The Essential Guide to Planning a Successful Company Retreat Agenda

• April 11, 2025
• Villa Punto de Vista
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A well-crafted company retreat agenda means every moment—whether it’s a high-level strategy session, an informal idea session over lunch, or a team building adventure—contributes to the bigger purpose of your retreat. Without one, you risk an expensive trip with little ROI. Too much structure and you’ll burn people out. Too little and you’ll miss the opportunity to create real impact.

In today’s remote-first world, 73% of employees are eager to connect with their colleagues in person, according to Indeed. A good agenda strikes the perfect balance between productivity and space to breathe, while allowing for that connection teams are craving. It keeps discussions focused, sparks creativity, and ensures breakthroughs aren’t left on the retreat but carried forward into daily life.

After hosting hundreds of retreats in Manuel Antonio, Costa Rica, we’re sharing our top tips. In this guide, we’ll cover:

• How to structure your retreat for clarity, alignment, and engagement
• Why strategic downtime is just as important as your workshops
• The best team building activities for high performing teams
• How to keep meetings dynamic, interactive, and results driven
• How to turn retreat insights into long-term impact and tweak future agendas

With the right approach, your next corporate retreat won’t just be a break from the office—it’ll be the catalyst for sharper thinking, more decisive leadership, and a more connected team ready for what’s next.

Start with a purpose: Why are you hosting a company retreat? 

Before diving into wine tastings, waterfall horseback rides, or sunset catamaran cruises, start with the why. As mentioned, a company retreat without a clear purpose is just an expensive trip. The best retreats have a defined goal that shapes the agenda, ensuring every session, activity, and conversation adds value to your company’s greater mission and goals.

Is your retreat about:

• Strengthening team dynamics for a newly formed group?
• Celebrating milestones and rewarding a year of hard work?
• Developing leadership through structured, high-impact sessions?
• Giving a remote team much-needed in-person connection time?

When everyone understands the reason they’re there, the retreat takes on a different energy. Discussions feel more focused, sessions have meaning, and the experience becomes more than just a getaway—it becomes a strategic investment in your team’s growth.

Your retreat location is actually a catalyst for your agenda

You could book a conference center in the city, gather your team in a windowless room, and power through slide decks under fluorescent lights. 

But why do that when you could be brainstorming with panoramic jungle views, discussing strategy as howler monkeys call in the distance, and wrapping up the day with a beachfront sunset?

Choosing the right retreat location isn’t just about aesthetics—it directly impacts engagement, creativity, and the overall retreat experience. Truthfully, a well-chosen setting reinforces your purpose and shapes every session’s energy seamlessly, making retreat planning easier.

Plus, studies from the Global Business Travel Association have found that up to 96% of business travelers agree that travel boosts job satisfaction. Talk about an opportunity!

Here’s what you can look for in a venue that will spark that engagement and make your agenda planning simpler: 

Checklist: How to Choose the Right Location for a Seamless Retreat Agenda

Why villa and private resorts make for an easier agenda and retreat planning than hotels

Corporate retreats aren’t just about getting people in a room—they’re about creating the right environment for big-picture thinking, meaningful conversations, and real connection. And where you host the retreat plays a bigger role than you might think.

Sure, you could book a hotel or conference center, shuffle between generic meeting rooms, and hope for the best. Or, you could host your retreat in a private villa or resort—where the setting works with your agenda, not against it.

Here’s why high-performing teams are skipping hotels and opting for private, high-touch retreats instead:

Distraction-Free Focus

Hotels and conference centers mean shared spaces, unexpected noise, and competing events. A private villa removes those variables. There are no distractions or interruptions. It’s just your team, fully present and engaged.

Flexible Meeting Spaces That Inspire

Why settle for fluorescent lighting and ballroom chairs when you could be strategizing on an oceanfront terrace or workshopping ideas in a breezy open-air lounge? Villas and private resorts offer adaptable spaces that make sessions feel less like meetings and more like conversations that matter.

