Woman holding four Guess Where Trips envelopes while on road trip

Our 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 DONE JUNE-SEPTEMBER
    Rural Adventures

    Rural Adventures

    $65 USD
    Scenic driving routes, a ton of photo-worthy views and rural, small town vibes await you on this surprise road trip.
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • BEST SELLER
    A winding road surrounded by trees with autumn leaves

    Scenic Sights & Tasty Bites

    $65 USD
    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 USD
    From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!
    • Kid-Friendly
    • Dog-Friendly
  • Last chance!
    Woman spinning on the beach.

    Waterside Bliss

    $65 USD
    Beach breezes, coastal eats, and charming strolls await on this picturesque day trip. You’ll wander waterfront boardwalks, explore historic homes, and discover secret spots only the locals know - all with a side of sandy serenity and small-town charm.
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Man walking through a forest on a dirt path

    Sandhills Sauntering

    $65 USD
    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 USD
    If you're the paranormal podcast listener in your friend group, this trip is for you! This area is filled with all things unusual, spooky, and abandoned. You'll also learn about some local legends, ghost stories and folklore throughout your day.
    • Dog-Friendly
  • GREAT SUMMER ROADTRIP
    A person wearing a yellow sweater is taking a photograph with a camera, standing against a backdrop of green trees.

    Peculiar Wonders

    $65 USD
    Travel through time and terrain on this Alberta road trip packed with scenic strolls, quirky museums, epic photo ops, and fun for all ages. From lush gardens and lakeside boardwalks to towering trestle bridges and even free-roaming bison, this one's full of "wait, where are we?" moments—in the best way possible.
    • Kid-Friendly
    • Dog-Friendly
    Sale
  • A LITTLE BIT OF EVERYTHING!
    A box of assorted donuts with different toppings and glazes.

    Treats & Trails

    $65 USD
    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
  • An winter route
    A scenic view of a road leading towards mountains with green trees on both sides.

    Secrets on the Scenic Route

    $65 USD
    This trip combines iconic attractions and quite a few hidden gems before ending in one of the coolest villages in Canada. Can you guess where? Perfect for those wanting to explore this famous route in more detail.
    • Dog-Friendly
  • BEST SELLER
    Offbeat Oddities

    Offbeat Oddities

    $65 USD
    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
  • BEST DONE SPRING-FALL
    Two people sitting on a rock overlooking a scenic view of mountains during sunset.

    Valley Views

    $65 USD
    Down in the valley where the green grass grows...you'll find charming towns, get lost in lush vineyards, take in vast views and hike scenic trails on this countryside road trip.
    • Dog-Friendly
    • Kid-Friendly
  • SOMETHING FOR EVERYONE
    A scenic view of a waterfall surrounded by greenery with a bridge in the background.

    Cascades & Colors

    $65 USD
    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
  • A PERFECT COUNTRYSIDE DRIVE
    Covered Bridges & Baked Goods

    Covered Bridges & Baked Goods

    $39 USD
    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 USD
    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 USD
    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
  • BEST DONE JUNE-SEPTEMBER
    The Long & Unknown Road

    The Long & Unknown Road

    $65 USD
    If you love a long and interesting drive, this trip is for you! This trip is approximately 5 hours round-trip from Calgary, so we recommend leaving super early or extending your stay into an overnight getaway.
    • Dog-Friendly
  • GREAT YEAR-ROUND TRIP
    A person outdoors holding a camera up to their face, with a body of water and a blurred background.

    Quirky Delights

    $65 USD
    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
  • CLOSE TO ORLANDO
    Wooden boardwalk trail in a lush green forest setting

    Boardwalks, Brews & Markets

    $65 USD
    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
  • last chance!
    A person standing on a trail in a forested area

    Old Florida Trail

    $65 USD
    Go back in time and visit old Florida. You'll visit delightful small towns, dig into local fare, explore a few outdoor adventures, and fill up your camera roll with quirky photo ops.
    • Kid-Friendly
  • BEST SELLER
    Two girls sitting in back of crossover SUV.

    A Little Bit of Everything

    $65 USD
    The perfect distance from Charlotte! From little local shops to an old rail trail and everything in between, this trip truly has something for everyone.
    • Accessible
    • Kid-Friendly
  • A CLOSE TO HOME ADVENTURE
    A street scene in a city with trees, buildings, and cars. People are walking on the sidewalk.

    Charming Curiosities

    $65 USD
    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 USD
    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 USD
    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
  • Great Year-Round Trip
    Ruins of an old building overgrown with trees and plants

    Mysterious Gems

    $65 USD
    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?

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!