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

  • FOR THE OUTDOOR ADVENTURER
    A scenic view of a waterfall surrounded by green foliage.

    Waterfall Wanderings

    $65 CAD
    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
  • BEST DONE SPRING-FALL
    The Shore Explorer

    The Shore Explorer

    $65 CAD
    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
  • EXPLORE CAPE COD
    Escape to the Cape

    Escape to the Cape

    $65 CAD
    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
    Two woman sitting on rocks by ocean.

    Coffee, Canyons & Coastlines

    $65 CAD
    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
  • MOTHER'S DAY PICK
    Groves, Gardens & Grapevines

    Groves, Gardens & Grapevines

    $65 CAD
    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
  • GREAT WEEKEND TRIP
    A person with a camera exploring a forested area

    Wacky Wonders

    $65 CAD
    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.
  • BEST SELLER
    Wonder & Whimsy

    Wonder & Whimsy

    $65 CAD
    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
  • MOTHER'S DAY PICK
    Sweet Sensations

    Sweet Sensations

    $65 CAD
    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
  • MOTHER'S DAY PICK
    Seaside Legends

    Seaside Legends

    $65 CAD
    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
  • 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 CAD
    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
  • BEST SELLER
    Grassy hills leading down to water.

    Coastal Jaunt

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

    Falls, Forests & Fables

    $65 CAD
    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
  • MOTHER'S DAY PICK
    A person taking a photo with a smartphone from a car, capturing a scenic view.

    Picture Perfect Discoveries

    $65 CAD
    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 CAD
    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
  • MOTHER'S DAY PICK
    All Things Charming

    All Things Charming

    $65 CAD
    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
  • LAST CHANCE
    Pretty Little Finds

    Pretty Little Finds

    $65 CAD
    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
  • FOR THE FOODIES
    Woman running along oceanside.

    Birds, Breezes & Cheeses

    $65 CAD
    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
  • BEST DONE SPRING-FALL
    A sandy trail leading to the water

    Lakeshore Views & Brews

    $65 CAD
    Stroll along a breathtaking boardwalk, dip your does in the cool water, sip craft drinks in unique destinations, and take lots of funky photos! This road trip will certainly let you unwind from the hustle and bustle of the city.
    • Kid-Friendly
    • Accessible
  • GREAT YEAR-ROUND TRIP
    A scenic view of mountains and a clear sky with clouds, framed by trees in the foreground.

    Mountain Marvels

    $65 CAD
    This family-friendly trip is the ultimate way to escape the city and head to the mountains. Stroll the streets of charming small towns, explore quirky art and museums, indulge in tasty bites & brews and enjoy the surprise!
    • Accessible
    • Kid-Friendly
  • CYCLE FRIENDLY
    Ojai Oasis

    Ojai Oasis

    $65 CAD
    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 CAD
    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 CAD
    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
  • A LEISURELY ROAD TRIP
    Woman hiking in a forest

    Woodland Walks & Wineries

    $65 CAD
    Funky forest finds are on every stop, which are perfect for the outdoor adventurer. Unique wineries, bakeries, and a museum celebrating a man we have a lot to thank for are sprinkled in for the more leisurely road tripper.
    • Kid-Friendly
  • SPOOKY STORIES
    Eerie Escapes

    Eerie Escapes

    $65 CAD
    Step into a day where every stop sends a shiver down your spine. Ghostly whispers in cemeteries, abandoned ruins, and wooded trails full of chilling stories will leave you wondering if any spirits followed you home.
    • Dog-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!