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

  • FOR A LEISURELY DAY
    Topanga Treetops to Beaches

    Topanga Treetops to Beaches

    USD
    Follow picturesque winding roads amongst the treetops while you shop, hike and enjoy tasty bites. End the day meandering along the beach or sipping a glass of wine!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Sold out
  • GREAT YEAR-ROUND TRIP
    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
  • The ultimate weekend away!
    Joshua Tree Journey

    Joshua Tree Journey

    $65 USD
    It's time to make your desert dreams come true. Whether this is your first time or your fifth, the Joshua Tree area is full of quirky delights, epic eateries, and incredible outdoor adventures. 
    • Dog-Friendly
    • Kid-Friendly
  • EPIC VIEWS
    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
  • GREAT WEEKEND GETAWAY
    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
  • Perfect Weekend Getaway!
    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
    Quirky & Colorful

    Quirky & Colorful

    $65 USD
    From charming coffee spots and hidden gardens to quirky museums and haunted tales, this adventure has something unexpected at every turn. Top it all off with shopping, murals, and more in one of Texas’ most vibrant small towns!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • THE ULTIMATE WEEKEND AWAY
    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
  • FOR THE PHOTOGRAPHER
    Elegant Estates & Outdoor Art

    Elegant Estates & Outdoor Art

    $65 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
  • 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
  • GREAT OUTDOORSY TRIP
    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
  • FOR PARANORMAL BUFFS
    Strange & Spooky Sights

    Strange & Spooky Sights

    $65 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
  • Best selling gift
    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
  • Best selling gift
    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
  • FAMILY FRIENDLY
    The Explorer's Route

    The Explorer's Route

    $65 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
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!