Caribbean

Toronto to Varadero Trip Itinerary

SPECS

Who: Two People, Two Beds

Where: Toronto to Varadero, Cuba

When: Thursday, June 13th - Thursday, June 20th, 2019

Budget Per Person: $500ish

Notes: Pretty sure this is carry-on only pricing.


Flight: Toronto to Varadero | June 13th - June 20th

$394.00 CDN: roundtrip (direct)

Stay: AirBnB for Two | June 13th - June 20th

Option 1: $236.00 CDN ($118.00/per person); Looks big, Cozy, Perfect reviews, Popular place

Option 2: $166.00 CDN ($83.00/per person); Close to beach, Perfect reviews, Looks cozy

Option 3: $219.00 CDN ($109.50/per person); Perfect reviews, Close to stuff, Looks cute

Option 4: $208.00 CDN ($104.00/per person); Popular place, Great location, Looks cozy, Perfect reviews

Option 5: $171.00 CDN ($85.50/per person); Close to beach, Perfect reviews, Looks cozy

Total: Overall, if you go for the LEAST expensive options I posted it's about $477.00 per person for the trip and for the MOST expensive options it's about $512.00 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.

Los Angeles to Punta Cana: Group Trip

SPECS

Who: Four People, Two Beds

Where: Los Angeles to Punta Cana, Dominican Republic

When: Tuesday, September 17th - Tuesday, September 24th, 2019

Budget Per Person: $700.00 USD


Flight: LAX to Punta Cana | September 17th - September 24th

$422.00 USD: roundtrip (quick layovers)

Stay: AirBnB or Hotel for Four | September 18th - September 24th

Option 1: $854.00 USD ($213.50/per person); Looks amazing, Close to beach, Great location, Perfect reviews

Option 2: $1131.72 USD ($282.93/per person); Superior Queen Room, Beach, Looks nice, All-inclusive

Option 3: $630.30 USD ($157.58/per person); Double Room with Pool View, Looks good, Breakfast included, Good location

Option 4: $666.00 USD ($166.50/per person); Pool, Looks like a beautiful home, Perfect reviews

Option 5: $484.00 USD ($121.00/per person); Close to beach, Pool, Looks beautiful, Perfect reviews

Option 6: $889.00 USD ($222.25/per person); Place looks huge, Pool, Great reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $543.00 per person for the trip and for the MOST expensive options it's about $704.93 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.

Toronto to Dominica Carnival (Mas Domnik) 2020

SPECS

Who: Four people/Two Beds, Two people/Two Beds

Where: Toronto to the island of Dominica for Mas Domnik 2020

When: Wednesday, February 19th - Wednesday, February 26th, 2020

Budget: Whatever I can find for cheap....

Notes: This might be carry-on only? Also, no solo option for this trip - go find some friends dammit.


Flight: Toronto to St. Maarten | February 19th - February 26th

$524.00 CDN per person; roundtrip (quick layovers)


Flight: St. Maarten to Dominica | February 19th - February 26th

$386.00 CDN per person; roundtrip (direct, plenty of time before and after SXM flight)

 

Stay: AirBnB for four | February 19th - February 26th

Option 1: $880.00 CDN ($220.00/per person); Close to center, Looks great, Perfect reviews

Option 2: $755.00 CDN ($188.75/per person); Looks big, Nice view, Quiet area, Great reviews

Option 3: $1801.00 CDN ($451.75/per person); Pool, Looks great, Perfect reviews

Option 4: $767.00 CDN ($191.75/per person); Place looks pretty damn big, Perfect reviews, Nice views

Option 5: $716.00 CDN ($179.00/per person); Pool, Looks nice, Great views, Perfect reviews

 

Stay: AirBnB for two | February 19th - February 26th

Option 1: $450.00 CDN ($225.00/per person); Big place, Good location, Perfect reviews

Option 2: $545.00 CDN ($272.50/per person); Bed + Sofa bed, Hammock, Looks cozy, Great reviews

Option 3: $732.00 CDN ($366.00/per person); I think this a place for hippies, Pool, Looks rustic, Great reviews

Option 4: $505.00 CDN ($252.50/per person); Bed + Sofa bed, Looks simple, Good location, Perfect reviews

Total: For four you're looking at between $1089.00 CDN and $1361.75 CDN per person for the trip. For two you're looking at between $1135.00 CDN and $1276.00 CDN 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.

