Plan the perfect corporate retreat (2025 edition)
Your team's Slack threads are collecting digital dust. The once-vibrant #random channel now echoes with the occasional reaction emoji. And those virtual team builds? They've devolved into 30-minute obligation sessions where half your team "has their camera off for bandwidth reasons." (Spoiler: they're folding laundry).
Time to admit company retreats aren't optional luxuries anymore. They're strategic necessities. In 2025's distributed work landscape, these in-person gatherings deliver ROI that virtual alternatives just can't match.
But planning an effective retreat requires more than booking flights and picking a cool location. You need a smart approach that creates lasting business value beyond the trip itself.
In this guide, we’ll give you everything needed to execute the perfect company retreat in 2025. From retreat types that actually work to venues worth the airfare to painless logistics, we’ve got you covered.
Why investing in a team retreat pays off
Company retreats aren't expensive vacations put on the corporate card. They're smart business investments with measurable returns. When teams connect in real life, they build collaboration foundations that persist long after they've returned to their Slack channels.
These face-to-face interactions translate directly to your bottom line in some of the following ways:
Enhanced communication: Teams who've shared meals or adventures communicate more effectively through digital channels
Creativity boost: Getting away from routine work environments sparks innovative thinking and fresh problem-solving
Morale lift: 83% of workers say corporate travel is a job perk, making retreats a powerful way to boost morale and attract and retain top talent
Sprint-like progress: Make significant headway on key initiatives in compressed timeframes
Culture reinforcement: Transform abstract company values into lived experiences
The trust built during retreats creates "positive currency" that pays dividends during virtual collaboration. When someone's message seems terse months later, that shared karaoke night may help teammates assume good intentions rather than defaulting to defensiveness.
Different types of company retreats
When starting your company retreat planning, get clear on which retreat format matches your goals:
Team-building retreats
These are relationship-focused gatherings with shared experiences outside work context. Think cooking classes, adventure challenges, and structured connection activities. Perfect for newly formed teams or companies experiencing growth spurts.
Leadership/strategy retreats
For executive teams or department heads, these ditch trust falls for focused planning and alignment. The agenda features workshops and problem-solving sessions where being in the same room creates breakthrough moments impossible on Zoom.
Hybrid retreats
This is the modern answer for companies with both remote and in-office teams. These experiences bridge different work styles with activities that level the playing field, ensuring everyone leaves equally connected.
One-day company retreat ideas
Budget-friendly and low-commitment, these mini-retreats deliver concentrated connection without extensive travel. Ideal for teams in the same area who need regular in-person touchpoints without logistical complexity.
How to plan a successful company retreat (6 easy steps)
Skip the planning overwhelm with these straightforward steps:
Step 1: Define your goals
Move beyond vague "team bonding" objectives. Are you solving communication breakdowns? Accelerating a critical project? Reigniting creativity? Your goals will drive every other decision.
Ask yourself:
What specific problems will this retreat solve?
What tangible outcomes will make it successful?
How will we measure impact afterward?
Step 2: Set your budget
Be realistic about costs when planning a company retreat. Your budget should cover:
Transportation (flights, transfers, vehicles)
Accommodations
Food and drinks
Activities and experiences
Meeting spaces and equipment
Emergency buffer (add 15%)
Expect $1,000-$3,000 per person for multi-day retreats. Naturally, one-day local gatherings often cost significantly less.
Step 3: Choose a location
Find a venue that matches your goals, budget, and team vibe. Consider:
Accessibility for all participants
Activities aligned with your objectives
Appropriate accommodation options
Functional meeting spaces
Seasonal factors
Safety considerations
For creative work, choose inspiring environments. For strategic planning, seek distraction-free spaces with good work facilities.
Step 4: Plan activities and free time
Avoid overscheduling. Balance is essential:
Targeted team-building activities that serve your goals
Focused work sessions when needed
Group meals and social events
Unstructured time for organic connections
Optional activities for different interests
The most memorable moments often happen during unscheduled time.
