Monday-Morning Moving: Great Shoulder-Season Travel Deals

A peaceful Mboyti Beach in the late-afternoon sun.
Whether you’re looking for the beach or the mountains, there’s a shoulder-season deal for you. (Ericka Hamburg photo.)

The best time to travel for a long time is … today. Or tomorrow. But not too many more days beyond tomorrow.

Here’s why: We are in shoulder season, that delightful time described by Sharyn Alden on Friday when the seasons are changing from crummy to delightful yet the prices for many destinations remain low.

Obviously, this is a generalization, and as Sharyn pointed out, not every destination has a shoulder season that runs at the same time – and some destinations claim to not have a shoulder season at all. (Though, as she points out, there’s no telling what shoulder-season deals you might get if you ask.)

Unfortunately, this particular installment of shoulder seasons is going to be short-lived, as Spring Break is just around the corner, and many of the destinations that are cheap tomorrow are going to be significantly more expensive a week or two from now.

Take San Diego. We’ve already pointed out that San Diego is a great Spring Break destination – though it’s every bit as attractive from a shoulder-season standpoint. What; do you think the mean temperature is going to increase five degrees in the next two weeks? It’s San Diego; it’s always 85 and sunny. Flights are not super-cheap – the best we could find for later this week is $345 from Chicago, on American (or about five times as much as it would cost you to fly from Providence to Europe) – but there are some great Airbnb options available, including some near the beach for around $100 a night. Hit the beach, hit the zoo, lounge around in Balboa Park, catch a little of the World Baseball Championship, and you’ve got a great shoulder-season vacation.

Another option that requires you to play your cards right is Austin, Texas. Yesterday my son asked me my favorite place in the U.S. to just have fun – and that’s a really tough question, because fun has so many dimensions. I thought a long time, and finally said, “Austin.”

Here’s why: Austin has the food, the music, the scene, the recreation, and the climate. It also has the mega-conference/festival/happening, SXSW, running through March 19. SXSW is an expensive proposition; however, go after that and everything changes: Airfares drop (the lowest we saw was $291, from Chicago), lodging costs fall (there are some amazing Airbnbs all around the area), and Austin is still the same ol’ happening place.

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Maybe you don’t want to ski on this, but Anchorage? Count us in.

Is skiing more of your scene? Despite having just returned from Salt Lake City, where the mountains beckon all around and even the license plates read, “Greatest Snow On Earth,” we are more partial to northern variants. Whistler is always a great option, though airfares are so-so (the best we could find for late March was $504, mostly on American), but if you’re looking for a real shoulder-season getaway, how about Anchorage? It’s not that much more ($575 versus $504, per Google Flights), but lodging in Anchorage or Girdwood, closer to the slopes, is reasonable and even includes a vintage Airstream. You’ll probably never have a better chance to cross off one big destination from your bucket list – and before summer, yet.

Finally, and always, there’s Europe. The string of ridiculous fares continues unabated – the most recent jaw-dropper was $386 from Denver to Copenhagen (or about as much as it costs to fly from Chicago to San Diego) – crowds are relatively sparse, the exchange rate favors the Americans, and lodgings are plentiful. There are hotel deals to be had regardless of the number of stars you’re seeking, and Airbnbs even include a starboard cabin on a two-masted schooner.

Amazing, huh? That’s the shoulder season for you. Pick a destination and go – and remember the travel insurance from BHTP. We can cover everything from Austin to Zanzibar with cool stuff like quick claim payments and pic-and-a-click claim filings. It’s the perfect complement to wherever the shoulder season takes you.

Author: Kit Kiefer

As content engineer for Berkshire Hathaway Travel Protection, I have one of the world's great jobs. Not only do I get to write about travel, but I get to edit the work of fantastically talented contributors from around the world. Plus I get all the maple syrup I can drink.