Prince Edward Island used to be the pinnacle of my vacation dreams. When I was a kid, all my friends and their families flocked there for sunshine, beaches and good, wholesome, squeaky-clean family fun. You’d stick the kids in the van, listen to Abba and drive all the way there. In my mind, PEI was as foreign as Japan.

When Cailin and I did our road trip to Guysborough, it wasn’t until late in the evening when we decided to give PEI a whirl because I needed to live out some childhood fantasies. We had to take the 12.9 kilometre beast of a Confederation Bridge. It was terrifying. I screamed. (Cailin has it on video.)

PEI has kickass tourism, maybe the best in Canada. The whole island goes through great lengths to please tourists and they do a damned good job. They even hired Regis & Kelly last year to visit and film on the island, garnering the interest of people worldwide and creating revenue that exceeded the predicted profit by more than $22-million.

On the other hand, when you show up in late September when tourism season is officially over, everything is already shut down. You become that tourist, the weirdo walking around Cavendish Beach in a raincoat during a storm. Worth checking out that beach, by the way. It has red sand.

The whole province comes with the subtitle “The Gentle Island.” (Something I learned: Never, ever refer to Newfoundland as “the island.” Prince Edward Island people will hunt you down and CUT YOU.) They stick to this wholesome, family image with a vengeance. When you first cross the bridge, you’re met immediately with the famous Cow’s ice-cream stop, boutique shops and endless references to Anne of Green Gables. I hate that redheaded bitch, but more on that later.

After an impromptu lobster dinner at Cailin’s uncle’s house where he insisted on giving us Road Rockets, we pulled up at Hostel HI Backpacker’s Inn in Charlottetown late in the evening. We scored discounts for being bloggers and were treated like celebrities. We loved it.

We took our beers and settled into the hostel’s ridiculously awesome games room: an outdoor shed with pool table, vintage video games and a huge stack of records. I sat next to a friendly German who had spent over a year travelling Canada and had fallen in love with the place. She had been to every province and every TERRITORY…but not Newfoundland. I cried and handed her my business card.

Levi, the lovable 20-something hostel owner, challenged me to a game of Pac-Man. If I won, I’d get a free room for the night. I didn’t. Two other young chaps joined in for a beer, along with two Australians, and before we knew it we had a fantastic little crew assembled.

For such an extremely tiny town, Charlottetown has a rocking nightlife. Cailin and I were separated from the group and sat at a table in a pub being accosted by old men until finally our friends showed up, including the 7-feet tall Aussie. The old men scattered like cockroaches.

Naturally, we went bar hopping. On a Wednesday night. In Charlottetown. We went to the sleezebag Velvet Underground, loaded up on platters of cocktails, and drank until the bar shutdown at 2 a.m. Then we went back to the hostel and carried on. Yes, we were THOSE backpackers.

I don’t know what happened to our friends. Cailin and I awoke the next morning, room spinning, and figured it was time to get the hell out of PEI. We just had one last, required, classic island stop: the Anne of Green Gables house.

I’m sure Anne was a darling, sweet girl for her time. But all I remember is reading one quote as a child (I can’t for the life of me find it anywhere) about how she hated her red hair, and I’ve carried an ongoing grudge since then.

I wanted to check out the famous house where Lucy Maude Montgomery wrote her bestselling books anyway. The house is set up like it would be back be in Anne’s day, and then there’s the Haunted Woods and an agricultural barn museum thrown in the mix. The whole thing was both creepy and amusing: it’s like she actually exists, and people freaking worship her. At any rate, it worked. I bought the first book, tried on a wig and teared up a little during the video presentation.

And upon further investigation, I’ll forgive her anti-redheaded stance based on this quote alone:

“Isn’t it splendid to think of all the things there are to find out about? It just makes me feel glad to be alive–it’s such an interesting world. It wouldn’t be half so interesting if we know all about everything, would it? There’d be no scope for imagination then, would there?”

– Lucy Maud Montgomery, Anne of Green Gable

If that doesn’t speak the traveller’s language, I don’t know what does.