Toronto to Antigua: Group Trip

SPECS

Who: Four People, Two Beds

Where: Toronto to Antigua

When: Sunday, June 2nd - Sunday, June 9th, 2019

Budget Per Person: $800.00


Flight: Toronto to Antigua | June 2nd - June 9th

$476.00 CDN: roundtrip (direct)

Stay: AirBnB for Four | June 2nd - June 9th

Option 1: $1248.00 CDN ($312.00/per person); By beach, Looks great, Perfect reviews

Option 2: $881.00 CDN ($220.25/per person); Close to beach, Looks cozy, Good reviews

Option 3: $751.00 CDN ($187.75/per person); Nice looking place, Nice view, Perfect reviews

Option 4: $648.00 CDN ($162.00/per person); Perfect reviews, Looks rustic, Quiet area

Option 5: $790.00 CDN ($197.50/per person); Close to stuff, Looks cozy, Perfect reviews

Option 6: $1279.00 CDN ($319.75/per person); At ocean, Looks great, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $638.00 per person for the trip and for the MOST expensive options it's about $795.75 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.

Los Angeles to Barbados: Baecation

SPECS

Who: Two People, One Bed

Where: Los Angeles to Barbados

When: Monday, September 9th - Monday, September 16th, 2019

Budget Per Person: $750.00 USD


Flight: LAX to Barbados | September 9th - September 16th

$442.00 USD: roundtrip (quick layovers, add $60 if you want checked-in luggage)

Stay: AirBnB for Two | September 10th - September 16th

Option 1: $548.00 USD ($274.00/per person); Awesome location, Close to beach, Looks super cute, Perfect reviews

Option 2: $416.00 USD ($208.00/per person); Pool, Looks cozy, Close to stuff, Perfect reviews

Option 3: $513.00 USD ($256.50/per person); Looks great, Close to food, Perfect reviews

Option 4: $474.00 USD ($237.00/per person); Pool, Perfect reviews, Quiet area, Looks cozy

Option 5: $615.00 USD ($307.50/per person); By beach, Looks fun, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $650.00 per person for the trip and for the MOST expensive options it's about $749.50 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.

Toronto to Grenada: Group Trip

SPECS

Who: Four People, Two Beds

Where: Toronto to Grenada

When: Thursday, September 12th - Thursday, September 19th, 2019

Budget Per Person: $750.00

Notes: Pretty sure this is carry-on only pricing.


Flight: Toronto to Grenada | September 12th - September 19th

$451.00 CDN: roundtrip (quick layover)

Stay: AirBnB for Four | September 12th - September 19th

Option 1: $1131.00 CDN ($282.75/per person); Beautiful home, Close to center, Nice balcony, Perfect reviews

Option 2: $848.00 CDN ($212.00/per person); Centrally located, Nice views, Perfect reviews

Option 3: $1136.00 CDN ($284.00/per person); Good location, Looks cute, Perfect reviews

Option 4: $794.00 CDN ($198.50/per person); Nice looking place, Quiet area, Perfect reviews

Option 5: $876.00 CDN ($219.00/per person); Perfect reviews, Great location, Looks cozy

Option 6: $831.00 CDN ($207.75/per person); Very nice looking place, Pool, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $649.50 per person for the trip and for the MOST expensive options it's about $735.00 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.

New York to Havana: Solo Trip

SPECS

Who: One Person, One Bed

Where: New York to Havana, Cuba

When: Saturday, October 5th - Saturday, October 12th, 2019

Budget Per Person: $500.00 USD

Notes: Pretty sure this is carry-on only pricing.


