here for archiving purposes.

Travel memory: First trip to Canada

queen street toronto

The first big trip in my since-destroyed travel van was a weekend getaway to Toronto with my friend Robin. This was also my first visit to Canada and my first couchsurfing experience.

We arrived late on a Friday night, sometime around midnight. I didn’t want to inconvenience my couchsurfing host, so after grabbing dinner and drinks (and being amused by Canada’s monopoly money), we slept in the van that first night. It seems silly in retrospect, but since it was our first CS experience, I didn’t want to get a bad review (“Inconsiderate guest didn’t show up until midnight…”)

canadian money

Somehow, we slept through my cell phone alarm, and when we woke up the next morning, I found that we had received a parking ticket. After 8:30, the street was meter parking, and the time was now 8:47. In that brief window, someone had ignored the two sleeping Americans in the back of the van and placed a citation on the window. I thought Canadians were supposed to be nice! They sure didn’t waste any time writing up that ticket.

Following that blow to our wallets, we headed over to the CN Tower, one of the city’s main tourist attractions.

cn tower

Unfortunately, it was the cloudiest day of the year, so we saw nothing from the top. We literally couldn’t even see the ground. It was pointless going up there, but we were eager tourists, so we paid anyway. Doh!

cn tower fog view

Wandering through some of the neighborhoods was a lot more fun. Our host directed us to areas like Kensington Market.

kensington market toronto

This was a quick trip. We didn’t have the time or money to fully immerse ourselves into the place. We didn’t take a ton of pictures. In fact, compared to my current travel style, where I run around like a madman to maximize my time in every city, this particular trip was very laid-back. Our host took us out to a couple of awesome restaurants and bars, but we didn’t take any pics there and the evening is a bit of a haze. We’ll all have to use our imaginations on that one.

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I wish Chicago trains were as colorful as this.

streetcar

I don’t think American businesses would dare to moon their customers the way these mannequins at Urban Outfitters did. Thumbs up for Canadian humor.

butt out urban outfitters

My favorite random discovery: Random blue sticks, which led to some artsy photos.

robin blue bars

The lingering feelings I had about Toronto were: 1) The city was very cool. 2) The people were not as cool as I expected. Oh, they were friendly and pleasant, and I liked them a lot, but they weren’t ‘cool’ in the hipster sense. They were a little behind the times in terms of trends and fashion. I remember being disappointed that Toronto wasn’t as edgy as Williamsburg in Brooklyn, as I had hoped. But in retrospect, that’s probably a good thing. Toronto is doin’ its own thing, and that’s fine.

I can’t wait to go back there next summer for the TBEX travel bloggers conference and get a better taste of the city.

Travel memory: Washington, D.C. as a kid

washington monument

My seventh-grade school trip to Washington, D.C. was the first big travel experience of my life. We went for three days and took tours of the major monuments. Except the White House – I still haven’t been inside there.

It’s hilarious looking back on the few surviving photos from the trip. This was way before digital cameras, so I had to take a cheapo 35mm cam with a 24-exposure roll of Kodak film. The pictures I got were dreadful – mostly blurry shots taken while I was walking.

What do I remember from this trip? A lot of odd memories. Singing Bon Jovi songs (“I’ll Be There for You”) in the big tour bus. Playing Paperboy in a video arcade at the rest stop just outside Maryland. Finally getting to D.C. and sharing a hotel room with four other kids and watching Guns N Roses’ “Patience” video on MTV.

I remember being at the top of the Washington Monument and enjoying the views. I took a few pics up there but they were all too blurry to be useful.

We stopped by the Lincoln and Jefferson Memorials. I’m sure we saw other important sights, but I couldn’t tell you what they were.

washington dc

Visit #2 to DC

One summer when I was 21, I was working as a counselor for a pre-college program at Penn State for high school students, and one of our weekend trips was to the capitol area to check out George Washington and Maryland Universities.

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Even though I was hearing great things about the DC nightlife, and I was now old enough to go to bars, our schedule did not allow us to do this since we were chaperoning the entire time. We were given one free night, about two hours, to wander around the reflecting pool. There wasn’t much to do, aside from people-watching and taking in the statues.

wash dc statues

Visit #3 to DC

In October, I’m going back to DC for the first time as an adult. I’ll finally get a chance to check out the nightlife, but I still want to see all those monuments too. They’re such iconic structures. I see them everyday when I count my $5s and $10s. It’s time to see them in person again.

It’s also gonna be cool to take the pulse of DC just a few weeks before the presidential election. I like being where the action is, so I have a feeling being in the middle of the battle will be fun.

