Travel Memories: First Trips to Canada, Washington DC, Orlando, 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. Here’s my collection of travel memories.

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.

travel memories - cn tower
Toronto is one of my favorite early travel memories.

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.

I wish Chicago trains were as colorful as this.


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. Another cool one to add to the list of travel memories.

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

My second trip to Canada came later, with a journey to London, Ontario, and attractions like Banting House.

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.

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?

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


“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.

cancun resort travel memories

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!

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.

Travel Memory: My Week-Long All-Inclusive Stay in Cancun


After winning a free trip to Cancun several years ago, my friend Erin and I booked the week-long vacation for early November.

It turns out that Hurricane Wilma, a category 5 storm, ripped through the Yucatan Peninsula just a week before we were scheduled to fly there. Yikes! Several days’ worth of flights were canceled, but everything was back on schedule just in time for us to make the trip.

The best thing about this vacation in Cancun was that it was all-inclusive, meaning everything was paid for. All-inclusive vacations are really a cheap way to travel to Cancun since you don’t have to worry about unexpected expenses.

The resort restaurants and bars were open all day (and in some cases, all night), and we could go in and get unlimited meals and drinks for the entire week without paying a thing.

We spent a week bouncing around from Cancun to Tulum to Playa del Carmen. Unfortunately, we didn’t make it to the island of Cozumel, one of the best scuba diving spots in the Caribbean, but that’s on our bucket list for next time!

At the resort, we enjoyed the free fruity drinks for all!


Wine on tap?! I had never heard of such a thing.


In retrospect, I’m not sure why we didn’t just spend the whole week at the bars enjoying the free booze. Oh, wait, I remember. Because we spent it at the beaches instead.


Because of the hurricane, the resort was sparsely crowded. It was maybe 20% full, which meant that at most of the fancier restaurants, we were the only ones there.

The waiters would come up and ask, “You want tequila?” at every meal – even breakfast!


At one dinner, we were serenaded by a mariachi band.

The fake mariachi was almost as fun as the real thing.


And after the meals, it was back to the beach.


The laid-back week was the complete opposite of my current travel style, in which I cram as much as possible into a few short days.

The resort itself was spectacular.

vacation in cancun-resort

Everyday during the vacation in Cancun, we would find a gift from housekeeping – a towel twisted into a random animal shape. On this day, it was a swan.

hotel-bed cancun resort all-inclusive

This was my first experience with a minibar. Normally, I don’t touch these, because they’re so expensive. We weren’t sure if the minibar was part of the all-inclusive package, or if we would have to pay for anything we ate.

So on the first day, we drank just one bottle of Dos Equis. When we weren’t charged, we knew we had the green light to go nuts and empty it everyday, because it would be replenished the next day at no cost.


I did want to incorporate some cultural experiences into this trip, but because of the hurricane and ongoing clean-up efforts, many of the tours were canceled.

We were able to sign up for a tour of Mayan ruins near Tulum. After a short hike through the forest, we arrived at the ruins.


The steps on these ancient structures were very narrow, so they have installed a rope to aid visitors with their ascent.


Looking back down from the top.


We also visited a local Mayan community. More than 6 million Maya still live in Latin America today. Our guide was friendly with one particular family and invited us to catch a glimpse of their way of life.


Their way of life consisted of large families living together in small huts while turkeys, ducks and chickens roamed around.


Our guide told us that she gives the family a payment whenever she brings in tourist groups. So while it felt a little odd that their whole life was on display for all of us camera-wielding tourists, at least they were benefitting from the arrangement.


The tour company also offered a snorkeling tour in a cenote, a deep natural sinkhole teeming with wildlife.

Unfortunately, the snorkeling part of the tour was canceled, but we did get to stop by the cenote to see the turtles swimming around.

We also stopped at a market that had locally-made artwork for sale. Most of us just browsed, although one lady was an experienced haggler who scored a couple of deals.


Our resort was actually an hour outside Cancun, near the town of Akumal. So we didn’t get to spend time in Cancun proper, but we did get to have a somewhat urban experience when we boarded the local colectivo bus into the town of Playa del Carmen.