Flight: JFK to Havana | October 5th - October 12th

$320.00 USD: roundtrip (layovers)

Stay: AirBnB for One | October 5th - October 12th

Option 1: $172.00 USD; Great reviews, Good location, Looks nice, Nice terrace

Option 2: $140.00 USD; Looks super cute, Great reviews, Great location

Option 3: $173.00 USD; Great area, Perfect reviews, Looks cozy, Has Wifi

Option 4: $131.00 USD; Place looks huge, Perfect reviews, Great location

Option 5: $122.00 USD; Great location, Perfect reviews, Looks cozy

Total: Overall, if you go for the LEAST expensive options I posted it's about $442.00 for the trip and for the MOST expensive options it's about $493.00 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.

Toronto to Barbados: Group Trip

SPECS

Who: Four People, Two Beds

Where: Toronto to Barbados

When: Monday, June 10th - Monday, June 17th, 2019

Budget Per Person: $600.00


Flight: Toronto to Barbados | June 10th - June 17th

$401.00 CDN: roundtrip (direct)

Stay: AirBnB for Four | June 10th - June 17th

Option 1: $700.00 CDN ($175.00/per person); Great location, Pool, Looks super cute, Perfect reviews

Option 2: $676.00 CDN ($169.00/per person); Looks very nice, Close to beach, Pool, Good reviews

Option 3: $535.00 CDN ($133.75/per person); Perfect reviews, Looks cozy, Close to beach

Option 4: $688.00 CDN ($172.00/per person); In quiet area of island, Cottage, Beautiful sea view, Perfect reviews, Looks cozy

Option 5: $757.00 CDN (189.25/per person); Good location, Looks cozy, Close to beach, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $534.75 per person for the trip and for the MOST expensive options it's about $590.25 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.

Miami to Aruba: Baecation

SPECS

Who: Two People, One Bed

Where: Miami to Aruba

When: Thursday, May 16th - Wednesday, May 22nd, 2019

Budget Per Person: $400.00 USD

Notes: Pretty sure this is carry-on only pricing.


Flight: MIA to Aruba | May 16th - May 22nd

$153.00 USD: roundtrip (direct)

Stay: AirBnB for two | May 16th - May 22nd

Option 1: $298.00 USD ($149.00/per person); Looks cozy, Great reviews, Close to beach

Option 2: $345.00 USD ($172.50/per person); Great location, Close to beach, Perfect reviews, Looks cute

Option 3: $316.00 USD ($158.00/per person); Close to downtown, Looks cozy, Perfect reviews

Option 4: $447.00 USD ($223.50/per person); Nice looking place, Close to beach, Perfect reviews

Option 5: $458.00 USD ($229.00/per person); Pool, Good area, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $302.00 per person for the trip and for the MOST expensive options it's about $382.00 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.

Toronto to Havana Trip Itinerary

SPECS

Who: Two People, Two Beds

Where: Toronto to Havana, Cuba

When: Sunday, May 19th - Friday, May 24th, 2019

Budget Per Person: $550.00

Notes: Pretty sure this is carry-on only pricing.


Flight: Toronto to Havana | May 19th - May 24th

$469.00 CDN: roundtrip (direct)

Stay: AirBnB for Two | May 19th - May 24th

Option 1: $150.00 CDN ($75.00/per person); Great location, Looks nice, Perfect reviews

Option 2: $136.00 CDN ($68.00/per person); Nice looking home, Great terrace, Great location, Perfect reviews

Option 3: $168.00 CDN ($84.00/per person); Great area, Perfect reviews, Looks super cute

Option 4: $124.00 CDN ($64.00/per person); Looks simple, Great location, Perfect reviews

Option 5: $129.00 CDN ($64.50/per person); Super cute looking place, Great location, Looks great, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $533.00 per person for the trip and for the MOST expensive options it's about $553.00 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.

