Self-Guided Adventures

One Day Mystery Road Trips

Our ultimate goal is to create a memorable experience that will inspire you to try, see, and do something you've never done before. We encourage you to step out of your comfort zone and take the road!

GIFT-A-TRIP

Give the Gift of a Surprise

Looking for the ultimate experience gift? We have everything from single gift cards to road trip gift boxes that will allow the recipient to select a road trip of their choice.

AS SEEN ON

Dragons' Den

All the dragons loved our mystery road trip experiences when Guess Where Trips' founder (Jessica Off) made a memorable appearance on Dragons' Den. Discover what had the dragons hooked – take a Guess Where Trip and experience the magic for yourself!

AS SEEN ON

step-by-step

So, How Does it Work?

Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.

1

Select your trip.

Choose a day trip based on your location and interests, or take our quiz to narrow down options.

2

Get your package.

Choose between a beautifully crafted package by mail or a PDF version sent to your inbox.

3

Hit the road!

Each package includes a 'Before You Go' booklet with essential information that won't spoil your surprise destinations.

What Will You Get?

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Sign Up for a Discount!

Stay up to date with new trips, special deals and get a discount for your first trip.

Choose Your Day Trip Starting Location

Our Trip Map

Our interactive map allows you to search for a trip's ending destination. Simply type in your city or address to see the closest trips to you.

CAN'T DECIDE?

Take our road trip quiz!

Enter your departing address, select your interests, and preferred driving duration to find the best trip for you.

Take Our Quiz

Why day trips make a great gift

Perfect for the avid adventurer or the person who has it all, let them choose their own path with the help of Guess Where Trips. With each envelope comes a new exciting destination and locale to explore with none of the long hours of planning.

What we're up to

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