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

  • A CLOSE TO HOME ADVENTURE
    Charming Curiosities

    Charming Curiosities

    $29 USD Sale
    With a few haunted stories, trails with a unique past, and charming historic mansions, we're confident you'll find new favorite spots to explore when you hit the road with this surprise trip.
    • Dog-Friendly
    • Kid-Friendly
    • Accessible
    Sale
    Can depart from: Washington DC Area, Baltimore Area, Winchester VA Area, Alexandria VA Area
  • PERFECT FOR SUMMER OR FALL
    Boardwalk leading to a beach.

    Coastal Connection

    $29 USD Sale
    From seaside strolls and spooky ruins to cider donuts and historic mansions, this charming coastal road trip is full of surprises. Whether you’re wandering a 17th-century town green, petting goats at a giant book barn, or soaking in saltwater views, you’ll fall in love with Connecticut’s quirkier side.
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
    Sale
    Can depart from: New Haven Area, Hartford Area, Providence Area, Springfield, MA Area
  • BEST DONE SPRING-FALL
    The Shore Explorer

    The Shore Explorer

    $29 USD Sale
    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
    Sale
    Can depart from: New York City Area, Trenton Area, Newark Area, Philadelphia Area
  • BEST SELLER
    The Southwest Quest

    The Southwest Quest

    $29 USD Sale
    Plenty of sun, strolls and citrus make this the ultimate Southwest Florida road trip. From unique eateries and boardwalk trails to an eerie ghost town and a sunset beach stop, there is truly something for everyone!
    • Kid-Friendly
    • Accessible
    Sale
    Can depart from: Fort Myers Area, Naples Area, Tampa Area
  • PERFECT FOR FAMILIES
    Enchanted Adventures

    Enchanted Adventures

    $29 USD Sale
    Around every winding road is a world of whimsical and enchanted adventures. This family-friendly trip is perfect for those who love easy trails, farm market stops, colourful photo ops and tasty treats.
    • Kid-Friendly
    Sale
    Can depart from: New York City Area, Philadelphia Area, Trenton Area
  • FOR THE OUTDOOR ADVENTURER
    Waterfall Wanderings

    Waterfall Wanderings

    $29 USD Sale
    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
    Sale
    Can depart from: Cleveland Area
  • BEST SELLER
    Treasure Coast Explorer

    Treasure Coast Explorer

    $29 USD Sale
    We've recommended our favourite hidden gems within this iconic area of Florida. Beach hopping, easy walks, charming cafes, and historic spots. This trip really does have it all!
    • Accessible
    • Kid-Friendly
    Sale
    Can depart from: West Palm Beach Area, Miami / Fort Lauderdale Area
  • EXPLORE CAPE COD
    Escape to the Cape

    Escape to the Cape

    $29 USD Sale
    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
    Sale
    Can depart from: Boston Area, Providence Area
  • GREAT FALL TRIP
    A Taste of Amish Country

    A Taste of Amish Country

    $29 USD Sale
    Escape to quintessential Amish country for cheese tastings, sweet treats, craft shops, funky museums and some incredible historic photo ops.
    • Kid-Friendly
    • Accessible
    Sale
    Can depart from: Cleveland Area, Columbus Area
  • BEST SELLER
    Two woman sitting on rocks by ocean.

    Coffee, Canyons & Coastlines

    $29 USD Sale
    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
    Sale
    Can depart from: San Diego Area
  • SCENIC ROAD TRIP
    Groves, Gardens & Grapevines

    Groves, Gardens & Grapevines

    $29 USD Sale
    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
    Sale
    Can depart from: Columbus Area, Cleveland Area, Toledo Area
  • GREAT FOR ACTIVE FAMILIES
    Sweet Sensations

    Sweet Sensations

    $29 USD Sale
    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
    Sale
    Can depart from: Detroit Area, Toledo Area, Windsor Area
  • GREAT FALL TRIP
    The Road to Asheville

