Weekly roundup
Hey Toronto! October's bringing some ridiculous flight deals...
Just finished my coffee and dove into this week's flight data. Super excited to share some of these places with you today. We've got everything from a 5-hour non-stop to Mexico for less than $300, to a European dream destination that costs almost the same as a domestic flight, plus an African adventure that's actually affordable.
Three totally different vibes, three incredible deals. These are the deals that caught my eye...
A tropical beach escape
Destination 1: 🇲🇽 Cancun, Mexico (49% off!) - A 1-week trip in December
Cancun might be known for spring break madness, but December is when this Caribbean coast really shines. It’s got the perfect beach weather without the crowds, ancient Mayan ruins you can explore, and some of the world's best cenotes (underground swimming holes) all within travelling.
Why now? December in Cancun = dry season begins + post-hurricane season calm + holiday vibes without the spring break chaos. Plus these prices from Toronto are absolutely ridiculous.
The Deal: CA$257 roundtrip from Toronto (Dec 1-7, Dec 6-12, or Dec 11-17)
49% savings – normally over $500!
Flair Airlines, non-stop, just 5 hours of travel time. That's it. No layovers, no hassles.
What's Special:
Perfect beach weather – 28°C days, 22°C nights, minimal rain
Cenote season – crystal clear water, perfect visibility for swimming
Mayan ruins exploration – Chichen Itza without the brutal summer heat
Insider Tips:
Dec 6-12 trip gives you weekend flexibility and avoids holiday rush
Book an all-inclusive outside the hotel zone – If you don’t wanna do any planning and want to eat unlimited Mexican food
Rent a car for day trips – cenotes and ruins are 1-2 hours away but totally worth it
Travel Time: Honestly, you can't beat 5 hours non-stop. You could literally have breakfast in Toronto and dinner on the beach.
Total Budget: CA$257 flights + $80-150/day (depending on all-inclusive vs independent)
Have you ever swum in a cenote? It's like swimming in liquid crystal – absolutely magical!
European charm
Destination 2: 🇵🇹 Lisbon, Portugal (47% off!) - A 1-week trip in October
Portugal's coastal capital is where old-world charm meets modern creativity. They have colourful trams climbing cobblestone hills, incredible seafood that costs half of what you'd pay elsewhere, and some of Europe's most stunning azulejo tiles covering everything from subway stations to historic buildings (if you're into architecture like that).
Why now? October in Lisbon is the perfect autumn weather + fewer tourists. Plus you're hitting shoulder season pricing on everything.
The Deal: CA$470 roundtrip from Toronto (Oct 25-31)
American Airlines, 1 stop, 12 hours travel time
47% savings – Usually $800-1200
What's Special:
Perfect autumn weather – 22°C days, crisp evenings, minimal rain
Shoulder season vibes – restaurants aren't packed, locals actually have time to chat
Incredible value – amazing food and wine at prices that'll shock you
Insider Tips:
Oct 25-31 perfect timing – avoids summer crowds but still warm enough for outdoor dining
Stay in Principe Real – trendy neighborhood with great restaurants and easy tram access
Try the pastéis de nata at the original spot in Belém – worth the tourist trap status better than the nova era ones we have here imo (shocker)
Total Budget: CA$470 flights + $70-120/day in city
Quick cultural note: Portuguese people are incredibly friendly – a simple "obrigado" (thank you) will get you smiles everywhere!
Book here for Oct 25-31
African Adventure
Destination 3: 🇿🇦 Johannesburg, South Africa (46% off) - A 1-week trip in December
Joburg (as locals call it) went from a gold rush town to Africa's economic powerhouse in just over a century. This is where you'll find incredible museums telling South Africa's complex history, some of the continent's best restaurants, and it's your gateway to safari adventures just a few hours away.
Why now? December in Johannesburg is when summer season begins + perfect safari weather. Plus you're hitting their high season for wildlife viewing.
The Deal: CA$1,217 roundtrip from Toronto (Dec 1-8 or Dec 5-11)
Air Canada/SWISS combo, 1 stop, 31 hours travel time vs 3 stops at 55 hours (avoid the 3-stop option – trust me)
46% savings – Usually around $2000-2500
What's Special:
Summer season energy – long days, warm weather, outdoor markets buzzing
Safari gateway – Kruger National Park is a 4-hour drive or 1-hour flight away
Rich history – Apartheid Museum and Constitution Hill are incredibly powerful experiences
Insider Tips:
Dec 1-8 has better timing – I wont lie the itinerary on this one isnt great (unless you have work you’d want to do in the comfort of an airport lounge) but the 31-hour option with 1 stop is way more manageable (has a 12 hour layover in Zurich). Dec 5-11 has a 22-hour layover in Montreal though if you want to make a trip out of it.
Book safari add-ons now – December is peak season, spots fill up fast
Stay in Maboneng – hip neighborhood with great nightlife and art scene
Total Budget: CA$1,217 flights + $60-100/day in city (not including safari add-ons)
Why December rocks: Perfect 26°C weather + peak safari season + South African summer vibes
Pro tip: The South African rand is really weak right now, so your Canadian dollars go incredibly far – dinner for two with wine can easily be under $30 CAD!
That’s it for this week.
Random thought: Isn't it wild how a $257 flight can completely change your December plans? That's like... two nice dinners in Toronto, but it gets you to the Caribbean instead.
Anyway – which destination made you start checking your vacation days? Hit reply and tell me! I genuinely love hearing which deals get people excited (plus your feedback helps me spot the good stuff for future newsletters).
Happy planning, and may you make the most out of your layovers! ✈️