Winter is coming, and so is the annual pilgrimage. Every year when the first real cold snap hits the GTA, half of Scarborough starts pricing out flights to somewhere with palm trees. For winter 2026-27, the Toronto to Caribbean map has real changes: a batch of brand new direct routes, one carrier going bigger than anyone, and one major destination where service has essentially collapsed. Here is the full picture, verified against airline announcements from 2026.
The biggest story: Porter goes all in on sun
The single largest Toronto-Caribbean growth story this winter is Porter Airlines. The carrier announced four new sun destinations in April 2026, then added a fifth, growing its winter sun capacity by more than 150 percent over last winter, with nearly 5,000 sun-destination flights planned this season. All of it flies on Porter’s 132-seat Embraer E195-E2 jets, which means no middle seats, free Wi-Fi, and complimentary wine and beer.
The new Toronto (YYZ) routes:
- Aruba (AUA): starts October 30, 2026, up to five times weekly. First time Porter has served Aruba.
- Montego Bay, Jamaica (MBJ): starts November 23, 2026, up to five times weekly. A new carrier on one of Toronto’s busiest Caribbean corridors.
- Providenciales, Turks and Caicos (PLS): starts November 6, 2026, five times weekly Tuesday through Saturday. Announced June 11, 2026.
- San Jose, Costa Rica (SJO): starts December 2, 2026, up to four times weekly. Central America rather than the Caribbean, but squarely in the sun market.
- Los Cabos, Mexico (SJD): starts November 16, 2026, up to three times weekly.
Porter’s Montego Bay and San Jose launches were noted as subject to regulatory approval at announcement time, and both appear to be proceeding, but it is worth a quick check when booking.
Porter’s existing YYZ sun routes also continue: Cancun and Nassau run daily at peak, alongside Puerto Vallarta, Grand Cayman and Liberia, Costa Rica.
The other new routes
Air Transat to Martinique. This is the sleeper pick of the season. Air Transat launches Toronto to Fort-de-France, Martinique (FDF) twice weekly starting December 19, 2026. It is seasonal from Toronto, while the route runs year-round from Montreal and Quebec City. Martinique is French Caribbean, creole culture, incredible food, and historically awkward to reach from Toronto without a connection. Not anymore.
Air Canada to Roatan. Air Canada starts Toronto to Roatan, Honduras (RTB) on Sundays from December 13, 2026 through April 11, 2027. This is the first time Air Canada has ever served Roatan. Honduras sits on the Caribbean coast, so it counts for the sun crowd, and it opens up one of the Caribbean’s best diving destinations to a direct flight.
Air Canada also continues flying Toronto to Port of Spain, Trinidad (AC1898/1899 on the 737 MAX, a few times weekly), and added new sun routes from other Canadian cities this winter, including Montreal to Aruba and Halifax to Barbados.
The big cut: Cuba
Here is the honest bad news. Cuba is the one Caribbean market where Canadian capacity has been cut for winter 2026-27, and the situation is genuinely confusing.
Air Canada suspended all Cuba flights in February 2026 during the island’s fuel crisis, ferrying roughly 3,000 customers home on empty outbound legs. It then postponed resumption to November 1, 2026. Air Transat halted Cuba flights the same month, and by September 2026 that suspension was being described as indefinite, with the carrier taking a roughly $35 million quarterly hit and drawing on a $250 million federal loan. The WestJet group paused its Cuba operations too, and a June 2026 report had Air Canada, Sunwing Vacations Group and Air Transat all suspending Cuba indefinitely, contradicting the earlier resume dates.
Bottom line: whether anyone is actually flying Toronto to Cuba this winter is not verifiable from published sources as of late September 2026. If Cuba is your plan, verify directly with the carrier before you book anything, and note that Canada’s travel advisory for Cuba remains in effect.
