By Molly Chester, Certified Travel Advisor and Scarborough resident
When it’s 90 degrees and your AC is struggling, winter travel might be the last thing on your mind – but if you want the best deal, now is the time to start planning. Knowing when to plan and book your trip can make a big difference in what is available, how much it costs, and how smoothly the planning process goes. While there is no one-size-fits-all answer, having a general timeline in mind – especially if you are planning around Scarborough’s school breaks – can help you get the best value and the most options.
For domestic trips, booking flights and hotels around 5 to 7 months in advance tends to offer the best mix of availability and pricing. For international travel, especially to popular destinations in Europe or the tropics, it’s often wise to start looking 8 to 10 months ahead. However, if you’re planning to travel during a school vacation or over a holiday period, the earlier the better! These dates tend to book up much faster than average, so planning ahead a full year or more is often the best bet. That’s not to say that fabulous destinations and deals won’t be available with a shorter lead time (for example, right now is a wonderful time to call yours-truly about travel this festive season!), but flexibility is the name of the game as availability tightens.
Speaking of holiday travel, Scarborough’s school calendar makes this year’s December break a golden opportunity! With more than two full weeks off – December 20 to January 4 – families can plan a truly special trip. You could even enjoy the magic of Christmas at home, then fly out on the 26th or 27th for a full week (or more) of sunshine, snow adventures, or city exploring, and still have a day to settle back in before school starts on January 5. This long of a school break is super rare, and worth planning around.
February break (February 14 to 22, 2026) and April break (April 17 to 26, 2026) are also great windows for family travel, especially if you’re hoping to escape the cold or get out on the slopes for ski week. Even though they may feel really far in the future, right now (late summer) is a terrific time to start making these bookings, as airline schedules are all released and lodging availability is wide open, so lots of options and early-booking discounts!
If you’re thinking about a trip for one of these windows – or looking ahead to next summer or non-school-related travel – I would always love to help. I am Scarborough-based, and have worldwide experience, with a specialty in travel to Europe and the Caribbean. I offer everything from hotel bookings with perks – a free service! – to fully customized itineraries, and I’m here to make the planning process smoother, more fun, and more rewarding, school break or otherwise!
Let’s figure out where to next!
Molly Chester lives in Scarborough and plans trips to destinations near and far as the founder of MChesterTravel.com.
