Seven Trips for Victoria Day Long Weekend 2024

SPECS

Who: Two People, One Bed (or Two)

Where: Toronto to Lisbon – Medellin – Havana – Chicago – Cancun – San Jose – Halifax

When: Thursday, May 17th – Monday, May 20th, 2024

Budget Per Person: Whatever I can find for a good price….


Option 1: Lisbon, Portugal

Flight: Toronto to Lisbon, Portugal | May 16th – May 20th

$808.00 CAD: roundtrip (direct)

Stay: Hotel or AirBnB for Two | May 17th – May 20th

Option 1: $808.00 CAD ($404.00/per person); Deluxe Double or Twin Room, 5-star place, Looks good, Pool, Great reviews

Option 2: $728.00 CAD ($364.00/per person); Double or Twin Room, Centrally located, Great reviews, Looks nice

Option 3: $570.00 CAD ($285.00/per person); Small, Looks good, Perfect reviews, Good location

Option 4: $1057.00 CAD ($528.50/per person); Looks great, Spacious, Perfect reviews, Popular place

Option 5: $570.00 CAD ($285.00/per person); Very popular place, Looks very nice, Great reviews

Total for Lisbon: Overall, if you go for the LEAST expensive options I posted it’s about $1093.00 per person for the trip and for the MOST expensive options it’s about $1336.50 per person for the trip.

I went to Lisbon a bit ago, if you want some ideas for what to get up to, click here.


Option 2: Medellin, Colombia

Flight: Toronto to Medellin | May 17th – May 20th

$571.00 CAD: roundtrip (quick layover)

Stay: Hotel or AirBnB for Two | May 17th – May 20th

Option 1: $467.00 CAD ($233.50/per person); Twin Room, 5-star place, Looks nice, Pool, Breakfast included, Great reviews

Option 2: $514.00 CAD ($257.00/per person); Standard Double Room with Two Double Beds, 5-star place, Great location, Breakfast included

Option 3: $905.00 CAD ($452.50/per person); Hot tub, Looks very fancy pants, Perfect reviews, Big place, Quieter location

Option 4: $221.00 CAD ($110.50/per person); Popular place, Pool, Looks nice, Great reviews

Option 5: $121.00 CAD ($60.50/per person); Great reviews, Very popular place, Good location, Looks cozy

Total for Medellin: Overall, if you go for the LEAST expensive options I posted it’s about $631.50 per person for the trip and for the MOST expensive options it’s about $1023.50 per person for the trip.

If you want to book some excursions in Medellin, click here.


Option 3: Havana, Cuba

Flight: Toronto to Havana | May 17th – May 20th

$445.00 CAD: roundtrip (layover)

Stay: AirBnB for Two | May 17th – May 20th

Option 1: $346.00 CAD ($173.00/per person); Popular place, Perfect reviews, Looks cute

Option 2: $235.00 CAD ($117.50/per person); Perfect reviews, Centrally located, Nice view

Option 3: $263.00 CAD ($131.50/per person); Very nice terrace view, Popular place, Perfect reviews, Looks spacious

Option 4: $247.00 CAD ($123.50/per person); Breakfast included, Centrally located, Very popular place, Perfect reviews

Option 5: $611.00 CAD ($305.50/per person); Nice ocean view, Looks very nice, Quieter location, Popular place, Perfect reviews

Total for Havana: Overall, if you go for the LEAST expensive options I posted it’s about $562.50 per person for the trip and for the MOST expensive options it’s about $750.50 per person for the trip.


Option 4: Chicago, Illinois

Flight: Toronto to Chicago | May 17th – May 20th

$371.00 CAD: roundtrip (direct)

Stay: Hotel or AirBnB for Two | May 17th – May 20th

Option 1: $1162.00 CAD ($581.00/per person); King Room with Sofa Bed, Breakfast included, Looks nice, Good reviews

Option 2: $1517.00 CAD ($758.50/per person); Traditional King Room: Awesome location, Great reviews, Looks great

Option 3: $1069.00 CAD ($534.50/per person); Very popular place, Looks really nice, Perfect reviews, Great location

Option 4: $799.00 CAD ($399.50/per person); Close to transit, Great reviews, Very popular place, Looks cozy

Total for Chicago: Overall, if you go for the LEAST expensive options I posted it’s about $770.00 per person for the trip and for the MOST expensive options it’s about $1129.50 per person for the trip.

