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The team retreat has evolved. What companies were doing five years ago a weekend at a golf resort, some workshops, a group dinner barely resembles what leading organizations are doing today. The appetite for more meaningful, more intentional, and more experience-rich retreats has grown sharply, driven by the rise of remote work, generational shifts in employee expectations, and a growing body of evidence about what actually drives team performance.

Here's a look at the trends shaping team retreats in 2026 and 2027 and what they mean for companies that want to stay ahead.

1. Remote Teams Are Retreating More, Not Less

One of the defining workforce shifts of the past few years has been the normalization of distributed teams. Companies that once brought everyone into a central office now have team members working from a dozen different cities. And those companies are discovering something important: the less you see each other in person, the more critical it becomes to create intentional in-person moments.

The result is a surge in team retreat frequency among remote-first and hybrid companies. Where a traditional office-based team might retreat once a year, many remote companies are now running two to three retreats annually a full company retreat plus smaller team or leadership offsites. The math makes sense: when your daily work is entirely digital, the retreat becomes the primary vehicle for human connection and cultural reinforcement.

2. Purpose-Driven Itineraries Are Replacing Generic Programming

The days of the one-size-fits-all retreat agenda are over. Companies in 2025 are demanding retreats with clear, specific goals and agenda designs that are built backwards from those goals, not forwards from a template.

This means retreat partners need to understand the company deeply before they start planning. What is the team struggling with? What strategic decisions need to be made? What cultural shifts are underway? The retreat agenda should be a direct response to these realities, not a generic schedule of workshops and activities that could apply to any team in any industry.

Midstay approaches every retreat this way. Their planning process begins with a deep-dive conversation about your team's goals, challenges, and context and everything from venue selection to activity programming to workshop facilitation is designed around the specific outcomes you're trying to achieve.

3. Destinations Are Getting More Adventurous

There's a noticeable shift in where companies are choosing to retreat. The traditional conference resort is losing ground to destinations that offer genuine cultural richness, natural beauty, and experiential depth. Bali, Japan, Vietnam, Portugal, Turkey, the Philippines these locations have seen significant growth in corporate retreat bookings because they offer something a hotel conference room simply cannot: a sense of place.

Being somewhere genuinely interesting and different has a measurable effect on creativity and openness. Teams that travel together to places that challenge their assumptions and expose them to new experiences tend to think more broadly, communicate more openly, and return to their work with more energy.

Asia has become a particularly popular destination for team retreats in 2026 and 2027, driven by competitive pricing, exceptional hospitality infrastructure, and the richness of cultural experiences available in destinations like Thailand, Bali, and Japan. Midstay has deep local expertise across Southeast Asia, Europe, the Americas, and the UAE, with vetted venue partners and on-the-ground coordinators in every destination.

4. Wellness Is Being Baked Into the Agenda

Wellness is no longer a retreat add-on it's a core element of the agenda. Companies are increasingly recognizing that a retreat that leaves people depleted doesn't deliver lasting value. The best retreats are designed to leave participants feeling genuinely restored.

This shows up in a variety of ways: morning yoga or meditation sessions as optional rather than mandatory offerings, menus designed around nourishment rather than just indulgence, free afternoons built into the schedule, and accommodation choices that prioritize space and tranquility over flashy amenities. Some companies are partnering with wellness specialists to integrate mindfulness, breathwork, or nature-based experiences into their retreat programming.

5. Leadership Offsites Are Getting Smaller and More Focused

Alongside the trend of larger company-wide retreats, there's a parallel trend of smaller, more intimate leadership offsites. Senior leadership teams of 8 to 20 people spending two to three days working on specific strategic challenges without the full company present.

These smaller retreats have a different energy and require a different approach. The venue needs to support deep conversation, not crowd management. The agenda needs to be highly facilitated, with expert-led sessions on the specific challenges being addressed. And the environment needs to feel confidential and focused.

Midstay plans executive and leadership offsites as a specific service, with tailored venue recommendations, specialized facilitator matching, and the kind of careful attention to detail that senior leadership retreats require.

