The Joys of Traveling During Shoulder Season

Many people time their vacations to coincide with the most favorable weather conditions or with long holiday weekends. Who doesn’t want pleasantly warm, sunny days and to take advantage of the extra time off over Labor Day and Memorial Day? Unfortunately, traveling during peak seasons carries a price. Airlines and hotels charge premium rates, and top sights and restaurants can become frustratingly overcrowded with tourists.

For many of us, avoiding the crowds is worth packing a jacket or umbrella (usually a good idea in any case), especially when cultural experiences are the focus. Whether or not you have a reserved entry, the world’s great art museums are far more enjoyable when you’re not fighting your way through tour groups to see the paintings. And we would much rather stand atop the Eiffel Tower while wearing a stylish scarf than wait in an interminable line underneath it while wearing shorts. Sometimes in the off-season, you might even discover you have a major attraction entirely to yourself. One travel consultant we spoke to related how on a sunny and pleasantly cool January day in Sicily, she sat entirely alone in Taormina’s ancient Greco-Roman amphitheater and watched the sun set behind Mount Etna. Breathtaking experiences like that you never forget.

Here are some tips to get the most out of a vacation outside the busiest season: When planning any journey (especially one that’s in the off-season), if there is an attraction or restaurant you are determined to visit, double-check that it will be open during your planned stay.

Consult the climate information in the Harper Collection.

In addition to weather averages, which tell you what to expect during a given month, Mr. Harper usually offers advice about which months offer the best combination of pleasant temperatures and smaller crowds.

In many cases, an area’s reputation for bad weather is overblown.

Chicago’s winters are no worse than Boston’s or New York’s. Parts of Canada are warm enough for world-class wine regions to develop. And though a rainy season may sound daunting, check the details. In many cases, rainy seasons manifest themselves as short afternoon downpours with plenty of sun before and after. Case in point: Our digital editor just returned from a June stay at Anantara in Chiang Rai, Thailand, and she only saw one day of (very light) rain.

Try something new.

The Travel Office receives countless calls from people who want to travel to beach resorts over the winter holidays, which inevitably book up well in advance. Instead, why not take advantage of Europe’s festive Christmas markets, the charming colonial cities of Mexico or the desert resorts in America’s Southwest?

Even cruises have shoulder-season itineraries, which tend to be less crowded and less expensive.

Cruising the Mediterranean in early May or mid-October is just as delightful – if not more so – than cruising it in July or August.

The off-season can be an ideal time for shopping.

In many North American and European cities, the best sales take place in January and again in July and August.

All that said, sometimes traveling in the height of the season is unavoidable.

Taking an Alaskan cruise, for example, can only be accomplished in the summer or early fall, and Antarctica can only be tackled during the northern hemisphere’s winter.