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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 Windsor
Please see the approximate driving distance below. Please note this includes driving distances and not time spent at each destination.
From Windsor: 2 hours and 20 minutes / 140 km
From Chatham: 2 hours and 53 minutes / 201 km
From Sarnia: 4 hours and 45 minutes / 356 km
From London 5 hours and 5 minutes / 428 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: Outdoor Enthusiasts, Photographers, Wine Lovers, Cyclists (optional cycling routes available)
- Hiking options that work well for everyone
- World class wineries and restaurants
- A charming and historic small town
- Quirky photo ops
What You'll Need to Bring:
- Bathing Suit
- Bicycle (not required)
- Road Trip Snacks
- Walking shoes
- Kid Friendly
- Pet 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.