I went to Chicago a bit ago, if you want some ideas for what to get up to, click here.


Option 5: Cancun, Mexico

Flight: Toronto to Cancun | May 17th – May 20th

$615.00 CAD: roundtrip (direct)

Stay: Hotel or AirBnB for Two | May 17th – May 20th

Option 1: $791.00 CAD ($395.50/per person); Standard Room Deluxe King, 5-star place, Pool, Great location, Looks very nice

Option 2: $467.00 CAD ($233.50/per person); Standard Double Room, Centrally located, Looks cozy, Breakfast included, Pool

Option 3: $430.00 CAD ($215.00/per person); Private small pool, Very popular place, Great reviews

Option 4: $567.00 CAD ($283.50/per person); Good reviews, Nice view, Looks good, Pool, Very popular place, By the beach

Option 5: $643.00 CAD ($321.50/per person); Quieter location, By the beach, Popular place, Great reviews

Total for Cancun: Overall, if you go for the LEAST expensive options I posted it’s about $830.00 per person for the trip and for the MOST expensive options it’s about $1010.50 per person for the trip.

I went to Cancun a bit ago, if you want some ideas for what to get up to, click here.


Option 6: San Jose, Costa Rica

Flight: Toronto to San Jose | May 17th – May 20th

$721.00 CAD: roundtrip (layover)

Stay: Hotel or AirBnB for Two | May 17th – May 20th

Option 1: $538.00 CAD ($269.00/per person); Superior Double Room, 5-star place, Pool, Breakfast and Dinner included, Looks fun

Option 2: $570.00 CAD ($285.00/per person); Deluxe Twin Room, Pool, Breakfast included, Great location

Option 3: $268.00 CAD ($134.00/per person); Popular place, Jacuzzi, Nice view, Perfect reviews

Option 4: $346.00 CAD ($173.00/per person); Looks very nice, Perfect reviews, Great location, Spacious

Option 5: $353.00 CAD ($176.50/per person); Very popular place, Great reviews, Pool, Looks super cute, Great location

Total for San Jose: Overall, if you go for the LEAST expensive options I posted it’s about $855.00 per person for the trip and for the MOST expensive options it’s about $1006.00 per person for the trip.

I went to San Jose a bit ago, if you want some ideas for what to get up to, click here.


Option 7: Halifax, Nova Scotia

Flight: Toronto to Halifax | May 17th – May 20th

$401.00 CAD: roundtrip (direct)

Stay: Hotel or AirBnB for Two | May 17th – May 20th

Option 1: $759.00 CAD ($379.50/per person); Deluxe Two Queen Beds, 5-star place, Quieter location, Breakfast included, Pool

Option 2: $871.00 CAD ($435.50/per person); Queen Room, Centrally located, Good reviews, Looks cozy

Option 3: $632.00 CAD ($316.00/per person); Perfect reviews, Great location, Popular place, Looks good

Option 4: $940.00 CAD ($470.00/per person); Looks very nice, Spacious, Good location, Perfect reviews

Total for Halifax Overall, if you go for the LEAST expensive options I posted it’s about $717.00 per person for the trip and for the MOST expensive options it’s about $871.00 per person for the trip.

I went to Halifax last year, if you want some ideas for what to get up to, click here.


– Mirna 

I am not a licensed travel agent of Ontario and make itineraries as a hobby. Any itineraries used by readers are of their own free will and choosing. Site owner is not responsible for any misadventures, mishaps, airline issues or accommodation issues that occur on trip itineraries that are posted or individually e-mailed to readers. Please research the Visa restrictions for your destination as well as the Covid entry requirements prior to booking.

Safe Travels! My Top 5 Safe Destinations For Women to Travel Alone

Bet some of you REALLY sick of waiting on others to get their shit together so you can travel right? I know those ones still. So now you’re in this situation like, ‘can I go there alone? am I going to be safe? is my self-imposed curfew going to be when the street light turn on?’ 

Relax. I got you. I’ve been traveling alone for almost 12 years now and I’ve managed to make it out in one piece. 

The first thing I will mention before going into this list is, if you are sick of your friends trying to get their funds together, get time off work etc. etc. etc. I made a blog post with a manifesto on how to go about traveling alone that you can read here. Also, I made a whole post about your biggest tool when traveling alone (and it can definitely apply to groups as well) – trusting your gut while traveling

Now let’s get into this list! 

All five weren’t necessarily somewhere I did travel to alone, however, I would definitely return to them alone at any given time.


