Vacations are something we never seem to get enough of. So, it might please you to know that you can more than double your vacation days in 2027 by planning around stat holidays and long weekends.
What are you waiting for? Get out your calendars! We’re sharing how to maximize your vacation days with memorable family trips, romantic getaways, beach vacations and more.
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February: The Family Day weekend
Book 1 day off for a 4-day vacation
If you live and work in Ontario, British Columbia, Alberta, New Brunswick, Saskatchewan, Manitoba*, Nova Scotia* or Prince Edward Island*, you can escape for a mini vacation right when winter is at its most bitter. Tack on a Friday to the Family Day long weekend and book a cheap flight to Miami, Los Angeles, Phoenix or Las Vegas for some much-needed heat.
Book off this date:
- Friday, February 12
Vacation from:
- Friday, February 12 – Monday, February 15
*Note: Manitoba, Nova Scotia and Prince Edward Island don’t celebrate Family Day, but do have other stat holidays on the third Monday of February: Louis Riel Day, Nova Scotia Heritage Day and Islander Day, respectively.
April: The Easter escape
Book 5 days off for a 10-day vacation
Hey, couples! Skip the madness of March break and opt for an extended Easter escape instead. An April trip to the Caribbean offers shoulder-season prices, fewer crowds and ever-so-slightly cooler weather (and by that we mean a comfortable 26–30 degrees instead of 30+ degrees). Since hurricane season won’t start for another few months, this really is one of the best times to go.
Book off these dates:
- Monday, March 29
- Tuesday, March 30
- Wednesday, March 31
- Thursday, April 1
- Friday, April 2
Vacation from:
- Friday, March 26 – Sunday, April 4
May: The Victoria Day getaway
Book 4 days off for a 9-day vacation
Spring is officially sprung, and warmer days are right around the corner. Now’s your chance to get a jump on popular Canadian destinations before the tourism season kicks into full gear. An extended Victoria Day getaway is the perfect time to catch a flight to Vancouver, Montreal, Toronto, Calgary or Halifax, and explore the True North however you please.
Book off these dates:
- Tuesday, May 25
- Wednesday, May 26
- Thursday, May 27
- Friday, May 28
Vacation from:
- Saturday, May 22 – Sunday, May 30
July: The big summer trip
Book 9 days off for a 16-day vacation
It’s the best time of year for a family vacation. Celebrate the end of the school year and the beginning of summer over the Canada Day stat — and beyond! If you’ve been saving up your vacation time for something extra special, this is it. Treat yourselves to a two-week getaway in Europe, New Zealand, or Costa Rica.
Book off these dates:
- Monday, June 28
- Tuesday, June 29
- Wednesday, June 30
- Friday, July 2
- Monday, July 5
- Tuesday, July 6
- Wednesday, July 7
- Thursday, July 8
- Friday, July 9
Vacation from:
- Saturday, June 26 – Sunday, July 11
September: The Labour Day break
Book 1 day off for a 4-day vacation
A quick break from the routine is often all you need. Take care of that travel craving with an extended Labour Day weekend to close out the summer. It’s the perfect time for one more fishing trip, hiking spree, golf tournament, concert or food festival. With any luck, you can catch a back-to-school flight deal (aka you save on cash and paid time off).
Book of this date:
- Tuesday, September 7
Vacation from:
- Saturday, September 4 – Tuesday, September 7
October: The Thanksgiving retreat
Book 1 day off for a 4-day vacation
Feel even more grateful over the Thanksgiving weekend with an extra day or two off! Fill up on turkey and travel memories, as it’ll be a while before the next public holiday in December. Use this opportunity to book a visit with the family you don’t usually get to see, a fun night in a Canadian capital, or some local tours that you’ve always had your eye on.
Book off this date:
- Friday, October 8
Vacation from:
- Friday, October 8 – Monday, October 11
December: The extended holiday
Book 8 days off for a 17-day vacation
Christmas falls on a Saturday this year, so we suggest you take the full week off to prepare for the festivities — and then also book a few days off the following week to recover (especially because you’ll already be observing the stat holidays on Monday and Tuesday). Since New Year’s Day is also on a Saturday, you have the perfect excuse to book an extra-long holiday. Enjoy a full 17 days of relaxation in a sunny destination, fly out to visit friends or ring in the new year in a winter wonderland. With the kids off from school, this is one of your best opportunities to book some quality family time.
Book off these dates:
- Monday, December 20
- Tuesday, December 21
- Wednesday, December 22
- Thursday, December 23
- Friday, December 24
- Wednesday, December 29
- Thursday, December 30
- Friday, December 31
Vacation from:
- Saturday, December 18 – Monday, January 3
Now that you know the best dates to book, it's worth locking them in early — both leave requests and flight prices get harder to secure the closer you get to each window. Check out our latest offers or chat with a Travel Expert to match a destination to your dates.
This blog post was originally published in December 2023. It was updated in October 2026.
FAQs
The Easter window (March 26 to April 2; five days of leave for 10 days off) and the December break (December 20 to January 3; eight days of leave for 17 days off) offer the best value in 2027.
Key 2027 dates include Family Day (February 15), Good Friday (March 26), Victoria Day (May 24), Canada Day (July 1), Labour Day (September 6), Thanksgiving (October 11), Christmas Day (December 25) and Boxing Day (December 26).
Booking five days off — Monday, March 29 through Friday, April 2 — turns the Good Friday long weekend into a 10-day vacation, running from Friday, March 26 through Sunday, April 4.
Yes. Thanksgiving falls on Monday, October 11, 2027. Enjoy the standard, three-day long weekend or book the Friday off as well for a four-day break.
The Easter window in late March and early April has one of the best ratios of leave days to time off, turning five vacation days into 10 days off. December is also a good choice, as the Christmas, Boxing Day and New Year’s Day fall on weekends in 2027 — giving you the opportunity to turn eight days of leave into a 17-day holiday.