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Why this makes a great gift
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, these roundtrip times and distances are here to guide you.
Round Trip Driving Distances and Times
From Toronto: 2 hours and 46 minutes / 205 km
From Oakville: 2 hours and 34 minutes / 183 km
From Hamilton: 3 hours and 4 minutes / 236 km
From Pickering: 3 hours and 6 minutes / 257 km
From Kitchener: 3 hours / 188 km
From Barrie: 2 hours 45 minutes / 200 km
From London: 4 hours 56 minutes / 388 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
Adventurous families, quick getaways, photographers
- A cute cafe located in the middle of the most picturesque hamlet
- An outdoor art opportunity (with a waterfall in the mix)
- A variety of lunch opportunities
- A hidden gem of a winery (alternative stops available)
Available to depart Wednesday-Sunday
Can be used all year
Great for families
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.