Where Should You Travel Next? Sometimes the Season Has the Answer

There are two ways to plan a vacation.

1. You can decide where you want to go and then look at the calendar.
2. Or you can look at the calendar first and ask a completely different question: Where is especially good at this time of year?

I often think the second approach leads to some of the most interesting trips.

Timing affects far more than the temperature. It can determine what you’ll eat, what you’ll see, how crowded a destination feels, whether you’ll spend your days outside or enjoy a slow lunch, and sometimes whether you’ll experience something that happens only for a few weeks each year.

A place you’ve visited before can even feel completely different in another season. So, instead of starting with a bucket list, let’s start with the calendar.

Fall: Travel for Food, Wine, and a Change of Pace

Much of Europe settles into a different rhythm after the busy summer months. Temperatures become more comfortable for walking and exploring, and in many places the season revolves around food and wine.

Fall may be my favorite season for travelers who aren’t tied to a school calendar.

Northern Italy is a perfect example.

Piedmont in the fall is for travelers who would happily plan an afternoon around a bottle of Barolo and dinner around whatever is in season. This is harvest time in the Langhe wine country, and autumn also brings white truffle season to Alba.

A good trip here isn’t about racing through a list of sights. Spend time in Turin, move into the countryside, visit wine producers, settle in for long lunches and, if you’re interested, head into the woods with a truffle hunter and dog.

Germany offers an entirely different version of fall.

Munich’s Oktoberfest gets most of the attention in September and early October, but I’d look beyond Munich, too. Wine regions along the Rhine and Mosel are particularly appealing during harvest season. Later in November, the mood begins shifting again as Christmas markets begin.

That’s one of the things I like about fall travel. The experience can change considerably in the space of a few weeks.

Consider fall if: food and wine are an important part of your vacations, you enjoy exploring cities on foot, or you’d rather travel when summer vacation crowds have begun to ease.

Winter: Go Somewhere Winter Doesn’t Feel Like Winter

By January, I generally have very little interest in convincing anyone that cold weather is fun.

This is when warmer destinations start sounding particularly good.

Costa Rica works beautifully for travelers who want sunshine without spending an entire vacation in a lounge chair. The Pacific side enters its drier season around mid-December, making winter a popular time for Guanacaste and other Pacific destinations.

But I wouldn’t fly all the way to Costa Rica just to see the beach.

Combine a few relaxing days on the coast with time near Arenal or Monteverde. One day might involve hiking or wildlife, another hot springs, and another doing absolutely nothing more strenuous than deciding where to have dinner. That combination makes Costa Rica especially good for families and multigenerational vacations because everyone doesn’t have to want exactly the same thing from the trip.

Southeast Asia offers another compelling winter possibility.

Thailand, Cambodia, Laos and neighboring countries can work particularly well during portions of the North American winter, although weather patterns vary considerably by country and region. A thoughtfully planned itinerary might pair temples and cultural experiences with several days at the beach.

This is also where good trip planning is essential. “Southeast Asia” isn’t one climate, and trying to see too much in one vacation can quickly turn a wonderful trip into an extended tour of airports.

I’d rather choose fewer places and experience them properly.

Consider winter if: you are craving warmth, want a longer international trip, or like combining active sightseeing with several days of genuine downtime.

Spring: Europe Before Summer Takes Over

There is a particular pleasure in visiting Europe in spring.

Cafés begin spilling outside again. Gardens are blooming. Days get longer. And in many destinations, you can comfortably spend hours walking without feeling as though you’ve accidentally signed up for a marathon.

Southern Spain is one place I’d put high on the list.

Seville, Córdoba and Granada combine beautifully into an Andalusia itinerary, especially for travelers interested in history, architecture, food and culture. Spring also brings major religious and cultural celebrations, so exact dates matter. Depending on your personality, being there during a major festival may be the highlight of the trip or precisely what you’d prefer to avoid.

Both are perfectly reasonable.

That’s an important part of choosing when to travel. The “best” time isn’t always the same for everyone.

Spring is also worth considering for other parts of Europe where summer demand becomes intense. Italy, France, Portugal and Greece can all offer appealing spring opportunities depending on the region and the experience you’re after.

You may trade guaranteed beach weather for cooler temperatures, but you can gain a much more comfortable trip for sightseeing.

Consider spring if: Europe is calling, you prefer comfortable sightseeing weather, or you’d like to experience cultural events that don’t happen during the traditional summer vacation season.

Summer: Head North, Toward the Water, or Into the Mountains

Summer is when choosing the right destination becomes particularly important.

Yes, you can visit almost anywhere in July. That doesn’t necessarily mean you should.

This is the time of year I start looking north.

Ireland is a great example. Long summer days give you much more time to explore, which matters when you’re driving the west coast and keep wanting to stop. And you will want to stop.

A western Ireland itinerary might include Connemara, Galway, the Aran Islands and the Wild Atlantic Way, with country-house hotels and small towns mixed into the journey. If your dates align, Galway’s International Arts Festival can add another reason to spend time in the city.

Scandinavia is another summer possibility worth considering, particularly for travelers who prefer mild temperatures and long daylight hours to Mediterranean heat. And then there are the mountains.

The Alps aren’t only for ski vacations. Summer opens up an entirely different experience in Switzerland, Austria, northern Italy and France, with hiking, lakes, scenic rail journeys and mountain resorts that feel completely different without snow.

For travelers who have already done several classic European summer trips, this can be a refreshing change.

Consider summer if: you love long days, scenic drives, time outdoors and destinations where summer actually improves the experience rather than simply increasing the temperature.

The Best Time to Go Is Really About You

Whenever someone asks me, “What’s the best time to visit?” my answer usually begins with another question:

What do you want the trip to feel like?

• Do you want warm weather or cool mornings?
• Are you willing to deal with crowds to attend a festival you’ve always wanted to experience?
• Would you rather be there during harvest season than swimming season?
• Is this a trip built around food, wildlife, hiking, history, beaches or simply slowing down?

Those answers matter more than a generic list of “best months.”

They also explain why I don’t think of destinations as having one perfect season. The same place can offer several completely different vacations depending on when you arrive. So if you’re staring at your calendar wondering where your next vacation should take you, try reversing the usual planning process.

Don’t choose the destination first.

Choose the season, decide how you’d like to spend your days, and see where that leads. You may find yourself considering somewhere that wasn’t even on your list.

And those are often the trips worth talking about.