Midwest
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Road Trip Gift Card
Regular price $74.00 USDUnit price perGive the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire. -
Bridges & Beauty
$65 USDGet 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
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A Riverside Ramble
$65 USDA scenic Chicago-area road trip with art, boutiques, eateries, and riverside views.- Accessible
- Kid-Friendly
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Cinema & Scenery
$65 USDDiscover 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
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All Things Charming
$65 USDFrom 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
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Eerie Escapes
$65 USDStep 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
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Falls, Forests & Fables
$65 USDGet 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
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Lakeshore Views & Brews
$65 USDStroll 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
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Cascades & Colors
$65 USDFunky, 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
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Woodland Walks & Wineries
$65 USDFunky 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
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A Taste of Amish Country
$65 USDA peaceful road trip near Akron through Amish country with food stops, shops, and scenic countryside.- Kid-Friendly
- Accessible
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Waterfall Wanderings
$65 USDThe 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
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Rivers & Rural Roads
$50 USD SaleRiverside 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
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Sweet Sensations
$65 USDBetween 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
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Endless Christmas Cheer
$65 USDThis 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
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Treats & Trails
$65 USDIs there anything better than a leisurely day sipping coffee, enjoying tasty treats and meandering along easy boardwalk trails? We think not, and you'll find all of that and more in this Michigan road trip!- Kid-Friendly
- Dog-Friendly
- Accessible
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Groves, Gardens & Grapevines
$65 USDThis 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
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Storybook Strolls
$65 USDA 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
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Cozy Country Charm
$65 USDThe 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
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Countless Covered Bridges
$65 USDTake 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
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Elegant Estates & Outdoor Art
$65 USDJust 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
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Southern Express
$65 USDThink cozy bakeries, swim spots, easy hikes, and wine with a view, all wrapped up in one charming escape. You’ll wonder how this area stayed off your radar for so long!- Kid-Friendly
- Dog-Friendly
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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!
