A Travel Price Comparison for Families, Couples, and Backpackers Portland, Maine vs. Winnipeg for Food, Nightlife, Families, and Couples

Should you visit Portland, Maine or Winnipeg?

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

Should I visit Portland, Maine 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.

Portland, Maine

Portland, Maine is a seaside, laid-back, and scenic coastal town. The beauty of Portland, Maine is also one of the main reasons why visitors come. Visitors also love the nightlife, food, and beaches. See Portland, Maine travel costs.

Winnipeg

Winnipeg is a cultural, friendly, and welcoming city. Other popular activities here include shopping, museums, and nightlife. See Winnipeg travel costs.

Portland, Maine and Winnipeg: Pros and Cons

Pros
  • Active nightlife
  • Popular beach
  • Good for hiking
  • Popular at Christmas
  • Known for its beauty
  • Family-friendly
  • Good for couples and romance
  • Impressive beauty
Things to Consider
  • Less popular with backpackers
Pros
  • Popular museums and historical sights
  • Active nightlife
  • Family-friendly
  • Good for couples and romance
  • Good for backpackers and budget travelers


Is there more to do in Portland, Maine or Winnipeg?

Travelers will generally find more things to do in Portland, Maine than Winnipeg. While Winnipeg is larger than Portland, Maine, Portland, Maine has more sights and attractions for tourists. Portland, Maine is more popular for its beaches, hiking, and impressive beauty, while Winnipeg is known for its museums and attractions. Portland, Maine is more touristy than Winnipeg and is popular for its seafood restaurants, scenic lighthouse, and coastal walks. It is also home to The Portland Head Light. Winnipeg is popular for its festivals, culture, and railway connections.

How is Portland, Maine different from Winnipeg?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Winnipeg and Portland, Maine. Then, you can decide for yourself which place is better for your next trip.

Are the Museums and Historical Sights Better in Portland, Maine or Winnipeg?

Portland, Maine
Winnipeg

Winnipeg is well known for its museums and landmarks. However, Portland, Maine does not have museums and landmarks.

Winnipeg offers many unique museums, sights, and landmarks that will make for a memorable trip. There are some unique museums around town including the Canadian Museum for Human Rights. Other popular museums are the Manitoba Museum and the Manitoba Children's Museum.

Portland, Maine does not have museums and landmarks.


Is the Food Better in Portland, Maine or Winnipeg? Which Destination has the Best Restaurants?

Portland, Maine
Winnipeg

Picking the best cuisine and restaurants between Portland, Maine and Winnipeg can be difficult as they are each good in their own way.

There are many up and coming restaurants in the Portland, Maine area. The town has grown into a foodie destination that takes advantage of its waterfront setting. Many restaurants make use of the fresh seafood with lobster rolls and oysters on the half shell being popular. You'll also find a lot of dishes that use haddock and whole lobsters.

There are plenty of up and coming restaurants around Winnipeg. You'll find a wide variety of restaurants around town that serve a mix of local dishes and international cuisines. A must-see part of the city is the historic Forks Market.

Is Portland, Maine or Winnipeg Better for Nightlife?

Portland, Maine
Winnipeg

Party-goers will find similar levels of energy in Portland, Maine and Winnipeg.

Portland, Maine has an active nightlife scene for those who seek it out. The city has many microbreweries, wine bars, taverns, and pubs. You'll find many places concentrated in the Old Port, which has a charming and fun atmosphere.

If you're looking for night time activities Winnipeg has a few options to choose from. The city has an active nightlife, even during the winter months. You'll find dance clubs, bars, and pubs around town that are popular with locals and visitors alike.

Is Portland, Maine or Winnipeg Better for Beaches?

Portland, Maine
Winnipeg

Portland, Maine is great for the beach. However, Winnipeg is not a beach destination.

The beaches at Portland, Maine attract visitors from all over. It has many sandy and calm beaches. The water may be too cold to swim, but the beaches are perfect for flying a kite or hanging out with family.

Winnipeg is not a beach destination.


Is Portland, Maine or Winnipeg Better for Hiking?

Portland, Maine
Winnipeg

Portland, Maine is a coastal town with good options for hiking. However, Winnipeg is not a hiking destination.

Plenty of visitors go hiking around Portland, Maine. In addition to bike trails, there are several good hikes in the area.

Winnipeg is not a hiking destination.

Is the Shopping Better in Portland, Maine or Winnipeg?