What is continuing
The workhorses are all still running. Caribbean Airlines continues its heavy Toronto to Port of Spain service, with schedule data showing multiple daily non-stops on the 737 MAX 8, and combined with Air Canada the route sees roughly 14 non-stop flights a week. Punta Cana, Cancun and Montego Bay remain served by multiple carriers. WestJet extended Toronto to Puerto Plata to year-round service, so it is no longer seasonal, and Flair’s new vacation program flies Toronto to Cancun, Punta Cana, Montego Bay, Puerto Vallarta and Puerto Plata at peak weekly frequencies.
One thing to get right: Sunwing Airlines no longer exists. Its final commercial flight operated May 28, 2025, and all narrowbody operations were unified under WestJet. Sunwing Vacations continues as a tour-operator brand, but the flights are now WestJet aircraft and crews. If you book a Sunwing Vacations package to Montego Bay or Punta Cana this winter, you are flying WestJet.
The route table
Destination | Airline(s) from YYZ | Frequency | Status |
|---|---|---|---|
Aruba (AUA) | Porter | Up to 5x weekly from Oct 30, 2026 | NEW |
Montego Bay, Jamaica (MBJ) | Porter | Up to 5x weekly from Nov 23, 2026 | NEW (carrier); route continuing on other airlines |
Providenciales, Turks and Caicos (PLS) | Porter | 5x weekly, Tue-Sat, from Nov 6, 2026 | NEW |
Fort-de-France, Martinique (FDF) | Air Transat | 2x weekly from Dec 19, 2026 | NEW |
Roatan, Honduras (RTB) | Air Canada | 1x weekly, Sun, Dec 13, 2026-Apr 11, 2027 | NEW |
San Jose, Costa Rica (SJO) | Porter | Up to 4x weekly from Dec 2, 2026 | NEW |
Puerto Plata, DR (POP) | WestJet, Flair | 1x weekly year-round (WestJet); 2x weekly peak (Flair) | EXTENDED to year-round |
Port of Spain, Trinidad (POS) | Caribbean Airlines, Air Canada | ~14x weekly combined (per schedule data) | Continuing |
Punta Cana, DR (PUJ) | WestJet, Air Canada, Air Transat, Flair | Multiple daily combined | Continuing |
Nassau, Bahamas (NAS) | Porter | Daily at peak | Continuing |
Grand Cayman (GCM) | Porter | Continuing (frequency unverified) | Continuing |
Cuba (all airports) | Air Canada, WestJet, Air Transat | Suspended since Feb 2026 | CUT; resumption unverified |
No direct Toronto service to Grenada, St. Lucia or Guyana was found in published sources. Do not assume those routes exist.
What about fares
Airlines did not publish round-trip lead-in fares for most of the new routes in the announcements reviewed. What exists is directional: search-engine snapshots put Toronto to Port of Spain around US$420 round trip on Air Canada in late September 2026, with December the priciest month to fly the route. Treat fare snapshots as rough guides, not guarantees.
Booking tips for this winter
- For peak December to February Caribbean travel, book three to six months ahead. For shoulder months like November, March and April, six to eight weeks is usually enough.
- The new once- or twice-weekly routes (Roatan on Sundays, Martinique twice weekly) have thin inventory. Book early or accept the schedule the airline gives you.
- Tuesday departures tend to price cheapest and Saturday returns best on routes like Toronto to Port of Spain, per fare search data.
- On the new Porter routes, the E195-E2 has no middle seats, so even the cheapest economy seat is more comfortable than the standard narrowbody squeeze. Worth knowing if you are price comparing against ultra-low-cost carriers.
The takeaway: this is the most new Caribbean capacity Toronto has seen in a single winter in years, led by Porter, with Martinique and Roatan as the genuinely novel destinations. Just do not build your winter around Cuba until an airline confirms it is actually going back.
Sources: Porter Airlines press releases (Apr and Jun 2026), Air Canada winter schedule announcements via Travelweek, PAX News and Open Jaw (Apr 2026), Air Transat winter announcements (May 2026), WestJet media room, Travel Industry Today on the Sunwing integration (Feb 2026), Flair Vacations winter program (Sep 2026), Carib Journal, flightmapper and Trip.com schedule data (Sep 2026).
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