Seamless Work-Life Flow

The best agendas balance productivity with space to recharge. At a villa, there’s no need to carve out “wellness time” between rigid meeting slots because it happens naturally. Morning yoga, afternoon catamaran sails, sunset debriefs by the pool. No shuttling between venues. No rushed transitions. Just a retreat that flows.

Personalized Experience, No One-Size-Fits-All Itineraries

At a hotel, you’re on their schedule—set meal times that are less flexible when catering to an entire conference center, preset meeting room blocks, and rigid service structures being shared with other groups on-site. At a private retreat, the schedule revolves around you. Want a brainstorming session over breakfast? Done. Need snacks at 3 p.m. instead of noon? No problem. Prefer lunch on the beach? We’ve got it.

Everything is customized to fit the way your team works best.

Stronger Team Connection

In a hotel, teams scatter to their rooms or blend into the crowd. In a villa, shared spaces foster organic conversations. These conversations are the kind that don’t happen in structured sessions but lead to real breakthroughs. The moments over a casual meal or a sunset toast? That’s where the magic happens.

Time blocking for your corporate retreat agenda 

Now that you understand why you’re hosting your retreat and how to choose a venue that will simplify agenda planning, let’s get into the nitty gritty details of planning the perfect retreat agenda. 

A successful company retreat schedule balances structured sessions with opportunities for team bonding and free time. 

If you’re not sure where to begin, here’s a tried-and-true framework to follow that will help you schedule each day with ease:

Morning (Focused Strategy & Innovation)

8:00 AM – Breakfast & networking
9:00 AM – Productive workshop led by a professional facilitator
10:30 AM – Break & reflection time
11:00 AM – Team meetings (different departments collaborate on challenges)

Afternoon (Team Building & Physical Activities)

12:30 PM – Lunch with roundtable discussions
1:30 PM – Outdoor team bonding activities (ziplining, surfing, or horseback riding)
3:30 PM – Small group organized sessions on key topics
5:00 PM – Free time (relaxation, beach walks, or poolside networking)

Evening (Celebration & Connection)

7:00 PM – Group dinner & wine tastings
8:30 PM – Retreat venue fireside chats & informal networking
10:00 PM – Optional activities (spa treatments, night walks, or game night)

Pro Tip: Not everyone wants to be scheduled the entire time—build in flexibility!

You’ll want to shift this cadence based on what your retreat goal is, too, obviously. So, if this is an incentive trip full of celebration, skip the roundtable discussions and add more free time to laze and recharge at the pool. If the goal is to get a new team to work together a bit more seamlessly, skip the inter-department meetings and focus on departmental team building. 

When you book with Villa Punto de Vista, you get assigned a pre-arrival concierge who can help you work out the details. They become an extension of your team to help you plan your most impactful retreat yet and help simplify the planning process. Your leadership team doesn’t need to worry about a thing!

Example Agenda: Villa Punto de Vista Corporate Retreat 

This mix of business and play is the best way to facilitate team bonding that will last past the confines of the jungle! 

Best Team Building Activities for Corporate Retreats in Costa Rica

So, what activities do you fill free time with? Let’s get into a few of our favorites. 

The country’s varied landscapes and vibrant culture are the perfect setting for unforgettable team building experiences. Here are the top activities to consider:

Canopy Tours (Ziplining)

Go ziplining through the rainforest canopy. This activity is a thrill and gets team members out of their comfort zones, building trust and support within the group. Costa Rica has some of the best and safest ziplining courses in the world.

Whitewater Rafting

Costa Rica’s rivers are some of the best in the world for white water rafting. Whether your team is rowing down Class II or Class IV rapids, this activity promotes teamwork, communication, and a little healthy competition if you have multiple boats navigating the waters. Our favorite spot is the Pacuare River, which is just a quick day or half-day trip from our villa in Manuel Antonio.

Beach Olympics

Right below our villa is a beach that will feel all your own, with plenty of room for your team to spread out over multiple stations. Our team has helped set up fun and challenging games like beach volleyball, tug-of-war, and relay races. These activities encourage collaboration, strategy, and team spirit, all while you enjoy the sun and surf under the shade of sprawling palms. If you’re lucky, you may spot a few sloths hanging out nearby! 