#5: Somewhere super close, CHICAGO!

Before you start with the nonsensical media-only-fueled notions of Chicago – zip it. The amount of times I have endured the ‘omg you’re going to Chiraq?’ questioning is ridiculous at this point. I love Chicago. I have traveled there with a friend, I have traveled there alone twice and I love the place so much I even brought my boyfriend there last year for his 30th birthday. Not a single person I know that has actually stepped a foot in Chicago had anything negative to say about it. (Minus my friend Martha, who didn’t like Harold’s chicken. Disgrace.)

I found the mid-westerners to be incredibly nice and cordial. There was a couple of occasions where I was staring down at my Google-maps directions and a stranger would come up to me on the street and ask me if I’m lost and then offer their own directions. In the bars and restaurants I found locals to be really welcoming and nice to talk to. When I was at some breakfast place near my AirBnB two years ago for the NFL Draft, one of the servers sparked a conversation about NFL with me. I ended up sitting there for an extra hour with three other patrons AND that servers just talking NFL. 

Do not let the media dictate your opinions of Chicago. Go there, eat some pizza, go to the million sports events they have, go walk down the Magnificent Mile, make some friends at the bars (or on Tinder?) and yes, go to the South Side to get some Harold’s Chicken with mild sauce. Heck, lay down on a glass floor and have other tourists take pictures of you on it like I did in the header for this piece. 


#4: Somewhere super friendly, ST. MAARTEN!

This is the only place on this list that I didn’t travel to alone. I mean, the second I find a cheap flight back there I would gladly go there alone ASAP. This island was warm, fun and you just felt really good being there.

Between the really nice staff at every establishment we went to eat or drink at, to the amazing drivers and just overall friendly locals – I can’t imagine a friendlier place. When I saw ‘The Friendly Island‘ as a licence place I was like OKAAAAAAAAAAAY this is the place for me. As soon as my friend Lorren and I landed in St. Maarten one of the first cab drivers we had was so friendly and hospitable that when he found out if was my birthday the next day, he offered us a free ride to and from the nightclub we were going to. NO charge. When we went out the following day, he was there to pick us up and also to drop us off. Just as a kind gesture to some tourists.

Also, we made a friend on the beach in Philipsburg who was so cool he actually gave us a tour of the entire island (French + Dutch), got us into a nightclub for free, oh, and did I mention? Randomly let me drive his car because ‘you said you didn’t know how, so figured it’s a good time to learn.’  

Would be back on that island as soon as I can. The generosity and hospitality there is nothing like I have ever seen before. Well, except for my #1 place if you keep reading :). 


#3: Somewhere super touristy, CROATIA!

I guess for this country I would be a little biased, having spent a lot of time during my childhood there and having family that still lives there. But how could you not love and feel completely safe in a place like Croatia? It’s incredible there.

For any woman trying to enjoy beaches (ALL BILLIONS OF THEM IN CROATIA it feels like), get good food and just mingle with nice locals and tourists alike – Croatia is your spot. I’ve been to Croatia alone and although I’m fluent in the native language there, English would have been perfectly fine as well. The place has become a tourist haven so everyone speaks English, along with, German, French, Italian…. it is totally normal to meet people in the service industry in Croatia who speak 5+ languages. 

Croatia is so safe that they have nude beaches. Yes, you could go full buck nekkid and no one will even blink an eye at it. As someone coming from the suffocating censorship and body issues of the North American continent ESPECIALLY, you will feel liberated in Croatia. All body types and ages prance around on some of the nude beaches. Living the good life, no tan lines.


#2: Somewhere hella far, SINGAPORE!

I went to Singapore alone and was out wandering the streets at 2am on Christmas, drunk and eating tacos. What else do you need to know? Can a place possibly feel ANY safer than that? 

Singapore is the cleanest city I have ever seen. From their airport, to the transit system and to their incredible downtown waterfront. Doesn’t matter what time of day it is, there is young people everywhere walking around and enjoying life. Not bothering anyone and in fact, asking you to join in THEIR shenanigans instead. There was just so much to do as a lone traveler in Singapore that it almost felt like they were catering to my Snapchat feed. Everything was impressive. Everything was beautiful. Everywhere felt safe.

I wouldn’t suggest chewing gum or spitting on their streets if you’d like to keep your sense of safety, but otherwise it is a great place to roam alone. Just remember when you go to bring lots of money as the cleanliness and luxury you feel in that city definitely will cost you more.