Playa Del Carmen had an active business district. I loved the store that sold gifts and novelties, like these skeleton dolls.


We stopped for an authentic Mexican meal.


The restaurant had a humorously mistranslated sign on the bathroom door.


And then it was back to the resort for some more lying around at the beach.


When we were tired of sitting at the beach, we moved back to the pool. The choice of where to spend our leisure time was so perplexing.


It was a really tough call, and you should feel sorry that we had to make such painful, agonizing decisions.


They even had little trams to drive us to the beach, in case we didn’t feel like walking. Talk about being spoiled!

cancun resort beach tram

We only got really crazy with the drinks on the last night, when we went to one of the resort nightclubs and freely accepted the complimentary tequila.

I remember spending some time on the dance floor trying to communicate in Spanish with these guys who only spoke Italian. Good times.

This blurry pic from the club is one of my few memories from the evening.


The good times ended on the flight home the next morning, when we were both borderline sick. Under normal circumstances, this might have been a miserable experience, but because there were fewer than 20 people on the plane, we got to stretch out and sleep it off.

The scariest thing about the plane was the “dinner” – some sort of microwaved box of food. I’ve never had another actual meal on a plane so I don’t know if this is what they all look like.

vacation in cancun - plane food

Other random memories from the trip: Watching South Park on the hotel tv with Spanish words dubbed over the original voices; being amused by the sight of spider monkeys on leashes in neighborhoods; wandering through backstreets of Playa Del Carmen and having more than one local ask us if we wanted to buy pot; wondering if they had dyed the water in the ocean because it was so clear and blue and there were so few fish.

Cancun was fun, and it instilled in me a burning desire to travel that has not subsided yet!

For more Mexico content, check out my visits to the Tequila Museum in Mexico City, the beaches of Zipolite and Mazunte, visiting Puerto Vallarta on a budget, a small-town Mexican cemetery, and tips for taking Uber and taxis in Tijuana.

Travel Memory: My Teenage Vacation in Orlando

Disney World Orlando travel memories

While I spend the next few months staying put in Chicago and saving up for Alaska, I want to start sprinkling in some “travel memory” stories of trips I took a while back, way before I ever had the blog.

Unlike many frequent travelers, I did not have the good fortune of traveling as a child. Up until I graduated high school, I had only left the Pennsylvania-Ohio-West Virginia tri-state area once, for a school trip to Washington DC.

But at age 18, I took my first flight with a friend to Orlando, where we stayed for two weeks with his aunt, checked out the Disney parks, and got seriously sunburned.

We went to the Disney parks, visited nearby areas like Kissimmee and St. Augustine, had fun lying in the sun, and participated in some outdoor activities.

That trip was many years ago, but I have a few lingering memories. The highlights and lowlights, accompanied by some shoddy old photos:

Travel memories: Disney World

Many of our days were obviously spent at Disney World, where my friend’s aunt worked. I remember wishing they had more thrill rides. The only one to speak of was the Tower of Terror at MGM Studios, a free-fall elevator ride.

The Animal Kingdom was closed, so we primarily spent time at Epcot and the Magic Kingdom. I loved the World Showcase section with different pavilions representing different countries.

Since I had no international travel experience, visiting the Japan and Germany and Norway pavilions was the next best thing!

I also have a strange lingering memory of getting the shaved Italian ice from the Vietnamese stand nearly every day. I loved that stuff.

The sunburn

Having never been south of the Mason-Dixon line, I had no idea just how fast the sun could fry your skin. We had a sweet swimming pool the backyard where we stayed, and one afternoon I spent an hour out there with no sunblock.

I ended up getting a burn so bad it hurt for the next two weeks. Oops!

Orlando sunshine weather activities pool

The MTV game show

Back in the ‘90s MTV had a game show called Sandblast, which was sort of American Gladiators on the beach.

We stumbled upon a taping of the show, and they put us in the audience for a couple rounds, until we decided the delays between filming were too excruciating and left. It was probably the shortest audience cameo ever.

I have no idea whether we actually made it onto TV because I never saw the episode air. Even now, I’m unable to find a single clip of this show online. Didn’t anybody tape Sandblast on their VCR? All I could find was this short commercial for the show on YouTube.

