Our ultimate goal is to create an experience that will inspire you to step out of your comfort zone and try, see and do something you’ve never done before. All while encouraging our customers to travel responsibly and support local businesses.
Guess Where Trips was created by Jessica Off after several years of planning travel. Our team understands how long it takes for the average trip to be planned and booked. One of our greatest joys is creating exciting itineraries that allow travellers to discover new places they would have never seen before.
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?
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.
Transportation and gas.
Entrances and parking fees for some of recommended attractions (the majority of stops are free).
Food, beverages and gratuities.
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