Planning a company retreat can feel like a major undertaking, but with the right approach, it’s an exciting opportunity to reconnect, reflect, and realign. Whether your goal is team bonding, strategic planning, or simply rewarding your staff with a well-earned break, a company retreat is a powerful way to bring your entire team together.
At Wander, we specialize in offering stunning large group vacation rentals for company retreats and corporate stays. From remote woodland cabins to luxurious lakeside estates, we provide more than just a retreat venue – we help create unforgettable company retreats.
Before diving into the retreat planning process, define your goals. What does a successful team retreat look like for your company?
Corporate retreats can help improve communication skills, strengthen team relationships, and provide space to realign with the company's vision.
They’re also an excellent chance to break free from office routines, boost employee engagement, and address team dynamics in a more relaxed, collaborative environment.
Not all retreats serve the same purpose. Choosing the right style depends on your team’s structure, goals, and what you want to achieve from the experience.
Leadership retreats give your leadership team a rare chance to step away from daily operations and focus on the bigger picture. It’s about aligning your team leads and planning for long-term success.
Why host a leadership team retreat?
Strengthen alignment around your company’s vision and future direction
Build trust and improve communication between different teams and departments
Identify roadblocks and brainstorm solutions through collaborative group sessions
Encourage honest conversations in a neutral, relaxed environment
Wander’s luxury rentals are perfect for executive retreats, offering privacy, spacious layouts, and peaceful surroundings that encourage strategic thinking.
With more companies going remote, building real human connections has become a top priority.
A remote team retreat is one of the best ways to strengthen team dynamics when your entire team is spread across different locations.
These retreats go beyond Zoom calls; they help form the foundation of meaningful relationships and long-term collaboration.
Why host a remote team retreat?
Remote teams rarely meet in person, so retreats create vital face-to-face connections
They help teams collaborate on complex projects like product design or big-picture planning
Coworkers get the chance to connect personally, which boosts trust and team bonding
They bring remote employees together to understand shared values and company culture
A whole team retreat is all about bringing everyone together. Whether your company is remote, hybrid, or office-based, spending time face-to-face helps strengthen team dynamics and boost morale.
This kind of retreat focuses on fun, bonding, and building a shared experience – ideal for improving collaboration across different teams.
Why host a whole team retreat?
Encourage stronger communication skills and team bonding
Create shared memories that bring team members closer together
Celebrate wins from the past year and align for what’s next
Help new employees feel connected and welcomed
Top Wander destinations for active, adventure-based retreats include:
Jackson, Wyoming: Skiing, hiking, and mountain adventures, plus luxury rentals like Wander Jackson Hole or Wander Teton Plains to unwind after.
Eatonton, Georgia: Water-based fun on Lake Oconee, including kayaking, archery, and off-roading near Wander Lake Oconee.
These unforgettable company retreats will leave your whole team refreshed, recharged, and more connected than ever.
Not every company retreat needs to be packed with workshops and strategy sessions. Sometimes, the best way to reconnect your team is to slow down and enjoy quality time together.
Leisurely retreats are perfect for rest, reconnection, and pure enjoyment – ideal after a busy quarter or before tackling the next big goal.
Why host a leisurely company retreat?
Recharge your team with a break from fast-paced work
Celebrate milestones, launches, or year-end wins in a meaningful way
Boost morale and create lasting memories in a relaxed setting
Encourage spontaneous bonding through unstructured fun and downtime
Top Wander destinations for luxurious relaxation include:
Wander Secluded Dunes, Port St. Joe, Florida: A luxurious coastal escape with stunning ocean views, an outdoor pool with swim-up bar, sea-facing balconies, a cozy fireplace, and a game room with ping pong and pool.
Wander Mita Luna, Punta Mita, Mexico: A serene six-bedroom villa with panoramic views, a private pool, jacuzzi, chef-prepared meals, and outdoor dining surrounded by lush greenery – perfect for unwinding and celebrating with your team.
Here’s how to organize your next company retreat in 7 simple steps:
Before you start planning logistics, take a step back and ask: Why are we doing this?
A successful retreat has a clear goal. That might be:
Solving a complex challenge that requires in-person brainstorming
Building stronger relationships between remote coworkers
Celebrating wins and recharging morale
Encouraging creative thinking outside of daily routines
Think about what your team is struggling with right now or what it could use more of.
