How to Choose Meeting Destinations (Without Playing Favorites)

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 to recommend smart meeting destinations

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.

Balance cost versus convenience

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:

• City 1 is the cheapest, but most attendees have stopovers or long travel days.
• City 2 is the most expensive, but all attendees have direct flights.
• City 3 is affordable and only a few attendees need connections.

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.

Consider the hotel options in your breakdown

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: 

• Accessibility and proximity to the airport and meeting space.
• Does the hotel offer meeting rooms that can accommodate your group, depending on the meeting type?
• What are the transportation options if you have to commute to a separate meeting venue?
• What are the meal and restaurant options for attendees?  
• Are there extra fees for amenities or parking?

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. 

Hidden variables that can break a good plan

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: 

Major events

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. 

Holidays

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. 

Safety

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.

Weather

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.

High, low, and shoulder seasons

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.

• High season: peak travel times like summer and holidays. Expect big crowds and higher prices on venues, hotels, and flights.
• Low season: the quietest (and often cheapest) time to travel, but potentially less desirable weather or limited options.
• Shoulder season: the sweet spot between high and low seasons. It varies by location and often offers better rates with fewer crowds.

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.

How to share the meeting destinations with your executive 

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. 

Make the smart meeting destination choice every time

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.