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A map-style destination graphic showing a red pin near Ottawa with a dashed line leading to Kingston, labeled 'END DESTINATION' at the top, 'Ottawa 40 min', and 'Kingston 1 hr 40 min'.

Ends Near Almonte, ON

(54)

Classic Road Trip

Brews, Bites, and Everything Nice

The coolest brews, tastiest bites, and everything nice in between.

$50

A map-style destination graphic showing a red pin near Toronto, with labeled nearby locations and travel times: Toronto 1.5 hr, Kitchener 1 hr 45 min, Hamilton 1 hr, and London 2 hr 15 min.

Ends Near Fonthill, ON

(34)

Classic Road Trip

The Sweet & Scenic Route

Cozy cafes, maple treats, waterfalls, and scenic trails.

$50

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.

Shop Now Shop

End destination map: Sarnia 1.5 hr, London 1.5 hr, Kitchener 1 hr 45 min, Hamilton 2.5 hr.

Ends Near Goderich, ON

(42)

Classic Road Trip

Bridges to Beaches

Picturesque bridges to sandy beaches plus some off-the-beaten-path spots in between.

$50

A stylized map graphic with a red location pin near Toronto, showing three labeled destination options: Toronto 2 hr, Kitchener 1.5 hr, and London 1 hr 45 min, with the heading 'END DESTINATION' at the top.

Ends Near Cayuga, ON

(37)

Classic Road Trip

Beautifully Haunted

Spooky legends, rural scenery, and ghost-hunting energy all day.

$50

A travel map graphic showing an end destination with location pins and travel times to Toronto, Hamilton, Kitchener, and London. The map has a light gray land area with pale blue water and a dark green banner at the top reading 'END DESTINATION'.

Ends Near Terra Cotta, ON

(30)

Classic Road Trip

The Whimsical Route

Nature, history, and a touch of cinematic magic, close to home.

$50

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 stylized map graphic showing an end destination with labeled location callouts: Windsor 45 min, Sarnia 2 hr, Chatham 1 hr, and London 2 hr 15 min, connected by dashed brown lines to a red pin marker on a pale map background.

Ends Near Kingsville, ON

(32)

Classic Road Trip

Southern Express

Cozy bakeries, swim spots, and wineries with seriously epic views.

$50

A travel map graphic showing an end destination with a red location pin and dashed lines pointing to Ottawa (1 hr), Cornwall (1 hr 40 min), and Montreal (1.5 hr), with a header reading END DESTINATION.

Ends Near Montebello, QC

(33)

Classic Road Trip

Backroad Bliss

Waterfalls, a challenging hike, scenic drives, and irresistibly cute towns and shops.

$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

A map-style destination graphic showing a red location pin between Kingston and Ottawa, with labels reading 'END DESTINATION,' 'Ottawa 1 hr 40 min,' and 'Kingston 30 min.'.

Ends Near Gananoque, ON

(19)

Classic Road Trip

Views & Secret Stops

Views for days on a scenic, slightly more active route.

$50

A map-style destination graphic showing Calgary with a red pin marker and a dashed line pointing to Red Deer, with text labels 'END DESTINATION', 'Calgary 35 min', and 'Red Deer 1 hr 50 min'.

Ends Near Bragg Creek, AB

(26)

Classic Road Trip

Quirky Gems

Quintessential towns, funky eats, and picturesque hikes near the city.

$50

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.

(8)

Road Trip Box

Ontario Getaway Box

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

$65

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.

(6)

Road Trip Box

Toronto Day Trip Box

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

$65

“From the coffee shop, to the towns locals giving us some fun history ... was amazing!”

Marlena W.

A stylized city map showing an end destination with a red pin marker and dashed route lines to labeled locations: Toronto (1 hr 45 min), Kitchener (50 min), Hamilton (1 hr), and London (45 min).

Ends Near Woodstock, ON

(28)

Classic Road Trip

The Cheese & Charm Trail

Flower farms, dairy stops, and can't-stop-snacking energy.

$50

A map-style destination graphic showing a red pin near the left side and dashed lines connecting it to labeled locations: Collingwood 2 hr, Barrie 2.5 hr, Toronto 3 hr, and Kitchener 2 hr.

Ends Near Kincardine, ON

(25)

Classic Road Trip

Curiosities & Coastlines

Eerie ruins, historic towns & bridges, and easy afternoons by the shore.

$50

End destination map: Calgary 1.5 hr, Red Deer 2.5 hr.

Ends Near Banff, AB

(12)

Classic Road Trip

Rocky Mountain Route

Incredible mountain towns and endless photo-worthy views add to this iconic road trip.

$50

A travel map graphic showing an end destination with labeled locations: Ottawa 1.5 hr, Cornwall 1 hr, and Montreal 45 min, connected by dashed brown lines on a pale map background with green land areas.

Ends Near Hudson, QC

(20)

Classic Road Trip

Hidden Hideaways

Countryside breweries, charming towns, and a seasonal sculpture garden.

$50

A map-style destination graphic showing a central pin near Philadelphia with labeled routes to Allentown, Trenton, Newark, and Wilmington, each with travel time text.

Ends Near Frenchtown, NJ

(19)

Classic Road Trip

Along the River

Scenic river towns, under-the-radar finds, and photo-worthy moments.

$50

A map-style destination graphic showing a central pin near Baltimore, with dashed lines and labels pointing to Allentown, Trenton, and Philadelphia, plus text reading END DESTINATION.

Ends Near Kennett Square, PA

(12)

Classic Road Trip

Whimsical Wonders

Luscious gardens, charming towns, and whimsical photo ops.

$50

A map-style destination graphic showing a central pin near Ontario, with labeled nearby locations: Barrie, Peterborough, Oshawa, and Toronto, each with travel time annotations.

Ends Near Fenelon Falls, ON

(20)

Classic Road Trip

Butter Tarts, Boos & Brews

This autumn road trip mixes haunted tales with scenic drives, eerie landmarks, farm markets, local brews, and ooey-gooey butter tarts

$50

A map-style destination graphic showing a location near Wolfville and Halifax with travel times labeled: Wolfville 1.5 hr, Halifax 1 hr 10 min, and Truro 2 hr.

Ends Near Lunenburg, NS

(8)

Classic Road Trip

Coastal Crawl

Iconic coastal views, ocean breezes, and small-town hidden gems.

$50

Showing 23-44 of 152 products

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

Black Friday

Brews, Bites, and Everything Nice

The Sweet & Scenic Route

Which Way? A Surprise Road Trip Card Game

Gift Cards

Bridges to Beaches

Beautifully Haunted

The Whimsical Route

Bayside Wonders

Southern Express

Backroad Bliss

Hidden Gems of Huronia

Views & Secret Stops

Quirky Gems

Ontario Getaway Box

Toronto Day Trip Box

The Cheese & Charm Trail

Curiosities & Coastlines

Rocky Mountain Route

Hidden Hideaways

Along the River

Whimsical Wonders

Butter Tarts, Boos & Brews

Coastal Crawl

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