Toronto’s Caribana Festival Guide | Boat Parties, Mas, and OVO Fest

Headed to T.Dot to experience this Caribbean bonanza?! My fellow traveler, you’ve made a great decision. This colorful and joyous event welcomes all from near and far. I’ve put together this guide and itinerary to help you navigate through your first Caribana to have the best experience.

A few things you should note of beforehand:

  • BOOK YOUR TICKETS AND LODGING IN ADVANCE PPL. You can use this page to scope and book hotel packages in advance, but you’ll quickly notice that prime packages get booked quickly
  • Bring Canadian dollars (CAD)
  • The vendors in Toronto only accept credit cards/debit cards that have a chip
  • Central Toronto is super walkable, so there’s really no need to rent a car as long as you stay in or around the downtown/chinatown area
  • OVO Fest *tends* to fall towards the end of the same weekend as Caribana. So if you’re a Drake fan or Hip-Hop fan generally, plan accordingly. OVO Fest is the same Sunday – Monday as Caribana (and Canada treats the Monday as a holiday, off work)

Where to Stay in Toronto

You won’t go wrong with the Marriott City Centre Toronto Downtown. Not only were the room and amenities on point, but the location of this hotel is primo. The going rate for this hotel was around $400 CAD for Caribana weekend, but if you have a clutch corporate code, you might come up and score it for around $180 CAD.

How to Get Around in Toronto

Stay in the downtown area and walk, Uber/Lyft, or use the Metro. Most of the events are around the downtown area. Make sure to look up the address of the events to see where they are in relation to your lodging.

Can’t Miss Eats in Toronto

Thursday: Explore The Six

There are Caribana parties you can attend on Thursday evening but we decided to chill out on this day and explore Toronto. If you’re interested in going to these parties–you can find out about them here.

Start with a late lunch at Figo – Italian Restaurant in Downtown Toronto

Address: 295 Adelaide St W, Toronto, ON M5V 1P7, Canada

From Figo, we headed over to pick up our costumes for Friday Night Mas (more on this later). Upon returning to downtown, we explored the area on foot, stopped by the CN Tower, and made our way for an apertivo at SOCO Rooftop. This spot was a vibe and has an excellent view of the CN Tower if you’re looking for a photo op. Make sure to save some room for their Roti – it was delicious!

Address: 75 Lower Simcoe St, Toronto, ON M5J 3A6, Canada

Friday: Day Lit & Mas

Afternoon: Day Lit Pool Party

Day Lit is *THE* pool party to be at on Friday and you never know who will show up–last year they had French Montana (2018) and this year it was none other than Drake and LeBron James. Don’t wait to get your tickets or you’ll end up at the other, not-as-lit pool party, OASIS, as we did.

In the case you miss snagging tickets to Day Lit, Oasis is not a bad alternative. If you want to secure a spot for you and your squad, I recommend going when the event starts. We went to Oasis around 5pm and the line was already wrapped around the venue.

Book your tickets in advance on Caribana’s website. Prices increase over time. To give you a ball park: Day Lit started around $40 and went up to $100 before selling out/being exclusively available in a package. Oasis was available for $40.

Evening: Friday Night Mas

If it’s your first time doing Carnival–you may be wondering–what is Friday Night Mas? Mas is short for masquerade and it consists of organized costumes by band. Each band has it’s own semi truck strapped with sound equipment that drives around in a loop blaring soca and calypso music for everyone to run in the streets and dance to. This year, DBandit ran Friday Night Mas and if you haven’t played Mas before, this is the perfect opportunity. You will have the option to pick among 3 costumes for Friday’s event – think cowboy, 70’s, and Spartans. You will need to pick up your costumes prior to the event. Beer and Coolers are included in your ticket price of ~$100.

Saturday – The Parade

Caribana Costumes 2019
Caribana Costumes 2019

The parade starts at 8:30am for masqueraders and makes its way towards Lake Shore Blvd where the onlookers are watching around 12:00pm. It is quite the site to see and there are thousands of people gathered from all over the world to observe. Even if you’re not dressed in costume, you’re allowed to run and join the parade and dance along the various bands.

If you desire to be part of a band and be in costume, you must plan for this months in advance. You will want to make arrangements via the Caribana Official Website. Note that costumes for females will cost upwards of $1000. This is normal. You can have fun without, but I can’t speak to the fun you have with it.

There will be food and drinks to purchase around the parade, make sure to bring cash. We ended up leaving the parade early to get the BEST JERK CHICKEN EVER because the lines were too long at the event.

Around 4pm, make your way over to the Kensington Market – a landmark market in Toronto filled with restaurants, shops, and homes. Make a stop over at Rasta Pasta for bomb Caribbean barbecued Chicken.

Jerk Chicken from Rasta Pasta in Kensington Market

Address: 61 Kensington Ave, Toronto, ON M5T 2K1, Canada

We had tickets for an evening concert headlined by the king of soca music, Machel Montano called Carnival Kingdom. But the late night and the combination of being out in the sun all day really took it out of us. Carnival Kingdom was happening at a venue 45 mins away from downtown Toronto. I encourage you all to check the locations before purchasing the ticket and plan ahead for distant events.

For more photos from the parade, check this post here.

Sunday – Boat Life & OVO Fest

Sunday was all about the – Shorts & Shades Boat Ride. You’ll want to find your tickets on eventbrite. It cost around $40 for General Admission. This is a great way to capture a beautiful view of the city of Toronto and continue the Caribana weekend vibes.

Toronto City Views from the Shorts and Shades Boat Ride | Caribana 2019

Pro-tip! you’ll do good to get on this boat early if you want breakfast, because food runs out quickly! But honestly, it’s not that great so just eat at your hotel or wait to grab a roti afterward. The party itself is what you’re going there for.

If you’re into DIM SUM – then GET SUM at Rosewood Asian Cuisine in Chinatown. $30 for all you can eat.

Address: 463 Dundas St W, Toronto, ON M5T 1G8, Canada

If you’re a Drake fan, seeing him perform in his hometown is a Hip-Hop extravaganza like none other. This year was especially epic with the Raptors W in the NBA Finals, so the city was particularly buzzing with energy during the event. You can read all about the Top Moments at OVO Fest here.

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