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

  • GREAT SUMMER ROADTRIP
    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
  • EXPLORE CAPE COD
    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
  • 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
  • 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
  • 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.
  • 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
  • GREAT OVERNIGHT TRIP
    Seaside Legends

    Seaside Legends

    $65 USD
    Little local legends are sprinkled throughout your day, telling the story of an iconic area of Florida. Expect picturesque beaches, tasty eats, a historic city, and so much more.
    • Kid-Friendly
    • Dog-Friendly
  • A CLOSE TO HOME ADVENTURE
    Timeless Towns & Scenic Sips

    Timeless Towns & Scenic Sips

    $65 USD
    Brews, bites and a whole lot of history! From small town charm to tasty tipples and one of the most unique (and eerie) trails we've ever found, this road trip has something for everyone.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • BEST SELLER
    Grassy hills leading down to water.

    Coastal Jaunt

    $65 USD
    Just across the Golden Gate Bridge, escape the city for a day by the coast. Beach breaks, epic overlooks, walks along the water and local eateries to fuel up at make this the perfect trip close to home.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • YEAR-ROUND JOY
    A festive Christmas-themed miniature village display with snow-covered houses and a large Christmas tree in the center.

    Endless Christmas Cheer

    $65 USD
    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
  • DOG-FRIENDLY TRIP
    Falls, Forests & Fables

    Falls, Forests & Fables

    $65 USD
    Get ready for a day filled with charm and easy outdoor adventures. Start in a small town bursting with colorful murals, then enjoy riverside lookouts and even some surprising wildlife. This trip is perfect for those who love to stay active while exploring!
    • Dog-Friendly
    • Kid-Friendly
  • FANTASTIC OVERNIGHT TRIP
    A person taking a photo with a smartphone from a car, capturing a scenic view.

    Picture Perfect Discoveries

    $65 USD
    Ready for a little mountain meandering? Picturesque historic spots, unique destinations to grab a bite to eat, and a couple charming towns are on your to-do list.
    • Kid-Friendly
    • Dog-Friendly
  • GREAT WEEKEND GETAWAY
    Man standing on a road looking up among towering trees

    Forests & Funky Finds

    $65 USD
    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
  • LAST CHANCE
    Pretty Little Finds

    Pretty Little Finds

    $65 USD
    With plenty of picture-perfect moments, quirky stops, and a bit of everything from bees to barns, this adventure promises the perfect blend of beauty and cozy vibes. Think funky florals, farm-fresh finds and plenty of antiques!
    • Kid-Friendly
    • Accessible
  • GREAT FOR FAMILIES
    All Things Charming

    All Things Charming

    $65 USD
    From serene lakeside views and quaint small-town charm to playful animal encounters and a whimsical museum, this captivating road trip promises to create unforgettable memories for everyone in your group!
    • Kid-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.

Take the Quiz
Woman on road trip leaning out window

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!