Winnipeg is a city full of surprises, offering a mix of historic sites, vibrant neighborhoods, and scenic parks. Its compact size makes it ideal for exploring on foot or by small-group tour, and the variety of options caters to different interests and budgets. We’re particularly fond of the Winnipeg: 2-Hour City Trolley Tour, which combines humor, history, and style—perfect if you want a lively overview without breaking the bank. Meanwhile, the Private City Tour in Winnipeg offers a personalized experience, ideal for travelers who prefer tailored insights or have limited time. For those seeking a playful challenge, both Operation City Quest’s scavenger hunt and Wacky Walks’ fun scavenger hunt turn sightseeing into a competitive game, making history and landmarks more memorable.
From guided tours to interactive challenges, Winnipeg’s city tours make it easy to discover the city’s most iconic spots and hidden corners. Whether you’re after an informative ride, a private adventure, or a lively scavenger hunt, there’s something here to fit your travel style. Below, we’ve broken down the best options to help you choose the perfect Winnipeg experience.
1. Winnipeg: 2-Hour City Trolley Tour
At number 1 on our list is the Winnipeg: 2-Hour City Trolley Tour, which has earned a stellar rating of 4.8/5 from 169 reviews. This tour offers a fun, humorous ride in a historically-inspired trolley through the city’s top sights. It’s perfect if you want a quick but lively overview of Winnipeg’s highlights, including landmarks like The Forks, Old Market Square, and the Exchange District. The guide’s storytelling makes the history and local stories engaging, even for those who’ve visited before.
The tour’s value lies in its combination of entertainment and education at just $33 per person for two hours. It’s ideal for first-time visitors or travelers short on time who want an authentic, relaxed introduction. The trolley’s vintage style lends a nostalgic feel, making the experience both memorable and photo-worthy. The reviews praise the guide’s humor and knowledge, making this a lively, carefree way to start your visit.
Bottom Line: A friendly, affordable option for a quick city overview with a touch of humor and style.
2. Private City Tour in Winnipeg
Coming in at number 2 is the Private City Tour in Winnipeg, which scores a solid 4.5/5 from 33 reviews. For around $96, this customized 2-hour tour offers a more personalized look at the city’s main attractions. Your private guide takes you to places like The Forks Market, Saint Boniface (Canada’s second-largest French-speaking community), Old Market Square, and the Winnipeg Railway Museum — all selected based on your interests.
What sets this tour apart is the flexibility; you can choose your preferred time (morning or afternoon) and get tailored insider tips on where to eat, drink, or explore further. The guide, often a local with deep knowledge of Winnipeg’s culture and history, shares fascinating stories about Louis Riel, Winnipeg’s film industry (“the Chicago of the North”), and the 1919 General Strike. This is an excellent choice if you prefer a relaxed, in-depth experience with fewer people and more personal attention.
Guests consistently praise the guide’s enthusiasm and flexibility, noting that it’s a comfortable way to learn about Winnipeg without feeling rushed. If you appreciate being able to customize your sightseeing, this private tour delivers.
Bottom Line: A flexible, intimate way to see Winnipeg’s key sights with expert guidance tailored to your interests.
3. Unique Scavenger Hunt Experience in Winnipeg by Operation City Quest
Number 3 on our list introduces an entirely different approach with the Operation City Quest scavenger hunt. For just $10.29 per person, you and your friends can explore Winnipeg on foot, completing challenges and taking photos at various landmarks. Using a smartphone app, you’ll follow clues and compete remotely with a host who can answer questions and keep you on track. This interactive experience turns sightseeing into a game — perfect for families, groups, or anyone who wants to add some fun and laughter to their visit.
What makes this tour unique is the mix of exploration and competition. You get to see the city from a different perspective, uncover hidden spots, and test your teamwork skills. The focus is on engaging with the city’s sights in a playful way, making it ideal for travelers who prefer active experiences and don’t mind a little friendly competition. While there are no reviews yet, the low price and social aspect make this a compelling option for budget-conscious adventurers.
Bottom Line: An affordable, fun-filled way to discover Winnipeg’s sights with friends, blending walking, challenges, and technology.
$10.29 per person
4. Fun City Scavenger Hunt in Winnipeg by Wacky Walks
Finally, the Wacky Walks’ Fun City Scavenger Hunt also offers a lively, interactive experience at a similar price point of $10.27 per person. Like the previous scavenger hunt, this activity involves walking around Winnipeg with an app, completing various challenges, and collecting points along the way. Participants can compare their scores with others across the country, adding a competitive edge to the adventure.
What makes this tour different is its emphasis on wacky, creative challenges that make exploring a city feel like a game show. It’s suitable for travelers who enjoy light-hearted fun, quirky tasks, and social interaction. With a remote host offering assistance, it’s a flexible and engaging way to see Winnipeg’s streets in an active, entertaining manner.
Though reviews are not yet available, the emphasis on fun challenges makes this a good choice for families or groups seeking a less conventional sightseeing experience. It’s perfect for those wanting to blend physical activity, strategy, and humor.
Bottom Line: An entertaining, competitive scavenger hunt ideal for active travelers looking for a lighthearted way to explore Winnipeg.
$10.27 per person
How to Choose the Right Winnipeg Tour
Choosing between these tours depends largely on your interests and travel style. If you want a quick, entertaining overview, the trolley tour offers a relaxed, humorous introduction. For a more tailored experience, the private city tour provides personalized insights and flexibility. If you’re traveling with friends or family who love games, the scavenger hunts and Wacky Walks turn sightseeing into a competitive, energetic activity.
Consider your budget, the level of interaction you want, and your interest in history or local culture. The private tour is best for those wanting detailed, personalized stories, while the scavenger hunts are perfect for a lively, social experience. Booking early is advisable, especially during peak seasons, to ensure availability and the best times.
Final Thoughts
Winnipeg offers a variety of city tours that cater to different tastes — whether you prefer a relaxed trolley ride, a personalized guided exploration, or a fun, interactive game. For history lovers, the private tour provides in-depth local stories, while families or groups seeking active fun might prefer the scavenger hunts. Budget travelers will appreciate the affordability of the scavenger hunt options, which offer a lot of entertainment for little money.
No matter which option fits your style, booking early will help ensure you get the most out of your Winnipeg experience. With its welcoming atmosphere and diverse attractions, Winnipeg is waiting to be explored — and these tours make it easier than ever to see the city’s best sights in a way that suits you.