Portland, Maine
Winnipeg

Shopping is a popular activity in both Winnipeg and Portland, Maine.

Many visitors go to Portland, Maine to go shopping. The town has many nice local boutiques to explore. Head downtown for the best local venues and the most interesting shopping opportunities.

Plenty of visitors enjoy shopping while in Winnipeg. You'll find all of the standard shopping options around town, from boutiques to big box shops and even some outlets.

Is Portland, Maine or Winnipeg More Beautiful?

Portland, Maine
Winnipeg

Portland, Maine is great for its scenery and beauty. However, Winnipeg is not a destination known for its beauty.

The beauty of Portland, Maine is also one of the main reasons why visitors come. Set against the water's edge, the town offers many beautiful scenes and picturesque settings.

Winnipeg is not a destination known for its beauty.


Is Portland, Maine or Winnipeg Better for Families?

Portland, Maine
Winnipeg

Kids will enjoy a visit to either Portland, Maine or Winnipeg.

You'll find plenty of kid-friendly things to do in Portland, Maine. It is a charming town with a number of kid-friendly museums, walks, and waterfront activities. You can visit the Portland Observatory, Bug Light Park, or grab ice cream in the Old Port. There are also children's museums such as the Children's Museum & Theatre of Maine.

Winnipeg offers lots of family activities. Kids will love a visit to the Assiniboine Park Zoo or the Manitoba Children's Museum. There are a number of parks and playgrounds around town as well as the Prairie Dog Central Railway. There are many kid-friendly restaurants in the city as well.

Is Portland, Maine or Winnipeg Better for Couples?

Portland, Maine
Winnipeg

With fun activities for couples, both Portland, Maine and Winnipeg make for a good place to visit.

Portland, Maine is a good coastal town for couples to visit. Couples will enjoy the beautiful waterfront setting, the fine dining restaurants, and everything that the city has to offer. Head to the Old Port for romantic restaurants and a great atmosphere or catch a show at Portland Stage.

Winnipeg is a nice destination for couples. Many couples enjoy wandering through Assiniboine Park. There are also many romantic restaurants and spas for couples.

Is Portland, Maine or Winnipeg Better for Backpackers and Budget Travelers?

Portland, Maine
Winnipeg

Winnipeg is a popular place for backpackers. However, Portland, Maine is not particularly known for backpackers and budget travelers.

Plenty of budget travelers visit Winnipeg. While it's often overlooked by backpackers, there are a couple of hostels around town.

Portland, Maine is a challenging destination for budget travelers and backpackers due to the higher prices. It isn't so much a backpacker destination, but there are some budget accommodation options around town.


Is Portland, Maine or Winnipeg Better for Public Transit? Which Is Easier to Get Around Without a Car?

Portland, Maine
Winnipeg

Winnipeg is a city with a few options for its public transit. However, Portland, Maine is not particularly known for times when you don't have a car.

Public transit is generally limited in Winnipeg. There's a bus system around town, but many visitors prefer to have a vehicle.

Public transit is quite limited in Portland, Maine. There is a very basic bus system but you really must have a car to explore the city.

Is Portland, Maine or Winnipeg a more walkable city?

Portland, Maine
Winnipeg

Portland, Maine and Winnipeg both are decent when exploring on foot.

Portland, Maine is generally not very walkable. Downtown is very walkable but if you want to travel to other areas you'll need a car.

Winnipeg is generally not a very walkable coastal town. While there are a few walkable neighborhoods, the city itself is not particularly walkable, particularly during the cold winter months.

For even more information, also check out Is Portland, Maine Worth Visiting? and Is Winnipeg Worth Visiting?.

Should I spend more time in Winnipeg or Portland, Maine?

How long in Portland, Maine or Winnipeg?

It's fun to spend time in either Portland, Maine or Winnipeg. Generally, people tend to spend more time in Winnipeg due to the larger number of activities and things to do. Usually, 2-3 days is a good amount of time for Portland, Maine, and 2-4 days is enough time in Winnipeg.

Families should spend more time in Portland, Maine than Winnipeg. Because of the many family-friendly attractions and fun things to do for kids in Portland, Maine, it's a great place to visit with the whole family.

Couples should spend more time in Portland, Maine than Winnipeg. You'll find plenty of romantic sights and fun activities in Portland, Maine that are great for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Winnipeg than Portland, Maine if your budget allows for it. With a larger number of budget-friendly sights, good nightlife, and active things to do, anyone traveling on a budget would have a good time in Winnipeg.


