How does it work?
Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.
See our road trips below, or check out our quiz and trip map to help find your perfect adventure.
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Vintage Vibes & Views
$39 CADImmerse yourself in quintessential New England charm as you wind along picturesque roads to a number of nature trails, cozy cafes, historic small towns and picturesque beaches.- Kid-Friendly
- Dog-Friendly
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Funky Farms & Storybook Tales
$65 CADIt’s no wonder authors flocked to this part of Massachusetts for inspiration. Set out on a scenic drive through storybook landscapes to discover farms, boardwalk trails, quirky history, and plenty of charming surprises along the way.- Accessible
- Kid-Friendly
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Coastal Connection
SaleRegular price $39.00 CADUnit price perFrom 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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Escape to the Cape
$65 CADThis 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