Private Charters

Book a private boat charter that leaves from the Marina Pez Vela by Villa Punto de Vista to explore Costa Rica’s coastline and nearby islands. Whether it’s a sailing trip, snorkelling adventure or sunset cruise, being on the water is a great way for team members to connect on a personal level, outside of the work environment.

Corporate Social Responsibility

Engage in meaningful community service projects that align with your company’s values, from beach cleanups and tree planting to hands-on community development initiatives. Past groups have donated professional services to local schools, revitalized public spaces with fresh paint, and contributed to projects that make a tangible difference. 

Our pre-arrival concierge will curate a Corporate Social Responsibility (CSR) experience tailored to your mission, ensuring your efforts create both local impact and lasting team unity. These immersive volunteer opportunities foster connection, pride, and a shared commitment to something greater than business as usual.

We also work with Pack for a Purpose, a global nonprofit connecting travelers to meaningful causes in their destinations. Our team can work with you to identify connections and needed goods, that your team can bring to donate.

A team retreat should be just as much about having fun as it is about getting down to business. You want your employees to leave the retreat feeling more connected to their team, and unstructured play sparks those connections.

How to elevate your team retreat agenda

A corporate retreat in Costa Rica offers the chance to get your team involved in activities that build collaboration, trust, and camaraderie. The country’s varied landscapes and vibrant culture are the perfect setting for unforgettable team building experiences. Here are the top activities to consider:

Hire caterers that offer diverse food options 

Food plays a crucial role in setting the tone for your retreat. Hiring a catering team that offers a variety of meal options ensures that all dietary preferences and restrictions are accommodated. 

Consider incorporating local Costa Rican flavors alongside familiar international dishes to create a well-rounded menu. A mix of buffet-style meals, plated dinners, and interactive dining experiences—such as a private chef-led cooking class or a beachside barbecue—adds an engaging element to mealtime.

Build fun into the agenda

A well-balanced retreat blends work sessions with moments of relaxation and excitement. Infuse the agenda with activities that encourage team bonding in a stress-free way. 

Ensure the chosen location is ideal

The success of a retreat often hinges on the setting. A location like Villa Punto de Vista offers the perfect combination of luxury, privacy, and accessibility. 

Its panoramic ocean views, spacious common areas, and high-end amenities provide a seamless blend of work and leisure. Additionally, proximity to key attractions—such as Manuel Antonio National Park—allows for easy access to adventure and team excursions without long travel times. 

Choosing a venue with a dedicated staff to handle logistics further ensures a smooth experience for attendees.

Ask for input for the next retreat 

A post retreat survey is critical for the long-term success of your strategy. Realistically, your employee feedback should guide the entire process year over year. What do you need to work on? Did they enjoy the amount of free time or would they like more or less? Were the team building activities good? Would they prefer different locations or would they prefer to come back to their favorite villa year after year? 

By asking for input, you allow employees to have a stake and help plan in their own way. This not only leads to a feeling of empowerment, but also greater employee engagement—and incredible insight on how to improve your agenda annually to keep your team on the same page and happy!

Retreat Planning FAQs & Best Practices

Planning a company retreat is no small feat. Between booking the perfect retreat venue, coordinating team building exercises, and ensuring your entire team stays engaged so the retreat helps build company culture, and thinking about how to lead productive workshops, it’s easy to feel overwhelmed. But don’t worry—we’ve got you covered.

Here are some of the most common retreat planning questions and expert-backed best practices to ensure a seamless experience from start to finish.

What’s the ideal length for a corporate retreat?

A 4-night/ 5-day retreat offers a sweet spot. Anything shorter, and you risk cramming too much into your entire time together. Anything longer, and you may lose engagement. If you’re considering a longer retreat, incorporating more downtime and experiential activities ensures a perfect balance of strategy, team-building, and relaxation.

Best Practice: Alternate work days with team bonding experiences to keep energy levels high (think: strategy meetings one day, ziplining the next).

Why should we book a retreat in Manuel Antonio, Costa Rica? 

