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The Best Times to Visit Europe, Alaska & the Caribbean
- Christine Hardenberger
- 20 hours ago
- 2 min read
One of the questions I get asked all the time is, "When is the best time to go to the Caribbean/Alaska/Italy, etc?"
My answer is always the same: shoulder season.
What is shoulder season? Shoulder season is the two or three months on either side of an area's peak season.
Peak season comes with the highest prices, the biggest crowds, and the most competition for flights, hotels, excursions, and restaurant reservations.
If you're looking for the sweet spot between good weather, lower prices, and fewer crowds, some of the best travel opportunities happen just outside of peak season. Shoulder season.
So, when is shoulder season in the Caribbean, Alaska, and Europe?
Let's discuss.
The Caribbean
Most travelers immediately look at January, February, and March. The weather at home is cold so everyone wants to head to the tropics.
EVERYONE.
Instead, visit the Caribbean from mid-September to mid-November. The summer crowds have gone home, prices start to drop, and the weather is still excellent.
I know what some of you are thinking.
"But isn't that hurricane season?"
Yes, but most of the popular resort islands rarely sustain direct hits from hurricanes. Also, storms don't suddenly appear overnight so we can pivot if necessary. Many of my clients (as well as I, myself!) enjoy wonderful Caribbean vacations throughout the fall, at a fraction of peak-season pricing.
Alaska
For Alaska, I love May and September.
May offers lower prices, fewer crowds, and gorgeous snow-capped scenery. September brings beautiful fall colors and often significantly lower cruise fares than the middle of summer.
The weather is a little cooler, but not frigid. It's a trade most travelers are happy to make to enjoy a more relaxed, cost-efficient experience.
Europe
Everybody wants Europe in the summer. I think the entire world is in Rome in July. Literally.
EVERYBODY wants Europe in the summer.
If you're looking for a better value and a more relaxed experience, consider April, early May, late September, or October. You'll find lower prices, shorter lines, easier restaurant reservations, and far fewer crowds than you'll see during the peak summer months.
In short, every destination has a sweet spot. The trick is knowing where to find it.
If you're considering Europe, Alaska, or the Caribbean, let's talk. I'd be happy to help you find the right balance between weather, crowds, and price so you can get the most value from your vacation.
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