The Ontario Gift Guide

Finding the perfect gift for someone who already has it all just got easier. Whether they love unexpected adventures, small-town charm, or discovering hidden gems close to home, our Ontario Gift Guide is filled with unforgettable experiences - all created right here at Guess Where Trips.

These gifts aren’t things… they’re memories waiting to happen. Perfect for couples, families, friends, co-workers, or anyone who needs a little adventure on their calendar.

🎁 First Things First: Gift Cards Make the Perfect Gift

Not sure which trip they'll love most? A Guess Where Trips gift card lets them choose their own adventure - whether that’s a cozy small-town stroll, a scenic nature escape, or one of our bestselling mystery days.

The perks:

Our gift cards never expire
They can redeem it closer to the date of travel, so they have the most up-to-date information as possible
Redeemable for any road trip on our site
The easiest way to give an unforgettable day out.

Three easy ways to gift:

Our new Road Trip Gift Card comes in an easy-to-wrap box, complete with a handy booklet to help them understand how our trips work, and how to redeem their gift card.
Our Road Trip Gift Bundle includes a gift card, tote bag, and game pack - all packed up in a keepsake gift box that they can later use to store their road trip memories.
Our Digital Gift Card can be emailed directly to the recipient (just click "I want to send this as a gift" before adding it to your cart!)

Prefer to pick the road trip out yourself? Here are our top Ontario road trip picks for everyone on your list:

Gifts for Couples
Gifts for Families
Gifts for Seniors
Gifts for Winter Lovers
Gifts For Everyone
Unique Gift Add-Ons

Give them a day to reconnect - no planning required.

Bayside Wonders (Kitchener-Waterloo, Toronto, Barrie)

The perfect blend of charming small towns, farmers markets, and wine tastings mixed with epic waterfalls and a couple unique trails.

Must love: 🏘️ Small Towns | 🌾 farmer’s markets | 💧 waterfalls

Seasons: Year-Round

Wine Time and Hidden Gems (Toronto, Kingston)

Rolling vineyard views, artful little towns, farm markets and that breezy, laid-back feel only lakeside moments can deliver.

Must love: 🍷 wine | 🌾 farmer’s markets | 🏞️ scenic views

Seasons: Spring-Fall

Local Markets and Picturesque Towns (London, Toronto)

One of our best-selling trips, and for a good reason. Stops include historic towns, local markets, eateries and hidden gems. This trip makes a great gift because of its versatility.

Must love: 🏘️ historic Towns | 🏞️ scenic views | 🛍️ unique shops & eateries

Seasons: Year-Round

Keep the kids curious (and entertained) with family-friendly stops, treat shops, outdoor activities, and hands-on surprises. Perfect for families who want to try something new without straying too far from home.

The Whimsical Route (London, Kitchener-Waterloo, Toronto)

Get ready for a road trip where nature, history, hidden gems, and a touch of cinematic magic come together for a perfectly whimsical escape just outside the city!

Must love: 🚜 farms | 📜 history | 🍽️ farm fresh food & drinks

Seasons: Year-Round

Country Farms & Furry Friends (London, Kitchener-Waterloo, Toronto)

Alpacas, donkeys and goats - oh my! They'll start their day off at a funky country market, before hanging with the birds and ending the day with some furry friends.

Must love: 🐮 animals | 👟 easy strolls | 🛍️ markets

Seasons: Year-Round

From Country to Coast (Sarnia, London, Kitchener-Waterloo)

Country roads, waterfall wonders, local wineries, breweries, farm shops, and beachside towns.

Must love: 👟 easy trails | 💧 waterfalls | 🧺 farm shops

Seasons: April-October

Well-paced road trips with lots to choose from for every walk of life and activity level. Retired? Skip the weekend road trips, and enjoy beautiful locations without the crowds.

Funky Florals and Fine Wines (London, Kitchener-Waterloo, Toronto)

This pretty little road trip offers quite a few hidden gems combined with some iconic attractions.

Must love: 💐 flowers | 🍷 wine | 🏘️ small towns

Seasons: Year-Round

Curiosities & Coastlines (Kitchener-Waterloo, Goderich, Collingwood)

Eerie ruins, offbeat roadside finds, historic small towns, and the shores of Lake Huron. This laid-back Bruce County adventure perfectly mixes local legends, great eats, and scenic spots!

Must love: 🏘️ historic towns | ☕ cafes | 👟 easy trails

Seasons: Spring-Fall

The Small Town Charm Trail (Sarnia, London, Toronto, Kitchener-Waterloo)

You know those towns that are described as 'blink-and-you'll-miss-it'? They often have the most amazing hidden gems!

Must love: ☕ Cafes | 🏘️ Small Towns | 📜 history

Seasons: Year-Round

Give the gift of fresh air, scenic hikes, and unique natural wonders across Ontario.

Escape to Nature (Toronto, Kitchener-Waterloo, Barrie)

Tiny towns and easy outdoor adventures, cozy local cafes and funky breweries. During the winter, activities include ice skating and snowshoeing!

Must love: ⛸️ winter activities | ☕ cafes | 🌿 nature

Seasons: Year-Round

Markets to Mountains (Kitchener-Waterloo, Toronto, London, Barrie)

From cute markets to mountainside hikes, Markets to Mountains has all the stops for a cozy yet adventurous day trip in Ontario.

Must love: 🥾 hiking | 🛍️ markets | ⛸️ winter activities

Seasons: Year-Round

The Sweet & Scenic Route (Toronto, Kitchener-Waterloo)

A little sweet, a little scenic - this road trip blends cozy cafés, local wines, and maple treats with easy trails, waterfalls, and serene ponds.

Must love: 🍷 wine | 🏞️ outdoor adventures | 🍁 maple treats

Seasons: Spring-Fall

Can’t decide which trip to choose? Take the road trip quiz or use our interactive road trip map to be matched with a trip OR consider these gifts for those hard-to-buy for loved ones!

Road Trip Gift Card

Includes:

A road trip voucher redeemable for one physical road trip including taxes & shipping
A handy road trip guide
Beautiful gift box with a slide out enclosure