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Weird and Wonderful Surprise Road Trip - Toronto Area

By Guess Where Trips Inc.


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

Why this makes a great gift

Know someone who could really use some "away" time? We've got you covered. This gift is perfect for the adventurer in your life who loves exploring and discovering hidden gems. From hiking to haunted hotels, let Guess Where Trips do the planning and be surprised with the perfect road trip. Bring a friend or five and let the good times roll. This North of Toronto-based trip is great for extending into an overnighter!

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 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 a surprise road trip! While we can't tell you where exactly you will be going until you open your first envelope, below will give a rough idea as to where you will be going!

Stops Located
North of Toronto.

Round-Trip Driving Distances

From Toronto: 5 hours and 32 minutes / 559 km

From Oakville: 5 hours and 32 minutes / 570 km

From Hamilton: 6 hours and 9 minutes / 633 km

From Pickering: 5 hours and 21 minutes / 474 km

From Kitchener: 6 hours and 36 minutes/ 674 km

From Barrie: 3 hours 29 minutes / 344 km

From London: 8 hours 11 minutes / 849 km


  • 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
Getting away from it all, longer roadtrips and overnight stays

Surprise Stops

  • The cutest Canadian coffee shop
  • A couple of pretty waterfalls
  • Hiking recommendations
  • A beautiful lookout stop
  • A haunted hotel
  • A town with hidden outdoor art
  • A variety of lunch stops (From healthy, hearty to just plain weird)
  • A place ranked as “one of the world’s most bizarre places”

More Information

Can be used every day except for holidays.

Dog friendly (except for the restaurant stops)

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