When is the best time to book your flight or reserve your hotel? Should you reserve a day trip before you leave? There are several ways to approach the question of when.

Are you given a specific time to take your vacation? Most employers have some sort of vacationing scheduling. My partner has to book his vacation every fall for the following year. Once the two or three week vacation period has been selected and approved, it is very difficult to change it. Other work places might be more flexible, but you have to plan your vacation within their rules.
I prefer to book holidays on the shoulder seasons. July and August are busy months for countries in the northern hemisphere, so why not visit in April, May, September or October? The tropics are busy during the end of December through to the end of March so why not look at November or April? If you check the prices for travel to the Caribbean, there’s a sweet spot in the first week of January. Most people don’t like to travel right after the Holiday season, so the prices drop. Who in Canada doesn’t want some sun in January?
Who, in Canada, would not enjoy a little sun in the first half of January?
Before you book your vacation, be sure to check the various airlines that fly to your destination. Belize is our favourite destination, but direct flights from Toronto to Belize City are only available from November until April. Be careful here. If a direct flight is desirable, consider NOT planning your vacation in the last month of service. For instance, the flight to Belize is fairly inexpensive in April . . . but the return flight is the highest rate. Why? Because ever Toronto bound Canadian will have to return home by the end of April.
You must be thorough and creative in your research. If the airline does not travel to the destination you desire, you may have to use a combination of methods. Pick a large airport that’s closest. If you wanted to fly to Belize off season, there are flights to Cancun, Mexico. From Cancun, there is a four-hour bus ride to Chetumal, Quintana Roo, Mexico. There is a water taxi from Chetumal to Belize City. You could also fly to Huston, Texas or Miami, Florida and catch a connecting flight to Belize City. Some plane travel search engines will even take you to Panama City in Central America for a connecting flight.
There is always a way to get there. But is it what you want?

If you don’t like buses, connecting flights or complicated travel arrangements please plan carefully and avoid these situations. We travel to Belize towards the end of November. This is in the shoulder season, but well past the rains of October. Most people don’t travel to the tropics in November, so there is a reduction in the price of the flight. If your vacation time is fixed and time restricted, you probably will not want connecting flights or buses or trains. Think carefully about what you want from your travel experience and plan accordingly.
