Experience Montreal Through Curiosity!

A three-day, small-group adventure focusing on food, culture, and connection

September 11–13, 2026

By clicking “Book Now!” below, you agree to the CuriosiTrip Terms & Conditions and Montreal Trip-Specific Terms.

Book Now!

What is a CuriosiTrip?

A CuriosiTrip is an exploratory travel experience where curiosity leads the way.

We design our time to explore Montreal’s neighborhoods, connect with local culture, and try unique foods and experiences without rushing through a rigid “see everything” schedule.

A glimpse of what’s waiting in Montreal…

Colorful street art and murals in Montreal neighborhood
Photo by Benoit Debaix on Unsplash

Why Montreal?

A city that blends European charm with North American energy. It’s the kind of place that rewards curiosity!

  • Walkable neighborhoods filled with character, murals, and hidden corners
  • A food scene that ranges from iconic staples to local favorites
  • A cultural mix that feels distinct, dynamic, and a little unexpected
St. Lawrence River running through Montreal at dusk, with the bridge and buildings illuminated
Photo by Walid Amghar on Unsplash

What to Expect?

A thoughtfully designed experience with room for serendipity and community. No rushing. No checklists. Just a better way to experience a place.

  • A curated three-day experience with a balance of structure and flexibility
  • Walkable exploration through distinct neighborhoods
  • A mix of planned moments and space for spontaneous discovery
  • Shared meals, conversations, and a small group atmosphere
  • Time built in to explore on your own

Who This Is For

  • Curious travelers who want more than a typical sightseeing tour
  • People who enjoy exploring with others, but also value independence
  • Those who are open to new experiences, foods, and perspectives
  • Travelers who appreciate a mix of structure and spontaneity
  • If you like to explore with intention but not overplanning, you’ll fit right in!
Colorful balconies with ornate designs on rowhouses in Montreal
Photo by Etienne Delorieux on Unsplash

What’s Included:

  • Curated 3-day CuriosiTrip experience
  • Small-group setting
  • 2-3 selected meals featuring local cuisine
  • Entry to select activities and experiences
  • Public transportation for group activities
  • Guided exploration and coordination throughout
  • Pre-trip correspondence with other attendees

What’s Not Included:

  • Airfare
  • Accommodation (suggestions provided)
  • Travel insurance (required)
  • Most meals and beverages
  • Transportation outside of group activities (e.g. airport transfers)
  • Optional activities not listed

Pricing

$795

Limited spots available. Prices listed in USD.

Before You Book

Please review both documents carefully before booking. They contain important information about cancellations, responsibilities, and trip expectations. Thank you!

By clicking “Book Your Spot!” below, you agree to the CuriosiTrip Terms & Conditions and the Montreal Trip-Specific Terms & Conditions.

Book Your Spot!

After You Book

  • Access to the group WhatsApp chat and pre-trip communication
  • Recommendations to help you make the most of your time in Montreal

Sample Itinerary

Day 1 – Arrival + Old Montreal

  • Arrival and group meet-up
  • Explore McGill University, Mount Royal and historic Old Montreal
  • Saint Helen’s Island (time permitting)
  • Welcome dinner

Day 2 – Murals + Neighborhoods

  • Jean Talon Market and local food
  • Street art and neighborhood exploration
  • Saint Louis Square
  • Flexible evening schedule

Day 3: Offbeat + Farewell

  • Olympic Stadium and Botanical Gardens
  • Optional free time to explore
  • Farewell dinner

Each day is designed with intention, while leaving room for curiosity to lead the way.

What Past Travelers Are Saying

John The Traveler is your perfect guide if you are looking for something a little different. He fully embraces “curiosity” and allows you to experience it with him.

If you’re looking for a trip with other curious individuals who like to explore new places then taking a CuriosiTrip may be perfect for you! You’ll be delighted by a mixture of local flavors both cultural and food.

I am generally not a fan of multi-day group tours (even when the group is smaller), but the CuriosiTrip was not a typical group tour. It felt like we were just hanging out with new friends, rather than trying to rush through a firm itinerary. I’d book another CuriosiTrip with John the Traveler!

Ready to Join?

Secure your spot and experience Montreal in a more meaningful and curious way.

By clicking “Book Your Spot” below, you agree to the CuriosiTrip Terms & Conditions and the Montreal Trip-Specific Terms.

Book Your Spot

Limited spots available.

Come see what curiosity uncovers.

Leonard Cohen mural in Montreal
Photo by Slava Abramovitch on Unsplash

Frequently Asked Questions (FAQs)

The official kickoff event will be at 9:00 AM local time on Friday, September 11, 2026, with an optional meetup the evening before. Be sure that you arrive with enough time to settle in and come prepared to mingle and start our CuriosiTrip.

We recommend arriving no later than the night before to avoid potential complications. Ideally, you would arrive in Montreal by noon on September 10, 2026. Montreal follows Eastern Daylight Time, which is the same as New York and three hours ahead of Los Angeles.