#1: Somewhere exceptionally hospitable, CUBA!

My favourite place.

I have been to Cuba on numerous occasions with family, a boyfriend and alone. This is by far the country I feel safest in when visiting. From the people I made friends with there, to the staff at various resorts and casa particulars, to even the customs agents at the airport. For an overall sense of being welcome and safe – Cuba tops all the countries I’ve been to.

When I would travel to Santiago de Cuba alone, I would be out at all hours of the night. On several occasions I would ask the motorcycle taxi drivers to give me a ride into the center way past midnight. I would sit in a bar alone and just people watch from 1am to 3-4am in the center. I loved those moments. 

I realize some women complain about Cuba not feeling safe for them because of the men giving them too much attention. For me personally, I don’t mind the attention. I’ve learned to block it out. It just never bothered me as much as it does other people and I am not here to tell them how to feel. I just know that not one man that ever whistled or yelled ‘que linda!’ at me ever took it past that point. Whether I was out in the market, at a baseball game, at a nightclub or on a beach. I always feel safe when I am in Cuba.  If you are a woman trying to embark on your first solo trip – this would be an awesome place to start. 


Tell me readers, what country did you feel safest in? Leave a comment.

– Mirna

Chicago Baecation Recap

I love Chicago. 

I love Chicago the way I love Nutella. I just really can’t get enough of it and I like it in so many ways that it would take posts on posts to explain it properly. 

This past weekend was my fourth time going to Chicago. I went once with my best friend, another time to get my mind together after a breakup and a third time to go to the NFL Draft. This time I took my boyfriend on a little baecation for the weekend because I wanted him to have an awesome 30th birthday and also for him to see how incredible the windy city is. 


Friday, March 31st – Arrival

On Friday we went to Billy Bishop Airport and took a Porter Airlines flight to Midway. Flying from Billy Bishop is so much better than Pearson because as a downtown dweller it means less time spent traveling to the airport and more time enjoying the free snacks and water bottles at the airport (picture below). I also love flying with Porter! The people who work for them are always so nice and you get to drink and have snacks on the airplane at no additional cost. Also, their complimentary shuttle from downtown to the airport comes in handy. After much beer, wine and chips – we landed at Midway.

The subway system in Chicago may be a bit dated, however, I would choose their system over Toronto’s ANY DAY. I love the 3-day unlimited rides pass for $20 and I also love that both of their airports are connected to the subway. No extra fees or needing to take a special subway or bus, you just hop on the subway lines and can make your way downtown so easily. 

As we boarded the subway to our destination, we were accompanied by some gentlemen we had met on the Porter flight who were heading to Chicago for a wedding. We mentioned that it was my boyfriends birthday, at which time they handed him a bottle of Crown Royal to start drinking on the subway. I will neither confirm nor deny if this happened, as that may be considered lewd behaviour – to some. Not me.

We arrived to our hotel for the weekend, the Millennium Knickerbocker. This is an old school looking hotel in downtown Chicago. I loved everything about it. I booked the king room which was a nice size for the two of us and came with complimentary Wi-Fi and a very nice bathroom. In their lobby they even had a jazz band playing by the bar on the Friday evening which gave us the real feel of the history in the hotel. 

After relaxing for a little while in our room it was time to take my boyfriend to eat the most important meal in Chicago – deep dish pizza. I love deep dish pizza. I LOVE IT MORE THAN THAT THIN CRUST THING THEY SERVE YOU IN NEW YORK. Yes, I said it. I prefer Chicago deep dish pizza to that thin stuff in New York. We went to the closest Giordano’s we could find via Google maps. Upon arriving there was a bit of a wait, however, you can pre-order your pizza which takes 45 minutes to make anyways so it was at least being worked on while we waited for a table. 

I realize between Gino’s East, Lou Malnati’s and Giordano’s everyone has their own favourite pizzerias in Chicago and you can stick to whichever one you like best. For proximity and the massive screens they had both NBA and NHL on, Giordano’s was very good for us. This was the perfect meal to send us into a food coma and sleep to prepare for our busy Saturday.


Saturday, April 1st – Birthday

I thought I was going to sleep in on this weekend getaway, but as someone who has been waking up at 6am on weekends for the past three years – no chance. My boyfriend was still asleep and since it was officially his birthday I took a stroll to the hotels lobby to get some breakfast for us. Let me say this, holy shit breakfast at hotels is expensive. I know I should have just assumed that and maybe planned better, but I didn’t want to be gone long so I could surprise him as he woke up. I purchased the two breakfasts and made my way back up to the room and surprised him. The food was OK, not the worst breakfast I’ve ever had nor the best. At least the miniature jars of jam that it came with were really cute.

