• Kimberly M.

4 Reasons Why You Should Travel During Rainy Season

Updated: May 16


Hardly a cloud in the sky during our rainy season trip to Costa Rica.

I usually try to take a vacation every year around my birthday. It’s my way of treating myself and celebrating another year of life in a new and beautiful location. However, considering my birthday takes place in mid-September, it means that on more than one occasion, I’ve had to gamble with an active hurricane season while planning and taking my trips. It’s absolutely a risk, but as a single mother and budget traveler, it’s a risk worth taking.


That being said, here are a few reasons why I say “Bring it” when it comes to travel during hurricane season or rainy season:


1. The prices are much lower

Hurricane season travel means enjoying highly discounted rates at otherwise expensive properties. Photo taken at La Concha Resort in San Juan, Puerto Rico.

Instead of focusing all of the “what if’s” of traveling during the hurricane or rainy season, I look at it as an opportunity to save on a vacation and get the best deals. Because hurricane season is considered “off season” for many Caribbean destinations, airlines and hotels act accordingly and significantly lower their prices. I’ve been able to enjoy accommodations, flights, and tours for 30%-50% less than I would during the typical high season. Saved money = more money for additional vacations!


Many times, extras are thrown in for free, such as day tours, spa discounts, or casino credits (if you’re into that kind of thing). During a late fall stay in Puerto Rico, the hotel I booked offered a day trip to the centrally-located town of Orocovis where I enjoyed a full day of ziplining at Toro Verde Adventure Park, including transportation and lunch. Not bad, considering the price of my stay alone was already less than $100/night.


2. It's less crowded

To me, there's nothing worse than a "vacation" where I have to fight to find the perfect spot at the beach or pool, wait in lines everywhere, deal with overbooked and sold out restaurants or tours, and constantly deal with rude tourists everywhere I go. By traveling during the “off season”, I don't have to worry about any of that. During a rainy season trip to Costa Rica, my son and I had an entire beach to ourselves during the morning that we were there. I’m pretty sure we would not have had the same opportunity if we had traveled during the high season.

Nobody on the beach but us and the waves from the ocean.

You know what else happens when it’s less crowded? The customer service gets better. Since the staff doesn’t have to juggle servicing me with hundreds of other tourists who may not have as much patience, I find that everyone is much friendlier, takes their time helping me, and are much more willing to cater to my needs.


3. It Is Much More Beautiful

One of the best parts about traveling during the rainy season is that the surroundings are lush and at their greenest. While days can be hot and humid, the rain cools things down and makes it the perfect climate to enjoy the outdoors.

A beautiful rainbow appears over El Yunque Rainforest in Luquillo, Puerto Rico.

What many don’t know is that just because it’s called “rainy season” doesn’t mean being stuck inside watching the rain pour down all day long. Most of the time it simply means that there won’t be 100% sun all day, and that there may be the presence of a rain shower/storm or two, usually in the late afternoon or evening after having had plenty of time to enjoy the day. During our trip to Costa Rica, we were stuck inside due to rain only on our very first day, and even that wasn’t until late in the day. After that, we only experienced rain in the evenings after we had turned in for the night. There were a couple of days where we didn’t get any rain at all!


4. Trips can always be rescheduled

Although there is that chance that my trip very well may be impacted by a hurricane, I try not to worry about it. Between closely following weather reports, trip insurance, and alternatives that are usually offered by airlines in the above cases, I know that I’ll be taken care of.


In 2012, I booked a one week trip to Puerto Rico at the end of October/early November. Unfortunately, my departure date fell on the same day that Hurricane Sandy was scheduled to hit the Washington, DC area. JetBlue gave me the option to change my departure date at no charge...so I did. I booked my departure date for a day sooner, allowing me to enjoy an additional day of vacation. Since the hotel rates were already cut in half during that time of year, the cost of my extra day was minimal. Similarly, when Hurricanes Irma and Maria hit Puerto Rico two months before a scheduled trip there, JetBlue happily refunded my flight in full, allowing me to rebook to another Caribbean destination without losing a dime.


So, while everyone else waits for the “safest”, yet busiest and more expensive times of year to travel, I’m more than happy taking the risk of traveling during the least popular times. At least I know that I’ll have a worthwhile and much more more enjoyable experience!

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