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A Handy Guide on Choosing the Best Time of Year to Organise a Company Retreat

By Preethi Jathanna

Senior Writer for HR and Remote Work

A handy guide on choosing the

When it comes to figuring out the best time of year to organise a company retreat, timing is everything, just like deciding when to throw that perfect backyard BBQ. Imagine gathering your team during the full bloom of spring, mirroring your team's potential for growth and renewal. Or perhaps, it's the warmth of summer, setting the stage for outdoor adventures and team bonding under the sun to celebrate a milestone.

In this post, let's dive into the what you should take into account when planning a corporate retreat that'll leave your team recharged, inspired, and ready to conquer any challenge

1. Factors To Consider Before Selecting the Best Time Of Year to Organize a Company Retreat

1.1 Industry-specific Considerations

Some industries have peaks and troughs of busyness throughout the year that can impact on retreat planning. For example, in retail, Christmas period tends to be extremely hectic. In most cases, you will most likely want to organize your corporate getaway during a time of the year when work slows down and you are fielding less requests from clients.

1.2 Weather & Climate

Depending on the type of activities you want to feature as part of your event, the best time of year to organize a company retreat can also be dependent on weather and climate. Outdoor escapades, such as group hikes, scavenger hunts, and company Olympics, are obviously better suited to sunny weather rather than rainy days.

1.3 Employee Availability & Schedules

It’s always a good idea to consult with your team before arranging any corporate retreat, just to check what their availability is like and whether they have any holidays scheduled. If you give plenty of advance notice, you should be able to ensure everyone is able to attend.

1.4 Budget Factor

Sometimes the best time of year to organize a company retreat is the cheapest time! If you’re trying to organize the best getaway possible on a tight budget, it’s worth seeing what kind of deals you can get during off-peak times of year. Accommodation in particular can have starkly different pricing depending on whether your retreat coincides with national holidays or summer vacation.

2. The Best Time of Year to Organize a Company Retreat for Team Building

2.1 Before the Holiday Season (Sept-Oct)

Arguably the best time of year to organize a company retreat is in September and October. First of all, it’s before the holiday season (encompassing Thanksgiving and Christmas), when people tend to have lots of familial commitments. Another factor in the favor of September and October is that it tends to be a little cheaper than the preceding months of July and August, which are the busiest time globally for travel, bumping up prices for transportation and accommodation. You also tend to get fairly good weather regardless of your location.

You can take advantage of the pleasant temperatures and the fall season by arranging for walks that encompass the changing colors of the leaves. Alternatively, enjoy the bounty of harvest time by organizing apple picking or pumpkin carving as part of your retreat.

2.2 Spring Season (March- April)

While you may experience a bit more rain during March and April than other times of the year, spring is a good time to get your team out and about so they can shake off the winter malaise. As with September and October, there are usually quite a few bargains to be had during March and April, as long as you avoid the easter holiday period. 

Due to the sometimes inclement weather, spring is the time for activities that largely take place indoors. Escape rooms, art classes, or other creative pursuits are just some of the things you could arrange with your team. Of course, you can still incorporate some outdoor activities like hikes or rafting, but it’s advisable to have a backup plan that can take place under a roof, just in case.

2.3 Off-peak Season (May-June)

May and June herald better weather for team building, while at the same time avoiding the peak holiday season when prices sharply rise. One of the principal downsides of this period is that a lot of industries find themselves at their busiest in May and June. It’s not uncommon for companies to try to get as much work done as possible before the school vacation, when many family men and women take time off.

During May and June, you can arrange for stays in log cabins, glamping tents, or other nature-themed accommodation. Take advantage of the good weather by communing with the environment, providing staff with ample time for rest and relaxation so they return to the office refreshed.

2.4 Company Milestones

You may want to give your corporate retreat meaning beyond team building by timing it to coincide with company milestones. These could be annual milestones, such as the date of the founding of the company, or they could be performance-related milestones, such as meeting a sales quota or achieving the important business objectives set out previously.

Since the aim of executive burnout retreats related to company milestones is often to celebrate, consider getaway options that are primarily fun and social in theme, such as picnics, boozy dinners, karaoke evenings, and wine tastings.

2.5 High Workload Periods

We’ve already noted that often the best time of year to organize a company retreat is during months when business is slow, but the converse can also be true. During high workload times, staff can become stressed and anxious, leading to negative impacts on their health and the company. A team-building getaway is able to combat this by taking employees out of the office and into a soothing escape where they can refresh and reset.

Wellness retreats that offer classes like yoga or meditation are particularly good options during high workload periods, as they not only give staff the opportunity to recover from their exertions, but also teach them skills that they can then incorporate into their daily lives whenever they need to alleviate stress.

3. FAQs

3.1 What time of year is best for retreats?

The best time of year to organize a company retreat depends on several factors, such as the types of activities you wish to arrange, the budget you have at your disposal, and the availability of your staff. In general, however, May, June, September and October tend to be the best options because the weather is good, allowing for a greater range of pursuits.

3.2 What makes a good corporate retreat?

The best team building retreats balance enjoyment with skills acquisition. Try to mix seminars and workshops that build staff communication and teamwork with fun activities that more indirectly promote team bonding, such as games or dinners.

3.3 How long should a company retreat last?

How long a corporate retreat lasts is entirely at your discretion. Normally, however, they run from two days to a week. If you are traveling further afield, it makes sense to have a longer company getaway, while for nearby locations a long weekend may be sufficient.

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