I’m a Travel Agent: 3 Times I Always Travel To Save Money

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Frequent and infrequent travelers alike are often on the hunt for the timing “sweet spot” when it comes to planning out a travel itinerary. Whether you travel solo or with a group or family members, uncovering the best time of year to travel is critical for sticking to budgets and making memories that will last a lifetime.

What would a travel expert do? GOBankingRates spoke to two travel professionals to find out some of the best times to travel to save money. Here’s what they said.

Shoulder Seasons

Jeff Lanno has been in the travel industry for over 20 years. As the founder and CTO of Hola Weddings, a travel agency dedicated to destination weddings, Lanno personally recommends traveling during shoulder seasons. These timelines include May, early June and mid-October to November.

“These periods boast pleasant weather, reduced crowds and lower prices, often 20% to 30% cheaper,” said Lanno. 

For even more affordable flights, Lanno said to prioritize early to mid-week departures.

Right Before Major Holidays

Traveling before national holidays, like Thanksgiving and Christmas, comes with an “if” caveat. Travelers can find incredible deals, if they’re prepared to handle heavy crowds and possible flight delays or cancellations due to bad weather. 

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There are even more incentives to traveling before major holidays if you’re based outside the United States. 

Casey Halloran, co-founder and CEO at Costa Rican Luxury Vacations, personally loves to travel right before big holidays.

“I think mid-December, right before Christmas, is one of the most underrated times to travel,” said Halloran. “The crowds are significantly smaller, the prices are 25% to 30% cheaper than peak season rates and in the case of my region (Central America) the weather is fantastic.”

Last-Minute in September or October

Let’s say someone wants to book a cheap getaway in the Caribbean. When would be the best time for them to do it while saving the most money possible? 

According to Lanno, travelers would want to book last-minute in September or October. The pros of doing so include rates dropping significantly on resorts and flights and being able to find tons of unbeatable prices and last-minute deals.

Now that the secret’s out, why doesn’t everyone book trips to the Caribbean in September or October? The one condition travelers need to be aware of before booking, Lanno said, is this is the Caribbean’s hurricane season.

Some travelers may decide to roll the dice and take advantage of these deals while others wait it out. 

Lanno, who has previously lived in Mexico and the Caribbean, said hurricane season is not as scary as it sounds. He told GOBankingRates sporadic rainfall is guaranteed daily, but it tends to last anywhere from 30 minutes to a few hours at most. Most of the rainfall also happens towards the end of the day.

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Still, Lanno understands if travelers choose to err on the side of caution. Those that choose to go for it may enjoy the benefits of the idiom of fortune favoring the bold.

“It’s not for everyone, but for people that can deal with the risk, it’s certainly a money saving bargain.”

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