St. Augustine

We took a day trip up to historic St. Augustine but didn’t have the greatest time. We took a walking tour of historic houses, but found it so boring that we ditched midway through.

I don’t know if it was truly that boring, or if our young selves just didn’t appreciate what we were seeing.

The highlight was seeing a parked car with a license plate holder from Beaver Falls, Pennsylvania – our small hometown! We did not expect to see that in Florida.

After that, we swung over to the beach on our ride home. That was my first time seeing the ocean and being on a real beach (unless you count Lake Erie.)

So many people in the middle of the country never get to see the beach – I hope those who had beach vacations as kids realize how lucky they were.

St. Augustine beach - Orlando things to do

The AA baseball game

We couldn’t go to the Disney theme parks everyday, because my friend’s aunt only had free passes for three days per week. So we had to make our own fun.

One night we checked out the local AA baseball team in action. A few of those players ended up making the major leagues, so we can say we saw them before they hit it big.

(At the time, they were an affiliate of the Chicago Cubs, so they were known as the Orlando Cubs. These days, they’re known as the Orlando Rays, due to their affiliation with the Tampa Rays.)

But the memorable part of the game was the usher who looked exactly like OJ Simpson. I couldn’t believe the resemblance. I guess I wasn’t alone, because later in the game, the guy did this skit where he pretended to try on a leather glove. Smart move by that guy, incorporating the OJ theme into his act! I’m sure he got bigger tips as a result.

Since that first visit to Orlando, I’ve been all over the state of Florida, checking out the alligators at the Everglades, camping at Dry Tortugas National Park, finding things to do on a lazy morning in Key West, and exploring Miami’s beaches and architecture and Calle Ocho in Little Havana.

After I became a travel blogger, I passed through St. Augustine again on a road trip from Orlando to Savannah, Georgia!

Travel memories: Have you ever been to Orlando?

Travel Memory: That Time I Saw an Andrew W.K. Concert Inside a Tiny Record Store in Vancouver

Woohoo, it’s an Andrew WK concert! As a huge music fan and budget traveler, one of my favorite things to do in big cities is look for in-store performances, where bands play free shows in local record stores to promote their music.

I’ve seen Iron & Wine at Amoeba Records in L.A., the Duchess & the Duke at Reckless in Chicago, and Carbon Leaf at Easy Street in Seattle.

Neptoon Records
Neptoon Records in Vancouver, where I saw an epic Andrew WK concert.

A couple years ago, I found myself with time to kill in Vancouver and checked the local weekly to see if anything was going on.

Amazingly, there was a late-afternoon free concert at Neptoon Records by Andrew W.K., who was the original party rocker long before LMFAO came around. Joining Andrew were the Evaporators, a punk band led by the endearing weirdo known as Nardwuar.

Neptoon is Vancouver’s oldest independent record store. I was excited to check out this gig!

Seeing the Andrew WK Concert at Neptoon Records

I got there early, which proved to be a smart move, as the place filled up beyond capacity, which was only 150 people at most. A large group of people got stuck outside.

Once the show began, Nardwuar and Andrew WK delivered an awesome collection of rabid two-minute songs. Nardwuar decided to crowd surf, which in the small store put him perilously close to the ceiling. Gotta love those punk rockers, living on the edge!


Andrew WK is the genius behind hits like “I Love NYC” and “Party Hard.” He had everyone in the crowd pumping their fists and shouting along.

andrew wk

What can you do at 4 pm on a Tuesday that would be more fun than this? The Andrew WK concert is the enduring memory of my first trip to Vancouver.

Since then, I’ve gone back to check out places like the totem poles at Stanley Park.

Meeting Andrew WK years later

Funnily enough, several years after this, when I was a music journalist, I attended Riot Fest in Chicago and got to meet Andrew WK in the media tent.

It was cool to see how things came full circle from initially seeing him in such a tiny record store. His performance there was just as manic, even though it was on a much bigger stage.

Note: If you’re up for a guessing game, see our collection of 90 Photo Teasers, where you try to identify the location in the photos. Here’s a collection of ridiculous SkyMall catalog items, and a collection of link roundups.