guess where trips ontario

You can take a surprise festive road trip outside of Toronto this winter

Guess Where Trips plans one day surprise road trips around Canada and there are a few trips in Ontario created to help you get in the holiday spirit this year. 

All you need is a car with a full tank of gas, some road trip snacks, and a sense of adventure since you won't know what the four stops are until you receive your chosen $55 package. 

One of the customized day excursions called Festive Florals and Fine Wines takes you to flower markets and floral displays that are decked out for the holidays and lets you sip wine by an outdoor fire pit. 

Bring along snowshoes or cross country skis, or just walk the optional wintery walk that's also included in the day.

The adventure ends at a Christmas market when it's lit up in sparkling lights to really get you in the festive mood. 

Another option is The Small Town Christmas Trail. Like the festive version of the Funky Florals trip, the exact pit stops are kept secret and only revealed when you get the physical or digital version of your trip.

This one includes destinations to bakeries, local shops, light displays and an old-timey Christmas tree farm in the most charming little towns in southern Ontario. 

Each package comes with discounts at a few local businesses and a variety of alternative stops in case a suggested stop doesn't interest you. And none of the stops need to be pre-booked in advance. 

If you miss out on the festive day trips, there are several other trips to take year-round like one that explores nearby waterfalls and a haunted history route perfect for horror fans or ghost story lovers. 

Take the road trip quiz if you're having a hard time deciding the best one for you. Just put in your departing city, preferred driving time and select your interests to get a trip recommendation. 

Lead photo by

Guess Where Trips

Latest Videos

Latest Videos

Join the conversation Load comments

Latest in Travel

Moving from Canada is becoming a popular but controversial choice

The top 5 hotels in Niagara-on-the-Lake

You can visit stunning ice caves hidden beside a quiet lake in Ontario this winter

Wye Marsh is Ontario's perfect winter spot for boardwalk trails and wildlife viewing

The ghost town of Eldorado offers a glimpse back in time to the era of Ontario's gold rush

10 winter hiking trails in Ontario to get away from it all

5 incredible hotels in Canada to add to your winter vacation bucket list

This cascading frozen waterfall in Ontario is a beautiful winter nature escape