Hitting the road with your furry friend

Hitting the road with your furry friend

Hitting the road with your furry friend

Our pet-friendly trips are full of surprise stops that will make your journey with your furry buddy unforgettable. 

What's a Guess Where Trip? A Guess Where Trip is like a big surprise adventure. Instead of planning every single thing ahead of time, you and your doggie choose from several recommendations at four different stops. You don't know exactly where you'll end up, and that's what makes it exciting!

What makes a trip pet-friendly? Our pet-friendly trips include at least one recommendation per stop where pets are welcome. These are usually outdoor activities, or summertime patios.

Important to note: Many shops, restaurants and indoor attractions are not pet-friendly. When taking a pet-friendly trip, prepare for a day in the great outdoors. We recommend packing your own picnic, just in case it's difficult to get a spot at a pet-friendly restaurant. And these trips are best taken in weather where you and your dog will be happy to spend the day outside.

Getting Ready for the Trip:

  1. Pick your trip: You can either check out our quiz or trip map to find pet-friendly trips in your area, or scroll through our trips and take note of the trips with a dog icon (indicating they are pet-friendly).

  2. Pack smart: Make sure to bring all the important stuff your dog needs, like food, treats, water, a leash, and a toy or two.

Let the Adventure Begin!

  1. Before You Go: As always, you should open your "Before You Go" envelope at least a day in advance. It will help you prepare for the day ahead.

  2. Hit the road: As you travel, you and your dog can explore new parks, go for walks on trails, and visit places that welcome furry friends. You'll have a great time taking walks, having picnics, and finding hidden treasures.

Remember the Moments:

  1. Take lots of pictures: Don't forget to take pictures of your pup having a blast! These pictures will help you remember the awesome time you had on your Guess Where Trip. We love being tagged on Instagram too!

  2. Take note: Found a new park that you and your dog fell in love with? Make note of it - we like adding our fave locations to Google Maps as a reminder to check it out again the next time we're in the area. Found some suggestions that you couldn't check out with your dog in tow? Make note of it so you can head back another time!

Going on a Guess Where Trip with your dog is an unforgettable experience for you both. Be safe, and have a doggone good time!

Our fave pet-friendly trips per region


Secrets in the South (London)

With funky markets, scenic roads and the most picturesque towns, you'll love all of the secrets you discover on the road. This trip is best enjoyed between June - October as there are a handful of fabulous seasonal suggestions.

Outdoor Adventures & Scenic Roads (Toronto)

Outdoor Adventures encompasses everything you could possibly want in a road trip getaway. Scenic roads? Check. Cool attractions? Check. Good food? Check check check.

All the Pretty Things (Ottawa)

Take in all the pretty views and things on this picturesque trip. The itinerary is packed with stunning viewpoints, historic attractions and delicious restaurants and wineries.

British Columbia

Chasing Waterfalls (Vancouver)

Don't let TLC lead you astray. You should definitely go chasing waterfalls! This trip is jam-packed with good food, picturesque waterfalls, and quirky gems.


The Long & Unknown Road (Calgary)

If you love a long and interesting drive, this trip is for you! This trip is approximately 5 hours round-trip from Calgary, so we recommend leaving super early or extending your stay into an overnight getaway.

Nova Scotia

Valley Views (Halifax)

Down in the valley where the green grass grows...you'll find charming towns, get lost in lush vineyards, take in vast views and hike scenic trails on this countryside road trip. 

Maryland & DC

Winding Roads & Historic Gems (Baltimore/Washington DC)

Discover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination filled with history and views.

North Carolina

Sandhills Sauntering (Raleigh)

Picturesque drives beneath towering trees make this an incredibly scenic trip. Sandhills Sauntering is full of epic places to eat, tons of photo-worthy moments and a hidden gem that will leave you speechless.


Quaint Corners (Atlanta)

Cozy cafes, countryside drives, gorgeous lookouts and quirky roadside stops are just some of the things you'll discover on your surprise road trip!


Mysterious Gems (Orlando)

Truly extraordinary destinations with strange stories and history. Cemeteries, abandoned ruins, historic homes and so much more await on this mysterious road tirp!


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