Crafting the Perfect Event Itinerary: Maximizing Impact and Minimizing Stress

Picture this: your team arrives at the offsite venue, energized and ready to connect, collaborate, and bond. But upon arriving you learn the schedule is loosely put together. There’s a welcome session from the CEO and some time for co-working but nothing more. Something is missing. And because of this, the event doesn’t really live up to your expectations.

This scenario is all too familiar for many planning an offsite. While a well-structured agenda is crucial, a truly successful offsite hinges on a comprehensive itinerary, one that is crafted with purpose and intention - while also planning for the unexpected. Here at BoomPop, we've helped countless teams do just that, crafting offsite experiences that foster connection, ignite creativity, and leave a lasting impact. Today, we're sharing our top tips for building an offsite itinerary that sets you up for success.

Applying strategy to your event itinerary

picture of an event itinerary plan

The first rule of thumb when thinking about your offsite itinerary is to coordinate strategically around travel, and factor in buffers for the unexpected. Don't shortchange your team by cramming too much into arrival and departure days. Factoring in travel logistics is key to respecting your team’s personal time – and also ensuring that uncontrollable factors like the weather don’t blow up your budget.

Here’s a cautionary tale: Imagine hosting a 100-person retreat with an offsite itinerary that ran until 3 p.m. on the final day. All guests are scheduled to fly out after 5 p.m., but when their flights were canceled due to weather, most of the team was stuck for another night. The company is stuck covering additional hotel rooms for all guests at $250/person, significantly adding to their total event cost. Scenarios like this are easier to avoid with a well-thought out itinerary. Here are a few best practices to keep in mind:

  • Schedule arrival activities: Plan a welcome reception or team-building activity in the late afternoon/evening to help your team unwind after travel.

  • Consider buffer time: Don't program events too close to arrival times. Build in buffer periods to account for unexpected delays.

  • Plan for reasonable departure times: Leaving the last day light on programming allows your team to catch flights that get them home at reasonable times without feeling rushed. 

  • Give arrival and departure time guidance: Let your guests know the target time windows they should plan to arrive and depart your offsite, including providing hotel check in and check out times, so your planning team can more easily schedule arrival and departure day activities.

Crafting a robust schedule

One team having a meeting for their event itinerary

Now that we've tackled the logistics, let's dive into the heart of your itinerary. A successful offsite strikes a balance between focused work sessions and engaging social activities. But this balance can vary depending on your goals.

For Moxy Management's summer camp retreat, they wanted to focus on team building—their event itinerary included more interpersonal exercises and fun activities to immerse their team in the experience. For other clients, giving their teams space to brainstorm and problem-solve is a bigger priority. 

Here's how to find the right balance for your event:

  • Match activities to goals: For example, if your focus is strategy, schedule dedicated brainstorming sessions. If it's team building, prioritize interactive activities. Make sure you have enough time to focus on the aspects of your offsite that support your overall goals, and be realistic with what you expect to accomplish.

  • Gather guest input: Use surveys and RSVP forms to understand your team's preferences to help you better plan activities, meals, and team-building moments.

  • Embrace compromise: Be realistic about what you can achieve and be willing to make adjustments.

Breaks the secret to an impactful event itinerary

People taking a coffee break as part of event itinerary

We all know the feeling of hitting a wall after hours of non-stop interaction. Don't underestimate the power of breaks! They give participants time to recharge, process information, and come back to the table with fresh perspectives. Remember, some personalities might need more downtime than others. A few tips:

  • Schedule regular breaks: Aim for short breaks every hour or two and a longer one for lunch.

  • Offer a variety of activities: Provide opportunities for both social interaction and quiet reflection.

Create your own event itinerary

Building a winning offsite itinerary takes planning and thoughtful consideration. With BoomPop, creating an impactful event itinerary is easier than ever—find and book activities, create a detailed schedule, and share it with your team, all through our powerful platform. Ready to get started? Contact us today for a free consultation.

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The Transformative Power of an Event Strategy with Tavar James

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