Traveling During Hurricane Season – Amateur Traveler
If I ask if you would travel during hurricane season, I suspect that many travelers would think that sounds crazy. Still, every tourist who visits Orlando, the Caribbean, or even New York City in the summer has done just that.
Many of us can recall Hurricane Katrina striking New Orleans or one of the numerous storms, such as Helene, Milton, or Ian, that have hit Florida since 2022. But, we should not forget Hurricane Sandy, which pounded New York City, or Helene, which caused catastrophic flooding in Asheville, North Carolina, which is more than 200 miles inland.
What Hurricane Season Means for Travelers
- When it Happens:
- Atlantic & Caribbean: June 1 – November 30 (peaking August–October)
- Eastern Pacific (Mexico/Central America): May 15 – November 30
- South Pacific & Indian Ocean: November – April
- Where to Watch Closely:
- Caribbean islands in the main hurricane belt (Dominican Republic, Puerto Rico, Jamaica).
- U.S. Gulf Coast and southeastern states.
- Pacific coasts of Mexico and Central America.
- Lower-Risk Choices:
- Southern Caribbean (Aruba, Bonaire, Curaçao, Trinidad & Tobago).
- Hawaii (rarely hit directly).
- The Mediterranean or Northern Europe as tropical alternatives.
Riding Out a Storm in Old San Juan
When I think about hurricane season travel, my mind goes back to historic Old San Juan, Puerto Rico. I had booked a room in Hotel El Convento, a former convent that had been converted into a hotel, right across from the cathedral. The plan was to work for a week from San Juan.
That week, though, it wasn’t history I was thinking about. It was Hurricane Fiona.
Everyone on the island had been watching the storm track. Fiona was predicted to clip the southwest corner of Puerto Rico, but forecasts are more art than certainty when it comes to hurricanes. I could have cancelled my trip, but it looked like I would be safe in Old San Juan, so I arrived on one of the last flights before the hurricane passed through.
When the storm arrived, the city’s location meant that in Old San Juan, it was a tropical storm rather than a hurricane. We avoided the catastrophic flooding seen in other regions. But Puerto Rico’s fragile power grid didn’t hold. The entire island went dark.
Here’s where Old San Juan’s infrastructure showed its strength. One by one, the hum of generators filled the air. My hotel kept the lights on, the air conditioning running, and even Wi-Fi connected. But while the hotel had said their restaurants would stay open, they closed for a day, as did every store and restaurant in the area. I should have stocked up on food, but trusting the hotel’s promise, I had not. I was left with the snacks I had in my backpack and the complimentary bottle of wine from the hotel.
In the rest of Puerto Rico, many residents endured days in sweltering heat without electricity or reliable water. Old San Juan wasn’t untouched but the area largely bounced back the next day as stores and many restaurants reopened.
Lessons from Fiona: What I Learned
1. Change Your Plans
I always have travel insurance, so I could have just cancelled my trip, and I would not have lost any money. As it was, I had to change my plans as the accommodation I was planning on staying at later in the week by the beach was open, but all the nearby restaurants and stores stayed closed for a week.
2. Choose Your Accommodations Carefully
Staying in Old San Juan meant I had access to hotels with backup power. Had I been elsewhere on the island, my experience could have been far more difficult. Major tourist areas might have the money to recover more quickly.
3. Expect Power and Transport Disruptions
Even though the hurricane didn’t hit directly, my travel plans shifted. You will need to stay flexible.
4. Travel Insurance is Essential
Many policies exclude “named storms” once they’re forecast, so buy insurance before a hurricane is on the radar. Look for coverage that includes trip interruptions, cancellations, and extra hotel nights. Check out Faye’s hurricane season travel guide.
4. Pack Like Power Might Fail
A flashlight, portable chargers, and a bit of cash will come in handy. ATMs don’t work without power, and neither do credit card machines. Also, I wish I had more snacks than 2 granola bars and a package of almonds.
5. Stay Flexible
Instead of exploring the island, I spent more time in Old San Juan, walking the blue cobblestone streets, talking with locals, and getting to know the city more deeply. This was not the time to explore the rest of the island. A hurricane won’t necessarily cancel your trip, but it may reshape it into something unexpected.
What To Do If You’re Caught in a Storm
- Before the Storm: Stock up on essentials, follow local news, and take evacuation orders seriously.
- During the Storm: Stay indoors and away from windows. Don’t risk venturing out until authorities say it’s safe.
- Afterwards: Transportation may be a mess. Be patient — you’re a visitor, while locals may be recovering from significant losses.
Alternatives Beyond the Hurricane Belt
If you’d rather avoid the risk entirely but still want sunshine, consider:
- Mediterranean (summer–fall): Greece, Italy, Croatia.
- South America: Peru, Argentina, Chile.
- Pacific Northwest & New England: Beautiful, storm-free autumns.
Final Thoughts
Traveling during hurricane season is a calculated risk, but not one that should scare you away. Sometimes airfares are lower, hotels are more affordable, and crowds are thinner. If you prepare, stay flexible, and choose your destinations carefully, the rewards often outweigh the risks.
My week in Old San Juan during Hurricane Fiona taught me that hurricanes don’t always look like the news headlines. Sometimes they mean candlelit dinners in colonial courtyards, streets alive with the buzz of generators, and conversations with strangers who become companions because the storm kept you all in one place. It was a reminder that travel isn’t about controlling the experience — it’s about adapting to it.