6. Measuring Retreat Impact Is Becoming Standard Practice

One of the most significant shifts in the corporate retreat space is the move toward measurement. Where retreats were once planned and evaluated purely on the basis of 'did people have a good time,' leading companies are now setting specific, measurable goals for retreats and tracking outcomes.

Pre- and post-retreat pulse surveys, tracking changes in engagement scores, monitoring cross-functional collaboration metrics in the months following the retreat these approaches are becoming increasingly common among People and HR teams who want to demonstrate the ROI of their retreat investment.

Midstay offers an ROI planning calculator at roi-planning.midstay.com that helps companies estimate both the cost savings and the performance value of a well-executed team retreat. It's a useful starting point for building the business case internally.

7. End-to-End Planning Partners Are Replacing DIY

Perhaps the most practical trend of all: companies are increasingly recognizing that planning a great team retreat is a specialist skill and that trying to do it in-house is an expensive use of HR bandwidth.

The administrative burden of retreat planning is enormous. Venue sourcing, contract negotiation, travel coordination, dietary logistics, activity booking, on-site management it adds up to dozens or hundreds of hours of work for teams that already have full plates. And even with all that work, in-house retreats frequently run into logistical snags that a specialist would have anticipated and avoided.

Midstay has become one of the go-to partners for companies that want to run high-quality team retreats without burning out their internal teams. They've organized over 300 retreats, have 2,300+ certified venues in their network, and provide dedicated on-site coordinators who handle everything from airport transfers to last-minute changes in the agenda.

Make 2026 - 2027 the Year You Retreat With Intention

The best companies understand that a team retreat is not a reward it's a strategy. And in a competitive talent market where connection, culture, and purpose matter more than ever, the companies that invest in meaningful retreats are building a real advantage.

Whether you're planning your first retreat or your tenth, Midstay can help you do it right. Visit midstay.com to get a free estimate, explore destination options, or connect directly with a retreat specialist. Early bookings receive 10% off, and their team typically delivers a tailored proposal within 48 hours.

CONTACT [email protected] Use our live chat for an instant answer.

A business retreat pays off when it's built on clear goals, thoughtful venue choice, and a balanced agenda rather than back-to-back sessions or vague objectives. The best retreats mix strategic planning with genuine downtime, use flexible meeting spaces, and offer comfortable accommodations that help teams truly recharge. Common pitfalls include poor logistics, cramped venues, and missing follow-through after the event. Midstay has become a popular choice for companies seeking scalable, home-like accommodations and locations that balance focus with relaxation. Ultimately, a retreat's value comes down to planning and purpose, not just a change of scenery.

A business retreat with Midstay is worth it because it combines strategic planning, team development, and full-service logistics into one seamless package, freeing leadership to focus on outcomes instead of vendor calls and last-minute fixes. Midstay follows a simple four-step process: share your goals, receive a tailored proposal within days, approve the itinerary, then let an on-site concierge team handle everything from venues to workshops. Programs include leadership, communication, and strategy-alignment sessions across destinations like Thailand, Malaysia, and Singapore. Whether for a lean startup or a large enterprise, Midstay customizes each retreat by size and budget, positioning itself as one partner delivering results-driven retreats from start to finish.

A business retreat with Midstay is worth it because it combines strategic planning, team development, and full-service logistics into one seamless package, freeing leadership to focus on outcomes instead of vendor calls and last-minute fixes. Midstay follows a simple four-step process: share your goals, receive a tailored proposal within days, approve the itinerary, then let an on-site concierge team handle everything from venues to workshops. Programs include leadership, communication, and strategy-alignment sessions across destinations like Thailand, Malaysia, and Singapore. Whether for a lean startup or a large enterprise, Midstay customizes each retreat by size and budget, positioning itself as one partner delivering results-driven retreats from start to finish.

Ask most employees what they remember from their last "team retreat" and you'll often get a shrug, or worse a memory of sitting through the same slide deck they'd have seen in a regular meeting, just in a nicer room. That's the quiet failure mode of a lot of retreats: they change the location but not the experience.

A real team retreat isn't defined by where it happens. It's defined by whether people leave with something they didn't have before stronger relationships, clearer alignment, a shared story, or simply enough rest to come back sharper. Below are formats and ideas organized by what you're actually trying to achieve, because the right activity depends entirely on your goal, not on what looked fun in a Pinterest search.