Toronto to Punta Cana: Big Group Trip

SPECS

Who: Six People, Three Beds

Where: Toronto to Punta Cana, Dominican Republic

When: Friday, June 14th - Friday, June 21st, 2019

Budget Per Person: $1000.00

Notes: Pretty sure this is carry-on only pricing.


Flight: Toronto to Punta Cana | June 14th - June 21st

$580.00 CDN: roundtrip (direct)

Stay: AirBnB or Hotel for four | June 14th - June 21st

Option 1: $1240.41 CDN ($206.74/per person); Privilege Condo Beach Club Access, Looks great, Breakfast included, Pool

Option 2: $2483.21 CDN ($413.87/per person); Three Bedroom Suite, Very nice place, Beach, Breakfast included, Great reviews

Option 3: $1786.00 CDN ($297.67/per person); 2 x Double Room with Pool View, Breakfast included, Looks good, Great reviews, Good location

Option 4: $1559.00 CDN ($259.83/per person); By beach, Looks beautiful, Pools, Great reviews

Option 5: $2111.00 CDN ($351.83/per person); Great view, Pool, By beach, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $786.74 per person for the trip and for the MOST expensive options it's about $993.87 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.

Toronto to Bonaire: Baecation

SPECS

Who: Two People, One Bed

Where: Toronto to Bonaire

When: Wednesday, July 24th - Wednesday, July 31st, 2019

Budget Per Person: $1000.00


Flight: Toronto to Bonaire | July 24th - July 31st

$598.00 CDN: roundtrip (quick layovers, carry-on only)

Stay: AirBnB for Two | July 24th - July 31st

Option 1: $622.00 CDN ($311.00/per person); Looks super cute, Great location, Perfect reviews

Option 2: $700.00 CDN ($350.00/per person); Central location, Seafront, Looks cozy, Perfect reviews

Option 3: $603.00 CDN ($301.50/per person); Close to beach, Has hammock, Looks cozy, Perfect reviews

Option 4: $532.00 CDN ($266.00/per person); Simple, Big, Good area, Perfect reviews

Option 5: $608.00 CDN ($304.00/per person); Good location, Great reviews, Looks chill

Option 6: $633.00 CDN ($316.50/per person); Outside the center, Looks very nice, Big, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $864.00 per person for the trip and for the MOST expensive options it's about $948.00 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.

Toronto to Cayman Islands: Quickie Group Trip

SPECS

Who: Four People, Two Beds

Where: Toronto to Grand Cayman, Cayman Islands

When: Monday, May 6th - Saturday, May 11th, 2019

Budget Per Person: $800.00

Notes: Pretty sure this is carry-on only pricing.


Flight: Toronto to Grand Cayman | May 6th - May 11th

$423.00 CDN: roundtrip (quick layovers)

Stay: AirBnB for four | May 6th - May 11th

Option 1: $1349.00 CDN ($337.25/per person); Looks great, Perfect reviews, Pool, At beach

Option 2: $1446.00 CDN ($361.50/per person); Great location, Close to stuff, Looks very nice, Perfect reviews

Option 3: $1106.00 CDN ($276.50/per person); Place looks big, Perfect reviews, Quiet area

Option 4: $1467.00 CDN ($366.75/per person); Bed + Sofa bed, Close to 7-Mile beach, Perfect reviews

Option 5: $1250.00 CDN ($312.50/per person); Looks great, Perfect reviews, Good area

Total: Overall, if you go for the LEAST expensive options I posted it's about $699.50 per person for the trip and for the MOST expensive options it's about $789.75 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.

Toronto to Reggae Sumfest 2019

SPECS

Who: Four people/Two Beds, Two people/Two beds

Where: Toronto to Montego Bay, Jamaica

When: Saturday, July 13th - Saturday, July 20th, 2019

Budget Per Person: $1000ish

Note: Reggae Sumfest 2019 will be taking place between July 14th - July 20th and if you want to purchase tickets, or get more information about it, that can be found hereAlso, I have no affiliation with the organizers of this event, I just do this because a lot of people requested cheaper alternatives for travel and after watching that incredible Buju concert? I can see why you’d want to attend this just to see him.


