Ask the agent – winter getaways for happy holidays Clara Power and Annalise Roberts
By Ann Ruppenstein /  December 12, 2024

Ask the agent – winter getaways for happy holidays

Where are your clients going this winter? Is it hot escapes, embracing the holiday season or cool getaways?

CP: When the winter is here, my clients are all asking for hot destinations. Whether it’s a beach holiday, theme park or cruise, they are asking for hot destinations to escape the cold and have something to look forward to. With our long winters, many want something warm to look forward to.   

AR: This winter my clients are choosing sunny all-inclusive getaways in the Caribbean. Whether it’s a romantic retreat for couples or a family-friendly resort with waterparks, the common theme is spending quality time with loved ones and making the most of their time away. They’re looking for resorts that allow them to truly unwind while also enjoying some fun together.

What is your biggest piece of advice for holiday travel? 

CP: Pack your patience. Holiday travel is busy, things can go wrong and patience is key. Many things are out of our control including weather, delays and crowds. If things go off the rails, it’s important not to let it impact the whole trip, take it in stride and look for the positives in the situation. 

AR: My top holiday travel tip is to ‘pack your patience’ and to expect the unexpected. The holiday season can be hectic with crowded airports, potential weather delays, and resorts at full capacity. It’s important to stay flexible and keep a positive attitude when things don’t go as planned. The key to enjoying holiday travel is remaining calm and remembering that a little patience can go a long way.

What’s popular for clients who want to experience Christmas markets? Do most look for a river cruise or a land tour? 

CP: European Christmas Markets keep gaining popularity and the majority of my clients request river cruises as it allows them to see multiple markets in a short period of time. Clients look forward to being able to collect unique gifts, décor and get into the Christmas Spirit… and of course all the special holiday treats that aren’t available at other times of the year.       

AR: For clients looking to experience Christmas markets, river cruising has been the most popular choice by far. They offer a stress-free way to explore some of Europe’s most iconic markets. One of the biggest draws is the convenience — you unpack once, and the boat brings you to multiple charming cities, so you can enjoy the holiday magic without the hassle of constantly moving from place to place. In addition, river cruises often provide knowledgeable tour guides, making it easy for clients to learn about each market’s history and traditions. It’s a perfect blend of adventure, comfort, and Christmas. 

Is the winter break a popular time to get out or do your clients tend to stick closer to home during the holidays?

CP: Multi-generational trips are becoming more and more popular for the holiday season.  Groups of 10, 20, 30 are becoming the norm. When family members can be spread across the country (or the world sometimes), families are finding it convenient to meet in a tropical destination where they can enjoy time together in a new location for longer than a day or two.  Also, as it’s a school break it is easier to travel without worrying that the kids will fall behind in class. 

AR: For many of my clients, winter break is the perfect opportunity to escape the cold Canadian winter and soak up some warm sunshine. The harsh weather at home often makes the idea of a warm getaway even more appealing. A lot of clients mention that a vacation feels more “worth it” when it’s snowing back home. They are eager to trade in their base layers for bathing suits and enjoy some time in the sun. 

Looking ahead to 2025, what is trending?

CP: Europe is still trending for 2025 but many are asking for destinations outside of the Mediterranean including Scandinavian countries and Iceland. Central Europe river cruises are continuing to be popular, even among families who want to try something different. Japan is still gaining popularity as well as Thailand and Vietnam. Since the change in Visa requirements for Canadians to Egypt, I’ve also seen an uptake in interest in Egypt again.

AR: I’m seeing an ongoing trend that’s stronger than ever – groups, groups, and more groups. Whether it’s multi-generational trips, getaways with friends, bachelor and bachelorette parties, or multi-couple vacations, it seems like almost every client I’m working with is planning a group trip. There’s something special about making memories together on vacation, and this demand for group travel feels like it is at an all-time high.

How far in advance do most of your clients book?

CP: Although there are some last-minute bookings, the majority of my clients book four-six months in advance, but sometimes as much as 12-24 months especially for cruising and more expensive trips. Clients prepare to plan with ease and without the last minute rush so they can get what they want without having to settle.

AR: In the past, most of my clients would typically book four-to-six months in advance at most. However, I’ve made a strong effort to emphasize that if clients are looking for those unique resorts, bucket list itineraries, and in particular any holiday travel, it’s best to secure your space as early as possible. While waiting for last-minute deals might seem appealing, the risk is that a dream vacation could sell out before you get a chance to book it. People often forget that even though the world feels vast, it’s still a relatively small place when it comes to popular destinations and travel seasons, and others are likely eyeing the same trips. I always encourage my clients to plan ahead to ensure they get exactly what they want, rather than waiting and risking disappointment.

Do you have anything else to add?

AR: One of the most rewarding parts of my job is helping clients create holiday memories! A meaningful trip can make the season feel extra special and I love being part of that experience.





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