Step 5: Communicate expectations early
Set clear ground rules before departure:
The "why" behind the retreat
Agenda highlights and must-attend sessions
Packing guidance
Family/partner policies
Work expectations
Cultural considerations for international destinations
This helps everyone prepare appropriately.
Step 6: Post-retreat follow-up
Multiply the impact with proper follow-through:
Gather feedback while memories are fresh
Document key insights and action items
Create accountability for initiatives
Share photos and stories
Recognize contributions
This ensures your investment continues paying dividends long after everyone returns.
Company retreat ideas to inspire your planning
Skip the trust falls. These company retreat activities deliver meaningful connections while advancing business goals:
For team bonding that isn't forced
Local cooking classes: Master regional cuisine together. The shared struggle over unfamiliar techniques naturally breaks down barriers.
Custom scavenger hunts: Design challenges incorporating your company values, turning abstract principles into experiences.
Outdoor microadventures: Try kayaking, hiking, or zip-lining to create natural opportunities for mutual support.
For strategic thinking beyond the whiteboard
Designathons: Run focused 24-hour sprints to tackle business challenges with mixed teams that break departmental silos.
Future scenario planning: Create exercises where teams navigate potential industry futures, identifying threats and opportunities.
Customer journey field trips: Experience your product as customers do, documenting pain points in real environments.
For impact beyond your company
Localized volunteer projects: Partner with organizations addressing issues relevant to your business values.
Environmental initiatives: Participate in restoration projects that leave the retreat location better than you found it.
Skill-sharing workshops: Tap your team's hidden talents through peer-teaching sessions.
For recharging alongside productivity
Movement sessions: Offer morning yoga, running groups, or strength training to energize the day.
Stress management workshops: Provide practical tools teams can apply back at work.
Structured free time: Block periods for unstructured exploration, especially for introverts who need recovery time.
The best company retreat ideas feel authentic and energizing while still supporting your business objectives.
Best company retreat locations
The right location transforms a good retreat into an unforgettable one. Here are venues that consistently deliver:
International destinations that wow
Bali, Indonesia: Wellness-meets-culture with affordable luxury. Ubud offers spiritual elements while coastal areas provide adventure options.
Quebec City, Canada: European charm without the travel time. Cobblestone streets, exceptional food, and bilingual environment create instant immersion.
Portugal (Lisbon, Porto, Algarve): The value champion. Great food, affordable lodging, and activities from urban exploration to coastal adventures.
Mexico (beyond tourist zones): Skip Cancun for Todos Santos or San Miguel de Allende. You'll find authentic experiences with excellent retreat facilities.
Domestic options worth considering
Napa Valley, California: Food-and-wine paradise with scenery rivaling Tuscany, close to major airports.
Asheville, North Carolina: A perfect blend of outdoor adventure and creative energy with a thriving arts scene.
Park City, Utah: Year-round destination with winter sports, summer activities, and great meeting facilities. Salt Lake City airport proximity adds convenience.
Austin, Texas: Urban energy without big-city hassles. The food, music, and unique venues create natural conversation starters.
When choosing your company retreat location, focus on:
Budget reality: Be honest about what you can spend
Travel accessibility: Consider total door-to-door time
Accommodation fit: Find lodging matching your company culture
Activity alignment: Ensure available experiences support your objectives
Seasonal factors: Research typical weather patterns
Tech infrastructure: Confirm reliable connectivity if work is planned
Expensify’s retreat experience
At Expensify, we take a different approach. Each year, we select a foreign country for a three-week workation, moving to a different city weekly. This isn't vacation; it's normal operations in extraordinary settings.
Why? We've found that unfamiliar environments create authentic connection opportunities. When colleagues navigate a new metro system or discover a hidden café together, they form bonds digital spaces can't replicate.
Our past locations include:
Perugia, Alghero, and Bari (Italy)
Lagos and Porto (Portugal)
Quebec City (Canada)
Canggu, Ubud, and Jimbaran Bay (Bali)
How Expensify streamlines corporate retreats and travel management
Retreat logistics can derail even the best plans. Between flight bookings, expense tracking, and reimbursements, the administrative load can overshadow the retreat's purpose. Expensify Travel transforms this experience.
