Summary

• Boost Team Cohesion & Morale: Retreats are proven to enhance collaboration, trust, and alignment within teams.
• Avoid Common Pitfalls: Learn how to dodge the 60% failure rate of retreats by mastering key planning steps!
• Save Time & Stress: Discover tools and strategies to streamline logistics (venue sourcing, transportation, and agenda planning) so you can focus on creating an unforgettable experience.
• Maximize ROI: Get expert tips on budgeting, leveraging off-season deals, and negotiating group rates to ensure your retreat delivers value without breaking the bank.
• Tailored Retreat Success: Learn how to design a retreat that aligns perfectly with your organization’s goals.
• Expert Insights & Real-Life Examples: Gain actionable advice from retreat planning pros, including myth-busting tips and a step-by-step guide to planning a seamless, impactful retreat.

Retreats are powerful tools for fostering team cohesion, boosting morale, and aligning organizational goals. However, planning a successful retreat is no small feat. From defining clear objectives to managing budgets and selecting the perfect location, the process is riddled with challenges that can overwhelm even the most experienced professionals.

According to a recent study, 73% of companies believe retreats boost collaboration, yet 60% of retreats fail to meet expectations due to poor planning.

This article delves into the key challenges of retreat planning, offering actionable insights, real-life examples, and practical tips to help navigate the complexities of organizing a memorable and effective retreat.

The (Potential) Retreat Planning Nightmare (and How to Turn It Into a Dream)

Let’s be honest: planning a retreat is hard. There are a lot of people concerned, and so many variables you need to juggle: picking a location, venue, budgeting, agenda planning, flights, food, emails, calls, messages, emails, calls. And all the while, you’re just hoping your team doesn’t end up bored, frustrated, or worse, checking emails under the table.

Why? Because planning is a minefield of challenges. But what if it didn’t have to be? Imagine this: a retreat where your team is energized, aligned, and buzzing with ideas. A retreat that feels seamless, stress-free, and worth every penny. Sounds too good to be true? It’s not.

With OnsiteHub, retreat planning becomes easy. We handle the heavy lifting—venue sourcing, budget management, logistics—so you can focus on what really matters: creating an unforgettable experience for your team. The challenges are real, but so are the solutions. Ready to stop stressing and start inspiring? Let’s make your next retreat the one everyone talks about—for all the right reasons.

What is the Goal of the Retreat?

Now, before you get lost in the idea of sitting on a beach, fine dining in a Mediterranean village, or exploring mountains, you need to answer the first question about retreat planning. Why are you doing this? The why is your goal. It’s the thing you want to achieve. Everything else that follows is in service of this goal.

Whether it’s team building, strategic planning, or leadership development, having a clear goal is essential. Planning the retreat without a unifying goal is to do it backward. Without a well-defined purpose, your retreat risks becoming a costly, unproductive endeavor. Take the time to align with stakeholders and establish measurable outcomes.

For example, you have your classic Team Building Retreats. They focus on improving communication, trust, and collaboration among team members. Then you have Corporate Retreats, which aim to align teams with the company vision, mission, and long-term goals. And one of the fastest growing trends we’ve been working on recently are Leadership Retreats. They’re designed to enhance leadership skills and boost innovation among executives.

But here’s a small word of warning for ambitious organizations. We understand your natural instincts would be to shoot for 2 or more ‘goals’. However, from our experience—for a more productive retreat—it is best to have only one formal goal. And besides, if you happen to win any secondary goals, then that’s just a quality bonus!

What is the Number of Attendees?

Planning without an attendee list is a dangerous business. For example, say you’re doing grocery shopping for a dinner party without knowing the head count. You could risk serving some awkwardly small portions. Alternatively, you could end up with a shameful amount of waste. The number of attendees significantly impacts the retreat’s logistics, budget, and overall experience. So to make it as streamlined as possible for everyone, we like to look at group sizes as small, medium, and large.

Think of small groups as between 10 and 20 people. They’re ideal for intimate, focused discussions and activities. Between 20-50 people is a medium group. Suitable for workshops and team-building exercises. Anything over 50 people is a large group. They require more extensive planning, including venue capacity, transportation, and accommodation.

