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From the founder...

Hi there! I'm Jessica, the founder of Guess Where Trips. Thank you for stopping by and taking the time to learn about us. Here are some fun facts about myself and the Guess Where Trips journey:

Before starting Guess Where Trips, I've worked in some of the weirdest and most wonderful places in the world. I taught a travel course in North Korea and worked at the Ministry of Tourism in the Cook Islands (a tiny island in the middle of the Pacific Ocean). I've always had a passion for discovering the unknown.

The idea of Guess Where Trips originated from a Christmas gift I gave to my parents. I had planned an overnight surprise trip to Prince Edward County through a series of surprise envelopes. I enjoyed doing it so much, I started a business out of it!

This isn't the first business I've started. I had a travel deal blog and a consulting business for small tour operators. I'm passionate about entrepreneurship and am constantly thinking of new business ideas.

Guess Where Trips now has an amazing team of four full-time staff and quite a few extras who help on a part-time basis.

Our ultimate goal is to create an experience that will inspire you to step out of your comfort zone and explore your own backyard.

Guess where you'll go next?

What's Included:

A ‘Before You Go’ guide with a packing list, approximate driving distances and more tips to plan for your day ahead.

A series of four envelopes that will make up your day’s itinerary with recommended roadside stops along the way.

Exclusive 'Guess Where' discounts and incentives at select businesses.

Restaurant, attractions and activity recommendations based on your trip style.

What's Not Included:

Transportation and gas.

Entrances and parking fees for some of recommended attractions (the majority of stops are free).

Food, beverages and gratuities.

Our Trips

At Guess Where Trips, we live for creating exciting road trips that allow travellers to discover new places they never would have discovered on their own.

Frequently asked questions

We're here to help

You have two shipping options when checking out.  Our expedited option is $8.70, with tracking, and it takes between 5-7 business days. We also have an Xpresspost option for $12, which will take 2-5 business days. If you spend more than $100, we will ship your package for free via expedited mail.

We highly recommend turning your day trip into an overnight getaway. We pack so much into the itinerary you won’t run out of activities. Once your trip is booked, we automatically email you a list of recommended accommodations within the finishing area. Unfortunately, we can’t book these for you.

After choosing a trip, please enter your 16-character code on the checkout page in the field under ‘Have a Gift Card?.’ This will then take your order to a zero balance.

Most trips are between 6-8 hours, which includes the driving and time spent at each stop. When selecting a trip, we’ll provide you with more information on approximate driving times and distances.

You can bring as many people that will come! However, we recommend 2-5 people per trip. The trip’s price is not based per person but per trip.

Most of the activities and attractions we recommend are free or have a minimal entrance cost (under $10/per person). We note the approximate costs per person in each trip package. If there is a higher entrance fee, we will recommend a free nearby alternative.

Yes! Almost all of our trips are kid-friendly. We recommend choosing trips shorter in driving length to ensure it’s a pleasant drive for everyone 🙂

Most of our trips are dog-friendly! Before purchasing a trip, check to ensure it’s dog-friendly.