Of course, it is highly encouraged that you consider adding more time to your Montreal trip, whether it is before and/or after our CuriosiTrip.

We are seeing some of less-touristy sides of the city, and while there will be a little free time to check out the popular attractions around the city, we hope you will take time and explore more of what this magnificent city has to offer. Quebec City is only about 2.5-3 hours northeast and Ottawa is about 2-2.5 hours west in case you’d like to plan a bigger Canadian adventure.

In order to maximize our experience and accommodate a variety of budgets and travel styles, this CuriosiTrip will not include lodging.

However, we will provide some suggestions of places to stay for your consideration.

We have partnered with some online booking engines that provide maps with lodging options that are centered around the proximity of where we will meet. Please note that the accommodation suggestions here include affiliate links. If you click through and make a purchase, I may receive a small commission at no additional cost to you. Thank you for your support!

The daily schedule will be tailored with a mind towards the composition and interests of the participants. As such, a detailed itinerary cannot be posted here.

However, participants who sign up will receive access to an exclusive WhatsApp group where they can ask questions, get to know each other, suggest places of interest, share travel tips, and much, much more.

Additionally, we are open to hosting a forum to address questions, discuss itinerary options, and do our best to ensure that everyone is prepared for the trip. This may be in the form of an Instagram Live, a group video chat, or a 1:1 call…or all of the above!

The best way to explore a city is to walk…a lot! While we will be stopping several times, there may not always be a place to sit down or rest. However, we’ll do our best to minimize walking while maximizing our curiosity.

A good rule of thumb is to expect 10,000 to 15,000 steps on average per day. Be prepared to be outside and moving for several hours each day. Wear sunscreen and a hat, and always wear sturdy walking shoes. (Please, no Crocs or flip-flops!)

If you have mobility issues or do not think you will be able to walk as much but still want to go, you may opt to take transportation to and from specific destinations.

Our time together is short. Be sure to build in some time to rest after the trip.

This trip is designed to allow you some free time to explore a little outside of our group, or with a new friend. Of course, you are not obligated to attend every activity if you would prefer to explore on your own.

Saturday evening and Sunday afternoon will have some dedicated free time, but you will have the morning before we meet and the evening after our group activities for yourself.

We will have a better idea of specific timing as the trip gets closer and people sign up. The flow of the trip will be dependent on who is coming and what kinds of experiences we have. We want to be open to serendipity at all times.

We firmly believe that age ain’t nothing but a number! That said, this CuriosiTrip is not designed for children or minors.

You should have some level of maturity and travel expertise to be able to respect cultural differences and norms. We will not be partying all day, nor will we be sitting around.

The estimated age range is 35-75, but any age is welcome as long as you are able to know your limits.

As mentioned above, the best way to experience this trip will be to be as mobile as possible. Solo travelers, couples, friend groups, and parents of adults are all acceptable!

Ticket sales will likely end sometime in August 2026 to ensure there will be enough time to prepare for the trip.

The early bird pricing may only be available for a limited time. If you have any concerns about pricing, please feel free to contact us directly.

Unfortunately, tickets are non-refundable so please be sure you can join us when you sign up.

Things can happen. We are requiring travel insurance to protect YOU. We have heard too many stories of travel mishaps that ended up costing thousands of dollars when insurance would have covered everything. Personally experience has also shown that having good coverage can pay off.

We’ve had good results with Allianz, which is why we’ve partnered with them. We get an annual plan with a level of coverage that matches our frequent travel habits.

For other options, you can check out Insure My Trip, which allows you to compare coverage from different insurers.

By signing up for this trip, you acknowledge that you will have appropriate travel and medical insurance and may be asked to show your coverage details to us when we meet in Montreal. If you have any questions or concerns about this requirement, please contact us directly.

Yes, you are still welcome to join us! We strongly encourage you to get WhatsApp, as we will have a group chat that will enable us to communicate with each other, changes, meeting points, etc.

Due to the nature of the trip, the itinerary may change frequently and we want you to be informed. There will still be time to unplug and be present on the trip.

CuriosiTrips are non-refundable, but we understand things come up. This is one of the reasons why travel insurance is beneficial and a requirement. However, if you have an emergency or are ill, please contact us. Transfers are also an option.

You must agree to the Terms & Conditions to sign up for the CuriosiTrip.

Terms + Conditions

By booking, you agree to the CuriosiTrip Terms & Conditions as well as the Montreal Trip-Specific Terms & Conditions. These documents outline payment terms, cancellation policy, participant responsibilities, and terms specific to this CuriosiTrip. Be sure you carefully review both of the following documents and ensure you understand. If you have any questions, please contact us!

View Full CuriosiTrip Terms + Conditions

View Montreal Trip-Specific Terms + Conditions

About CuriosiTrips

CuriosiTrips are independently organized travel experiences designed for small groups of curious travelers seeking deeper, more intentional ways to explore the world.