A Travel Price Comparison for Families, Couples, and Backpackers Islamorada vs. Winnipeg for Vacations, Tours, and Honeymoons

Should you visit Islamorada or Winnipeg?

Which is cheaper to visit? Which is more expensive for vacation?

If you're trying to decide where to visit between Islamorada or Winnipeg, this travel comparison, which includes costs, can help. The overall cost of travel is usually a consideration when deciding where to go next, and the cost comparison down below can help you decide based on the average prices from other travelers along with your own travel budget.

Where Should I go: Islamorada or Winnipeg?

Islamorada

From its thriving coral reefs to its miraculous botanical gardens, you will find adventure on both land and sea at Islamorada, Florida. Islamorada, or "Village of Islands," is located in Monroe County and holds a population of no more than 6,119. As Islamorada's village is occupied within a cluster of nearby islands, Islamorada is located on Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key and Plantation Key in the Florida Keys. The village is relatively small, expanding to about 7.2 square miles total. Approximately an hour and a half-drive from Miami and a two hour-drive from Key West, Islamorada works swimmingly for those who seek to acquaint themselves with the tropical pleasures of the Keys.

Winnipeg

Winnipeg is the capital of the Canadian province of Manitoba. Its heart is The Forks, a historic site at the intersection of the Red and Assiniboine rivers, with warehouses converted to shops and restaurants, plus ample green space dedicated to festivals, concerts and exhibits. Nearby, the Exchange District is known for its well-preserved, early 20th-century architecture and numerous art galleries. Rising above the prairie, Winnipeg is a metropolis where you least expect it. Cultured, confident and captivating, it’s more than just a pit stop on the Trans-Canada haul, but a destination in its own right, with a couple of world-class museums and a wonderfully diverse dining scene.

For some great organized tour ideas, see The Best 3-Week Tours in United States of America, The Best Bicycle Tours in United States of America, Tours for Outdoor and Nature Lovers in Canada, and The Best Coach Bus Tours in Canada.


Which place is cheaper, Winnipeg or Islamorada?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Islamorada is $145, while the average daily cost in Winnipeg is $251. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Islamorada and Winnipeg in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Islamorada $79
    Winnipeg $92
  • Accommodation Typical double-occupancy room
    Islamorada $158
    Winnipeg $184
Compare Hotels in Islamorada and Winnipeg

Looking for a hotel in Islamorada or Winnipeg? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Islamorada


Hotels in Winnipeg


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Islamorada Hotel Prices and Winnipeg Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Islamorada $28
    Winnipeg -

Hired Cars and Shuttles in Winnipeg

Also for Winnipeg, here are a few examples of actual transportation services:

  • Winnipeg One way Private transfer from/to the Airport: $200
  • Arrivals Private Transfer from Richardson Airport: $141
  • Winnipeg Airport (YWG) to Winnipeg accomodation - Round-Trip Private Transfer: $122
  • Private Transfer from Winnipeg Airport (YWG) to Winnipeg Hotels: $61
  • Private Transfer from Winnipeg Hotels to Winnipeg Airport: $61
  • Winnipeg accomodation to Winnipeg Airport (YWG) - Departure Private Transfer: $61
  • Winnipeg Airport (YWG) to Winnipeg accomodation - Arrival Private Transfer: $61
  • Private Transfer from Winnipeg Airport to Winnipeg Accommodation : $37

Is it cheaper to fly into Islamorada or Winnipeg?

Prices for flights to both Winnipeg and Islamorada change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Islamorada $47
    Winnipeg $5.40

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Islamorada $19
    Winnipeg $2.52

Tours and Activities in Islamorada

Also, here are some specific examples of entertainment, tickets, and activities for Islamorada.

