SPECS

Who: Three People, Two Beds

Where: Toronto to Cancun, Mexico / Orlando, Florida / Barbados / San Juan, Puerto Rico / Montego Bay, Jamaica

When: Anytime between Saturday, February 16th and Sunday, February 24th, 2019

Budget Per Person: $1000.00

Notes: I’m just going to assume all of these are carry-on only flights, but SUCK IT UP! You’re going somewhere warm for cheap, you’ll manage with your teeny tiny clothes. Also, if you can’t find a third person OR have more people, just shoot me an e-mail to augment one of these trips to fit what you need.

Option 1: Cancun, Mexico

Flight: Toronto to Cancun, Mexico | February 17th – February 21st

$627.00 CDN: roundtrip (quick layovers)

Stay: AirBnB for three in Cancun | February 17th – February 21st

Option 1: $333.00 CDN ($111.00/per person); Good location, Looks nice, Pool, Great reviews

Option 2: $320.00 CDN ($106.67/per person); Looks great, Perfect reviews, Great location

Option 3: $418.00 CDN ($139.33/per person); Great location, Close to ferries, Pool, Looks nice, Great reviews

Option 4: $391.00 CDN ($130.33/per person); Place looks great, Pool, Central location, Perfect reviews

Option 5: $338.00 CDN ($113.00/per person); Great area, Close to stuff, Perfect reviews, Looks super cute

Total: Overall, if you go for the LEAST expensive options I posted it’s about $733.67 per person for the trip and for the MOST expensive options it’s about $766.33 per person for the trip.

Option 2: Orlando, Florida

Flight: Toronto to Orlando, Florida | February 18th – February 22nd

$469.00 CDN: roundtrip (quick layover)

Stay: AirBnB or Hotel for three in Orlando | February 18th – February 22nd

Option 1: $562.00 CDN ($187.33/per person); Great looking cottage, Good area, Perfect reviews

Option 2: $757.00 CDN ($252.33/per person); Close to Disney, Looks great, Perfect reviews

Option 3: $602.00 CDN ($200.67/per person); Looks big, Good location, Perfect reviews

Option 4: $493.16 CDN ($164.39/per person); Deluxe Room with Two Double Beds, Good location, Pool, Good reviews

Option 5: $629.59 CDN ($209.86/per person); Queen Room with Two Queen Beds, Breakfast included, Looks cute, Great reviews

Total: Overall, if you go for the LEAST expensive options I posted it’s about $633.39 per person for the trip and for the MOST expensive options it’s about $721.33 per person for the trip.

Option 3: Barbados

Flight: Toronto to Barbados | February 16th – February 20th

$729.00 CDN: roundtrip (layovers)

Stay: AirBnB for three in Barbados | February 16th – February 20th

Option 1: $426.00 CDN ($142.00/per person); Perfect reviews, Looks simple, Close to stuff

Option 2: $602.00 CDN ($200.67/per person); By the beach, Looks great, Awesome location, Perfect reviews

Option 3: $569.00 CDN ($189.67/per person); Close to transit, Perfect reviews, Looks cozy

Option 4: $550.00 CDN ($183.33/per person); Perfect reviews, Looks great, Close to transit

Option 5: $301.00 CDN ($100.33/per person); Quiet area of Island, Looks simple, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it’s about $829.33 per person for the trip and for the MOST expensive options it’s about $929.67 per person for the trip.

Option 4: San Juan, Puerto Rico

Flight: Toronto to San Juan, Puerto Rico | February 18th – February 23rd

$672.00 CDN: roundtrip (quick layovers)

Stay: AirBnB for three in San Juan | February 18th – February 23rd

Option 1: $480.00 CDN ($160.00/per person); Perfect reviews, Close to beach, Looks simple

Option 2: $560.00 CDN ($186.67/per person); Great location, Bed + Bunk bed, Looks cozy

Option 3: $542.00 CDN ($180.67/per person); Great reviews, Looks nice, Good location

Option 4: $708.00 CDN ($236.00/per person); By beach, Looks very nice, Perfect reviews

Option 5: $676.00 CDN ($225.33/per person); Bed + Sofa bed, Nice location, Looks good, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it’s about $832.00 per person for the trip and for the MOST expensive options it’s about $908.00 per person for the trip.

Option 5: Montego Bay, Jamaica

Flight: Toronto to Montego Bay, Jamaica | February 18th – February 23rd

$522.00 CDN: roundtrip (quick layovers)

Stay: AirBnB for three in Montego Bay | February 18th – February 23rd

Option 1: $566.00 CDN ($188.67/per person); Close to nightlife, Looks cozy, Perfect reviews

Option 2: $550.00 CDN ($183.33/per person); Looks great, Perfect reviews, Close to stuff

Option 3: $775.00 CDN ($258.33/per person); Good location, Looks nice, Perfect reviews

Option 4: $725.00 CDN ($241.67/per person); Looks great, Good location, Perfect reviews

Option 5: $940.00 CDN ($313.33/per person); Great balcony, Nice views, Great reviews, Looks cozy

Total: Overall, if you go for the LEAST expensive options I posted it’s about $705.33 per person for the trip and for the MOST expensive options it’s about $835.33 per person for the trip.

Extras: If you plan on using AirBnB for the first time, click here for a free credit towards your stay OR if you choose Booking.com for the first time click here for a free credit. Also, if you plan on using Uber for the first time, click here for a free credit towards the ride.

– Mirna 

I am not a licensed travel agent of Ontario and make itineraries as a hobby. Any itineraries used by readers are of their own free will and choosing. Site owner is not responsible for any misadventures, mishaps, airline issues or accommodation issues that occur on trip itineraries that are posted or individually e-mailed to readers.