Flight: Toronto to Montego Bay | July 13th - July 20th

$678.00 CDN per person; roundtrip (direct, carry-on only)

Flight: Hamilton to Montego Bay | July 13th - July 20th

$450.00 CDN per person; roundtrip (direct, price WITH checked-in luggage)

 

Stay: AirBnB for four in Montego Bay | July 13th - July 20th

Option 1: $1357.00 CDN ($339.25/per person); Place looks very big, Nice, Good area, Perfect reviews

Option 2: $1432.00 CDN ($358.00/per person); Perfect reviews, Looks nice, Good area

Option 3: $1068.00 CDN ($267.00/per person); Very good location, Looks great, Perfect reviews

Option 4: $1402.00 CDN ($350.50/per person); Pool, Looks fancy pants, Good location, Perfect reviews, Bed + 2 Sofa Beds

Option 5: $948.00 CDN ($237.00/per person); In a gated community, Looks great, Perfect reviews, Good location

 

Stay: AirBnB for two in Montego Bay | July 13th - July 20th

Option 1: $512.0 CDN ($256.00/per person); Good size, Quiet area, Looks cozy, Great reviews

Option 2: $571.00 CDN ($285.50/per person); Perfect reviews, Looks big, Good location

Option 3: $733.00 CDN ($366.50/per person); Has a pool, Great location, Looks cute, Perfect reviews

Option 4: $501.00 CDN ($250.50/per person); Close to beach, Looks nice, Perfect reviews, Great location

Option 5: $682.00 CDN ($341.00/per person); Good location, Simple, Perfect reviews

Total: For four you're looking at between $687.00 CDN and $1036.00 CDN per person for the trip. For two you're looking at between $700.50 CDN and $1044.50 CDN 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.

Toronto to St. Maarten: Baecation

SPECS

Who: Two People, One Bed

Where: Toronto to St. Maarten

When: Thursday, June 13th - Tuesday, June 18th, 2019

Budget Per Person: $1000.00

Notes: I believe this is carry-on only. Should also note, one of the (many) awesome things about St. Maarten is you can take a ferry and visit the beautiful Anguilla, the expensive St. Bart’s and little Saba island while there!


Flight: Toronto to St. Maarten | June 13th - June 18th

$420.00 CDN: roundtrip (quick layovers)

Stay: Hotel or AirBnB for Two | June 13th - June 18th

Option 1: $1021.80 CDN ($510.90/per person); King Studio, At beach, Looks great, Great reviews

Option 2: $682.74 CDN ($341.37/per person); Lower Lobby Studio, Looks super cute, Beach, Great reviews

Option 3: $929.99 CDN ($465.00/per person); Junior Suite, Oceanfront, I stayed here and loved it, Awesome location

Option 4: $963.59 CDN ($481.80/per person); Deluxe Studio with Sea View, Great looking place, Nice views

Option 5: $620.00 CDN ($310.00/per person); Perfect reviews, By beach, By nightlife, Looks cozy

Option 6: $575.00 CDN ($287.50/per person); Simple, Close to beach, Perfect reviews, Close to transit

Total: Overall, if you go for the LEAST expensive options I posted it's about $707.50 per person for the trip and for the MOST expensive options it's about $930.90 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.

Toronto to Turks and Caicos: Quickie Group Trip

SPECS

Who: Four People, Two Beds

Where: Toronto to Turks and Caicos

When: Wednesday, April 3rd - Sunday, April 7th, 2019

Budget Per Person: $1000.00

Notes: Pretty sure this is carry-on only pricing.


