Flair Vacations Announces Winter Packages To Mexico And The Caribbean
Toronto is on the schedule for all five destinations, with travel advisors central to the rollout.
Flair is putting more than flights on the winter itinerary. The Flair Vacations winter schedule brings together airline seats and resort stays in Mexico, the Dominican Republic and Jamaica, with five sun destinations announced for Canadian travellers.
The company’s September 18 announcement lists departures from Toronto, Montreal, Vancouver, Calgary and Edmonton. For Toronto readers, there is a useful distinction: Toronto (YYZ) is the only departure city in this initial schedule connected to all five destinations, a point also noted in Travelweek’s coverage of the announcement.
The packages will combine Flair Airlines flights with a growing selection of resort partners. The company says its official opening and full product list will be announced separately, so this is a first look at the program, not confirmation that every package is available to book.
What The Trade-First Approach Means
In this announcement, “trade-first” means building the program around travel advisors and their clients. Flair Vacations says it plans to meet with advisors, hear what they need and develop a resort lineup they can recommend.
“We know this industry runs on relationships, and that those relationships have to be earned,” said Nicole Bursey, president of Flair Vacations, in the announcement.
For someone planning a winter trip, that gives the announcement a practical angle: speak with your advisor about the destinations now, then ask for the exact hotel, dates and inclusions when the range opens for bookings.
The Full Winter Route Schedule
The initial program covers Cancun and Puerto Vallarta in Mexico; Punta Cana and Puerto Plata in the Dominican Republic; and Montego Bay in Jamaica. Here are all 15 origin-destination pairings listed in Flair Vacations’ September 18 announcement.
| Origin | Destination | Peak Weekly Flights |
| Toronto (YYZ) | Cancun (CUN) | 18 |
| Toronto (YYZ) | Punta Cana (PUJ) | 8 |
| Toronto (YYZ) | Montego Bay (MBJ) | 6 |
| Toronto (YYZ) | Puerto Vallarta (PVR) | 4 |
| Toronto (YYZ) | Puerto Plata (POP) | 2 |
| Montreal (YUL) | Cancun (CUN) | 7 |
| Montreal (YUL) | Punta Cana (PUJ) | 3 |
| Montreal (YUL) | Puerto Plata (POP) | 2 |
| Montreal (YUL) | Puerto Vallarta (PVR) | 1 |
| Vancouver (YVR) | Puerto Vallarta (PVR) | 9 |
| Vancouver (YVR) | Cancun (CUN) | 7 |
| Calgary (YYC) | Cancun (CUN) | 4 |
| Calgary (YYC) | Puerto Vallarta (PVR) | 3 |
| Edmonton (YEG) | Cancun (CUN) | 3 |
| Edmonton (YEG) | Puerto Vallarta (PVR) | 3 |
Source: Flair Vacations, September 18, 2026 announcement. Figures show peak weekly flight frequencies.
These are peak weekly frequencies, not guaranteed counts for every week of the winter season. Confirm the outbound and return dates for your trip.
Toronto Has The Widest Choice
Cancun leads Toronto’s schedule with 18 flights per week at the peak. Next comes Punta Cana with eight, followed by Montego Bay with six. Puerto Vallarta has four, while Puerto Plata has two. By comparison, Montreal has four destinations in the initial program. Vancouver, Calgary and Edmonton each have Cancun and Puerto Vallarta. Meanwhile, Montego Bay appears only under Toronto. Even so, more weekly flights do not confirm hotel availability or package length. Check the departure and return combination before requesting time off.
Puerto Plata Is The New Addition
Puerto Plata (POP) is the newest destination in Flair’s network and joins Punta Cana as the program’s second Dominican Republic option.
A separate flight announcement, reported by TravelPulse Canada, lists December 18, 2026, as the start date from Montreal and December 19 from Toronto. These are airline service dates; they do not confirm the first stay date for every vacation package.
What To Check Before You Book
The September 18 release does not list package prices, named resorts, trip lengths, baggage allowances or transfer arrangements. It also leaves the official opening date and full product list for a later announcement.In a separate Open Jaw interview published that day, Bursey described a two-stage rollout: airline sales first, followed by the Flair Vacations launch. An available airline ticket is therefore not proof that the new resort package range has opened.
When you request a quote, ask for the full breakdown:
- Dates and flights: Confirm both travel dates, airports and flight times rather than relying on the peak-frequency table alone.
- Resort and room: Ask for the property name, room category, meal plan and number of nights. “Vacation package” does not, by itself, establish an all-inclusive stay.
- Total cost and terms: Check the complete price, baggage, seat selection, airport transfers, payment deadlines and change or cancellation conditions. Ask which items are included and which cost extra.
What Comes Next
Flair Vacations says it will keep adding resort partners before winter. Next, watch for the full hotel list, package prices, sales opening date and confirmed departure options.
In the meantime, Toronto travellers can compare five destinations across Mexico, the Dominican Republic and Jamaica. Start with your preferred destination, then compare the actual hotel, dates and total cost when Flair Vacations releases the package details.
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