When’s the Best Time to Take a Vacation?

6 Tips for Busy Executives

High-ranking corporate executives have very little free time. Between the endless appointments, meetings, and business trips, it’s almost impossible to find a large enough time window to take a brief leave of absence.

Here are six opportune times when executives can get away for a vacation without jeopardizing their job security or affecting their company’s performance.

1. The Travel Offseason

Almost every travel destination has an “offseason” when bookings decrease and tourist traffic slows down. The offseason might last a few weeks or a few months depending on the location. Weather is the main determining factor, but different school schedules and cultural practices also come into play. These are the offseasons for the most popular vacation regions:

• Europe: January and February are the slowest tourist months in Europe. The weather is cold and dreary throughout most of the continent. However, tropical locations such as coastal Greece and Italy are still mild enough for travelers to enjoy.
• North America: This continent’s offseason varies by region. Coastal attractions are much less busy during the spring and fall compared to the summer and winter because of holidays and school schedules. Travel to middle North America is relatively slow except during the winter, when everyone flocks to the snowy Rocky Mountains.
• Caribbean and Central America: Travel to the Caribbean islands and Central America slows down during hurricane season, which goes from June 1 to November 30. Flight and cruise prices drop and the beaches are less busy. With careful planning and a little bit of luck, travelers can avoid the storms and enjoy a quiet tropical vacation.
• Southeast Asia: Monsoon season in Southeast Asia poses a more serious threat to travel plans. The storms are more frequent and flooding is a common occurrence. It goes from April 1 to September 30. A vacation in Japan or Thailand during this period might be cheap, but rain is almost a guarantee.

Offseason travel might be more convenient for executives, but there are a few downsides. The local town or vacation resort might not have the same amenities and activities. Hotels, beaches, restaurants, and marketplaces might be closed for the season. Be sure to choose a place with year-round attractions if you’re traveling during the offseason.

Additionally, travelers can never be 100% certain about the weather. A sudden storm could sweep through and put a damper on the whole trip. Executives must carefully weigh the pros and cons of offseason travel before booking a vacation to one of these regions.

2. Shoulder Season

If vacationing during the offseason sounds too risky, consider going during the “shoulder season” instead. This term refers to the brief transitional period between the peak travel season and the offseason. Some places have multiple shoulder seasons throughout the year, such as Europe during the early spring and late autumn.

Tourist activity won’t be overbearing, the weather won’t be such a concern, and more activities will be available. However, experienced travelers love shoulder seasons for these reasons. That means there will be lots of competition for the most sought-after hotel rooms and vacation rentals. Executives might only be able to book their desired rooms for a few days.

Don’t worry if booking an extended stay becomes an issue. A quicker vacation will still provide the same positive effects. Research demonstrates that even vacations just four nights long can provide enough recovery time for working professionals to improve their moods.

3. During Business Lulls

Executives can take a vacation during business activity lulls when their absence won’t be so detrimental. Top-level employees have enough company insights to identify these lulls well in advance, especially if they have a background in sales. Every industry has a handful of peak sales periods that occur at around the same time every year.

For example, an experienced executive of an office supply store should know that sales will spike around early August with the school year approaching. Tech companies see massive sales increases around the holiday season. High-ranking employees can book a vacation before the spike and make a timely return when business starts to pick up again.

4. After a Big Assignment

On the flip side, executives can wait until after the busy sales period or important project to take their vacation. The trip might be more difficult to schedule, but it will be more satisfying and stress-free because the difficult work is finished. Taking extensive time off after a big assignment will also be more understandable to the other employees.

One of the hardest parts of being a top-level employee is managing lofty expectations. Bosses and managers set the standard for the rest of the workforce, so taking a long vacation might hurt their reputation. Booking a trip after proving their worth on a high-stakes project will minimize the reputational damage and keep executives in good standing with the company.

5. Bank Holidays

The American bank holiday schedule provides a handful of convenient vacation opportunities throughout the year. These holidays refer to occasions when banks and other essential businesses are closed for the day. Workers also traditionally get PTO on the closest Monday to the holiday.

With everyone at home, executives can take a quick weekend vacation without feeling any guilt or missing anything important. They’ll get at least three full days of relaxation and be back at work on Tuesday without missing a beat. The only downside is that many people have this exact idea every year, so tourist attractions are usually busy on bank holiday weekends.

6. School Breaks

Executives with children in grades K-12 can take advantage of school breaks. Aside from their wide-open summer schedule, students get lengthy breaks for Christmas and New Year’s. Catholic schools also give students at least one day off for Easter. Traveling during these holidays might be difficult, but families must take advantage of their limited opportunities.

If there’s no other choice but to take a vacation during these busy holidays, try to book a less-popular location where crowds won’t ruin the trip. Going to a popular beach during Easter, when college spring breakers are in town, wouldn’t be ideal for a family vacation. Pick a quiet spot with kid-friendly activities.

Delegation Before Vacation

Regardless of when or where executives decide to take their vacation, they must abide by one rule: Delegate first. Give subordinates proper instructions and make sure the company’s operations will continue as anticipated before leaving. Fulfilling this responsibility will reduce everyone’s stress levels. There will never be a perfect time to get away for an extended trip, so executives must do everything in their power to minimize the effects of their absence.