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

  • LAST CHANCE
    Film & Food Crawl

    Film & Food Crawl

    Regular price $65.00 USD
    Georgia is often called the "Hollywood of the South" so we've rounded up a few of our favorite filming spots. Local cafes, breweries, eateries and farmers markets are also sprinkled in to keep your energy up!
    • Accessible
    Sold out
  • COZY TRIP NEAR THE CITY!
    Elegant Estates & Outdoor Art

    Elegant Estates & Outdoor Art

    $65 USD
    Just a short drive from Indy, you’ll find a world of elegant estates, whimsical gardens, and colorful outdoor art - all looking a little extra magical when dusted with snow. We’ll share 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

    $65 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
  • CAN BE DONE IN WINTER
    Ocean photographed from atop a hill.

    Down by the Bay

    $65 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
  • LAST CHANCE
    Outback Oasis

    Outback Oasis

    USD
    The perfect combination of easy outdoor adventures, browsing through farm markets, and enjoying a slower pace. You'll feel so at ease by the end of your road trip!
    • Accessible
    • Kid-Friendly
    Sold out
  • Scenic drives!
    Wooden bridge overtop of moving river and surrounded by forest trees.

    Valleys, Vistas & Falls

    Regular price $65.00 Sale price $39.00 USD
    Sale
    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
    Sale
  • THE ULTIMATE WEEKEND AWAY
    Joshua Tree Journey

    Joshua Tree Journey

    $65 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
  • PERFECT FOR MOVIE BUFFS
    Cinema & Scenery

    Cinema & Scenery

    $65 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
  • FOR PARANORMAL BUFFS
    Strange & Spooky Sights

    Strange & Spooky Sights

    Regular price $39.00 USD
    Sale
    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

    $65 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
  • Perfect summer trip!
    Blue skies overlooking a Vancouver Island pier with a blue building in the distance.

    Seaside Sips & Strolls

    Regular price $65.00 Sale price $39.00 USD
    Sale
    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
    Sale
  • CAN BE DONE IN WINTER
    Solvang Splendors

    Solvang Splendors

    $65 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
  • 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
  • AN ICONIC ROUTE
    Hill Country Harvest

    Hill Country Harvest

    $65 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
  • OUTDOOR ADVENTURES!
    River overlook with trees beginning to change color in the fall.

    Walk on the Wild Side

    $65 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
  • GREAT YEAR-ROUND!
    Art Trails & River Tales

    Art Trails & River Tales

    $65 USD
    With snow-dusted riverside bluffs, artistic oddities, and cozy small towns, this photo-friendly adventure through southeastern Minnesota is packed with stories waiting to be discovered.
    • Kid-Friendly
    • Dog-Friendly
  • CAN BE DONE IN WINTER
    Tastes & Trails of Malibu

    Tastes & Trails of Malibu

    $65 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
  • PERFECT FAMILY ROAD TRIP!
    Bison in the middle of a grassy field and grey skies.

    Creatures & Quirks

    $65 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
  • CLOSE TO THE CITY!
    Gazebo overlooking a lake on a sunny day.

    Lakeside Treasures

    $65 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
  • 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
    All Things Merry & Bright

    All Things Merry & Bright

    Regular price $65.00 Sale price $39.00 USD
    If you're looking for a road trip that is full of festivity and holiday cheer, look no further! Meander down decorated streets with a warm beverage in hand, shop for that hard-to-buy-for person at quaint markets, and find your perfect Christmas tree.
    • Accessible
    • Kid-Friendly
    Sale
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!