Woman holding four Guess Where Trips envelopes while on road trip

Winter Road Trips

Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

Browse all trips

  • BEST SELLER
    Woman looking at plants at a market.

    Local Markets and Picturesque Towns

    $65 USD
    One of our best-selling trips, and for a good reason. Stops include historic towns, local markets, eateries and hidden gems. This trip makes a great gift because of its versatility.
    • Accessible
    • Kid-Friendly
  • BEST SELLER
    The Small Town Charm Trail

    The Small Town Charm Trail

    $65 USD
    You know those towns that are described as 'blink-and-you'll-miss-it'? They often have the most amazing hidden gems! Get to know a few small pockets of Ontario with this surprise road trip.
    • Accessible
    • Kid-Friendly
  • GREAT YEAR-ROUND TRIP
    Woman sitting on a rocky shore overlooking a river.

    Riverside Roaming

    $65 USD
    Start your day in a picture-perfect town by the river before strolling along boardwalks, dining at a funky distillery, indulging at farm shops and so much more. This trip is a nice distance from the city and can be done year-round!
    • Kid-Friendly
    • Accessible
  • BEST SELLER
    Brews, Bites, and Everything Nice

    Brews, Bites, and Everything Nice

    $65 USD
    This trip is very true to its name, the coolest brews, the tastiest bites and everything else is very nice.
    • Accessible
    • Kid-Friendly
  • BEST SELLER
    Quirky Gems

    Quirky Gems

    $65 USD
    Our best-selling trip from Calgary! Hit the road and visit some quintessential Alberta towns, eat at funky restaurants, support local businesses and explore picturesque hikes and natural attractions. All without venturing too far from the city!
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • HIDDEN GEMS IN THE NIAGARA REGION
    Couple holding hands on a forest trail

    The Sweet & Scenic Route

    $65 USD
    A little sweet, a little scenic—this road trip blends cozy cafés, local wines, and maple treats with easy trails, waterfalls, and serene ponds. Perfect for a girls' getaway or a romantic day trip!
    • Accessible
    • Dog-Friendly
  • BEST SELLER
    The Taste Trail

    The Taste Trail

    $65 USD
    This road trip will take you to some funky eateries, family farms, wineries, cideries, and a whole lot more. To offset the treats, we've included a few whimsical hikes to end your day.
    • Accessible
  • BEST SELLER
    Funky Farms & Storybook Tales

    Funky Farms & Storybook Tales

    $29 USD Sale
    It's no wonder authors flocked to this area of Massachusetts for inspiration! Head out on a picturesque drive and discover farms, boardwalk trails, lots of quirky history and much more.
    • Accessible
    • Kid-Friendly
    Sale
  • GREAT FALL TRIP
    Quirky Delights

    Quirky Delights

    $29 USD Sale
    Not too far from home you'll discover a ton of quirky destinations. Think outdoor folk art, funky eats in a small town, hidden gem riverside strolls, and a local alpaca farm.
    • Accessible
    • Kid-Friendly
    Sale
  • GREAT FALL TRIP
    Boardwalks, Brews & Markets

    Boardwalks, Brews & Markets

    $29 USD Sale
    The name really says it all! Explore marvelous markets with food stalls and local artisans, enjoy a couple brews, and stroll along easy boardwalk trails.
    • Accessible
    Sale
  • PERFECT FOR FAMILIES
    Enchanted Adventures

    Enchanted Adventures

    $29 USD Sale
    Around every winding road is a world of whimsical and enchanted adventures. This family-friendly trip is perfect for those who love easy trails, farm market stops, colourful photo ops and tasty treats.
    • Kid-Friendly
    Sale
  • GREAT FALL TRIP
    A Taste of Amish Country

    A Taste of Amish Country

    $29 USD Sale
    Escape to quintessential Amish country for cheese tastings, sweet treats, craft shops, funky museums and some incredible historic photo ops.
    • Kid-Friendly
    • Accessible
    Sale
  • YEAR-ROUND HOLIDAY JOY!
    Endless Christmas Cheer

    Endless Christmas Cheer

    $29 USD Sale
    This is the perfect trip for anyone who thinks that extra festive feeling should be a year-round experience. Decorations, cozy shops and eateries, and a picture-perfect covered bridge - oh my!
    • Kid-Friendly
    • Accessible
    Sale
  • GREAT FALL TRIP
    A Riverside Ramble

    A Riverside Ramble

    $29 USD Sale
    Wander through colorful sculptures, charming boutiques, and local eateries before discovering breathtaking riverside gems that are so photo-worthy, your camera roll is sure to fill up!
    • Accessible
    • Kid-Friendly
    Sale
  • GREAT FALL TRIP
    Mountain Marvels

    Mountain Marvels

    $29 USD Sale
    This family-friendly trip is the ultimate way to escape the city and head to the mountains. Stroll the streets of charming small towns, explore quirky art and museums, indulge in tasty bites & brews and enjoy the surprise!
    • Accessible
    • Kid-Friendly
    Sale
  • GREAT WEEKEND GETAWAY
    Man standing on a road looking up among towering trees

    Forests & Funky Finds

    $29 USD Sale
    This trip is the perfect overnight getaway! As you're driving through the woods, you'll hop between the cutest small towns full of charming shops and eateries.
    • Kid-Friendly
    • Dog-Friendly
    Sale
  • FOR THE PHOTOGRAPHER
    Elegant Estates & Outdoor Art

    Elegant Estates & Outdoor Art

    $29 USD Sale
    Just a short drive from Indy you'll find a world full of elegant estates, whimsical gardens, and colorful outdoor art. We'll tell you all of the quirky fun facts and historic moments that make these spots so unique!
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
    Sale
  • PERFECT FOR MOVIE BUFFS
    Cinema & Scenery

    Cinema & Scenery

    $29 USD Sale
    Discover hidden art, channel your inner movie star, indulge in tasty bites, and enjoy a waterside stroll. This captivating adventure offers a perfect blend of creativity, culture, and coastal charm.
    • Kid-Friendly
    • Accessible
    Sale
  • THE ULTIMATE WEEKEND AWAY
    Solvang Splendors

    Solvang Splendors

    $29 USD Sale
    Escape to the Santa Ynez Valley and explore cute small towns, the roaming vineyard hills, local farms and so much more. We highly recommend turning this trip into a weekend adventure! 
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
    Sale
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

Take Our Quiz to Find Out

Select your region and interests to find the best trip for you.

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Gift-a-Trip

The ultimate present for the avid traveller. Select a digital or mailed 'Gift-A-Trip' option that covers the full cost of one of our road trips. We promise you this will be one of the most memorable and unique gifts they'll ever receive!