Manuel Antonio, Costa Rica, is the ultimate retreat destination where luxury and nature intertwine seamlessly. Just a short domestic flight or scenic drive from San José, this tropical haven offers exclusive ocean-view villas, private infinity pools, and world-class hospitality, all surrounded by lush rainforest and pristine beaches. Whether you’re unwinding with bespoke spa treatments, practicing sunrise yoga with the sound of the waves, or embarking on private adventures like catamaran cruises and guided wildlife hikes, every moment here is designed for renewal and inspiration. With golden sunsets painting the sky and the tranquil energy of the Pacific, Manuel Antonio isn’t just a place to escape—it’s a destination that transforms your team.

How do we ensure our retreat is productive (not just a vacation)?

A truly effective corporate retreat goes beyond luxury and leisure—it’s about aligning leadership, driving strategy, and strengthening executive collaboration. The key is designing an agenda that blends high-level discussions with strategic team-building, ensuring every moment has purpose.

Key Strategies for a High-Impact Executive Retreat:

• Start with clear objectives – Define the retreat’s focus (strategic planning, leadership development, innovation) and communicate it upfront.
• Facilitate structured discussions – Bring in a professional facilitator to guide conversations, ensuring high-level discussions remain actionable.
• Balance deep work with dynamic engagement – Break up intensive executive sessions with activities that encourage creative thinking and collaboration.
• Create space for reflection and integration – End each day with key takeaways, leadership insights, and next steps to drive long-term impact.

Pro Tip: Use post-retreat feedback to assess impact, refine future retreats, and ensure every executive leaves with actionable implementation strategies.

How much does a company retreat cost?

The cost of a company retreat depends on the experience you want to create. At Villa Punto de Vista, we specialize in high-impact, luxury retreats that bring teams closer, spark innovation, and drive real results—all in a breathtaking private estate in Costa Rica. Pricing varies based on factors like accommodations, dining, activities, transportation, and facilitation, but every retreat is fully customizable to match your company’s goals and budget. Whether you’re planning a leadership summit or a multi-day immersive experience, we’ll craft something truly unforgettable. 

Get in touch today for a custom quote, and let’s bring your vision to life.

Pro Tip: Book off season for potential savings. 

How does a company retreat impact company culture?

A well-planned corporate retreat creates a lasting impact far beyond the retreat itself. It strengthens team dynamics, reinforces company values, and fosters innovation in ways that traditional meetings simply can’t.

How can we help team members with any pre retreat anxiety? 

It’s natural for your team to feel a little jittery before spending time with colleagues away from the office. Especially if you have a company where remote work is the norm, do what you can to ensure employees feel taken care of during the planning process. 

Send a short survey as you plan to ask for dietary restrictions, ensure them that you’ll book lodging on their behalf, share employee roles for the retreat so there are no questions, and share reflections from the past year and how powerful these events have been in the past. This does a lot to put the entire staff at ease and ready for a great retreat. 

Do we have to incorporate team-building exercises?

It’s been found that ⅔ of employees believe it’s difficult to build professional connections virtually, so just getting them to gather at a villa is team building in itself. 

While a corporate event like a retreat is built for team building, many don’t realize that when you host a destination retreat like one in Costa Rica, your team will innately create connections just hanging around the villa. Yes, you can 1,000% incorporate them, a private resort or villa naturally provides opportunities for engagement that a hotel or conference center does not.

Host Your Next Company Retreat in Manuel Antonio, Costa Rica

A corporate retreat isn’t just a getaway. It’s a strategic investment in leadership, vision, and company growth. And a private villa in Manuel Antonio, Costa Rica isn’t just a venue—it’s a strategy. A perfect match, really.

Hosting at a private villa in Costa Rica eliminates distractions, enhances creativity, and ensures your retreat agenda actually delivers results. The best teams know that real work doesn’t just happen in meeting rooms—it happens in the spaces in between. And a private villa allows your team to create more of those moments naturally without having to manufacture them in your agenda.

If you’re ready to explore what your agenda could look like in the tropical oasis of Manuel Antonio, check available dates and get started planning now.