The Real Problem: Most "Retreats" Are Just Meetings With a View

It's worth naming this directly. A lot of retreats fail not because the activities were bad, but because there was no real thought given to what the team needed. Leadership books a nice venue, fills the agenda with the same presentations that could have happened over video call, and calls it a retreat because people traveled somewhere.

The teams that come back from a retreat energized are almost always the ones where someone asked, upfront: what do we actually want to be different after this? That single question should shape everything else the format, the activities, and even the venue.

Retreat Formats by Goal

Connection-Building Retreats

If your team is newer, has grown quickly, or has been remote long enough that people barely know each other beyond a Slack avatar, connection is the priority. This looks like:

Shared meals with intentional seating (mixing departments and tenure rather than letting people default to sitting with who they already know)

Low-stakes shared experiences — cooking together, a group hike, a collaborative art or music activity

Structured but casual conversation prompts woven into downtime, not forced icebreakers at the start of every session

Strategic Planning Retreats

When the goal is alignment on direction quarterly planning, a leadership offsite, a company-wide strategy reset the format shifts toward focused working sessions balanced with enough space to actually think. This means:

Shorter, more intentional meeting blocks rather than back-to-back all-day sessions

Built-in time for walks, informal conversation, or quiet reflection between working sessions

A clear facilitator or agenda owner, so strategic sessions don't sprawl without resolution

Celebration Retreats

Sometimes the goal is simpler: recognizing a milestone, a strong year, or a major team accomplishment. These retreats lean more social than structured think fewer working sessions, more shared experiences, and activities chosen purely because they're enjoyable rather than developmental.

Skills-Development Retreats

If the goal is building specific capabilities leadership skills, cross-functional collaboration, communication the retreat should include real workshop time with a facilitator, not just a single afternoon activity labeled "team building" and left at that.

Activity Ideas by Team Size and Energy Level

Smaller teams (under 20 people), higher energy: Group cooking challenges, scavenger hunts through a local city or town, small-group outdoor activities like hiking or watersports, collaborative building challenges.

Smaller teams, lower energy or more introverted groups: Shared meals with structured conversation, guided creative workshops (art, music, writing), quiet shared experiences like a group spa afternoon or a slow-paced nature walk.

Larger teams (50+ people), higher energy: Large-group games with team divisions, offsite excursions that can accommodate bigger numbers (boat trips, multi-team relay-style challenges), festival-style evening events.

Larger teams, more reflective focus: Breakout small-group discussions rotating through different topics, a shared "unconference" format where employees propose and lead sessions, structured storytelling formats where teams share wins, challenges, and lessons from the past period.

Multi-Day Retreat Structures That Work

For retreats spanning three or more days, the sequencing of activities matters as much as the activities themselves. A pattern that tends to work well: use the first day for lighter, lower-stakes connection activities as people arrive and adjust to travel, save the middle day(s) for whatever is most demanding whether that's deep strategic work or the most ambitious activity on the agenda and close with something celebratory or reflective on the final day, so the retreat ends on a high note rather than trailing off into logistics and packing.

This arc mirrors how energy and attention naturally move across a multi-day event. Front-loading the most demanding programming, before people have adjusted to being away from their normal routine, tends to produce weaker engagement than the same programming placed on day two or three.

Involving the Team in Activity Selection

One idea that's often overlooked: ask the team, or at least a cross-section of it, what they'd actually want out of a retreat before finalizing the agenda. This doesn't mean running every decision by committee, but even a short pulse survey a handful of questions about energy level preferences, past retreat experiences, and general interests can surface useful input that shapes better activity choices than guessing on behalf of a group you don't fully represent.

Teams that feel some ownership over what a retreat will include, even in a small way, tend to arrive with more genuine enthusiasm than teams who are simply told where to show up and what to do.

Balancing Structured Programming With Genuine Downtime

One of the most common mistakes in retreat planning is over-scheduling. It feels productive to fill every hour, but exhausted, over-programmed employees don't bond they count down until they can go home.

