Table of Contents Show
Seeking Canada’s best-kept secrets, hidden gems, we turned to seven travel experts and entrepreneurs for their personal recommendations. From the serene Thousand Islands to the unexpected urban oasis of Hamilton’s waterfalls, our contributors, including Travel Bloggers and Founders, unveil hidden gems and lesser-known destinations worth adding to your Canadian itinerary.
- Discover Thousand Islands’ Serenity
- Kingston’s Rich History and Nightlife
- Explore Kaslo, Charlottetown, and Carcross Desert
- Banff’s Glaciers and Mountain Life
- Tobermory: A Lakeside Hiking Haven
- Windsor: Breweries and Border Adventures
- Hamilton: From Steel City to Waterfalls
Discover Thousand Islands’ Serenity
Hammer Tsui, Travel Blogger and Digital Nomad, A Fun Couple

The Thousand Islands in Ontario, Canada, completely won me over as an off-the-beaten-path gem. Cruising along the St. Lawrence River, surrounded by these charming islands, felt like stepping into a fairy tale. Exploring each unique islet, with the majestic Boldt Castle in the backdrop, was a magical experience.
The serene atmosphere set it apart from more crowded spots, offering a peaceful escape. From enjoying local cuisine at waterfront eateries to witnessing stunning sunsets, the Thousand Islands delivered a perfect mix of nature and relaxation, making it a truly memorable and underrated destination that deserves more attention.
Kingston’s Rich History and Nightlife
Scott Sidders, Co-Founder and CEO, Scott & Yanling Media Inc.

Go to Kingston, Ontario. There are so many unique places and things to do there, and you rarely hear about them. You can visit Fort Henry and watch the demonstrations, reenacting what it was like in the past. Kingston is also home to Canada’s most notorious prison, which has since been closed down, but tours of the prison are available.
The downtown area has many great shops if you walk down Princess Street. The nightlife is vibrant, and if you’re with family, there’s a haunted tour that’s fun for all ages. The city has many quality restaurants too, like AquaTerra.
Explore Kaslo, Charlottetown, and Carcross Desert
Ritesh Raj, COO & CPO, CuddlyNest

As a seasoned traveler who has explored over 120 countries, I’ve discovered many hidden gems in my travels, including some lesser-known destinations in Canada.
One such place is Kaslo, a small village in British Columbia’s West Kootenay region. Nestled beside the beautiful Kootenay Lake and at the foot of the Purcell Mountains, Kaslo offers a blend of natural beauty and historic attractions.
Charlottetown, Prince Edward Island, is another destination that doesn’t get the number of visitors it deserves. Despite its small size, it’s packed with historic attractions, stunning architecture, and a vibrant arts scene.
Lastly, I’d recommend exploring the Carcross Desert in Yukon, the world’s smallest desert. It’s a unique and fascinating destination that offers a stark contrast to the typical Canadian landscape.
Banff’s Glaciers and Mountain Life
Axel Hernborg, Founder and CEO, Tripplo

Banff National Park, the first national park in Canada, offers visitors the chance to explore the enormous glaciers that cover all of the lakes, creating an incredibly picturesque landmark. Visitors can also take in the exotic beauty of the park’s Rocky Mountains.
Amidst the tops of towering mountains, you will see the lovely village life that will astound you with its breathtaking views. Many different wildlife species can be found in the mountain forests. In addition, you can engage in daring pursuits like biking, hiking, camping, and glacier skiing.
Tobermory: A Lakeside Hiking Haven
Dr. Mark Farrell (FIA), Founder, CEO, Associate Professor & Actuary, ProActuary Jobs
I moved from Ireland to live in Toronto for a year and often visited the hidden gem of Tobermory. This lakeside town captivated me with its unique charm. It is a haven for adventurers and hikers like myself. The walking trails offer access to some of the world’s most stunning scenery, providing a tranquil escape into nature. Tobermory’s beauty and serene environment make it a must-visit for those seeking lesser-known destinations in Canada.
Windsor: Breweries and Border Adventures
Sarah Marie Naska, Founder, SMHavice Investments

Windsor, Ontario, and surrounding areas are a lesser-known destination in Canada that is enjoyable, especially in the summer.
Windsor borders the city of Detroit, and it’s quite easy to hop between the two cities, meaning you could spend part of the day in Windsor and the other part of the day in Detroit or on Belle Isle. This proximity to the U.S. also makes traveling to and from the area convenient, providing a ton of travel options for flights and more.
The Windsor area also offers a lot of nice activities to partake in, including an abundance of wonderful breweries, distilleries, and wineries (I especially recommend Pelee Island Winery and actually making the trip over to Pelee Island). The drive through the entire Essex area is quite picturesque, and since Windsor isn’t a major city, it’s easy to get around.
Windsor’s riverfront is a nice walk, especially on a sunny day, and you can look across the blue water and see the Detroit city skyline. Just up from the riverfront is a hip, modernized area called Walkerville that has some delicious restaurants, cafes, a bookshop, and another great brewery. Spending an afternoon there is enjoyable, and you can also take a tour of the J.P. Wiser’s Whiskey factory!
Hamilton: From Steel City to Waterfalls
Travis Hann, Partner, Pender & Howe

As a Torontonian, I’d long eschewed Hamilton, Ontario. Call it elitism, but that smoggy drive into the Steel City really turned me off.
But recently, as the city has grown, it’s become a force of its own, and I find myself heading there to meet candidates and clients regularly. They’ve shown me a different, and often unknown, side of the city. Turns out, it’s the waterfall capital of the world. I’ve now spent hours exploring trails that start in the city proper but lead to places you’d never associate with the gritty downtown.
Hamilton is now a place I take friends and family when we’re looking to unwind in nature.
Last Updated on by Milan Maity