    The Road to Asheville

    $29 USD Sale
    Grab a sweet treat in a converted church, sip a beer beside a babbling creek, get your steps in on a couple local trails and so much more. This iconic North Carolina destination is the perfect weekend away, so we highly recommend booking a hotel!
    • Dog-Friendly
    • Kid-Friendly
    • Accessible
    Sale
    Can depart from: Charlotte Area, Winston-Salem Area
  • GREAT YEAR-ROUND TRIP
    Tree lined road

    A Drive Back in Time

    $29 USD Sale
    The perfect day for the more leisurely road tripper. A Drive Back in Time isn't too far from the city and is full of cute towns, cafes, funky photo ops and so much more.
    • Accessible
    Sale
    Can depart from: Atlanta Area, Chattanooga Area
  • FANTASTIC OVERNIGHT TRIP
    Picture Perfect Discoveries

    Picture Perfect Discoveries

    $29 USD Sale
    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
    Sale
    Can depart from: Charlotte Area, Winston-Salem Area
  • YEAR-ROUND JOY
    Endless Christmas Cheer

    Endless Christmas Cheer

    $29 USD Sale
    This is the perfect trip for those of you who think that extra-festive feeling should be a year-round experience. Decorations, cozy wine stops, and covered bridges - oh my!
    • Kid-Friendly
    • Accessible
    Sale
    Can depart from: Detroit Area, Windsor Area, Sarnia Area
  • GREAT FALL TRIP
    A Riverside Ramble

    A Riverside Ramble

    $29 USD Sale
    Wander through colorful sculptures, charming boutiques, and local eateries before discovering breathtaking riverside gems that are so photo-worthy, your camera roll is sure to fill up!
    • Accessible
    • Kid-Friendly
    Sale
    Can depart from: Chicago Area, Milwaukee Area
  • SOMETHING FOR EVERYONE
    Park bench and fountain at the end of a brick path in a garden.

    Antique Adventures

    $29 USD Sale
    This leisurely trip packs a punch! Expect a variety of antique shops (both small and large), cozy cafes, funky eateries, effortless outdoor escapades and haunted stops along the way. The best part? It's only a quick jaunt from the city.
    • Accessible
    Sale
    Can depart from: Charlotte Area, Winston-Salem Area
  • GREAT WEEKEND TRIP
    Wacky Wonders

    Wacky Wonders

    $29 USD Sale
    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.
    Sale
    Can depart from: Atlanta Area, Athens Area
  • A CLOSE TO HOME ADVENTURE
    Timeless Towns & Scenic Sips

    Timeless Towns & Scenic Sips

    $29 USD Sale
    Brews, bites and a whole lot of history! From small town charm to tasty tipples and one of the most unique (and eerie) trails we've ever found, this road trip has something for everyone.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
    Sale
    Can depart from: Raleigh Area, Winston-Salem Area
  • OFF-THE-BEATEN-PATH ROAD TRIP
    Woman taking photo can be seen in side view mirror of car.

    All Things Strange & Beautiful

    $29 USD Sale
    A few famous filming spots, scenic drives, local eateries and an eerie abandoned area are just some of the strange and beautiful things you'll discover on this road trip.
    • Accessible
    • Kid-Friendly
    Sale
    Can depart from: Atlanta Area
  • GREAT OVERNIGHT TRIP
    Seaside Legends

    Seaside Legends

    $29 USD Sale
    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
    Sale
    Can depart from: Orlando Area, Jacksonville Area, Gainesville Area
  • GREAT FOR FAMILIES
    All Things Charming

    All Things Charming

    $29 USD Sale
    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
    Sale
    Can depart from: Chicago Area, Milwaukee Area
  • BEST SELLER
    Grassy hills leading down to water.

    Coastal Jaunt

    $29 USD Sale
    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
    Sale
    Can depart from: San Francisco Area, San Jose Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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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!