Romantic Road Trip Bundles are here! Click on Merch & Gift Cards.


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.

Select your trip style.

Select a day trip based on your interests and travel preferences OR fill out our 'road trip quiz.'

Get your package.

Receive your beautifully curated package in the mail OR choose the digital version of the trip which gets sent right to your inbox.

Pack your bags.

Each package includes a ‘Before You Go’ guide and a series of envelopes that will lead you to several surprise destinations on your road trip.

Our Trips

Select an area or city you would be departing from to find what trips are available.

View All Trips

Can't decide?

Take our road trip quiz!

Enter your departing address, select your interests, and preferred driving duration to find the best trip for you.

Take our Quiz

Romantic Road-Trip Bundles ($75)

These Valentines Day bundles are the perfect way to say 'I Love You'. Each bundle comes with a pre-planned romantic trip or gift card, tote bag and card and is nicely wrapped as pictured.

More Info


What People are Saying...

Each stop was so well thought out, perfectly timed, and so much fun. Like the rest of the world, my wife and I have been stuck inside during the pandemic, but Guess Where Trips introduced us to some hidden gems, and reminded us of how much fun it is to get out and discover new spots (and took away the stress of planning!). It was the perfect getaway. I cannot recommend it highly enough.

OMG! I did the Funky Florals trip yesterday with my mom and some friend and wow! The spots were absolutely amazing. The first stop was my favourite. If that was the only one it still would have been worth it! The rapids are insane! Doing the surprise trip next weekend and cannot wait! Thank you! Can't wait to see what's coming for the winter.

I cannot thank you enough for this! We went on our adventures trip and it exceeded our expectations! My kids were very excited to open the envelopes after each stop to see where we were going next. I took my mom as well, and she enjoyed every minute of it. The third stop was stunning! We stayed at the patio of the vineyard and enjoyed the beautiful view while we ate and sipped on some wine. Oh and the donkey sanctuary...cutest thing ever. Today has been one of the most memorable days yet!

My mom turns 60 this week and she always says she doesn't 'NEED' anything. So, I decided to get her a Guess Where Trip so that she could spend an entire day with her family doing something fun. She LOVED it!!! She said it was such a great idea and wants to go on another one with me ASAP! Thanks so much for an amazing day!

Ah! I just have to let you guys know, you're amazing at putting together fantastic road trips! We started out on the Hops & History tour, and ended up in the CUTEST beach town (you guys weren't lying).

Went on our third Guess Where Trips today, and like the others, it exceeded our expectations! Never know where we are headed until the day we go on our trip. Very well planned out road trips. They have taken me to many places I've never been to.

Not to be dramatic, but I went on one of your trips last weekend and it was the best day of my life.

My girlfriend and I went on your Weird and Wonderful trip on Saturday and we just wanted to say that it was such an amazing experience! From the moment we opened our first envelope it was clear that your team is dedicated to creating a very memorable experience for each of the stops! My girlfriend and I want to say thank you for helping us create some amazing memories and can't wait to do more trips in the future!

Absolutely LOVED our surprise adventure from @guesswheretrips! We visited so many beautiful and interesting places that we never would have stopped at otherwise. Also, the roadside food stops were 10/10. I highly recommend checking them out if you're looking for an amazing action-packed day!