Hi Travelzoo Members!

Your Travelzoo membership entitles you to 50% off your purchase with the code TRAVELZOO. Below, you will find our five DMV-area trips, as well as some answers to our most frequently asked questions.

DMV-Area Trips

  • Available year-round! | Great gift
    Tiny Town Tour

    Tiny Town Tour

    $65 CAD
    • Dog-Friendly
  • Great Weekend Away Trip!
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $65 CAD
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • Available Year-Round
    Haunts, Hikes & History

    Haunts, Hikes & History

    $65 CAD
    • Kid-Friendly
    • Dog-Friendly
  • Best done Spring - Fall
    Waterside Bliss

    Waterside Bliss

    $65 CAD
    • Kid-Friendly
    • Dog-Friendly
  • Something for everyone | Great gift
    Whimsical Wonders

    Whimsical Wonders

    $65 CAD
    • Kid-Friendly
    • Accessible
  • Great Year-Round Trip
    Secrets of Gettysburg

    Secrets of Gettysburg

    $65 CAD
    • Kid-Friendly
    • Dog-Friendly
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  • How does it work?

    Our trips include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips, fun facts and exclusive 'Guess Where' discounts at select local businesses.

    1. Select your trip. Select any day trip below, add it to your cart, and use code TRAVELZOO  at checkout for 35% off.
    2. Get your package. Shipping is free and takes 7-10 business days. The PDF option is an instant digital download. 
    3. Pack your bags. Open the ‘Before You Go’ guide which includes a packing list and more information to help prepare for your day.
    4. Want to stay overnight? We include a variety of hotel recommendations in your confirmation email if you'd like to make it into an overnight trip.

Frequently Asked Questions

What is Guess Where Trips?

At Guess Where Trips, we specialize in one-day surprise road trips. Leave the stress of planning to us! We build each road trips around a general theme, so you might have an idea of what you’ll get up to during the day, but you won’t know where we’re sending you! We love finding new small businesses, hidden gems, cute cafes, and picturesque small towns. 

How do I know where I'm going?

The trips are intended to be surprises, but there are a few ways to get a better idea of where you'll be going:

Check our 'Trip Map: Our trip map allows you to see the general area of where each trip ends. 

FAQ: Each trip has its own set of frequently asked questions. Please read this section for a list of approximate round-trip driving distances from nearby cities. 

Ask us! We're always here to help with any questions you might have. Start a chat with us or send us an email with your departure area and travel interests, and we'll send you our trip recommendations. 

What is included in my package?

Your road trip includes a well-curated itinerary for the day with a focus on small businesses, cute shops, hidden gems, and unique locations.

Food, drinks, gas, and admission (if there is a fee!) are not included in the price of our trips.

I’m travelling with a group of people. Does each person in our group need to purchase a trip?

If everyone is travelling together in the same car, you only need to purchase one trip. Otherwise, we recommend one trip per driver.

How long are your road trips?

Our road trips are designed to be one day trips. Each trip takes roughly 6-8 hours to complete - this includes time spent at the recommendation and driving.

In the Before You Go booklet, we will tell you what time we recommend leaving for your road trip. Keep in mind that the later you leave, the less time you may have to spend at each stop.