Frequently Asked Questions

How it Works

What is Guess Where Trips?

We design self-guided, one-day road trips, and keep the destination a surprise!

You choose a trip based on themes that appeal to you (think hidden gems, local shops, cute cafes, and scenic small towns), and the stops are revealed as you go.

The idea? To discover amazing places right in your own backyard.

How do I know where I'm going?

Trip Map: See the general area where each trip ends up. Explore the map →

Trip FAQs: Every trip page has its own FAQ section, which includes approximate round-trip driving distances from nearby cities.

Ask us: Tell us where you're departing from and what you're into, and we'll point you in the right direction. Start a chat or send us an email →

Physical vs. Digital - what's the difference?

A physical trip arrives by mail as 5 sealed envelopes: one "Before You Go" guide + 4 surprise stop envelopes you open throughout the day.

A digital trip is a downloadable PDF, same content, sent to your inbox. All stops are in one file, so be careful about scrolling ahead!

Do I need to book anything?

Our trips are self-guided and flexible, no booking required.

Just check the "Before You Go" guide for the best days and seasons to go, plus any stops that recommend a reservation.

How long does a trip take?

Most trips are 6-8 hours, including drive time and time at each stop.

Do your road trips expire?

We recommend going within 6 months of purchase. After that, some small businesses may have changed, though we usually offer 2-4 options per stop so there's always something to enjoy.

How much does shipping cost?

For orders over $100, we will ship your package for free. Shipping takes 4-10 business days.

If you need your order earlier, there is a faster option for an extra fee, and shipping will take 2-4 business days.

Choosing a Trip

I don't know which trip to pick - help!

Choose a trip by selecting the city closest to you from the "Select Your Departure" menu, or explore the Trip Map to get a feel for where each trip takes you.

Are trips kid-friendly?

Yes! Most trips work great for families. Look for shorter driving distances if you're bringing little ones.

Are trips dog-friendly?

Many are! Check the individual trip page, it'll say whether dogs are welcome.

Keep in mind most indoor spots won't allow pets, so expect to spend the day mostly outdoors.

Are trips wheelchair/stroller accessible?

Yes, several are. Filter by accessibility on the Trip Map.

Do I need one trip per person?

No, one trip per group is all you need. If you're taking multiple cars, grab one per car.

Gifting

Can I give a trip as a gift?

Absolutely. You can purchase a specific trip and ship it directly to the recipient, just enter their address at checkout.

If you are purchasing a digital trip, you can forward them the link in your confirmation email.

What does a gift card cover?

Gift cards cover any physical road trip. Using one on a digital trip will leave a remaining balance on the card.

Why does the gift card cost more than a trip?

The extra amount covers tax at the time of redemption.

Can I include a gift note?

We're not able to include gift notes. We recommend giving the recipient a heads up that something is on its way from you, and forwarding them the tracking info once it's available.

  • What's Included:

    A ‘Before You Go’ guide with a packing list, approximate driving distances and more tips to plan for your day ahead.

    A series of four envelopes that will make up your day’s itinerary with recommended roadside stops along the way.

    Restaurant, attractions and activity recommendations based on your trip style.

    Physical version: includes 5 printed booklets (a Before You Go and 4 surprise stops) and shipping

  • What's Not Included:

    Transportation and gas.

    Entrances and parking fees for some of recommended attractions (the majority of stops are free).

    Food, beverages and gratuities.

    Digital version: does not include printed booklets, itinerary is emailed