  • How many days in Portland, Maine or Winnipeg? Ideal Length of Stay
    Portland, Maine 2-3 
    Winnipeg 2-4

One day in Portland, Maine or Winnipeg?

The beautiful coastal town of Portland, Maine offers nightlife and food. Most people come for the beaches. With so much to do, one day is probably not enough time to see everything. It will give you the chance to have new experiences.

The friendly destination of Winnipeg offers nightlife and food. Take your pick from the many activities offered here. One day is usually not enough time for a trip here as there is plenty to do.


A weekend in Portland, Maine or Winnipeg?

Portland, Maine is a popular place that is full of things to see and experience. If you have a weekend, this coastal town makes for a great vacation. Many visitors spend time at the beach while visiting the area. While some people choose to spend more or less time in Portland, Maine, a weekend is sufficent for most. Take your pick from the many activities offered here.

The city of Winnipeg offers food and shopping. A weekend here is typical. The entire region has so many activities, and you'll want time to do everything. A weekend is often enough time to do most activities.

Five days in Portland, Maine or Winnipeg?

Portland, Maine is a popular choice for travelers. Five days is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips. The entire region has so many activities, and you'll want time to do everything.

Winnipeg is a great place to explore. This city offers something for everyone. Most people find that five days is more than enough time to see everything.

A week in Portland, Maine or Winnipeg?

Portland, Maine is a great place to explore. It's also a great beach destination, too. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. This coastal town offers something for everyone.

Many people enjoy the museums and nightlife when visiting Winnipeg. The length of your trip often depends on your style of travel. One week is plenty of time to see everything, even with extra days to spare.


For some great organized tour ideas, see The Best One-Week (7-Day) Tours from Las Vegas, The Best One-Week (7-Day) Tours from Anchorage, Tours for Outdoor and Nature Lovers in Canada, and The Best Coach Bus Tours in Canada.


Which place is cheaper, Winnipeg or Portland, Maine?

These are the overall average travel costs for the two destinations. These travel costs come from the actual spending of real travelers.

  • Portland, Maine Prices
    USA Prices
    Winnipeg Prices
    Canada Prices
  • Average Daily Cost Per person, per day
    Portland, Maine $227
    Winnipeg $255

The average daily cost (per person) in Portland, Maine is $227, while the average daily cost in Winnipeg is $255. 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 Portland, Maine and Winnipeg in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Portland, Maine $115
    Winnipeg $92
  • Accommodation Typical double-occupancy room
    Portland, Maine $230
    Winnipeg $184
Compare Hotels in Portland, Maine and Winnipeg

Looking for a hotel in Portland, Maine 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 Portland, Maine


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: Portland, Maine Hotel Prices and Winnipeg Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Portland, Maine $34
    Winnipeg -

Hired Cars and Shuttles in Portland, Maine

Some specific examples of transportation prices in Portland, Maine:

  • Private Transfer from Portland Port to Portland Jetport (PWM): $136
  • Private Transfer from Portland city to Portland Cruise Port: $75
  • Private Transfer from Portland Cruise Port to Portland city: $75

Hired Cars and Shuttles in Winnipeg

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

  • Private Transfer from Winnipeg Airport (YWG) to Winnipeg Hotels: $97
  • Private Transfer from Winnipeg Airport to Winnipeg Accommodation : $37
  • Private Transfer from Winnipeg Hotels to Winnipeg Airport (YWG): $97
  • Winnipeg Airport (YWG) to Winnipeg accomodation - Arrival Private Transfer: $83
  • Winnipeg Airport (YWG) to Winnipeg accomodation - Round-Trip Private Transfer: $165
  • Winnipeg One way Private transfer from/to the Airport: $200
  • Winnipeg accomodation to Winnipeg Airport (YWG) - Departure Private Transfer: $83

Is it cheaper to fly into Portland, Maine or Winnipeg?

Prices for flights to both Winnipeg and Portland, Maine 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
    Portland, Maine $84
    Winnipeg $9.33
Typical Food Prices in Portland, Maine

Below are a few samples from actual travelers for food and meal costs in Portland, Maine:


  • Breakfast for 2
    $17
  • Dinner for 2
    $30

Food Tours and Cooking Classes in Portland, Maine

Also, here are some specific examples of food and dining related activities in Portland, Maine.