  • 1.5 Hour (20 miles) Waverunner Tour. See Mangrove Tunnels, 20 Islands & SandBar: $225
  • Day Tour Glass Bottom Boat In Islamorada: $80
  • From Miami: Key Largo & Islamorada Private Open-Top Bus Tour: $1,515
  • Islamorada Florida Keys Sunset Sightseeing Cruise Music : $86
  • 2-Hour Snorkeling Adventure on Pontoon : $80
  • Guided Tour with Local Highlights: $95
  • Snorkel Adventure & Sandbar Trip: $130
  • Snorkel Adventure & Sandbar Trip from Cheeca Spa: $140
  • Snorkel adventure & Sandbar Trip : $150
  • Snorkel adventure & Sandbar Trip : $160
  • Snorkeling Experience : $80
  • Snorkeling and Beach Adventure: $90

Tours and Activities in Winnipeg

Also, here are some specific examples of entertainment, tickets, and activities for Winnipeg.

  • Discover Assiniboine Park with a Smartphone Audio Tour: $5.23
  • Explore The Challenge of Moderninity with Walking Tours in Winnipeg, MB: $6.73
  • Louis Riel & Red River Metis Trails Tour: $74
  • Manitoba Legislative Grounds: a Smartphone Audio Tour & Trivia Challenge: $5.23
  • Murder Mystery Detective Experience Winnipeg, MB: $11
  • Private City Tour in Winnipeg: $49
  • Sights of South Winnipeg Smartphone Audio Driving Tour: $6.21
  • The Forks Historic Site: a Smartphone Audio Tour: $5.23
  • The Indigenous Residential School Museum Private Tour: $82
  • The Sights of South a Smartphone Audio Tour: $6.36
  • Unique Scavenger Hunt Experience in Winnipeg by Operation City Quest: $10
  • Walk Downtown Winnipeg with 4 Unique Smartphone Audio Tours: $18

Alcohol
  • Alcohol Drinks for one day
    Islamorada $15
    Winnipeg -


When we compare the travel costs of actual travelers between Islamorada and Winnipeg, we can see that Winnipeg is more expensive. And not only is Islamorada much less expensive, but it is actually a significantly cheaper destination. So, traveling to Islamorada would let you spend less money overall. Or, you could decide to spend more money in Islamorada and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Winnipeg would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Winnipeg than you might in Islamorada.

If you're trying to decide if either of these two destinations are within your price range, also see Is Islamorada Expensive? and Is Winnipeg Expensive?.


Which is Bigger, Islamorada or Winnipeg?

Winnipeg has a larger population, and is about 90 times larger than the population of Islamorada. When comparing the sizes of Islamorada and Winnipeg, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.


When is the best time to visit Islamorada or Winnipeg?

Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Islamorada or Winnipeg in the Summer?

Both Winnipeg and Islamorada are popular destinations to visit in the summer with plenty of activities. The beaches, snorkeling, and the family-friendly experiences are the main draw to Islamorada this time of year.

In the summer, Islamorada is a little warmer than Winnipeg. Typically, the summer temperatures in Islamorada in July average around 84°F (29°C), and Winnipeg averages at about 21°C (71°F).

It's quite sunny in Winnipeg. The sun comes out a lot this time of the year in Islamorada. Islamorada usually receives around the same amount of sunshine as Winnipeg during summer. Islamorada gets 328 hours of sunny skies, while Winnipeg receives 328 hours of full sun in the summer.

In July, Islamorada usually receives more rain than Winnipeg. Islamorada gets 3.3 inches (83 mm) of rain, while Winnipeg receives 72 mm (2.8 in) of rain each month for the summer.


  • Summer Average Temperatures July
    Islamorada 84°F (29°C) 
    Winnipeg 21°C (71°F)

Should I visit Islamorada or Winnipeg in the Autumn?

Both Winnipeg and Islamorada during the autumn are popular places to visit. Many travelers come to Islamorada for the shopping scene and the natural beauty of the area.

In October, Islamorada is generally much warmer than Winnipeg. Daily temperatures in Islamorada average around 80°F (27°C), and Winnipeg fluctuates around 7°C (45°F).

It's quite sunny in Islamorada. In the autumn, Islamorada often gets more sunshine than Winnipeg. Islamorada gets 258 hours of sunny skies this time of year, while Winnipeg receives 147 hours of full sun.

