Woman holding four Guess Where Trips envelopes while on road trip

Philadelphia-Area Road Trips

Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

Browse all trips

  • Gift Card [Digital $USD]

    Gift Card [Digital $USD]

    $65.00 USD
    Instantly send the gift of a one-day surprise road trip! Digital gift cards can be sent immediately or scheduled to be sent on a specific day.
  • BEST SELLER
    River running through forest.

    Along the River

    $65 USD
    Meander through tiny towns along the river that are brimming with hidden gems. There are countless photo-worthy moments and memories to make on this easygoing scenic road trip.
    • Accessible
    • Kid-Friendly
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area, Allentown, PA Area, Newark Area, Wilmington, DE Area, New York City Area
  • BEST SELLER
    Whimsical Wonders

    Whimsical Wonders

    $65 USD
    Escape to hidden gem destinations that make you feel like you've stepped into a fairytale world. Lucious gardens, charming towns and whimsical photo ops make this the perfect road trip.
    • Kid-Friendly
    • Accessible
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area
  • FOR THE PARANORMAL EXPLORER
    Black and white photo of an old house.

    An Unusual Adventure

    $65 USD
    If you're the paranormal podcast listener in your friend group, this trip is for you! This area is filled with all things unusual, spooky, and abandoned. You'll also learn about some local legends, ghost stories and folklore throughout your day.
    • Dog-Friendly
    Can depart from: Philadelphia Area, Trenton Area, Wilmington, DE Area
  • MOTHER'S DAY PICK
    Red covered bridge over water.

    Covered Bridges & Baked Goods

    $65 USD
    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
  • GREAT YEAR-ROUND TRIP
    Secrets of Gettysburg

    Secrets of Gettysburg

    $65 USD
    Explore 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
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area, Winchester VA Area
  • BEST DONE SPRING-FALL
    The Shore Explorer

    The Shore Explorer

    $65 USD
    Hop 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
    Can depart from: New York City Area, Trenton Area, Newark Area, Philadelphia Area
  • MOTHER'S DAY PICK
    Enchanted Adventures

    Enchanted Adventures

    $65 USD
    Around 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, colourful photo ops and tasty treats.
    • Kid-Friendly
    Can depart from: New York City Area, Philadelphia Area, Trenton Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

Take Our Quiz to Find Out

Select your region and interests to find the best trip for you.

Take the Quiz
Woman on road trip leaning out window

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!