Woman holding four Guess Where Trips envelopes while on road trip

United States

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
    River running through forest.

    Along the River

    $65 CAD
    A scenic road trip near Allentown along the NJ and PA border with small towns and riverside stops.
    • Accessible
    • Kid-Friendly
  • BEST SELLER
    A person standing at the entrance of a lush garden pathway, looking towards the light at the end of the tunnel created by the archway.

    Whimsical Wonders

    $65 CAD
    Escape to hidden gem destinations that make you feel like you've stepped into a fairytale world. Lucious gardens, charming towns and whimsical photo ops make this the perfect road trip.
    • Kid-Friendly
    • Accessible
  • BEST SELLER
    Hudson River Hideaways

    Hudson River Hideaways

    $65 CAD
    An iconic road trip route with a twist! We've found countless hidden hideaways along the Hudson including: crumbling ruins, quaint towns, spooky cemeteries and more.
    • Dog-Friendly
  • BEST SELLER
    A large American flag hanging on the side of a red brick building with greenery in the background.

    Tiny Town Tour

    $65 CAD
    Meander along scenic roads while stumbling upon charming tiny towns! This trip has endless photo opportunities, easy outdoor adventures, and plenty of fantastic spots to shop, drink and eat.
    • Dog-Friendly
  • GREAT FOR A WEEKEND AWAY
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $65 CAD
    Discover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination filled with history and views.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • NEW ENGLAND CHARM
    A picturesque street in a New England town with a two-story house adorned with an American flag, surrounded by cozy buildings and greenery.

    Vintage Vibes & Views

    $65 CAD
    Immerse yourself in quintessential New England charm as you wind along picturesque roads to a number of nature trails, cozy cafes, historic small towns and picturesque beaches.
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    A winding road surrounded by trees with autumn leaves

    Scenic Sights & Tasty Bites

    $65 CAD
    Bakeries, breweries & views - oh my! With the perfect mix of outdoor adventures, local farms, and tasty bites, this is the ideal trip for your whole road trip crew. The perfect road trip for any Little Women movie fans, too!
    • Accessible
    • Kid-Friendly
  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    $65 CAD
    From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Man walking through a forest on a dirt path

    Sandhills Sauntering

    $65 CAD
    Picturesque drives beneath towering trees make this an incredibly scenic trip. Sandhills Sauntering is full of epic places to eat, tons of photo-worthy moments and a hidden gem that will leave you speechless.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • FOR THE PARANORMAL EXPLORER
    Black and white photo of an old house.

    An Unusual Adventure

    $65 CAD
    A spooky Southern New Jersey road trip with abandoned spots, local legends, and eerie stops.
    • Dog-Friendly
  • A LITTLE BIT OF EVERYTHING!
    A box of assorted donuts with different toppings and glazes.

    Treats & Trails

    $65 CAD
    Is there anything better than a leisurely day sipping coffee, enjoying tasty treats and meandering along easy boardwalk trails? We think not, and you'll find all of that and more in this Michigan road trip!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • BEST SELLER
    Offbeat Oddities

    Offbeat Oddities

    $65 CAD
    The quirkiest road trip in central Florida! Historic homes with peculiar stories, off-the- beaten-path eateries, and funky trails & ruins will keep you on your toes throughout the day.
    • Kid-Friendly
  • SOMETHING FOR EVERYONE
    A scenic view of a waterfall surrounded by greenery with a bridge in the background.

    Cascades & Colors

    $65 CAD
    Funky, colorful towns full of local eateries and shops, a few waterfalls that will leave you in awe and one of the most unusual gardens we have ever seen. You’ll want to get your camera out for this trip!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • MOTHER'S DAY PICK
    Covered Bridges & Baked Goods

    Covered Bridges & Baked Goods

    $65 CAD
    This trip is like taking a step back in time! Wind your way through the peaceful countryside to a number of quaint covered bridges and locally owned bakeries, farmers markets, and shops.
    • Kid-Friendly
    • Accessible
  • GREAT YEAR-ROUND TRIP
    Vibrant Vistas & Picturesque Towns

    Vibrant Vistas & Picturesque Towns

    $65 CAD
    Hit the road and explore easy outdoor adventures, outstanding views and small towns that inspired Stars Hollow in Gilmore Girls.
    • Dog-Friendly
  • BEST SELLER
    Red barn with trees behind it.

    Funky Farms & Storybook Tales

    $65 CAD
    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 so much more.
    • Accessible
    • Kid-Friendly
  • CLOSE TO ORLANDO
    Wooden boardwalk trail in a lush green forest setting

    Boardwalks, Brews & Markets

    $65 CAD
    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
  • BEST SELLER
    Two girls sitting in back of crossover SUV.

    A Little Bit of Everything

    $65 CAD
    A well-rounded Charlotte-area road trip with local shops, a scenic rail trail, and a little bit of everything.
    • Accessible
    • Kid-Friendly
  • MOTHER'S DAY PICK
    A street scene in a city with trees, buildings, and cars. People are walking on the sidewalk.

    Charming Curiosities

    $65 CAD
    With a few haunted stories, trails with a unique past, and charming historic mansions, we're confident you'll find new favorite spots to explore when you hit the road with this surprise trip.
    • Dog-Friendly
    • Kid-Friendly
    • Accessible
  • BEST SELLER
    The Southwest Quest

    The Southwest Quest

    $65 CAD
    Plenty of sun, strolls and citrus make this the ultimate Southwest Florida road trip. From unique eateries and boardwalk trails to an eerie ghost town and a sunset beach stop, there is truly something for everyone!
    • Kid-Friendly
    • Accessible
  • PERFECT FOR SUMMER OR FALL
    Boardwalk leading to a beach.

    Coastal Connection

    $65 CAD
    From seaside strolls and spooky ruins to cider donuts and historic mansions, this charming coastal road trip is full of surprises. Whether you’re wandering a 17th-century town green, petting goats at a giant book barn, or soaking in saltwater views, you’ll fall in love with Connecticut’s quirkier side.
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
  • BEST SELLER
    Two people sitting on a rock with arms raised, enjoying a scenic view of a landscape.

    Quaint Corners

    $65 CAD
    Cozy cafes, countryside drives, gorgeous lookouts and quirky roadside stops are just some of the things you'll discover on your surprise road trip!
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • TONS OF TASTY BITES + SHOPS
    A person holding up a sugar-coated doughnut, likely enjoyed as part of the 'A Taste of Amish Country' experience.

    A Taste of Amish Country

    $65 CAD
    A peaceful road trip near Akron through Amish country with food stops, shops, and scenic countryside.
    • Kid-Friendly
    • Accessible
  • Great Year-Round Trip
    Ruins of an old building overgrown with trees and plants

    Mysterious Gems

    $65 CAD
    Truly extraordinary destinations with strange stories and history. Cemeteries abandoned ruins, historic homes and so much more await on this mysterious road trip!
    • Dog-Friendly
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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Gift-a-Trip

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