Midwest

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  • SCENIC ROUTE
    Bridges & Beauty

    Bridges & Beauty

    $65 USD
    Get ready to wind your way through scenic tree-lined roads, cross charming covered bridges, sip at cozy wineries, hike stunning trails, and maybe even get a chill from a ghostly tale or two.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Cleveland Area
  • CAN BE DONE IN WINTER
    A Riverside Ramble

    A Riverside Ramble

    $65 USD
    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
    Can depart from: Chicago Area, Milwaukee Area
  • 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
    Can depart from: Chicago Area, Milwaukee Area
  • Great For Families!
    All Things Charming

    All Things Charming

    $65 USD
    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
    Can depart from: Chicago Area, Milwaukee Area
  • SPOOKY STORIES
    Eerie Escapes

    Eerie Escapes

    $65 USD
    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
    Can depart from: Chicago Area
  • Dog-Friendly Trip!
    Falls, Forests & Fables

    Falls, Forests & Fables

    $65 USD
    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
    Can depart from: Chicago Area
  • BEST DONE SPRING-FALL
    Lakeshore Views & Brews

    Lakeshore Views & Brews

    $65 USD
    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
    Can depart from: Chicago Area
  • Can be done in winter
    Cascades & Colors

    Cascades & Colors

    $65 USD
    Funky colorful towns full of local eateries and shops, a few waterfalls that will leave you in awe and one of the most unusual gardens we have ever seen. You’ll want to get your camera out for this trip!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Can depart from: Columbus Area, Cincinnati Area
  • A LEISURELY ROAD TRIP
    Woodland Walks & Wineries

    Woodland Walks & Wineries

    $65 USD
    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
    Can depart from: Cleveland Area, Toledo Area
  • TONS OF TASTY BITES & SHOPS
    A Taste of Amish Country

    A Taste of Amish Country

    $65 USD
    Escape to quintessential Amish country for cheese tastings, sweet treats, craft shops, funky museums and some incredible historic photo ops.
    • Kid-Friendly
    • Accessible
    Can depart from: Cleveland Area, Columbus Area
  • Can be done in winter
    Waterfall Wanderings

    Waterfall Wanderings

    $65 USD
    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
    Can depart from: Cleveland Area
  • BEST DONE MAY-OCTOBER
    Rivers & Rural Roads

    Rivers & Rural Roads

    $65 USD
    Riverside roaming strolls, historic highlights, scenic spots for sipping wine or beer, and some of the prettiest rural roads are just a few of the hidden gems you’ll discover on this trip!
    • Kid-Friendly
    Can depart from: Detroit Area, Toledo Area
  • Great For Active families
    Sweet Sensations

    Sweet Sensations

    $65 USD
    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
    Can depart from: Detroit Area, Toledo Area, Windsor Area
  • FOR HOLLY JOLLY FEELINGS
    Endless Christmas Cheer

    Endless Christmas Cheer

    $65 USD
    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
    Can depart from: Detroit Area, Windsor Area, Sarnia Area
  • A LITTLE BIT OF EVERYTHING
    Treats & Trails

    Treats & Trails

    $65 USD
    Is there anything better than a leisurely day sipping coffee, enjoying tasty treats and meandering along easy boardwalk trails? We think not!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Can depart from: Windsor Area, Detroit Area, Toledo Area
  • Can be done in winter
    Groves, Gardens & Grapevines

    Groves, Gardens & Grapevines

    $65 USD
    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
    Can depart from: Columbus Area, Cleveland Area, Toledo Area
  • FOR A CLOSE-BY WHIMSICAL ADVENTURE
    Storybook Strolls

    Storybook Strolls

    $65 USD
    A day full of whimsy, wonder and quirky destinations that will make you feel like you're living in a storybook world. This trip is perfect for the whole road trip crew, from families with kids to girlfriend getaways!
    • Kid-Friendly
    Can depart from: Cincinnati Area
  • FOR COUNTRYSIDE DRIVES
    Cozy Country Charm

    Cozy Country Charm

    $65 USD
    The perfect blend of rustic allure, cute small towns, cozy cafes, and farmstead feelings makes this a fantastic road trip for those looking to slow down and appreciate the little moments.
    • Kid-Friendly
    • Accessible
    Can depart from: Indianapolis Area
  • EXPLORE AN ICONIC AREA
    Countless Covered Bridges

    Countless Covered Bridges

    $65 USD
    Take a leisurely drive through the idyllic countryside, hopping from one quaint covered bridge to another. We've sprinkled in a few local eateries and easy trails to give your camera a break! 
    • Dog-Friendly
    • Kid-Friendly
    Can depart from: Indianapolis Area
  • 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
    Can depart from: Indianapolis Area
  • Gift Card [Digital $USD]

    Gift Card [Digital $USD]

    $65.00 USD
    Instantly send the gift of a one-day surprise road trip! Digital gift cards can be sent immediately or scheduled to be sent on a specific day.
  • Best done spring-fall
    Southern Express

    Southern Express

    $65 USD
    This trip takes you to some iconic stops and hidden gems in southern Ontario. It's the perfect combination of outdoor activities, funky restaurants, beaches and historic attractions.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Windsor Area, Detroit Area, Sarnia Area, London Area

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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!