Warm winter escapes, checked by hand for Canadians. Prices below are in Canadian dollars, per person, unless a fare is marked as a round-trip flight-only price. We have not added anything to these prices — the final price is always shown on the booking page before you pay.
Book the pieces yourself
Prefer to build your own trip? Start with flights, a hotel, or an experience — you check out on the partner’s own secure website.
Puerto Plata, Dominican Republic
Source: Sunwing | From: Toronto | Stay: 7 nights, all-inclusive
- Cofresi Palm — $1,235 CAD per person — Jan 26, 2027
- Lifestyle Tropical — $1,285 CAD per person — Jan 26, 2027
- Casa Marina Sosúa — $1,365 CAD per person — Dec 15
- Marien — $1,395 CAD per person — Dec 15
Checked Oct 28, 2026 — prices change fast, final price is on the booking page.
Punta Cana, Dominican Republic
From: Toronto | Stay: 7 nights, all-inclusive
- Sunwing Whala Bavaro — $1,735 CAD per person — Dec 15. Source: Sunwing.
- WestJet Vacations via Flight Centre, Bahia Principe — $1,789 CAD per person — Dec 4 (was $1,939). Source: Flight Centre.
See this deal on Sunwing See this deal on Flight Centre
Checked Oct 28, 2026 — prices change fast, final price is on the booking page.
Cancun & Riviera Maya, Mexico — Price benchmark only
Source: Air Canada Vacations | Stay: 7 nights, all-inclusive, including flights
- From $1,239 CAD per person — Montreal (Oct 28)
- From $1,419 CAD per person — Toronto (Oct 31)
- From $1,589 CAD per person — Edmonton (Nov 3)
- From $1,829 CAD per person — Vancouver (Jan 12)
Use these figures only as a sense of what a similar package was listed at on Oct 28. Do not treat them as available prices.
Check current sun listings on Travelzoo Canada
Checked Oct 28, 2026 — prices change fast, final price is on the booking page.
Puerto Vallarta, Mexico
Source: Air Canada Vacations via redtag | From: Toronto | Stay: 7 nights, all-inclusive
From $1,109 CAD per person — Nov 22
Please read this plainly: unusually deep lead-in price (was $2,759) — best-case fare, expect most dates higher.
Checked Oct 28, 2026 — prices change fast, final price is on the booking page.
Jamaica
Source: redtag | Stay: 7 nights, all-inclusive, to Negril
- Edmonton to Negril — $1,479 CAD per person — Dec 7
- Toronto to Negril — $1,491 CAD per person — Nov 23
Checked Oct 28, 2026 — prices change fast, final price is on the booking page.
Los Cabos, Mexico
Source: redtag | Stay: 7 nights, all-inclusive, entry resorts
Edmonton — $1,474 CAD per person — Nov 22
Checked Oct 28, 2026 — prices change fast, final price is on the booking page.
Flight-only deals — sample fares
These are sample fares, dates limited. The final fare depends on the exact dates you choose, and is shown by the airline or booking partner before you pay.
- Toronto–Cancun, Flair — $363 CAD round trip, nonstop — sample dates Oct 30–Nov 21
- Vancouver–Bangkok — $674 CAD round trip, including a checked bag — Nov–Mar
- Toronto–Fort Lauderdale, Porter — $226 CAD round trip — Dec–Jan, excluding Christmas/New Year
Checked Oct 28, 2026 — prices change fast, final price is on the booking page.
Sales ending soon
- Escapes.ca “Sun or Treat” — up to 64% off, as advertised by Escapes.ca — Ends Oct 31, 2026. Book by Oct 31, 2026. See the Escapes.ca offer and check its terms on the source page.
- WestJet Vacations Royalton — up to $400 savings per room, as advertised by WestJet Vacations — Ends Oct 31, 2026. Expires Oct 31, 2026. See WestJet Vacations and check its terms on the source page.
When to go
The cheapest windows are usually the first two weeks of December and mid-January. Christmas/New Year and March Break are the most expensive times to travel, so if your dates are flexible, those quieter windows are worth checking first.
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- S — Secure Booking: you check out on the partner’s own secure website.
- A — Affordable, With Nothing Added: prices are shown by the partner before you pay, and booking through us costs the same as booking direct.
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