Give 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.

Immerse 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.

Bakeries, breweries & views - oh my! With the perfect mix of outdoor adventures, local farms, and tasty bites, this is the ideal trip for your whole road trip crew. The perfect road trip for any Little Women movie fans, too!

It'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.

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.