  • Portland: Walking Food Tour – Warm Donuts & History: $57

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Portland, Maine $39
    Winnipeg $2.52

Tours and Activities in Portland, Maine

Here are a few actual costs in Portland, Maine for available activities, ticket prices, and tours:

  • 2 Hour Scenic Powerboat Cruise Experience Portland's Waterfront: $143
  • 2-Hour Portland Old Port Ghost Walking Tour: $29
  • A Walk Through Time Tour in Portland: $49
  • Afternoon Lighthouse Cruise Along the Coast of Portland Maine: $62
  • Afternoon Windjammer Cruise Along the Coast of Portland Maine: $67
  • Around The Peninsula Bike Tour: $85
  • Audio Guided Walking Tour from Old Port of Portland, Maine: $7.75
  • Discover Portland City and Lighthouse Tour: $56
  • Guided RIB Boat Adventure of Casco Bay: $75
  • Harbor Lights and Sights Cruise: $56
  • Historical Walking Tour of Portland’s Old Port District: $7.99
  • Lighthouse Bicycle Tour from South Portland with 4 Lighthouses: $99

Tours and Activities in Winnipeg

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

  • The Forks Historic Site: a Smartphone Audio Tour: $6.61
  • Manitoba Legislative Grounds: Smartphone Audio Tour: $6.61
  • Winnipeg's Most Haunted: a Smartphone Audio Ghost Tour: $6.61
  • Winnipeg's Wealthy Beginnings: a Smartphone Audio Walking Tour: $6.61
  • The Sights of South a Smartphone Audio Tour: $6.61
  • Discover Assiniboine Park with a Smartphone Audio Tour: $6.61
  • Winnipeg in the Limelight: a Smartphone Audio Walking Tour: $6.61
  • Explore The Challenge of Moderninity with Walking Tours in Winnipeg, MB: $6.61
  • Unique Scavenger Hunt Experience in Winnipeg by Operation City Quest: $10
  • Murder Mystery Detective Experience in Winnipeg MB: $11
  • Wonderful 3 Smartphone Audio Guided Walking Tours: $14
  • Winnipeg's Outdoor Secret Agent Audio Experience: $15

Alcohol
  • Alcohol Drinks for one day
    Portland, Maine $24
    Winnipeg -

Sample the Local Flavors in Portland, Maine

Here are a few nightlife and alcohol tours and activities from local tour providers in Portland, Maine:

  • Portland Old Port Wine Tasting Walking Tour: $99
  • Local Brewery & Spirits Bus Tour: $99
  • Old Port Brewery & Pub Walking Tour: $99


When comparing the travel costs between Portland, Maine and Winnipeg, we can see that Winnipeg is more expensive. However, the two cities are actually relatively comparable in price, as the difference is somewhat minimal. Generally, this means that you could travel with generally the same travel style and level of luxury in each place. Since both cities are in North America, it's no surprise that their costs are relatively close, as many destinations here have somewhat similar travel prices overall.

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


Which is Bigger, Portland, Maine or Winnipeg?

Winnipeg has a larger population, and is about 10 times larger than the population of Portland, Maine. When comparing the sizes of Portland, Maine 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 Portland, Maine 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 Portland, Maine or Winnipeg in the Summer?

Both Winnipeg and Portland, Maine during the summer are popular places to visit. Many visitors come to Portland, Maine in the summer for the beaches, the hiking, and the family-friendly experiences. Also, most visitors come to Winnipeg for the family-friendly experiences during these months.

In July, Portland, Maine is generally around the same temperature as Winnipeg. Daily temperatures in Portland, Maine average around 69°F (20°C), and Winnipeg fluctuates around 21°C (71°F).

In Winnipeg, it's very sunny this time of the year. It's quite sunny in Portland, Maine. In the summer, Portland, Maine often gets less sunshine than Winnipeg. Portland, Maine gets 282 hours of sunny skies this time of year, while Winnipeg receives 328 hours of full sun.

Portland, Maine usually gets less rain in July than Winnipeg. Portland, Maine gets 2.6 inches (66 mm) of rain, while Winnipeg receives 72 mm (2.8 in) of rain this time of the year.


  • Summer Average Temperatures July
    Portland, Maine 69°F (20°C) 
    Winnipeg 21°C (71°F)

Should I visit Portland, Maine or Winnipeg in the Autumn?

The autumn attracts plenty of travelers to both Portland, Maine and Winnipeg. Most visitors come to Portland, Maine for the hiking trails, the shopping scene, and the natural beauty of the area during these months. Also, the autumn months attract visitors to Winnipeg because of the shopping scene.

