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 SELLING GIFT
    Pretty Little Finds

    Pretty Little Finds

    $39 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
  • LAST CHANCE
    Woman looking up through binoculars.

    Adventure in the Glades

    USD
    Scenic views, unique boardwalks and funky roadside attractions can all be found when you escape to the Everglades. Just make sure you keep your eyes peeled for those pesky gators!
    • Accessible
    Sold out
  • CAN BE DONE IN WINTER
    Ocean photographed from atop a hill.

    Down by the Bay

    $39 USD
    You don't have to go far from home to have an epic adventure! The scenic viewpoints and easy trails are endless on this trip. And while you won't see watermelons grow, there are tons of fantastic local eateries along the way.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • FOR THE PHOTOGRAPHER
    Elegant Estates & Outdoor Art

    Elegant Estates & Outdoor Art

    $39 USD
    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
  • CAN BE DONE IN WINTER
    Sonoma Sips & Strolls

    Sonoma Sips & Strolls

    $39 USD
    Scenic sipping and picturesque strolls can be found in this iconic area of California! We've found hidden gem wineries, tasty food shops, a few easy trails and so much more.
    • Dog-Friendly
    • Accessible
  • THE ULTIMATE WEEKEND AWAY
    Joshua Tree Journey

    Joshua Tree Journey

    $39 USD
    Think cowboy towns, desert trails, rooftop cacti, and a whole lot of quirky charm. This road trip blends epic eats, funky photo ops and offbeat art with your journey to Joshua Tree National Park—whether it’s your first time or your fifth.
    • Dog-Friendly
    • Kid-Friendly
  • EXPLORE MIAMI
    Mysteries of Miami

    Mysteries of Miami

    Regular price $65.00 Sale price $50.00 USD
    If you're into true crime and mysteries then this is the trip for you! From murder mysteries and spooky cemeteries to ghosts and the supernatural, this Miami road trip is truly full of unusual destinations.
    • Accessible
    Sold out
  • PERFECT FOR MOVIE BUFFS
    Cinema & Scenery

    Cinema & Scenery

    $39 USD
    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
  • CAN BE DONE IN WINTER
    Solvang Splendors

    Solvang Splendors

    $39 USD
    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
  • FOR PARANORMAL BUFFS
    Strange & Spooky Sights

    Strange & Spooky Sights

    $39 USD
    Get ready for a spine-tingling adventure as you explore some of the most haunted and historic spots in the state. Along the way, you'll encounter restaurants and cafes with ghostly legends, strange stories, peculiar museums and haunted objects galore — perfect for anyone who loves a good thrill mixed with quirky charm!
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • Great for foodies!
    Cowboy Country Crawl

    Cowboy Country Crawl

    $39 USD
    Saddle up for a Wild West adventure packed with charm. Snap a few cowboy-inspired photos, savor local flavors, and cool off at a hidden swimming hole. It’s everything you need for an unforgettable day in cowboy country!
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • OUTDOOR ADVENTURES!
    River overlook with trees beginning to change color in the fall.

    Walk on the Wild Side

    $39 USD
    From Scandinavian treats to rocky riverside hikes and a stop at a wildlife park, this photo-worthy adventure is packed with fresh air, big views, and even a tipple or two at a local winery.
    • Dog-Friendly
    • Kid-Friendly
  • CAN BE DONE IN WINTER
    Tastes & Trails of Malibu

    Tastes & Trails of Malibu

    $39 USD
    This iconic route along the PCH is full of hidden gems and epic viewpoints. Put your walking shoes on, save room for awesome eats, and get ready to be beachside!
    • Kid-Friendly
  • GREAT GIFT!
    Bison in the middle of a grassy field and grey skies.

    Creatures & Quirks

    $39 USD
    From towering sculptures and wild bison to waterfalls, eye-spy photo ops, and pints with peacocks, this adventure is as weird and wonderful as they come!
    • Kid-Friendly
    • Accessible
  • PENNSYLVANIA & NEW JERSEY
    Festive Farms & Holiday Charm

    Festive Farms & Holiday Charm

    $65 USD
    Celebrate the season with farm-fresh bites, twinkly markets, and festive small-town charm. From history-rich stops to holiday treats and cozy sips, this merry adventure will soon become your new favorite winter tradition.
    • Accessible
    • Kid-Friendly
  • AN ICONIC ROUTE
    Hill Country Harvest

    Hill Country Harvest

    $39 USD
    Embark on a day of scenic sips and charming discoveries! With visits to stunning wineries, a renowned distillery, a beautiful wildflower farm, and photogenic roadside stops, this is the perfect getaway to explore the best of Hill Country's iconic Highway 290.
    • Accessible
    • Kid-Friendly
  • IDEAL SUMMER TRIP!
    Sculpture of a woman with long hair in front of blue skies and behind a bush of yellow flowers.

    Art Trails & River Tales

    $39 USD
    With riverside bluffs, artistic oddities, and charming small towns, this photo-friendly adventure through southeastern Minnesota is packed with stories waiting to be discovered.
    • Kid-Friendly
    • Dog-Friendly
  • LAST CHANCE
    The Explorer's Route

    The Explorer's Route

    USD
    Take a step back in time with this family-friendly adventure! With so many quaint towns, easy outdoor adventures, photo-ops and local eateries, you'll have so much to explore.
    • Dog-Friendly
    • Accessible
    Sold out
  • ONTARIO
    Maple Syrup Farm in Winter

    Festive Edition: The Sweet & Scenic Route

    $65 USD
    A little sweet, a little scenic—this road trip blends cozy cafés, local wine, and maple treats with easy winter trails and frozen waterfalls. Perfect for a festive family road trip or romantic getaway!
    • Kid-Friendly
    • Accessible
  • CLOSE TO THE CITY!
    Gazebo overlooking a lake on a sunny day.

    Lakeside Treasures

    $39 USD
    This laid-back road trip blends small-town charm with offbeat surprises and scenic sips. Discover lakeside towns, quirky art gardens, a few furry friends, and the perfect patio pint.
    • Kid-Friendly
    • Accessible
  • Perfect summer trip!
    Blue skies overlooking a Vancouver Island pier with a blue building in the distance.

    Seaside Sips & Strolls

    $65 USD
    Think waterside strolls, blooming gardens, farm-fresh bites, cozy tasting spots, and storybook towns. This surprise-filled Vancouver Island adventure is packed with charm, quirky detours, and nature escapes you’ll be dreaming about later!
    • Kid-Friendly
    • Accessible
  • Scenic drives!
    Wooden bridge overtop of moving river and surrounded by forest trees.

    Valleys, Vistas & Falls

    $65 USD
    Wander through lush forests, meet rooftop goats, enjoy a riverside pint, and chase waterfalls on this Vancouver Island road trip packed with quirky charm and breathtaking West Coast views!
    • Kid-Friendly
    • Accessible
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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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!