Parent and child opening a Guess Where Trips booklet on a picnic bench

Delaware

Choose a road trip that suits your driving and travel preferences from our selection below. Can't decide? Take our road trip quiz for personalized recommendations.

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.

  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 CAD
    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.
  • BEST SELLER
    River running through forest.

    Along the River

    $65 CAD
    A scenic road trip near Allentown along the NJ and PA border with small towns and riverside stops.
    • Accessible
    • Kid-Friendly
    Can depart from: Philadelphia Area, Trenton Area, Allentown, PA Area, Newark Area, Wilmington, DE Area, New York City Area
  • FOR THE PARANORMAL EXPLORER
    Black and white photo of an old house.

    An Unusual Adventure

    $65 CAD
    A spooky Southern New Jersey road trip with abandoned spots, local legends, and eerie stops.
    • Dog-Friendly
    Can depart from: Philadelphia Area, Trenton Area, Wilmington, DE Area
  • MOTHER'S DAY PICK
    Covered Bridges & Baked Goods

    Covered Bridges & Baked Goods

    $65 CAD
    This trip is like taking a step back in time! Wind your way through the peaceful countryside to a number of quaint covered bridges and locally owned bakeries, farmers markets, and shops.
    • Kid-Friendly
    • Accessible
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area, Allentown, PA Area, Wilmington, DE Area