After lounging around for a little bit more, we started our walk to Navy Pier. The scenic route along Chicago’s Lake Shore Drive is always something to be delighted about, especially on a day where it was sunny and 15 degrees. My next birthday gift was a lunch boat cruise on the Spirit of Chicago. All I can say is WOW about the whole experience. The staff (shout out to our waitress Nicky) and the ambiance was incredible. The cruise came with a buffet lunch and a two hour ride on the water. I purchased some extras for our ride like the shrimp cocktail and also a window seat. Another thing we decided to purchase while on the boat was a 45-ounce rum punch drink. Yes, you read that right, 45 ounces. It didn’t even matter than we had a massive buffet lunch, once that rum punch hit we were both wavy. 

There was a DJ on the boat playing some music and people did dance, we saw some get down real hard to the Cupid Shuffle. Many people aboard were either celebrating birthdays or anniversaries and ALSO drinking that 45-ounce rum punch –  very jubilant crowd. 

As we disembarked from the cruise we were also handed freshly baked cookies by the staff and I was able to take my 45-ounce glass with me home as a souvenir. Overjoyed, and birthday boy was having a great day.

The plan after the cruise was to go shopping, that definitely did not happen. Due to the large consumption of alcohol we fell asleep in our hotel room for almost four hours. Wasted the afternoon, literally. When we woke up and realized it was evening and that the NCAA Final Four games were on, we decided to just order some food and watch those. 

Now it was time to party. I had read about there being a reggae lounge called The Wild Hare with live bands and a Twitter follower of mine had sent me a flyer for a hip hop club named The Evil Olive that also had a dancehall/afrobeats/soca room in the back. At the reggae lounge the cover was $10 and the crowd was definitely there for the vibes and food, not so much dancing. We stayed there for about 30-45 minutes taking in the wonderful singing on stage but we decided that we wanted to go dance and not just observe that evening. At this point we left for the hip hop club. 

Cover for me was $10 but for my boyfriend it was $20, also, he had a light sweater that he had to put in ‘mandatory coat check’ – odd. I was a bouncer for five years and had never witnessed a mandatory coat check, especially of a light sweater. This place was booming. The front had a large dancefloor with an elevated area for the DJ and many strobe lights. I hoped to walk through and hear Faneto, that did not happen. We went to the tiny room in the back that was designated for dancehall instead. 

This room was so small and the people were not even dancing. I loathe that there are so many people (men and women) who spend all this money to go out and look nice but do not dance and just spend the whole night Snapchatting themselves pretending to have fun. It was a strange thing to see as my boyfriend and I came there for the sole purpose of dancing. The DJ was OK, his choice of dancehall songs to mix was very odd. I would say he was maybe a notch above the dancehall selections top 40 clubs in Toronto play. Eventually some people began dancing (3am) but by 4am we were ready to leave and go to sleep. 


Sunday, April 2nd – Departure

On our final day in Chicago, I took my boyfriend to my favourite brunch place there called Yolk. I had been there numerous times on my previous trips and their red velvet french toast stuffed with cream cheese was calling my name. The place was very busy and we were eventually seated. The french toast was delicious and so was the raspberry lemonade that felt like it was being served by the liter. 

Following this large brunch we walked over to Millennium Park to do some touristy Chicago things. The Bean, the stage, the walkway to the Art Institute of Chicago and the front entrance of it. I wanted my boyfriend to see all the wonderful architecture that Chicago has to offer that is not inundated solely by glass structures of condos on condos on condos. (Sorry, Toronto)

Sadly it was time to return to Midway for our flight back to Toronto. I love that our hotel had a bag hold for no extra charge so we didn’t have to spend the day carrying our luggage around while sightseeing. After picking our bags up we hopped back on the Red Line and then the Orange Line to be on time for our 7:30 pm Porter flight. 


Overall, this was an awesome weekend getaway for both of us. He got to celebrate his birthday being inebriated on a boat and I got to eat more pizza. Most importantly, this was another person I had converted to loving Chicago. To understanding that there is more to Chicago than just media headlines. I hope to be back in July for my 5th time, so I can attend the Taste of Chicago!

– Mirna