That clarity will shape every decision that follows – from how long your retreat should be to what kinds of activities you’ll plan.
Not all retreats need to be a full week, but they do need to be long enough to achieve your goal.
Here’s a general rule of thumb:
2–3 days: Best for bonding and quick strategic planning
3–5 days: Ideal for deep dives, larger teams, or a mix of work and relaxation
More than 5 days: Rare, but works well if paired with vacation or travel
Tip: Factor in travel time so your team doesn’t spend half the retreat on planes or in cars. And if a full retreat isn’t feasible, even one focused day offsite can be a powerful reset.
Company retreat cost can vary widely, but it’s helpful to start with a per-person budget.
Typical expenses include:
Travel (flights, transport, fuel)
Accommodation
Meals and snacks
Activities and experiences
Venue hire or meeting space
Swag or team gifts (optional)
Make sure to:
Add 10–15% wiggle room for surprise costs
Check if your company’s leadership has budget guidance or a cap
Prioritise activities and accommodations that support your retreat goals (connection, creativity, etc.)
The retreat location sets the tone for the whole experience. Consider what kind of vibe and environment will suit your team best.
Ask yourself:
Do we want urban energy or nature and seclusion?
Is this location easily accessible for everyone?
Can the venue support both work and relaxation?
Also consider:
Accessibility needs
Dietary requirements
Proximity to airports or major transport routes
Try to pick a location where travel isn’t too draining – this helps your team show up energised, not exhausted.
If your retreat is for the team, include them in the process. This will boost engagement and ensure that the retreat reflects real needs.
Ways to involve your team:
Send out a short survey: ask about ideal locations, goals, activity ideas, dietary needs, and more
Ask for volunteers to help plan activities or lead sessions
Create opportunities for team members to share ideas or skills during the retreat (e.g. mini workshops, wellness sessions, etc.)
Also keep in mind:
Some employees (like customer support or operations) may need to stay partially online. Build the schedule with that flexibility.
Not everyone will love the same kind of activity. Offer a mix so everyone can enjoy at least one thing fully.
The best retreats have moments your team talks about long after it's over. That comes from thoughtful, creative activities.
Try mixing it up:
Connection-building: Group hikes, team cooking classes, escape rooms, guided meditations
Skill-sharing: Workshops led by team members on hobbies or passions
Creative thinking: Brainstorming in nature, improv sessions, storytelling games
Relaxation: Spa time, free afternoons, casual hangouts
Remember to tie activities back to your goal. If you’re focusing on collaboration, make sure there’s plenty of opportunity for people to problem-solve together.
Also, always check for inclusivity. Can everyone participate safely and comfortably?
The more you iron out the details ahead of time, the more smoothly the retreat will run.
Don’t forget:
Book travel and lodging early (especially for peak seasons)
Send out an itinerary with key info (dates, times, what to pack, emergency contacts)
Assign point people for different tasks (tech setup, transport, team morale, etc.)
Create contingency plans for weather or schedule changes
Use tools like shared calendars, retreat apps, or even group chats to keep everyone informed before and during the event.
The retreat might be over, but its impact shouldn’t stop there.
Make time to:
Gather feedback with a post-retreat survey (what worked, what didn’t)
Share photos, quotes, or recap videos to keep the energy going
Reflect on the original goals - did you achieve what you hoped?
Turn new ideas into action steps (assign owners and set deadlines)
Follow-up helps show that the retreat wasn’t just a one-off; it was a launchpad for bigger and better things to come.
Whether you're planning team-building activities or a relaxing retreat agenda, Wander’s collection of luxury vacation rentals offers the perfect escape.
We have homes for urban company retreats in New York, Miami, and Los Angeles, and relaxing destinations like Healdsburg, Tennessee, and Cape Cod, Massachusetts.
So whether your team bonds through adventure or unwinds together fireside, we’ll help you find the perfect setting to reflect, recharge, and reconnect.
Yes! Our concierge team is here to support you throughout your retreat planning journey. From transportation and catering to on-site retreat activities, we’re happy to help you create a seamless, stress-free experience for your entire team.
Each Wander property is designed with careful planning, offering:
Fully equipped kitchens (ideal for cooking classes or private chefs)
Large event space or communal areas
Fast Wi-Fi (great for work sessions or last-minute calls)
Access to outdoor areas for team building or relaxation
Support for dietary restrictions with private catering options
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