Top 3 Questions Our Advisors Hear Every September
September is a natural time for reflection and planning. As the energy of summer gives way to the rhythm of fall, many travellers begin to think ahead: where to go next, how to make the most of upcoming seasons, and how to travel in ways that feel more meaningful and connected.
Here are the top three questions our advisors hear every September:
1. “When should I book my holiday travel?”
Book early, not just for availability — but to travel more intentionally. Planning ahead gives us the time and space to choose experiences that align with our values, reduce last-minute emissions-heavy decisions (like unnecessary flights), and ensure we’re supporting local communities who rely on predictable, respectful tourism.
If you’re considering a holiday getaway, our advisors can help you find locally owned accommodations, slower-paced itineraries, and immersive experiences that give back — like small-scale winter festivals, Indigenous-led tours, or nature-based wellness escapes.
Why it matters: Early planning reduces strain on systems, supports small businesses in advance, and avoids the rush of mass tourism in high-demand destinations.
Browse Landsby’s robust list of winter getaways.
2. “Are there still good fall getaways available?”
Yes — and fall is the perfect time to travel mindfully. Autumn is a season of abundance, reflection, and connection with the land. From harvest feasts to forest walks, it invites us to slow down and appreciate local rhythms. There’s still space at many smaller resorts, farm stays, and nature retreats — especially those that are working to preserve and celebrate their local ecosystems.
Ask us about experiences that highlight seasonality: orchard tours, foraging walks, harvest dinners, or community events. Travelling during the quieter fall months also helps spread economic benefits across the shoulder season — making your trip a more sustainable one.
Try this: Choose a place you can drive or train to, stay longer, and spend time learning from locals rather than ticking off must-see lists.
Our advisors are happy to help plan a meaningful last-minute getaway. Get started by looking through Landsby’s list of fall getaways.
3. “Is it too early to plan for summer next year?”
Now is the perfect time to dream and to plan with purpose. Thinking ahead allows us to build travel into the natural flow of life, rather than reacting to promotions or trends. If there’s a place that’s captured your imagination — a family-run lodge, an off-grid cabin, a community-led cultural experience — early planning helps ensure your visit is welcome, intentional, and truly meaningful. This lead time is especially important if you’re looking for us to help you craft a custom, tailor-made itinerary.
We’re happy to help you build relationships with hosts, understand the rhythms of the land and seasons, and co-create an experience that supports the place you’re visiting.
Consider this: What kind of legacy do you want your travel to leave? Let’s plan a summer that honours that intention.
Take a look at Landsby’s lineup of immersive summer getaways.
Travel That Gives Back
At Landsby, we believe travel can be a force for good — when it’s rooted in connection, care, and respect. Whether you’re planning for fall, winter, or beyond, our team is here to help you travel thoughtfully and meaningfully across Canada. Take a look at Landsby’s community initiatives to see how we are trying to support a strong regenerative travel community in Canada.
Let’s create something regenerative together.