Flight: Toronto to Turks | April 3rd - April 7th

$496.00 CDN: roundtrip (direct)

Stay: AirBnB for four | April 3rd- April 7th

Option 1: $1959.00 CDN ($489.75/per person); Looks huge, Looks nice, Great location, Perfect reviews

Option 2: $1505.00 CDN ($376.25/per person); Bed + Sofa bed, Pool, Looks very nice, Perfect reviews

Option 3: $997.00 CDN ($249.25/per person); Big place, Quiet area, Looks simple, Great reviews

Option 4: $1481.00 CDN ($370.25/per person); Great looking home, Good location, Great reviews

Option 5: $1512.00 CDN ($378.00/per person); Great location, Looks nice, Big, Close to Grace Bay, Great reviews

Option 6: $1316.00 CDN ($329.00/per person); Bed + Sofa bed, Looks cute, Quiet area, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $745.25 per person for the trip and for the MOST expensive options it's about $985.75 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.

Toronto to Barbados: Baecation

SPECS

Who: Two People, One Bed

Where: Toronto to Barbados

When: Wednesday, June 12th - Monday, June 17th, 2019

Budget Per Person: $700.00

Notes: I realized that only because I like staying in one particular area of Barbados, doesn’t mean everyone does so the locations of the AirBnB’s are all over the island - not just the Gap.


Flight: Toronto to Barbados | June 12th - June 17th

$477.00 CDN: roundtrip (direct)

Stay: AirBnB two in Barbados | June 12th - June 17th

Option 1: $376.00 CDN ($188.00/per person); Awesome location, Looks cozy, Perfect reviews

Option 2: $413.00 CDN ($206.50/per person); Nice views, Looks peaceful, Perfect reviews

Option 3: $300.00 CDN ($150.00/per person); Very simple, Close to airport, Perfect reviews

Option 4: $376.00 CDN ($188.00/per person); Looks super cute, Close to beach, Perfect reviews

Option 5: $376.00 CDN ($188.00/per person); Very nice views, Perfect reviews, Looks great, Quiet area

Option 6: $301.00 CDN ($150.50/per person); Close to beach, Perfect reviews, Looks big

Option 7: $339.00 CDN ($169.50/per person); Right at the beach, Great location, Looks cozy, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $627.00 per person for the trip and for the MOST expensive options it's about $683.50 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.

Toronto, Miami and New York to Trinidad Carnival 2020

SPECS

Who: Four people/Two Beds, Two people/Two beds

Where: Toronto, Miami and NY to Trinidad Carnival

When: Wednesday, February 19th - Wednesday, February 26th, 2020

Budget: Whatever I can find for cheap....

Note: I did flights from all three cities in their respective currencies, but the stays are only in Canadian Currency. For what it’s worth - that means you know it’ll cost you less because US Currency is higher. Also, in about three-four weeks I know Copa Airlines will release their flights for the NY and Miami crowd, might end up being a favorable price as well! I tried to find as many places as I could, not all are central POS but I promise none of them are all the way in Tobago. Hopefully after carnival is finished this week, more properties will put their prices/availability up for 2020.


TORONTO TO PORT OF SPAIN

Flight: Pearson International to Port of Spain | February 19th - February 26th

$672.26 CDN per person; roundtrip (direct, red-eye, choose the Caribbean Airlines option)

$824.87 CDN per person; roundtrip (direct, afternoon)


MIAMI TO PORT OF SPAIN

Flight: Miami International to Port of Spain | February 19th - February 26th

$591.60 USD per person; roundtrip (direct, choose the Caribbean Airlines option)


NEW YORK TO PORT OF SPAIN

Flight: JFK to Port of Spain | February 19th - February 26th

$973.11 USD per person; roundtrip (layover, red-eye)

$795.60 USD per person; roundtrip (direct, afternoon/evening, choose the Caribbean Airlines option)


 

Stay: AirBnB for four | February 19th - February 26th

Option 1: $2049.00 CDN ($512.25/per person); Place looks huge, Pool, Perfect reviews

Option 2: $1421.00 CDN ($355.25/per person); Perfect reviews, Looks cozy, Quiet area

