Everyone has that spontaneous adventure seeker on their holiday shopping list. You know, the one who knows the best places to explore, the most exceptional restaurants to eat at, and where to find unique experiences.

They are vivacious, fun, and find “the unknown” to be exciting! They are also impossible to shop for. What do you buy for someone who is only interested in collecting memories and doesn’t want tangible things? Have you guessed where we are going with this? (hint!)

Gift them with a surprise road trip that they can look forward to in southwestern Ontario curated by the experts at Guess Where Trips! Each Guess Where Trips itinerary was created to inspire people to step out of their comfort zones and try something they’ve never done before. All while encouraging local travel that supports local businesses.

What's Included:

  • A "Before You Go" guide with a packing list, approximate driving distances and more tips for a day trip. 
  • A series of four envelopes that will make up a day’s itinerary with recommended roadside stops along the way.
  • Exclusive "Guess Where" discounts and incentives at select businesses.
  • Restaurant, attractions and activity recommendations based on the trip style.

Guess Where Trips Holiday Photo

Photo courtesy of Guess Where Trips Social Media Manager, Eleni Kyri.

Here are 4 of our favourite Guess Where Trips you can purchase now that will make the perfect gift for the adventurous person in your life. 

The Southern Express

The Southern Express itinerary is best experienced in the spring and fall! It's the perfect combination of outdoor activities, funky restaurants, beaches and historic attractions.


Southern Express by Guess Where Trips


Trip Highlights for the Southern Express:

  • Hiking options that work well for everyone.
  • World class wineries and restaurants.
  • A charming and historic small town.
  • Quirky photo ops.
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Secrets of the South

The Secrets of the South itinerary is best experienced from June to October! With funky markets, scenic roads and the most picturesque towns, you'll love all of the secrets you discover on the road.


Secrets in the South by Guess Where Trips


Trip Highlights for the Secrets in the South:

  • Scenic hikes with some non-hiking alternatives.
  • A countryside winery.
  • A beach town with a couple of secrets.
  • A seasonal lavender farm on a picturesque property.

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An Adventure is Brewing

The An Adventure is Brewing itinerary is best experienced from late-May to early-October! It's takes you on the perfect summer adventure filled with lavender fields (mid-June to mid-July), funky hidden gems, beaches and unique wineries and breweries.


An Adventure is Brewing


Trip Highlights for An Adventure is Brewing:

  • Unique breweries & wineries.
  • Some country shops and markets.
  • A fun beach town to soak up the sun.
  • A couple of lighthouses to snap a photo.

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Waterfront Wonders

The Waterfront Wonders itinerary is best experienced in the warmer months; June - September! It's an incredibly scenic route that takes you to a variety of picturesque stops you'll fall in love with. The best part? There are hardly any crowds.


Waterfront Wonders Guess Where Trips


Trip Highlights for Waterfront Wonders:

  • A variety of scenic lookouts and beaches.
  • A few hiking options to explore.
  • Funky breweries and restaurants along the way.
  • Beachside towns you'll fall in love with.

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Looking for even more unique ways to escape the city for a local getaway? Browse our collection of experiences and itineraries that have been specially crafted for adventurous souls craving the kind of connection that can only be found off the beaten path.