A rough rule that works well for most retreats: no more than 60–70% of daytime hours should be structured. The rest should be genuinely open not "optional activity B" that's really just structured programming with a different label, but real unscheduled time. Some of the most meaningful connections at a retreat happen in the gaps between sessions, not during them.

The Format Should Follow the Goal, Not a Template

If there's one thing to take away from this list, it's that there's no universal "best" team retreat activity. A scavenger hunt that energizes one team will fall flat for another. A quiet reflective format that builds deep trust in one group will bore a team that's craving high energy after months of remote work.

Before locking in activities, get honest answers to: What does this team actually need right now? What's the one thing we want people to feel or understand differently by the time they head home? Let those answers not a generic retreat activity list drive the final agenda.

Not sure which format fits your team? Talk to Midstay's planning team about your goals, and we'll help you design a retreat built around what your team actually needs not a one-size-fits-all template.

Frequently Asked Questions

What's the biggest mistake teams make when choosing retreat activities? Picking activities because they sound fun on paper rather than because they match the team's actual goal. A high-energy scavenger hunt is a poor fit for a team that's exhausted and craving rest, for example.

How much of the retreat should be structured vs. free time? As a general guideline, aim for no more than 60–70% structured programming. Genuine downtime is where a lot of real connection happens.

Do larger teams need different activities than smaller teams? Often, yes. Larger groups usually need activities that scale well logistically (multi-team formats, larger venues, bigger excursions), while smaller teams have more flexibility for intimate, conversation-heavy formats.

How do we know if our team needs a connection-focused retreat or a strategic one? Ask what's actually missing right now. If the team barely knows each other outside of work tasks, connection should come first. If the team knows each other well but lacks clarity on direction, lean toward a strategic format.

Most business retreats fail not from bad luck but bad sequencing  teams pick a destination first and bolt on an agenda later, ending in patchy Wi-Fi, overpacked schedules, and a rough return to normal life. Midstay flips that order: define the outcome first, size the group honestly, then choose a venue vetted for real work, reliable internet, proper meeting space, and a genuine off-switch for downtime. Agendas need breathing room, budgets should cover the whole trip, and someone must own on-ground logistics. Success isn't measured in photos but in what's different the Monday after  a decision is made, trust rebuilt, momentum that wouldn't exist without stepping away. Midstay handles that heavy lifting end to end.

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A well-planned business retreat is more than a temporary escape from the office it is a strategic investment in people, collaboration, and long-term business growth. By bringing employees into an inspiring environment, companies encourage open communication, stronger relationships, creative thinking, and effective leadership development. Midstay designs customized retreat experiences that balance productive workshops, wellness activities, strategic planning, and team-building sessions, helping organizations align around shared goals while strengthening workplace culture. These retreats improve employee engagement, innovation, and problem-solving skills, creating lasting benefits that continue well beyond the event itself. With the right environment and expert planning from Midstay, businesses can build motivated, connected, and high-performing teams prepared to succeed in an ever-changing and competitive business landscape.

A business retreat is more than just a break from the office it is a powerful tool for building stronger teams, improving communication, and driving long-term business success. With Midstay, companies can create customized retreat experiences that combine team building, leadership development, strategic planning, and employee wellbeing. By bringing employees together in an inspiring environment, organizations encourage collaboration, creativity, and stronger workplace relationships. Midstay manages every aspect of the retreat process, from venue selection and accommodation to activities and logistics, ensuring a seamless experience. Whether supporting remote teams or strengthening company culture, a well-planned business retreat helps boost engagement, productivity, and morale, making it a valuable investment for sustainable growth and organizational success.

A team building retreat is a powerful way to strengthen workplace relationships, improve communication, and create a more connected team. As modern workplaces become increasingly digital, employees often have fewer opportunities for meaningful face-to-face interactions. Midstay helps businesses overcome this challenge by creating inspiring retreat experiences that bring people together in productive and engaging environments. Through collaborative activities, leadership development, strategic discussions, and team-building exercises, employees build trust, enhance communication skills, and develop stronger professional connections. A well-planned retreat also encourages creativity, supports employee well-being, and reinforces company culture. With carefully selected locations and seamless planning, Midstay transforms ordinary corporate gatherings into memorable experiences that boost morale, increase engagement, and help organizations build stronger, more successful teams for long-term growth.