Option 3: $1153.00 CDN ($288.25/per person); By UWI, Looks big, Nice, Perfect reviews

Option 4: $1426.00 CDN ($356.50/per person); Close to transit, Looks nice, Perfect reviews, Quiet area

Option 5: $1254.00 CDN ($313.50/per person); Looks cozy, Perfect reviews, Quiet area, There’s fruit trees

Option 6: $1487.00 CDN ($371.75/per person); Looks nice, Looks big, Perfect reviews, San Juan location

 

Stay: AirBnB for two | February 19th - February 26th

Option 1: $359.00 CDN ($179.50/per person); Private room (not whole place), Very good location, Good reviews, Looks simple

Option 2: $755.00 CDN ($377.50/per person); Perfect reviews, Good area, Looks cute

Option 3: $838.00 CDN ($419.00/per person); Looks great, Big, Perfect reviews, Good area

Option 4: $623.00 CDN ($311.50/per person); Perfect reviews, Closer to airport, Looks nice

Option 5: $877.00 CDN ($438.50/per person); By Chaguanas, Looks very nice, Perfect reviews


Total: For four you're looking at between $960.51 CDN and $1337.12 CDN per person for the trip. For two you're looking at between $851.76 CDN and $1263.37 CDN 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.

Toronto to Montego Bay: Group Trip

SPECS

Who: Four People, Two Beds

Where: Toronto to Montego Bay, Jamaica

When: Thursday, April 11th - Tuesday, April 16th, 2019

Budget Per Person: $600.00


Flight: Toronto to Montego Bay | April 11th - April 16th

$417.00 CDN: roundtrip (direct)

Stay: AirBnB for four | April 11th - April 16th

Option 1: $557.00 CDN ($139.25/per person); Perfect reviews, Close to nightlife, Looks cozy

Option 2: $579.00 CDN ($144.75/per person); Looks super cute, Cozy, Perfect reviews, Good location

Option 3: $553.00 CDN ($138.25/per person); Quiet area, Looks big, Perfect reviews

Option 4: $401.00 CDN ($100.25/per person); Perfect reviews, Looks cozy, Quiet area

Option 5: $609.00 CDN ($152.25/per person); Rose Hall area, Close to the beach, Looks cozy, Perfect reviews

Total: Overall, if you go for the LEAST expensive options I posted it's about $517.25 per person for the trip and for the MOST expensive options it's about $569.25 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.

Toronto to St. Lucia: New Year's 2020 Baecation

SPECS

Who: Two People, One Bed

Where: Toronto to St. Lucia

When: Tuesday, December 31st, 2019 - Tuesday, January 7th, 2020

Budget Per Person: $1000.00

Notes: Carry-on trip I believe. Also, YES I know this is super duper early but for this price I figured maybe there’s someone else as nutty as I am to take advantage of cheap trips for NYE before they skyrocket. I made the locations for places to stay all over the island because I realize some people like to be close to the action and some also like peace and quiet.


Flight: Toronto to St. Lucia | December 31st - January 7th

$631.50 CDN: roundtrip (layover, lands with plenty of time to get ready to go party for NYE)

Stay: AirBnB for two | December 31st - January 7th

Option 1: $569.00 CDN ($284.50/per person); Incredible view of Pitons, Close to beach, Looks nice, Perfect reviews

Option 2: $667.00 CDN ($333.50/per person); Perfect reviews, Looks beautiful, Good location

Option 3: $668.00 CDN ($334.00/per person); This place is huge, Close to transit, Perfect reviews

Option 4: $485.00 CDN ($242.50/per person); Perfect reviews, Looks super cute, Good location

Option 5: $518.00 CDN ($259.00/per person); Close to beach, Looks cozy, Big, Perfect reviews

Option 6: $594.00 CDN ($297.00/per person); Very nice view, Great reviews, Looks nice, Close to transit

Total: Overall, if you go for the LEAST expensive options I posted it's about $874.00 per person for the trip and for the MOST expensive options it's about $965.50 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.