Browse all trips
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Funky Farms & Storybook Tales
$65 USDIt's no wonder authors flocked to this area of Massachusetts for inspiration! Head out on a picturesque drive and discover farms, boardwalk trails, lots of quirky history and so much more.- Accessible
- Kid-Friendly
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Boardwalks, Brews & Markets
$65 USDThe name really says it all! Explore marvelous markets with food stalls and local artisans, enjoy a couple brews, and stroll along easy boardwalk trails.- Accessible
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Quirky Delights
$65 USDNot too far from home you'll discover a ton of quirky destinations. Think outdoor folk art, funky eats in a small town, hidden gem riverside strolls, and a local alpaca farm.- Accessible
- Kid-Friendly
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Old Florida Trail
$39 USDGo back in time and visit old Florida. You'll visit delightful small towns, dig into local fare, explore a few outdoor adventures, and fill up your camera roll with quirky photo ops.- Kid-Friendly
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Charming Curiosities
$65 USDWith 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
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A Little Bit of Everything
$65 USDA well-rounded Charlotte-area road trip with local shops, a scenic rail trail, and a little bit of everything.- Accessible
- Kid-Friendly
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The Southwest Quest
$65 USDPlenty 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
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Coastal Connection
$65 USDFrom 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
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The Shore Explorer
$65 USDHop 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
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Quaint Corners
$65 USDCozy cafes, countryside drives, gorgeous lookouts and quirky roadside stops are just some of the things you'll discover on your surprise road trip!- Accessible
- Dog-Friendly
- 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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Mysterious Gems
$65 USDTruly extraordinary destinations with strange stories and history. Cemeteries abandoned ruins, historic homes and so much more await on this mysterious road trip!- Dog-Friendly
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Enchanted Adventures
$65 USDAround 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, colorful photo ops and tasty treats.- Kid-Friendly
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Escape to the Cape
$65 USDThis 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
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Secrets of Gettysburg
Regular price $39.00 USDUnit price perExplore Gettysburg and its surrounding area in a whole new way. We’ve made this classic, All-American, bucket list destination easy and fun to do - whether it's your first or fiftieth time! Discover hidden gems and surprising stops while learning more about the turning point of the Civil War.- Kid-Friendly
- Dog-Friendly
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Treasure Coast Explorer
$65 USDWe'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
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Coffee, Canyons & Coastlines
$65 USDCoffee, 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
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A Drive Back in Time
$65 USDA relaxed Atlanta-area road trip through charming small towns, cozy cafés, and quirky photo stops.- 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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Wacky Wonders
$65 USDA 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. -
Wonder & Whimsy
$65 USDEmbark 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
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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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A Riverside Ramble
$65 USDA scenic Chicago-area road trip with art, boutiques, eateries, and riverside views.- Accessible
- Kid-Friendly
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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!