Choosing the right meeting destination can make or break the success of your in-person meeting. Maybe your go-to move is to cycle through the same familiar cities — New York, Chicago, and Seattle — regardless of the meeting type, budget, or where attendees are traveling from. Or maybe you choose a city simply because it’s where you have an office. This process is easy and it’s what’s worked before.
But how often are you strategically choosing a meeting destination rather than treating it like a revolving door?
Perhaps you’re still learning your executive’s preferences. Sometimes, the CEO wants the final say. Either way, it’s up to you to present the best options — and make the case for each one. Why? Because choosing a destination isn’t just about where people go, it’s a chance to showcase your strategic thinking, support better decision-making, and ensure the meeting runs smoothly for everyone involved.
This blog breaks down how to confidently recommend meeting destinations and why doing a strategic, pre-meeting analysis matters more than ever.
How can you present the best meeting destinations to your executive, and other stakeholders when necessary? Especially when balancing different budgets, meeting types, or attendees — and a multitude of other planning factors — we dig into all of these scenarios and more.
When planning meeting travel, some destinations look great from a price perspective — until you realize they come with three layovers and a red-eye. Others offer direct flights for everyone but cost twice as much. Convenience and cost don’t always align, which is why presenting a balanced view is key.
Here’s a simplified way to frame it:
Review the flight options for all attendees to better understand the travel logistics and feasibility. If the destination has a major airport then flights will be easier to manage and most attendees won’t have long layovers or suboptimal arrival and departure times. While a smaller destination, with a regional or small airport, may require more transfers or connections further increasing the cost and time.
Utilizing meeting planning software can help you more easily capture a bird's eye view of the travel logistics. With TROOP, you can present these scenarios in minutes with flight times, costs, and trade-offs all visualized side-by-side.
Once flights are mapped out, identify hotel options that meet your organization’s requirements, policies, and attendee preferences.
Considerations that should be included in your planning process include:
When possible, negotiate on room rates or other services, especially if your organization has worked with the hotel before for previous meetings. If you’re looking into new hotels, plan a site visit if feasible otherwise schedule a virtual walkthrough or ask for detailed pictures covering all angles. The more details you gather upfront, the smoother the experience for your attendees and fewer surprises during the meeting.
Convenience and cost are the biggest factors to choosing a meeting destination, but there are other considerations you’ll need to account for. Especially as some of these will affect both convenience and cost. Look at the following:
What large events are going on during that time at the proposed destination? Look at big sporting events, shows, conventions, and more to ensure availability and avoid what we call the “Taylor Swift effect” — increased hotel bookings, particularly for multi-night stays, and higher prices for flights and accommodations during big event dates.
Are you traveling during major holidays? Expect higher prices, limited availability, and potential closures. Additionally, you need to create contingency plans as holiday travel often means delays, cancellations, and increased travel stress.
Consider safety perimeters for the city and destination you’re traveling to. Beyond that, look at the proximity of the meeting venue and hotel, especially if they’re not in the same space. You want to avoid unsafe situations, but this could mean booking spaces and rooms in higher-cost areas; so factor that into your analysis.
Is the weather appropriate for the meeting type and attendees? Just because your meeting is indoors, doesn’t mean you won’t face weather-related issues. If you’re planning a meeting on the East Coast during the winter months, then be prepared for missed flights, longer wait times, and more as the odds for heavy rain and snow will affect travel.
Or maybe you have an executive team that likes to golf, they might prefer warmer destinations, like Phoenix in February, over a snowy location so they can unwind after long meetings.
When evaluating meeting destinations, always check the seasonal timing. Costs and availability often depend on whether you’re planning during high, low, or shoulder seasons.
Take Park City, Utah as an example: the winter ski season is peak time, and summer draws plenty of tourists. But spring and fall offer lower prices and lighter crowds. Then there’s Orlando, Florida: spring falls in the shoulder season so it’s less busy and has fun outdoor activities. While summer means the peak season, driving up prices and crowds.
Understanding these seasonal patterns is crucial because it directly impacts budgeting, attendee experience, and availability more than you might expect.
Once you understand how your executive likes to receive communications, use this opportunity to showcase your strategic, pre-meeting analysis skills. They can decide what matters most: saving time, saving money, or something else.
From there, learn their decision making process to better align on meeting destination options going forward. They’ll appreciate your forward thinking and preparation. For example, you may find that if it's a C-suite offsite, convenience is going to be a big factor. A team gathering or training means choosing a lower-cost city. While executive team meetings, board meetings, or project kickoffs might mean going with the more expensive option.
Working more strategically shows that you’re putting in the work and that you’re mindful of cost, aligned with your exec’s priorities, and tuned into what the company needs.