Oakville Itineraries
Oakville is an all-seasons destination with something for everyone! Follow along with our seasonal itineraries or pick and choose elements from each to create your ultimate vacation.
Travelling right now requires a lot of planning and forethought, so follow along with our new itineraries and start shaping your next trip.
Oakville’s Historical Past
From being an entry point for many American slaves travelling the Underground Railroad in search of freedom to being a major point of entry for sailors and merchants in the 19th century, Oakville is the ideal location for anyone interested in learning more about Canadian history.
Romantic Getaway Itinerary
Are you looking for a romantic weekend getaway? Look no further than Oakville! Located on the shores of Lake Ontario, this beautiful town is full of culture and activities.
A Guide to Exploring Oakville’s Surrounding Cities
Explore Oakville’s surrounding cities with this detailed guide of three day trip options.
Weekend Trip Itinerary
Oakville is a great destination for family travel, romantic escapes and solo trips
Family-Friendly Places in Oakville
Guaranteed to Elevate You to Cool Grandma and Grandpa Status
A Weekend in Oakville with Sporty Kids
This two-day action-packed itinerary is perfect for families looking to stay active while they spend a weekend in Oakville.
Black History Walking Tour
Explore Kerr Village’s Black History with the help of the Canadian Caribbean Association’s self-guided Oakville walking tour!
Black History Bike Tour
Explore local Black History with the help of the Canadian Caribbean Association’s self-guided Oakville bike tour!
History and Art Itinerary
Spend two days exploring local art, history, theatre and historic eats.
Visitor Guide & Map Brochure
Download the digital guide and brochure below to begin planning your next adventure. Contact info@visitoakville.com to request a physical copy.