It rains a lot this time of the year in Islamorada. Islamorada usually gets more rain in October than Winnipeg. Islamorada gets 5.1 inches (129 mm) of rain, while Winnipeg receives 30 mm (1.2 in) of rain this time of the year. Also, June to November in Islamorada is the hurricane season.


  • Autumn Average Temperatures October
    Islamorada 80°F (27°C) 
    Winnipeg 7°C (45°F)

Should I visit Islamorada or Winnipeg in the Winter?

The winter attracts plenty of travelers to both Islamorada and Winnipeg. Many visitors come to Islamorada in the winter for the museums, the shopping scene, and the cuisine.

Winnipeg can be very cold during winter. Islamorada is much warmer than Winnipeg in the winter. The daily temperature in Islamorada averages around 70°F (21°C) in January, and Winnipeg fluctuates around -17°C (2°F).

In Islamorada, it's very sunny this time of the year. Islamorada usually receives more sunshine than Winnipeg during winter. Islamorada gets 252 hours of sunny skies, while Winnipeg receives 115 hours of full sun in the winter.

In January, Islamorada usually receives more rain than Winnipeg. Islamorada gets 1.7 inches (43 mm) of rain, while Winnipeg receives 19 mm (0.7 in) of rain each month for the winter.


  • Winter Average Temperatures January
    Islamorada 70°F (21°C) 
    Winnipeg -17°C (2°F)

Should I visit Islamorada or Winnipeg in the Spring?

The spring brings many poeple to Islamorada as well as Winnipeg. Most visitors come to Islamorada for the beaches and the natural beauty during these months.

In the spring, Islamorada is much warmer than Winnipeg. Typically, the spring temperatures in Islamorada in April average around 77°F (25°C), and Winnipeg averages at about 5°C (42°F).

The sun comes out a lot this time of the year in Winnipeg. People are often attracted to the plentiful sunshine in Islamorada this time of the year. In the spring, Islamorada often gets more sunshine than Winnipeg. Islamorada gets 326 hours of sunny skies this time of year, while Winnipeg receives 248 hours of full sun.

Islamorada usually gets less rain in April than Winnipeg. Islamorada gets 0.8 inches (21 mm) of rain, while Winnipeg receives 36 mm (1.4 in) of rain this time of the year. Also, the hurricane season in Islamorada is June to November.


  • Spring Average Temperatures April
    Islamorada 77°F (25°C) 
    Winnipeg 5°C (42°F)

Typical Weather for Winnipeg and Islamorada

Islamorada Winnipeg
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 70°F (21°C) 1.7 inches (43 mm) -17°C (2°F) 19 mm (0.7 in)
Feb 71°F (21°C) 1.4 inches (36 mm) -14°C (8°F) 15 mm (0.6 in)
Mar 74°F (23°C) 1.7 inches (42 mm) -6°C (22°F) 23 mm (0.9 in)
Apr 77°F (25°C) 0.8 inches (21 mm) 5°C (42°F) 36 mm (1.4 in)
May 81°F (27°C) 2.7 inches (68 mm) 13°C (56°F) 60 mm (2.4 in)
Jun 83°F (28°C) 4.5 inches (114 mm) 19°C (65°F) 84 mm (3.3 in)
Jul 84°F (29°C) 3.3 inches (83 mm) 21°C (71°F) 72 mm (2.8 in)
Aug 84°F (29°C) 3.9 inches (98 mm) 20°C (68°F) 75 mm (3 in)
Sep 83°F (29°C) 5.7 inches (144 mm) 14°C (57°F) 51 mm (2 in)
Oct 80°F (27°C) 5.1 inches (129 mm) 7°C (45°F) 30 mm (1.2 in)
Nov 76°F (24°C) 2 inches (50 mm) -3°C (26°F) 21 mm (0.8 in)
Dec 72°F (22°C) 1.4 inches (35 mm) -13°C (9°F) 19 mm (0.7 in)