Road Trips near Windsor
Choose a road trip that suits your driving and travel preferences from our selection below. Can't decide? Take our road trip quiz for personalized recommendations.
How does it work?
Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.
See our road trips below, or check out our quiz and trip map to help find your perfect adventure.
-
Secrets in the South
$65 CADWith 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 - September as there are a handful of fabulous seasonal suggestions.- Kid-Friendly
-
Southern Express
$65 CADThink cozy bakeries, swim spots, easy hikes, and wine with a view, all wrapped up in one charming escape. You’ll wonder how this area stayed off your radar for so long!- Kid-Friendly
- Dog-Friendly
-
Treats & Trails
$65 CADIs there anything better than a leisurely day sipping hot coffee, enjoying tasty treats, and wandering along quiet snow-covered boardwalk trails? We think not!- Kid-Friendly
- Dog-Friendly
- Accessible
-
Sweet Sensations
$65 CADBetween making a furry friend at a farm, enjoying local eateries, walking to quirky ruins in the woods and exploring the sweetest small town, this trip will make all five senses come to life all day!- Kid-Friendly
- Accessible
