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Southern Express Surprise Road Trip - Windsor Area

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.

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

Why this makes a great gift

This trip takes you to some iconic stops and hidden gems in southern Ontario. It's the perfect combination of outdoor activities, funky restaurants, beaches and historic attractions. Worried about planning? This gift has you covered! Your itinerary will come mailed to your house in beautiful envelopes for an easy surprise road trip to enjoy!

Product Description

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 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.
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
What You Will Do
This Trip is Great For: Outdoor Enthusiasts, Photographers, Wine Lovers, Cyclists (optional cycling routes available)

Trip Highlights:
  • Hiking options that work well for everyone
  • World class wineries and restaurants
  • A charming and historic small town
  • Quirky photo ops
Available to Depart: Available to depart any day, with some closures between Monday - Wednesday's.

What You'll Need to Bring:
  • Bathing Suit
  • Bicycle (not required)
  • Binoculars
  • Camera
  • Cash
  • Road Trip Snacks
  • Walking shoes
  • Water
Additional Information:
  • Kid Friendly
  • Pet Friendly
  • Vegan
  • Wheelchair Accessible
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