A team retreat is one of the most effective ways to bring employees together, strengthen workplace relationships, and encourage fresh thinking. Midstay specializes in creating carefully planned retreat experiences that help teams step away from daily routines and focus on collaboration, communication, and growth. Whether your goal is team bonding, leadership development, strategic planning, or employee engagement, Midstay provides the ideal setting for productive and memorable gatherings. By combining comfortable accommodations, inspiring locations, and seamless coordination, every team retreat becomes an opportunity to build trust and improve teamwork. Discover how Midstay helps organizations create lasting connections, boost morale, and inspire innovation through customized retreat experiences designed to support long-term business success and stronger company culture.

A business retreat is no longer just a corporate gathering it is an opportunity to inspire teams, strengthen workplace relationships, and spark fresh ideas. Midstay helps companies transform ordinary retreats into memorable experiences by offering thoughtfully selected destinations and seamless planning solutions. Whether the goal is team building, leadership development, strategic discussions, or employee appreciation, Midstay creates environments where productivity and relaxation work together. Away from daily distractions, teams can collaborate more effectively, communicate openly, and return with renewed energy and focus. By combining comfort, convenience, and purpose-driven experiences, Midstay makes every business retreat more impactful. Discover how the right setting can help organizations build stronger cultures, encourage innovation, and create lasting professional connections that support long-term business success.

 In today’s competitive business world, companies need more than meetings and emails to build strong teams. A business retreat offers the perfect opportunity for employees to connect, collaborate, and recharge in a productive environment. Midstay helps organizations create memorable retreat experiences that combine comfort, teamwork, innovation, and professional growth. From strategic planning sessions to team-building activities, a well-organized business retreat can improve communication, strengthen company culture, and boost employee engagement. By providing inspiring locations and seamless planning support, Midstay enables businesses to focus on their goals while creating meaningful experiences for their teams. Discover how a business retreat with Midstay can help modern organizations foster creativity, enhance leadership, and build stronger workplace relationships for long-term success and sustainable growth.

The team retreat has evolved. What companies were doing five years ago on a weekend at a golf resort, some workshops, and a group dinner barely resembles what leading organizations are doing today. The appetite for more meaningful, more intentional, and more experience-rich retreats has grown sharply, driven by the rise of remote work, genertional shifts in employee expectations, and a growing body of evidence about what actually drives team performance.

Here's a look at the trends shaping team retreats in 2026 and 2027 and what they mean for companies that want to stay ahead.

Looking for the perfect business retreat experience? Discover how Midstay helps companies create productive, engaging, and memorable business retreat programs that strengthen teamwork, improve communication, and inspire innovation. A well-planned business retreat gives employees the opportunity to step away from daily routines, connect with colleagues, and focus on strategic goals in a relaxed environment. Midstay offers carefully selected retreat locations and flexible accommodations designed to support collaboration, creativity, and employee well-being. Learn why businesses across the United States are choosing Midstay to organize successful retreats that deliver lasting benefits for both teams and organizations.

When budgets get tight, the company retreat is often one of the first things cut. It feels discretionary. It feels like a perk. It's visible, expensive, and hard to justify with a spreadsheet.

This is a mistake. And increasingly, the data shows it.

Leaders who treat the company retreat as a strategic investment rather than a morale bonus are seeing measurable returns in employee retention, team performance, leadership alignment, and even revenue. Here's why, and how to build the business case for your next retreat.

The success of a company retreat often depends on choosing the right environment. Well-planned company retreat locations help teams step away from daily routines, improve communication, and build stronger workplace relationships. Instead of focusing only on meetings, a retreat creates opportunities for collaboration, creative thinking, and personal connection. Midstay helps organizations find spaces that support both productivity and relaxation, allowing employees to engage in meaningful discussions while recharging their energy. These experiences can improve teamwork, strengthen company culture, and encourage fresh ideas that benefit the business long after the retreat ends. By combining comfort, flexibility, and inspiring surroundings, Midstay transforms ordinary corporate gatherings into valuable experiences that help teams grow together and perform more effectively in the workplace.