Barrie / Muskoka

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Self-guided & fully flexible

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Canada Ontario GTA K-W / Hamilton Southwestern Ontario Barrie / Muskoka Eastern Ontario

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Toronto Day Trip Box by Guess Where Trips, illustrated with the CN Tower skyline, a red barn, a waterfall and a winding country road.

What's included in the Toronto Day Trip Box: 20 sealed trip envelopes and a map of all 20 trip areas.

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(5)

Road Trip Box

Toronto Day Trip Box

20 day trips from Toronto: Mennonite country, lakeside towns, and hidden trails.

$65

Ontario Getaway Box by Guess Where Trips, illustrated with lakeside cottages, red Muskoka chairs on a dock, rocky island bluffs and a boat.

What's included in the Ontario Getaway Box: 20 sealed trip envelopes and a map of all 20 trip areas.

NEW

(8)

Road Trip Box

Ontario Getaway Box

20 getaways across Ontario: cottage country, Niagara wine country, and beach towns.

$65

The Surprise Which Way? Road Trip Game box on a light cream textured background. The packaging features a bright orange top and bottom band with white text, and a central white panel decorated with cute illustrations of cars, a backpack, a coffee cup, and a suitcase, all framed by a dashed orange border.

A hand holds a mini card with a travel-themed mystery question, surrounded by promotional text callouts on a warm off-white background.

(4)

For the Road

Which Way? A Surprise Road Trip Card Game

Go on your own mini surprise trip with Which Way. Simply pick a card to reveal your next...

$22

Gift Cards

Not sure what to get them? Our digital gift cards are sent when you want, to whoever you want, in any amount you want.

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A map-style destination graphic showing an end point marked with a red pin, with dashed lines and labeled callouts to Kincardine, Barrie, Toronto, and Kitchener, each with estimated travel times.

Ends Near Owen Sound, ON

(34)

Classic Road Trip

Bayside Wonders

Farmers' markets, wine tastings, and waterfalls worth making it a weekend getaway.

$50

A travel map graphic showing an end destination with a red location pin and dashed lines pointing to four labeled locations: Collingwood (1 hr), Barrie (45 min), Peterborough (2.5 hr), and Toronto (1 hr 45 min).

Ends Near Midland, ON

(34)

Classic Road Trip

Hidden Gems of Huronia

Haunted history, picturesque trails, and farm-fresh flavours.

$50

End destination map: Collingwood 1 hr 45 min, Barrie 1 hr 15 min, Peterborough 2.5 hr, Toronto 2.5 hr.

Ends Near Port Carling, ON

(70)

Classic Road Trip

Muskoka Meandering

Cottage-country wineries, scenic lookouts, and charming small towns.

$50

A map-style destination graphic showing a central pin labeled 'END DESTINATION' with dashed lines pointing to four locations and their travel times: Parry Sound (1 hr), Barrie (1.5 hr), Newmarket (2 hr), and Peterborough (2 hr 15 min).

Ends Near Huntsville, ON

(87)

Classic Road Trip

Weird & Wonderful Things

Unusual attractions and secluded waterfalls that are worth the longer drive.

$50

A stylized map graphic showing an end destination marked with a red pin, with dashed route lines to three labeled locations: Barrie in 50 min, Toronto in 2 hr 15 min, and Kitchener in 2 hr 10 min.

Ends Near Collingwood, ON

(66)

Classic Road Trip

Markets to Mountains

Cute markets, mountainside hikes, and a cozy-meets-adventurous day.

$50

We had an amazing time! I highly recommend this trip for couples or groups of friends.

Cyndi G.

200,000+ Road Trips Sold200,000+ Road Trips Sold200,000+ Road Trips Sold200,000+ Road Trips Sold

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Barrie / Muskoka

Toronto Day Trip Box

Ontario Getaway Box

Which Way? A Surprise Road Trip Card Game

Gift Cards

Bayside Wonders

Hidden Gems of Huronia

Muskoka Meandering

Weird & Wonderful Things

Markets to Mountains

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Barrie / Muskoka

Toronto Day Trip Box

Ontario Getaway Box

Which Way? A Surprise Road Trip Card Game

Gift Cards

Bayside Wonders

Hidden Gems of Huronia

Muskoka Meandering

Weird & Wonderful Things

Markets to Mountains

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Get a mystery discount!

Our Trips

Help & Info

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