Woman holding four Guess Where Trips envelopes while on road trip

California & Texas

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 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
  • 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
  • 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
  • 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 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
  • FOR THE FOODIES
    Woman running along oceanside.

    Birds, Breezes & Cheeses

    $65 USD
    Say cheese! That's right, we've rounded up the best cheese shops and the most photo-worthy moments a road trip can have. You'll feel the breeze in your hair as you walk down coastal trails and quaint streets.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • CYCLE FRIENDLY
    Ojai Oasis

    Ojai Oasis

    $65 USD
    Small-town charm is at the center of this Ojai road trip. Shop 'till you drop, indulge in local wine and sweet treats, and meander along a few short trails. This trip is cycle-friendly too!
    • Accessible
    • Dog-Friendly
  • GREAT OVERNIGHT GETAWAY
    Grassy landscape with hills.

    Country Treasures

    $65 USD
    Escape to the country and visit tons of charming bakeries, get your steps in on easy trails, sip something tasty, and end the day in the most amazing small town.
    • Kid-Friendly
    • Dog-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
  • FAMILY FRIENDLY
    Colorful houses along a beach.

    Colors & Wonders

    $65 USD
    This trip is full of colorful wonders - like a short hike to get your heart rate up before you relax with an afternoon beverage, support a local shop, or sip coffee & indulge in delicious baked goods.
    • Kid-Friendly
    • Accessible
  • Last chance!
    South Bay Secrets

    South Bay Secrets

    $65 USD
    Coastal walks and lighthouse views make this South Bay road trip incredibly picturesque. It's the perfect choice for a trip close to home!
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • LAST CHANCE
    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
  • 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
  • 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
  • Last chance!
    Two people toasting with glasses of wine, set against a wallpaper with a tropical leaf pattern.

    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
  • Last chance!
    A person standing among tall cactus plants in a desert landscape with mountains in the background.

    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
  • 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
  • last chance!
    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!
    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
Three women walking through tulip fields
Winding roads through mountains at sunrise

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