Julie Shipley-Strickland Wealth & Risk Management

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5 Popular 2026 Travel Destinations from Calgary

It’s no new news, but my family and I love to travel and make memories together. My husband Kurtis and I really value travel gifts over material goods because as the kids get older, their days are spent more with teammates and friends than they are with us. It’s a lovely way to capture the essence of our family in any given year – our kids even remember travel vacations from when they were toddlers! As many Canadians seek out travel destinations outside of the United States, I thought it’d be valuable to round up some of the “hot” spots that have been the talk of the town in my circles. It’s a new year, meaning it’s time to get planning on your next vacation so you can book the time off and look forward to your next adventure. Let’s dive in!

 

Panama

In 2025, our entire family made a trip to Panama, and we’re so glad we did. It’s somewhere that maybe hasn’t taken off in popularity yet but holds so much beauty. This Central American gem offers such a unique blend of modern city life, tropical beaches, and rich history. You can explore the historic Casco Viejo district in Panama City, which features colourful colonial buildings with stunning architecture, the kind that you can’t see everywhere. Travel time from Calgary is around 8-9 hours with one connection, so I’d recommend planning for at least 7-14 days to be able to fully enjoy the city and surrounding area sightseeing.

Japan

If you’ve been scrolling your Instagram or TikTok feeds, then I can guarantee you’ve seen someone in your life adventuring to Japan, and for good reason. For all of us in Calgary, it’s been a game change since WestJet first introduced their one-way direct fares to Tokyo. Many visit for the Sakura (cherry blossom) season between March and May, or for the fall colours between September and December. No matter what time of year you visit, Japan is known to be an amazing cultural experience with historic temples and shrines, incredible food, and picturesque nature scenes. I think it’s so cool that you can go from ultra-modern skyscrapers to peaceful bamboo forests on the same day. Travel time from Calgary is around 10-12 hours depending on your route, so plan for at least 10-14 days if you can, and make sure to stick to a few cities rather than doing one every couple of days. My goal is to eventually visit and book a ryokan and onsen during the trip – I’ve heard they’re idyllic!

Mexico

Oh, Mexico. I attend a women’s retreat here every year, and it’s something that I look forward to the second the New Year hits. It really does make a difference growing my skills and building my resilience with like-minded female entrepreneurs. With so many direct flights and relatively short travel times (around 4-5 hours depending on where you’re going), Mexico is perfect for everything from a quick getaway to an extended vacation. Many popular destinations include Playa del Carmen, Tulum, Todos Santos, and Sayulita. Of course, we can’t forget Mexico City, which is a design hub that has so much to offer in the way of aesthetics. The food is always 10/10, the people are wonderfully kind, and the oceans are stunning and warm. Really, what more could you ask for? The best part of a trip to Mexico is there are so many different areas, allowing you to find a spot that’s perfect for your budget and vibe.

Dominican Republic

The Dominican Republic continues to be one of Calgarians’ favourite weather escapes with direct flights from Calgary taking around 6-7 hours. From word of mouth and chatting with people in my circles, it seems more Calgarians have opted for second homes in the Dominican because once you’ve made the trek, you’re transported to a completely different world made up of brilliant turquoise water, white sand beaches, and endless sunshine. Punta Cana is always a popular spot, but it’s worth doing some more research to explore areas like Puerto Plata, Bani, La Romana, and more. You can tackle any kind of adventure you’d like, from kite surfing, to snorkeling, to relaxing on the beach. Whatever you’re looking for, the Dominican has in store.

Italy

In my opinion, Italy must have a place on this list for its European charm. It can be roughly 10+ hours from Calgary including connections, but once you’ve arrived, the incredible food, stunning architecture, rich history, and romantic atmosphere make it worth it. My recommendation is to always hit a central classic like Rome, Florence, or Venice, but to balance the trip with some smaller destinations that have a truly unique charm to them like Siena, Puglia, Cinque Terre, and Lake Como. Stay in smaller, less populated towns if you want your dollar to go a little further and you want an experience that’s off the beaten path. You can rent an Airbnb for a more authentic experience where you can make your accommodation a true home and cook real meals. I’m dreaming of that fresh pasta, ripe tomatoes, and memorable wine as I write this! If you’re planning a trip here, give yourself at least 14 days to really explore and avoid feeling rushed. Italy is meant to be savoured slowly, like a good espresso or glass of vino.

 

I’d love to hear about your travel experiences and where you’re headed next on my Wealth with Julie Instagram page. Before you head off onto your planning journey, remember that websites like SkyScanner, Kiwi, Expedia, Kayak are your best friends when searching for deals on your next adventure – you really can find everything, from accommodation bundles to cheaper flights. Set your flight alerts and get planning – we want to get those big-ticket items at reduced pricing, if possible!

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