If you’re looking to add some playful, festive fun to your Milwaukee visit, the Holly Jolly Hunt offers a cheerful way to explore the city during the holiday season. This app-based scavenger hunt turns your smartphone into a holiday adventure, combining sightseeing with laughter and lighthearted challenges.
It’s designed for groups of up to ten people, making it a perfect activity for families, friends, or even co-workers eager to share some holiday cheer.
What we really like about this experience are two key aspects: first, it’s accessible to all ages and fitness levels, and second, it brings a spirited, interactive element to your holiday exploration. You don’t need to be a seasoned traveler or a history buff—just bring your sense of fun and enjoy the city’s sights in a new way.
A potential consideration is that it relies on a smartphone, so if you’re traveling without one or prefer guided tours, this might not be the ideal fit.
This scavenger hunt is best suited for those who enjoy a casual, playful adventure that encourages team spirit and creativity. It’s perfect for families wanting to make holiday memories, groups of friends looking for a memorable activity, or co-workers seeking a fun team-building exercise. If you enjoy interactive experiences that blend sightseeing with humor, Holly Jolly Hunt is worth considering.
Key Points
- Affordable fun: Cost is $20 per group, making it a budget-friendly way to enjoy the holidays.
- Flexible timing: Play during the holiday season from late November through December, with opening hours from 9 am to 5 pm Tuesday to Sunday.
- Interactive and engaging: Features holiday-themed tasks and challenges to bring laughter and memorable moments.
- All ages welcome: No age restrictions; suitable for young kids, teens, and adults alike.
- Easy to participate: No need for prior experience—just download the app and follow the instructions.
- Inclusive: Service animals are allowed, and the activity is near public transportation.
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The Experience in Detail

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How It Works
The Holly Jolly Hunt is a one-hour adventure designed to be played at your own pace within Milwaukee. The process is straightforward: you purchase a mobile ticket for $20, suitable for groups up to 10 people, and receive a link to the app. Once you’re ready, you start at the Cathedral Square Park (located at 520 E Wells St), the designated meeting point. The app guides you through your holiday quest, prompting you to find specific items around the city—both traditional (like Christmas trees or holiday decorations) and some surprises that are less obvious.
Throughout the hunt, you’ll take photos via the app to earn points, and you’ll also be tasked with performing holiday-themed challenges meant to spark laughter and interaction. For example, you might be asked to do a silly dance or sing a holiday song, adding extra fun to the activity. Your points are tracked on a leaderboard, so you can see how your team stacks up against others in real time—friendly competition is part of the charm.
What Makes Milwaukee Special?
Milwaukee’s vibrant downtown provides a scenic backdrop for this holiday adventure. The start point at Cathedral Square Park is a natural gathering spot, often decorated with seasonal displays, and close to other attractions. The activity ends back at the same meeting spot, making it convenient to combine with other outings or meals afterward.
What to Expect
Participants should plan for roughly an hour of activity, but you could spend longer if you indulge in additional sightseeing or photos. The experience is designed to be light and fun, not overly strenuous, making it accessible for most. Since the tour is private, only your group will participate, ensuring a relaxed and personalized experience.
What’s Included and Not Included
The price covers the app activities, a remote guide via text message who can offer hints or assistance if needed, and all associated fees and taxes. You’ll need your own smartphone, as the activity functions through the app. Private transportation isn’t included, so be prepared to walk between locations or use public transit.
Practical Considerations
- Booking in advance is recommended, as most groups book about 13 days ahead on average.
- The activity operates from late November through December, aligning with the holiday season.
- It’s suitable for most travelers, as the activity is designed to be simple and engaging.
- Service animals are permitted, which is helpful for travelers with mobility needs or emotional support animals.
Authentic Voices and Expectations
While there are no formal reviews yet, the concept of a holiday-themed scavenger hunt has broad appeal. Past participants likely enjoy the interactive, family-friendly nature of the activity, and the fact that it’s played outdoors makes it a healthy way to get some fresh air during the winter months.
You might find the cost particularly appealing when compared to more traditional guided tours or museum admissions. For just $20, you get an hour of entertainment, a chance to see parts of Milwaukee you might not explore on your own, and plenty of laughs along the way.
Some travelers could see it as a light-hearted alternative to more traditional holiday events. The inclusion of silly challenges and the competitive element will keep everyone engaged, especially kids or those young at heart. However, if your group prefers guided commentary or historical insights, this activity may be more playful than educational.
The Sum Up

The Holly Jolly Hunt in Milwaukee offers a lively, inexpensive way to enjoy the city’s holiday atmosphere. Its app-driven format makes it easy and flexible, while the interactive challenges encourage spontaneous fun and create memorable moments. It captures the festive spirit without requiring much planning or physical exertion—perfect for families, friends, or coworkers looking for a lighthearted holiday outing.
For those who enjoy interactive sightseeing combined with humor, this scavenger hunt provides a unique way to explore Milwaukee’s downtown and soak in the seasonal cheer. It’s especially ideal if you want a personalized experience that’s easy to book and adaptable to your schedule. While it won’t replace a detailed city tour, it offers a delightful, low-pressure way to celebrate the holidays and make lasting memories.
If your group appreciates fun, casual activities that bring everyone together, Holly Jolly Hunt is an excellent choice. Just be sure to book in advance, dress warmly, and come ready to laugh and explore.
Get in the holiday spirit with a scavenger hunt by Holly Jolly Hunt in Milwaukee
FAQ

Is this activity suitable for children?
Yes, it’s designed for all ages. The challenges are holiday-themed and meant to be fun for kids and adults alike.
How long does the scavenger hunt last?
The activity is approximately one hour, but you can take longer if you wish to complete more challenges or take extra photos.
What’s the cost?
It’s $20 per group, up to 10 people, making it an affordable way for a group to enjoy the holiday season together.
Do I need a smartphone to participate?
Yes, the scavenger hunt is app-based, so a smartphone is required to play and submit photos or complete tasks.
Can I do this activity in any city?
Yes, Holly Jolly Hunt is designed to be played in any city, and you can book it in Milwaukee or other locations.
What’s included in the price?
Your fee covers the app activities, all scavenger hunt tasks, and a remote guide via text message for assistance.
Are there any accessibility considerations?
Service animals are allowed, and the activity is suitable for most travelers. Since it involves walking, consider weather conditions and mobility needs.
When can I book this activity?
Bookings are typically made 13 days in advance, and the activity runs from late November through December.
Is transportation included?
No, private transportation is not included. You’ll need to walk between locations or use public transit.
Can I cancel if my plans change?
Yes, there is a free cancellation policy up to 24 hours before the start time.
This holiday season, consider adding a playful twist to your Milwaukee visit with the Holly Jolly Hunt. It’s a straightforward, cheerful way to connect with friends and family, enjoy the city’s festive sights, and create some of those “remember when” moments that make holidays special.

















