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

Should you visit Key West or Winnipeg?

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

Should I visit Key West or Winnipeg? This is a common question asked by many travelers. By figuring out which city has activities that align with your interests along with knowing which is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the details and the data, which all comes from actual travelers.

Where Should I go: Key West or Winnipeg?

Key West

Key West is both a city and an island as well as the southern most Florida Key. It is also the southern most city in the continental United States. The island is only about four miles long and one mile wide. The total land mass covers just 4.2 square miles. The most famous street in town is Duval Street, which runs just 1.1 miles from the Gulf of Mexico to the Atlantic Ocean. There are 14 blocks. The size of the island doubled during the 1950s when many of the salt ponds along the eastern side of the island were filled in.

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 One-Week (7-Day) Tours from Los Angeles, The Best One-Week (7-Day) Tours from New York City, Tours for Outdoor and Nature Lovers in Canada, and The Best Coach Bus Tours in Canada.


Which place is cheaper, Winnipeg or Key West?

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

The average daily cost (per person) in Key West is $551, 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 Key West and Winnipeg in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Key West $132
    Winnipeg $92
  • Accommodation Typical double-occupancy room
    Key West $264
    Winnipeg $184
Compare Hotels in Key West and Winnipeg

Looking for a hotel in Key West 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 Key West


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: Key West Hotel Prices and Winnipeg Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Key West $51
    Winnipeg -
Typical Local Transportation Prices in Key West

Below are a few samples from actual travelers for transportation costs in Key West:


  • Rental Car for One Day
    $38

Hired Cars and Shuttles in Key West

Some specific examples of transportation prices in Key West:

  • Private Arrival Transfer from Key West Airport EYW: $144
  • Key West Airport (EYW) to Key West - Round-Trip Private Transfer: $129
  • Key West Int Airport (EYW) to Key West hotels Round-Trip Transfer: $129
  • Marathon/ Key Largo to Fort Lauderdale Airport(FLL) - Departure Private Transfer: $109
  • Key West Int Airport (EYW) to Key West - Arrival Private Transfer: $64
  • Key West to Key West Airport (EYW) - Departure Private Transfer: $64
  • Key West hotels to Key West Int Airport (EYW) Departure Transfer: $64
  • Private Transfer from Key West Int Airport to Key West Port: $38
  • Private Transfer from Key West Cruise Port to Key West hotels: $38

Hired Cars and Shuttles in Winnipeg

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

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

Is it cheaper to fly into Key West or Winnipeg?

Prices for flights to both Winnipeg and Key West 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
    Key West $385
    Winnipeg $5.40

Food Tours and Cooking Classes in Key West

Also, here are some specific examples of food and dining related activities in Key West.

  • Sunset Dinner Cruise with Open Bar & Live Music: $81
  • Key West Sunset Cruise: Dinner and Drinks Included: $93
  • Southernmost Food & Cultural Walking Tour by Key West Food Tours: $93
  • Historic Seaport Food & Walking Tour by Key West Food Tours: $93
  • Old Town Secret Food Tour: $107
  • Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling: $160
  • Snorkeling, Sunset Dinner Cruise & Open Bar: $200

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Key West $33
    Winnipeg $2.52

Tours and Activities in Key West

Some specific costs of activities, tours, and entrance tickets for Key West are as follows:

  • Key West Kayak Eco Tour | An Eco-Friendly Adventure Awaits!: $56
  • Private E-Pedicab 1 Hour Sightseeing Ride of Old Town Key West: $100
  • Southernmost Ghosts Tour: $33
  • 2-Hour Live Music Guided Tour in Key West: $35
  • A Self-Guided Tour of Key West's Legends and Sights: $24
  • Adults only Sunset Cruise from Key West with Champagne: $81
  • Bahama Village Walking Tour: $30
  • Best of Key West Walking Tour with Glass Bottom Boat Cruise: $229
  • Best of Key West with Glass Bottom Boat Cruise: $294
  • Champagne Sunset Catamaran Cruise in Key West with Cocktails!: $60
  • Cruise Through Key West's Black History Audio Tour: $11
  • Dark Corners of Key West – Walking Tour: $352

Tours and Activities in Winnipeg

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

  • Self-Guided Smartphone Audio Ghost Tour: $5.11
  • Assiniboine Park Self-Guided Smartphone Audio Tour: $5.11
  • Wealthy Beginnings Audio Walking Tour: $5.11
  • Winnipeg in the Limelight: a Smartphone Audio Walking Tour: $5.11
  • The Forks Self-Guided Smartphone Tour with Audio: $5.11
  • Manitoba Legislative Grounds Audio Walking Tour: $5.11
  • The Forks Historic Site: a Smartphone Audio Tour: $5.23
  • Manitoba Legislative Grounds: a Smartphone Audio Tour & Trivia Challenge: $5.23
  • Winnipeg in the Limelight: a Smartphone Audio Walking Tour: $5.23
  • Discover Assiniboine Park with a Smartphone Audio Tour: $5.23
  • Winnipeg's Wealthy Beginnings: a Smartphone Audio Walking Tour: $5.23
  • Winnipeg's Most Haunted: a Smartphone Audio Ghost Tour: $5.23