At Expensify, we apply our own solutions to our retreats. Before each trip, we create dedicated workspaces in New Expensify: one for #announcements and another for #social events where employees share and coordinate activities. Our "social budgets" let team members get activities reimbursed by posting invites in the #social channel.
This creates connections that transform remote work. As a company with an asynchronous work culture, we've seen these shared experiences pay dividends months later. Trust built over Portuguese wine or during cooking classes helps colleagues assume good intentions rather than misinterpreting digital messages.
Here's how Expensify Travel eliminates retreat planning headaches:
Centralized booking that works
Book flights, hotels, and transportation from a single platform. No more juggling multiple booking sites or confirmation emails.
Realtime expense visibility
See spending as it happens with automatic categorization. No more post-retreat spreadsheet nightmares.
Smart travel policy enforcement
Set spending guidelines that prevent budget disasters while maintaining flexibility. The system handles enforcement automatically.
Fast reimbursements
Process repayments quickly. No more waiting weeks for accounting to settle expenses.
Group travel coordination
Manage multiple itineraries simultaneously with at-a-glance arrival tracking.
Receipt capture that delivers
Our SmartScan technology automatically captures and categorizes receipts, simplifying accounting and tax compliance.
By handling these logistical details, Expensify lets you focus on creating meaningful experiences rather than drowning in administrative tasks.
Go big or go home
Every successful retreat needs one showstopper event – an unforgettable experience people will still discuss years later. Building anticipation for these signature moments elevates the entire retreat.
The magic formula? Create something that:
Could only happen in that specific company retreat venue
Feels slightly exclusive or unexpected
Creates a shared "can you believe we did that?" moment
These aren't just fun experiences; they're strategic investments in team connection. When colleagues face challenges months later, these shared memories create a foundation of trust that transforms virtual collaboration.
Skip the generic "nice restaurant dinner" for experiences that leverage your location's uniqueness and align with your company's personality. You won’t regret it.
FAQs about corporate retreat planning
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A company retreat is an organized event where members of an organization get together outside of the regular workplace for a specified period, ranging from a few hours to a month.
They’re typically held at off-site locations, away from the office environment, to provide a change of scenery and create a more relaxed and conducive atmosphere for the planned activities.
A company retreat can also be referred to as a “team retreat”, “corporate retreat”, or “team building retreat”.
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Absolutely – when done right. Well-executed retreats deliver measurable ROI through improved collaboration, enhanced communication, accelerated project completion, and significantly higher retention rates.
For remote teams, especially, the in-person connections formed during retreats help counteract digital isolation and build trust that transforms virtual collaboration. The key is having clear objectives tied to business outcomes, rather than just planning a fancy vacation.
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Yes, company retreats are generally tax-deductible as legitimate business expenses when they have a clear business purpose. Deductible costs typically include meals, transportation, lodging, and business activities.
Keep meticulous documentation, including agendas, business purposes, and attendee records. The rules get trickier when mixing business with recreation or including family members, so consult your tax professional for your specific situation.
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Pack strategically for maximum comfort and appropriate professionalism. Most company retreats adopt business casual for work sessions, with specific guidance for special events or activities. Consider asking your retreat planner for a business trip checklist to help you pack appropriately.
A smart approach: pack versatile layers that can transition from casual daytime activities to slightly more polished evening events.
Level up your company retreat game with Expensify
Ready to create a company retreat that actually delivers on its promises? Let Expensify Travel handle the headaches while you focus on designing experiences your team will still be talking about next year.
Our all-in-one platform eliminates the chaos of traditional retreat planning – from booking flights to managing expenses to processing reimbursements faster than you thought possible. And with Expensify Chat, your team stays connected before, during, and after the retreat, maximizing those relationship dividends.
Make your next retreat the easiest to plan and the hardest to forget.
