Woman holding four Guess Where Trips envelopes while on road trip

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

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  • 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
  • FATHER'S DAY PICK
    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
  • 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
  • Digital Only
    A person standing on a trail in a forested area

    Old Florida Trail

    $39 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
    Sale
  • 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
    Two girls sitting in back of crossover SUV.

    A Little Bit of Everything

    $65 USD
    A well-rounded Charlotte-area road trip with local shops, a scenic rail trail, and a little bit of everything.
    • Accessible
    • Kid-Friendly
  • 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
  • FATHER'S DAY PICK
    The Shore Explorer

    The Shore Explorer

    $65 USD
    Hop from shore to shore on this iconic beachside road trip just a short drive from the tri-state area. Alongside beaches, you'll also explore waterside boardwalks, age-old lighthouses, scenic viewpoints, and delicious local eateries.
    • 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 USD
    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 USD
    A peaceful road trip near Akron through Amish country with food stops, shops, and scenic countryside.
    • Kid-Friendly
    • Accessible
  • FOR THE OUTDOOR ADVENTURER
    A scenic view of a waterfall surrounded by green foliage.

    Waterfall Wanderings

    $65 USD
    The ultimate waterfall adventure not too far from home! Wander along historic paths, snap photos of four falls, enjoy a glass of local vino and explore a mysterious cave.
    • Kid-Friendly
    • Dog-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
  • Last chance!
    Mother and child walking on a winding road surrounded by greenery

    Enchanted Adventures

    $65 USD
    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, colorful photo ops and tasty treats.
    • Kid-Friendly
  • FATHER'S DAY PICK
    Escape to the Cape

    Escape to the Cape

    $65 USD
    This road trip is full of Cape Cod charm. Think picturesque views, independent shops, heritage buildings, boardwalks and more. This trip focuses more on the hidden gems, quaint towns and history of the area.
    • Kid-Friendly
    • Dog-Friendly
  • Digital Download Only
    A monument at Gettysburg, featuring a statue on top of a classical Revival dome, surrounded by an open field under a partly cloudy sky.

    Secrets of Gettysburg

    Regular price $39.00 USD
    Explore Gettysburg and its surrounding area in a whole new way. We’ve made this classic, All-American, bucket list destination easy and fun to do - whether it's your first or fiftieth time! Discover hidden gems and surprising stops while learning more about the turning point of the Civil War.
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Treasure Coast Explorer

    Treasure Coast Explorer

    $65 USD
    We've recommended our favourite hidden gems within this iconic area of Florida. Beach hopping, easy walks, charming cafes, and historic spots. This trip really does have it all!
    • Accessible
    • Kid-Friendly
  • BEST SELLER
    Two woman sitting on rocks by ocean.

    Coffee, Canyons & Coastlines

    $65 USD
    Coffee, Canyons & Coastlines - Oh my! Get your caffeine fix throughout the day to prepare for beachside moments and easy outdoor adventures. This is the perfect trip close to San Diego!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • GREAT YEAR-ROUND TRIP
    Tree lined road

    A Drive Back in Time

    $65 USD
    A relaxed Atlanta-area road trip through charming small towns, cozy cafés, and quirky photo stops.
    • Accessible
  • SCENIC ROAD TRIP
    Groves, Gardens & Grapevines

    Groves, Gardens & Grapevines

    $65 USD
    This incredibly picturesque road trip is full of whimsical gardens, lookout points, wineries, and easy strolls along forest paths. We think it's an area you'll want to come back to time and time again.
    • Kid-Friendly
  • GREAT WEEKEND TRIP
    A person with a camera exploring a forested area

    Wacky Wonders

    $65 USD
    A little funky, a little unexpected, and totally unforgettable—this road trip is a whirlwind of colorful folk art, quirky roadside stops, scenic detours, and bites worth savoring. The only rule? Embrace the unexpected.
  • BEST SELLER
    Wonder & Whimsy

    Wonder & Whimsy

    $65 USD
    Embark on a day trip where lakeside strolls, whimsical gardens, and charming small-town shops and eateries are just the beginning. Along the way, you'll explore a quirky hotel, a few scenic sights, and even read a haunted tale or two!
    • Kid-Friendly
  • GREAT FOR ACTIVE FAMILIES
    Sweet Sensations

    Sweet Sensations

    $65 USD
    Between making a furry friend at a farm, enjoying local eateries, walking to quirky ruins in the woods and exploring the sweetest small town, this trip will make all five senses come to life all day!
    • Kid-Friendly
    • Accessible
  • CYCLE FRIENDLY
    Sunset over a river with trees in the foreground

    A Riverside Ramble

    $65 USD
    A scenic Chicago-area road trip with art, boutiques, eateries, and riverside views.
    • Accessible
    • Kid-Friendly
Three women walking through tulip fields
Winding roads through mountains at sunrise

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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!