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One Day Surprise Road Trip

By Guess Where Trips Inc.


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Sold and Shipped By: Guess Where Trips - This gift ships immediately via email. Redemption instructions are included in the email. All of our travel packages include free shipping Canadawide. Please select the desired road trip destination before adding to cart, the recipient can change to a different region if they choose at the point of redemption.

  • category:entertainment
  • experience
  • gifts_for_two
  • promote
  • subcategory:adventure_and_outdoors
  • subcategory:travel

Why this makes a great gift

Give the gift of choice and adventure with a surprise roadtrip! 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. This gift is the ultimate road trip catered and planned to the tastes and travel preferences of the wanderluster on your list. With each envelope comes a new exciting destination and locale to explore with none of the long hours of planning. You'll wonder why road tripping hasn't always been this easy!

Product Description

Select your trip. Get your package. Pack your bags. Road tripping has never been so easy!

With this surprise road trip you’ll get to select the type of trip you want to go on and leave the hard work to us. Once the trip style has been finalized you will receive your package of destinations at least 10 days before your selected departure date. The package includes a ‘Before You Go’ guide and a series of envelopes that will lead you to several surprise destinations on your road trip.

On the morning of your trip, open up the first envelope and drive to your surprise destination. Along the way, we include a number of ‘roadside recommendations’ that will break up the driving time in between.

Location & Duration
This is the ultimate surprise road trip! Choose between the areas surrounding Toronto, Ottawa, Vancouver or London, Ontario and the rest will be a surprise delivered to your door.


  • A ‘Before You Go’ guide with a packing list, approximate driving distances and more tips to plan for your day ahead.
  • A series of 4-5 envelopes that will make up your day’s itinerary with recommended roadside stops along the way.
  • Restaurant, attractions and activity recommendations based on your trip style.
  • Bring as many people as you want! 2-5 are recommended.

What's not included:

  • Transportation and gas
  • Entrance fees to any of the recommended attractions (we keep most of them free anyways)
  • Food, beverages and gratuities
  • Parking costs

This Trip is Great For
The spontaneous & indecisive

Can’t decide on a roadtrip? We can pick the best trip for you based on your preferences. Simply answer the questions in our travel questionnaire and we’ll make sure we send you on a surprise trip that works for you!

Here are some of the questions we’ll ask you

  • When you would like to travel
  • What activities you enjoy when travelling
  • What activities you DON’T like when travelling
  • How long you want to drive for
  • The type of trip you’re looking for

Who Will Guide You
This trip is self-guided! Guess Where Trips will in advance provide envelopes with your surprise roadtrip destinations. You will pilot this trip throughout the journey.

Shipping and Return Policy