Portland, Maine is a little warmer than Winnipeg in the autumn. The daily temperature in Portland, Maine averages around 49°F (9°C) in October, and Winnipeg fluctuates around 7°C (45°F).

Portland, Maine usually receives more sunshine than Winnipeg during autumn. Portland, Maine gets 196 hours of sunny skies, while Winnipeg receives 147 hours of full sun in the autumn.

In October, Portland, Maine usually receives more rain than Winnipeg. Portland, Maine gets 3.3 inches (84 mm) of rain, while Winnipeg receives 30 mm (1.2 in) of rain each month for the autumn.


  • Autumn Average Temperatures October
    Portland, Maine 49°F (9°C) 
    Winnipeg 7°C (45°F)

Should I visit Portland, Maine or Winnipeg in the Winter?

The winter brings many poeple to Portland, Maine as well as Winnipeg. The winter months attract visitors to Portland, Maine because of the Christmas ambience, the shopping scene, and the cuisine. Also, the museums, the shopping scene, and the cuisine are the main draw to Winnipeg this time of year.

It's quite cold in Winnipeg in the winter. The weather in Portland, Maine can be very cold. In the winter, Portland, Maine is much warmer than Winnipeg. Typically, the winter temperatures in Portland, Maine in January average around 21°F (-6°C), and Winnipeg averages at about -17°C (2°F).

In the winter, Portland, Maine often gets more sunshine than Winnipeg. Portland, Maine gets 163 hours of sunny skies this time of year, while Winnipeg receives 115 hours of full sun.

Portland, Maine usually gets more rain in January than Winnipeg. Portland, Maine gets 3.4 inches (86 mm) of rain, while Winnipeg receives 19 mm (0.7 in) of rain this time of the year.


  • Winter Average Temperatures January
    Portland, Maine 21°F (-6°C) 
    Winnipeg -17°C (2°F)

Should I visit Portland, Maine or Winnipeg in the Spring?

Both Winnipeg and Portland, Maine are popular destinations to visit in the spring with plenty of activities. The beaches and the natural beauty are the main draw to Portland, Maine this time of year.

In April, Portland, Maine is generally a little warmer than Winnipeg. Daily temperatures in Portland, Maine average around 43°F (6°C), and Winnipeg fluctuates around 5°C (42°F).

It's quite sunny in Winnipeg. The sun comes out a lot this time of the year in Portland, Maine. Portland, Maine usually receives less sunshine than Winnipeg during spring. Portland, Maine gets 212 hours of sunny skies, while Winnipeg receives 248 hours of full sun in the spring.

In April, Portland, Maine usually receives more rain than Winnipeg. Portland, Maine gets 3.3 inches (85 mm) of rain, while Winnipeg receives 36 mm (1.4 in) of rain each month for the spring.


  • Spring Average Temperatures April
    Portland, Maine 43°F (6°C) 
    Winnipeg 5°C (42°F)

Typical Weather for Winnipeg and Portland, Maine

Portland, Maine Winnipeg
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 21°F (-6°C) 3.4 inches (86 mm) -17°C (2°F) 19 mm (0.7 in)
Feb 24°F (-5°C) 3.5 inches (89 mm) -14°C (8°F) 15 mm (0.6 in)
Mar 33°F (1°C) 3.6 inches (91 mm) -6°C (22°F) 23 mm (0.9 in)
Apr 43°F (6°C) 3.3 inches (85 mm) 5°C (42°F) 36 mm (1.4 in)
May 53°F (12°C) 3.3 inches (85 mm) 13°C (56°F) 60 mm (2.4 in)
Jun 63°F (17°C) 3.1 inches (79 mm) 19°C (65°F) 84 mm (3.3 in)
Jul 69°F (20°C) 2.6 inches (66 mm) 21°C (71°F) 72 mm (2.8 in)
Aug 67°F (20°C) 2.6 inches (66 mm) 20°C (68°F) 75 mm (3 in)
Sep 59°F (15°C) 3.1 inches (78 mm) 14°C (57°F) 51 mm (2 in)
Oct 49°F (9°C) 3.3 inches (84 mm) 7°C (45°F) 30 mm (1.2 in)
Nov 39°F (4°C) 4.8 inches (123 mm) -3°C (26°F) 21 mm (0.8 in)
Dec 27°F (-3°C) 4.1 inches (103 mm) -13°C (9°F) 19 mm (0.7 in)