7 Questions to Ask Yourself When Planning the Perfect Corporate Retreat to Orlando

Company retreats are wonderful opportunities for your organization to recharge, stimulate, and connect with each other in a relaxed setting that fosters better communication and teamwork. They also encourage interaction between different departments and contribute to creating a more productive work environment.

For these reasons, the perfect corporate retreat should be planned with meticulous attention to detail with the focus being on employee rejuvenation. And a corporate retreat to Orlando meets all these requirements. But planning and executing the perfect retreat is no easy task. Before you take on this challenge, here are a few questions to ask yourself when planning the ideal retreat experience:

What is the purpose of the retreat?

First things first. You must decide what kind of corporate retreat you are looking to host. One way to determine this is by asking yourself the goal of your retreat. Is it recreational? A chance to interact with your teams’ families? Is it business oriented with leadership training and team building activities? Or educational with seminars and workshops? A good retreat is generally a mix of work and play. Once the objective of the retreat is worked out, the retreat can be planned with a clear vision and focus.

And the best part about having mostly sunny weather year-round, is it gives residents and visitors endless opportunities to take part in a wide variety of outdoor activities and excursions.

Where do you want to host it?

The location of your company retreat is essential in ensuring the comfort and enjoyment of your team. Fortunately, there are many options available in Orlando that provide luxury accommodation with access to ample recreational and conferencing facilities that are perfect for company retreats. When selecting the venue, there are a few things to look out for and keep in mind:

  • Location and Accessibility- The ideal location would be one that offers the right balance of privacy while at the same time being close to popular attractions that your team members would love to visit.
  • Lodging and Ambience- The space chosen should be suitable to accommodate your team and the purpose of the retreat. This means that the attendees should have their comfort and privacy while still being close together to encourage interaction. The atmosphere of the venue must also tie in with the theme of the retreat.
  • Health and Safety Protocols- Planning a corporate retreat can be stressful, especially in the post-Covid environment. For this reason, it is important to take into consideration the health and safety guidelines mandated by the venue. This brings peace of mind to those anxious about gathering in large groups. Selecting a venue that follows strict hygiene standards and social distancing regulations is also a proven way to ease any concerns.
  • Amenities offered- Always inquire about the facilities available to guests at the venue. These should include dining options, access to pools and spas, and availability of space for training sessions.
  • Reviews- To get a better sense of the property and venue, look at online reviews. These can help to guide you toward making an informed choice about the amenities and services important to you.
  • Pre-booking- Booking your venue in advance not only helps you in the planning stage, but it also gives the attendees adequate notice to smooth out any conflicts in their schedules for maximum participation. The venue chosen could also help you book tickets to nearby attractions and theme parks.

Florida boasts some of the best beaches in the nation. The state is bordered by both the Gulf of Mexico as well as the Atlantic Ocean giving rise to some truly spectacular coastlines. From the pure white sand of the Clearwater beach to the orange shores of Daytona, the beaches of the state are not only wide-ranging in their hues and textures but also in the adventures and experiences on offer.

Florida beaches are not just renown for fishing, surfing, kayaking, parasailing, rollerblading and horseback riding. You can take part in the American Sand-sculpting Championship at Fort Myers, join the annual Mullet Toss, or participate in the great Southern Tailgate Cook-off.  There really is a beach for everyone.

How would you get about?

An important aspect when planning out-of-town corporate events is transport. Do you have to book flights? How will you get to and from the venue? And if you are planning on visiting any of the numerous nearby attractions in Orlando, what would be the best mode of travel for your team?

Pre-booking your venue can help make these arrangements easier. And many flights offer special rates for bulk booking for corporate events. For local travel, charter buses would be ideal for travel to and from the venue.

Another great option would be to inquire if the venue itself provides transportation to and from local attractions which would help in planning a perfect day out in Orlando.

The Tallahassee Museum is a treat for wildlife and history enthusiasts, while art-lovers would appreciate the wonder that is the Salvador Dali Museum. Living in Florida can certainly feel like a non-stop vacation.

What events would the retreat feature?

The perfect corporate retreat should be both professional and entertaining. A unique blend of motivational programs and fun activities. Fortunately, Orlando boasts of many resorts that cater to both the professional and recreational groups.

These resorts provide access to world-class conference rooms, which are ideal for executive meetings, as well as to outstanding golf courses, pools, spas, tennis courts, theater rooms, game rooms, and much more.

As such, these resorts provide you the opportunity to include a variety of activities in the itinerary. Training sessions, team-building exercises, and even golfing. All of this, without leaving the resort.

And giving your team options on how they spend their time adds to their enjoyment. You can do this by providing a perfect blend of scheduled time together and unstructured time. Thereby ensuring your corporate retreat is the ultimate social experience.

The physical and social benefits of the game aside, playing on the beautifully landscaped courses of Florida offer an incomparable experience.

What would you need?

Based on your proposed itinerary, it is important to pre-book any meeting space or equipment you may require. This is largely dependent on the number of participants attending the retreat. So, take into consideration the square feet of the meeting space as well as the social distancing protocols when booking.

Luckily, most resorts provide ample meeting room facilities that make planning your company retreat simple and hassle-free.

Are there any special dining requirements or restrictions?

Catering to the dining requirements for a large group of people is no easy feat. It involves a great deal of research and preparation. But there are ways to make it simpler:

  • Find out about any dietary requirements or restrictions from everyone on your team well in advance. You could carry out a quick survey and keep this information on file.
  • Notify the venue of the same. This helps the resort or restaurant where you intend on dining, plan the menu accordingly.

Most resorts feature plenty of on-site dining options that cater to all your culinary requirements. This goes a long way in helping make the retreat an enjoyable and effortless experience.

These financially beneficial tax policies make the state a popular retirement option even for those simply looking to escape during the winter months. This also makes Florida incredibly appealing to senior citizens looking to spend their retirement income on something they enjoy. After all, they have earned it.

What are the concierge services available?

Resorts in Orlando are well-equipped to cater to corporate events. One feature that makes them stand out are the amazing concierge services offered that make planning a gathering seem like a piece of cake. These services may include:

  • Coordinating transportation to nearby parks and attractions
  • Scheduling spa appointments
  • Booking tickets to theme parks
  • Arranging rental equipment
  • Planning a unique chef dining experience

By utilizing these services, you can plan out the ideal corporate retreat by creating a unforgettable adventure for your team.


There is no doubt that a well-planned corporate retreat creates a unique environment that boosts morale, creativity, and productivity in your team. It also builds better work relationships that foster greater teamwork and a positive work environment.

But planning a memorable experience for your team can be a stressful experience. However, with some preparation, access to the right facilities, and skillful event management, your retreat can be an enriching and inspiring experience for your team.

If you are interested in creating and planning the perfect corporate retreat, look no further than The Bear’s Den Resort in Orlando. Set in a spectacular location, surrounded by numerous attractions, and providing luxurious accommodation and world-class amenities, it provides the ideal setting to inspire your team. Our team of expert event planners and exceptional staff will take care of all the details, leaving you free to enjoy the perfect retreat.