Festive Road Trips

2026 Festive Season

Twinkling lights and charm

Magical memories

7 Products

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

Ends Near St. Marys, ON

(1)

Classic Road Trip

A Cozy Countryside Christmas

Trade your holiday to-do list for a day of twinkling lights, cozy sips, and festive finds.

From $39

End destination map: Toronto 1 hr 20 min, Kitchener 1 hr 15 min, Hamilton 1.5 hr, London 2 hr 15 min.

Ends Near Orangeville, ON

Classic Road Trip

All Things Merry & Bright

If you're looking for a road trip that is full of festivity and holiday cheer, look no further!

From $39

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

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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Two people clinking glasses of red wine.

Ends Near Frankenmuth, MI

(3)

Classic Road Trip

Endless Christmas Cheer

Year-round festive cheer, cozy shops, and a picture-perfect covered bridge.

$50

A travel map graphic showing an end destination near Toronto, with dashed lines and labels pointing to Toronto, Kitchener, Hamilton, and London with travel times.

Ends Near Niagara, ON

(73)

Classic Road Trip

Funky Florals and Fine Wines

Must enjoy: wine, food and flowers for this pretty little road trip.

$50

A map-style destination graphic showing a central pin over Kitchener, with dashed lines and labels to Toronto (1.5 hr), Hamilton (1 hr 15 min), and London (2 hr) under the heading 'END DESTINATION'.

Ends Near Elora, ON

(208)

Classic Road Trip

Local Markets & Picturesque Towns

Historic towns, local markets, and plenty of under-the-radar finds.

$50

A map-style destination graphic showing a central pin near Toronto with dashed lines pointing to nearby cities and travel times: Barrie 1.5 hr, Peterborough 1 hr, Oshawa 35 min, and Toronto 1 hr 15 min.

Ends Near Port Perry, ON

(53)

Classic Road Trip

Taste of the Country

Farmers' markets, cute small towns, and an easy wooded trail to round out your day.

$50

Amazing and historic places that were made more amazing with the all the Christmas decorations and trees.

Alexis T.

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Festive Road Trips

A Cozy Countryside Christmas

All Things Merry & Bright

Brews, Bites, and Everything Nice

Gift Cards

Endless Christmas Cheer

Funky Florals and Fine Wines

Local Markets & Picturesque Towns

Taste of the Country

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Festive Road Trips

A Cozy Countryside Christmas

All Things Merry & Bright

Brews, Bites, and Everything Nice

Gift Cards

Endless Christmas Cheer

Funky Florals and Fine Wines

Local Markets & Picturesque Towns

Taste of the Country

Give Us a Follow!

Get a mystery discount!

Our Trips

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