What are your impressions of Washington D.C.? Do you have any suggestions of places I should check out while I’m there?

I once won a free trip to Cancun because my friend had a weak bladder

sombreros

“If I win, I promise to take you!”

I made this half-joking vow to my new friend Erin as we dropped our entry forms into the box at the movie theater on the South Side of Pittsburgh.

We had only known each other for a couple of months, having met on MySpace back in 2005 when people legitimately used social media sites to make new friends, as opposed to simply reconnecting with old ones (I miss those days…)

Erin and I went for a walk around the South Side one evening, with no real plans except to chat and hang out. At one point, she had to pee, so we ducked into the movie theater. While she went to answer nature’s call, I noticed a box on the ticket counter.

“Win a trip to Cancun! Win a trip to Punta Cana!”

Whatever, I thought. I had never won anything in my life, except for a plastic mug bearing the logo of my high school back in a 7th-grade school drawing. This contest appeared to be sponsored by a local radio station and the prize was a trip for two to the tropical destination of your choice.

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cancun resort

I had time to kill, so I grabbed the only writing utensil available, a dull pencil in my backpack. As I recall, I had to bite off some of the wood to get the lead to emerge so I could actually write with it.

I didn’t bother to fill out most of the form, because I didn’t want spam or junk mail coming my way. So I listed my name and phone number, but I ignored the email section and probably used a fake mailing address.

When Erin returned she filled out one too, and we agreed to take each other if one of us won. I completely forgot about the contest about two minutes after I walked out of the theater, and that was that.

Imagine my surprise a couple weeks later when I got a call from a guy at the radio station, informing me I was one of five finalists for the prize. To win, I had to compete in a scavenger hunt at the South Side Works that weekend.

I didn’t know what this scavenger hunt would entail, but assumed it would involve being given a list of items and having to run around and find the stores that sell them. So I spent the three days leading up to the contest going into every store in the mall, memorizing which items could be found in which places.

The day of the event, I sized up my four competitors. One young woman had just gotten married and was hoping to use the trip as her honeymoon. Her tearjerker story may have made her the sentimental favorite to those watching, but I was unmoved. I had a vacation to win!

cancun beach

(I think she ultimately finished second, by the way. How excruciating that must have been.)

It turns out that my advance studying was unnecessary. All we had to do was unscramble a list of store names, run to those stores and pick up a piece of paper from the register at each place, and run back to the starting point. As a fit young adult male, I had an unfair advantage.

I raced around the mall from store to store, and when I made it back to the start, I discovered I was the first one there. I had won! Because my friend had a weak bladder and I was a fast runner, I won a trip to Cancun!

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I called Erin to give her the good news, and over the coming weeks we planned our amazing vacation. Seven nights at an all-inclusive resort just south of Cancun.

I don’t even remember the name of radio station. Sorry, guys. But thanks for sending me to Mexico!

People really do win those things.

Visiting Memphis

Nat Geo Traveler recently praised its grassroots projects, sustainable restaurants, and emerging biking scene, while also mentioning Graceland and the National Civil Rights Museum, built around the former hotel where Martin Luther King Jr. was assassinated.

Memphis boasts numerous other music and historic attractions, including Sun Studio and the Stax Museum of American Soul Music. I have to concur with the selection of Memphis as one of the must-see places for this year.

About Quirky Travel Guy

Scott Shetler is a Seattle-based freelance writer & fan of indie rock, road trips, ice cream, squirrels on power lines, runaway shopping carts, and six-way intersections. Some posts on this site contain affiliate links, which may earn me a commission (at no extra cost to you) if you make a purchase.

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12 Comments

  1. My hometown! I`m happy you go to see Kensington, it`s one of my favourite parts of the city. But I hate to be the bearer of bad news, we have tons of hipsters in the city. They must have been hiding while you were here because of the grey weather.

  2. Hello Scott!
    Thanks for a lovely post on my hometown! I hope you can visit again and connect with someone who can give you a better and authentic hipser-y experience. Our indie trend is also slightly different from US, certainly so in the francophone areas. I see that you were at Queen west and Ossington, hopefully you will like it more next summer! Sorry for the ticket, you could apologise and get it reversed. 🙂
    cheers, Priyank.

  3. Okay this is really helpful! I’m headed to Toronto in a few weeks and all I’ve heard how cool the city is. I’ll be interested to see what the hipster scene is like. I love the ad on that train with all the #2s – looks cool.

    And I totally get you about wanting to be a good CS guest. I would’ve done the same thing.

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