Alcohol
  • Alcohol Drinks for one day
    Key West $16
    Winnipeg -

Sample the Local Flavors in Key West

Also in Key West, these are the prices for nightlife and alcohol related activities from various tour providers:

  • Haunted Pub Crawl Walking Tour: $30
  • Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt: $32
  • Bone Island Haunted Pub Crawl: $32
  • 2.5-Hour Duval Street Pub Crawl: $43


When we compare the travel costs of actual travelers between Key West and Winnipeg, we can see that Key West is more expensive. And not only is Winnipeg much less expensive, but it is actually a significantly cheaper destination. So, traveling to Winnipeg would let you spend less money overall. Or, you could decide to spend more money in Winnipeg 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 Key West would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Key West than you might in Winnipeg.

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


Which is Bigger, Key West or Winnipeg?

Winnipeg has a larger population, and is about 30 times larger than the population of Key West. When comparing the sizes of Key West 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 Key West or Winnipeg?

Both places have a temperate climate with four distinct seasons. As both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Key West or Winnipeg in the Summer?

The summer brings many poeple to Key West as well as Winnipeg. Many visitors come to Key West in the summer for the beaches, snorkeling, the small town charm, and the family-friendly experiences.

Key West is a little warmer than Winnipeg in the summer. The daily temperature in Key West averages around 84°F (29°C) in July, and Winnipeg fluctuates around 21°C (71°F).

The sun comes out a lot this time of the year in Winnipeg. People are often attracted to the plentiful sunshine in Key West this time of the year. In the summer, Key West often gets around the same amount of sunshine as Winnipeg. Key West gets 328 hours of sunny skies this time of year, while Winnipeg receives 328 hours of full sun.

Key West usually gets more rain in July than Winnipeg. Key West gets 3.3 inches (83 mm) of rain, while Winnipeg receives 72 mm (2.8 in) of rain this time of the year.


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

Should I visit Key West or Winnipeg in the Autumn?

Both Winnipeg and Key West are popular destinations to visit in the autumn with plenty of activities. Most visitors come to Key West for the shopping scene, the small town atmosphere, and the natural beauty of the area during these months.

In the autumn, Key West is much warmer than Winnipeg. Typically, the autumn temperatures in Key West in October average around 80°F (27°C), and Winnipeg averages at about 7°C (45°F).

The sun comes out a lot this time of the year in Key West. Key West usually receives more sunshine than Winnipeg during autumn. Key West gets 258 hours of sunny skies, while Winnipeg receives 147 hours of full sun in the autumn.

It's quite rainy in Key West. In October, Key West usually receives more rain than Winnipeg. Key West gets 5.1 inches (129 mm) of rain, while Winnipeg receives 30 mm (1.2 in) of rain each month for the autumn. June to November in Key West is the hurricane season.


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

Should I visit Key West or Winnipeg in the Winter?

Both Winnipeg and Key West during the winter are popular places to visit. The winter months attract visitors to Key West because of the shopping scene and the cuisine.

It's quite cold in Winnipeg in the winter. In January, Key West is generally much warmer than Winnipeg. Daily temperatures in Key West average around 70°F (21°C), and Winnipeg fluctuates around -17°C (2°F).

It's quite sunny in Key West. In the winter, Key West often gets more sunshine than Winnipeg. Key West gets 252 hours of sunny skies this time of year, while Winnipeg receives 115 hours of full sun.

Key West usually gets more rain in January than Winnipeg. Key West gets 1.7 inches (43 mm) of rain, while Winnipeg receives 19 mm (0.7 in) of rain this time of the year.


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

Should I visit Key West or Winnipeg in the Spring?

The spring attracts plenty of travelers to both Key West and Winnipeg. The beaches, the small town charm, and the natural beauty are the main draw to Key West this time of year.

Key West is much warmer than Winnipeg in the spring. The daily temperature in Key West averages around 77°F (25°C) in April, and Winnipeg fluctuates around 5°C (42°F).

People are often attracted to the plentiful sunshine in Winnipeg this time of the year. In Key West, it's very sunny this time of the year. Key West usually receives more sunshine than Winnipeg during spring. Key West gets 326 hours of sunny skies, while Winnipeg receives 248 hours of full sun in the spring.

In April, Key West usually receives less rain than Winnipeg. Key West gets 0.8 inches (21 mm) of rain, while Winnipeg receives 36 mm (1.4 in) of rain each month for the spring. The hurricane season in Key West is June to November.


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

Typical Weather for Winnipeg and Key West

Key West 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)