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Why this makes a great gift
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 are Located: Close to Toronto
Please see the approximate round-trip driving distances below. Please note this just includes driving distances and not time spent at stops.
From Toronto: 3 hours and 35 minutes / 288 km
From Oakville: 2 hours and 45 minutes / 216 km
From Hamilton: 2 hours and 35 minutes / 190 km
From Pickering: 4 hours / 365 km
From Kitchener: 3 hours and 55 minutes / 311 km
From Barrie: 5 hours and 50 minutes / 450 km
From London: 4 hours and 55 minutes / 435 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.
- 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: A friend getaway, A romantic date, Families with older children (15+), Seniors, Photographers
- A couple of Instagrammable floral stops
- A winery that offers a lot more than just wine
- A few quirky roadside pit stops
- A picture-perfect town with a lot of history
What You'll Need to Bring:
- Reusable shopping bags
- Walking shoes
- Kid Friendly
- Wheelchair Accessible
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.