On many occasions, the group number chooses itself. If you do a company-wide retreat, then it’s as many people as you have on the books. If it’s a leadership retreat, then it’s the number of managers. However, life isn’t always that straightforward. Some people can’t make it for many different reasons. In some organizations, team members are encouraged to bring partners. However, outside of these minor variables, the guest list should be fairly easy to nail down. In short, consider the dynamics of your team and the activities you have planned. A group that’s too large may hinder engagement, while a group that’s too small may lack diversity of thought. And, if you’re feeling lost, talk to a professional!

What is the Timing, the Length of the Retreat, and When Should it Happen?

Timing is everything for a successful retreat. Get it wrong, and you risk low attendance, high costs, or a disengaged team. Get it right, and you’ll create an unforgettable experience. Getting this right takes knowledge, experience, strategy, and communication. Here’s how to nail it:

1. Start Early

Plan 6-12 months in advance. Smaller teams (under 50) can aim for six months, while larger groups (100+) need 9-12 months to secure top venues and avoid last-minute stress.

2. Leverage Shoulder Seasons

Avoid peak seasons to save money and secure availability. Most of the time, off-season travel is 20–50% less than high-season travel.

3. Align with Your Team’s Schedule

Avoid busy periods. Choose a time when your team can fully disconnect and engage. Pro Tip: Survey your team to find the best dates.

4. Keep It Focused

• 1-2 Days: Great for quick team-building.
• 3 Days: Ideal for most corporate retreats.
• 4+ Days: Best for leadership or international retreats.

Leave room for downtime—it’s where the real magic happens.

5. Plan for Follow-Through

Before wrapping up, define clear next steps. Who’s responsible for what? Document everything to keep the momentum alive. 

The Bottom Line

In short, the question of when to start planning your retreat isn’t just logistics – it’s strategy. Start early, pick the right season, align with your team, and leave room for follow-up. With the right timing, your retreat will be a game-changer.

Where Should You Organize Your Retreat?

You wouldn’t plan a book club meeting in a nightclub, and you wouldn’t host a laughter therapy session in a library. The right setting matters. Get it wrong, and your retreat could miss its mark (or blow your budget).

Traditionally, company retreats were called off-sites. But for remote-first teams, off-sites have become the new on-sites. In this new world, not having an office is the saving, and having an onsite is the investment: Investments in collaboration, connections, strategizing, and recharging. Some teams opt for a familiar yet refreshing setting, keeping travel minimal while stepping outside the usual routine. Others go all in with international retreats. This is the full-immersion option. Here work, adventure, and creativity collide.

‍Why Europe is The Top Retreat Destination in The World ‍

Europe is the top destination for corporate retreats for loads of different reasons. It’s the best value for money for a start. But what really brings hundreds of our clients to - and across - Europe is all the different worlds we have on this little continent.

There are beautiful beaches for teams who want to relax. The blue seas and golden sand are waiting for you on arrival, and stress is left at home. For coastal treasures with picturesque towns to explore, we can take you to the likes of Italy and Spain. However, if you prefer your coastal escapes to be more private, then there are beaches in Croatia and Montenegro where you’ll have entire vistas to yourself!

We have cosmopolitan cities where teams charge up on culture and inspiration. Moving and loud spaces, with awesome facilities for all business needs. Think of famed places like Amsterdam, Barcelona, Paris, and Athens.

For organizations that crave adventure, we have dreamy mountains for them to explore. There you have hidden gems like the Serbian mountains, where team-building activities are packed with adrenaline – and the glory of nature to recharge your team's batteries.

Or, you may want rural fairy tales that look too pretty to be true. The rolling vineyards of Italy or the French Chateaux perhaps, where your team can harness the power of tranquility to reflect, strategize, and prepare your organization for success.

What is the Budget, and Can We Afford It?

Our co-founder says “Team retreats are not an expense, they’re an investment.” This statement is true as an investment is a commitment now, to benefit later. Now, that’s not a reason to go crazy. Budgeting is one of the most challenging aspects of retreat planning. Costs can quickly get out of control if they’re not managed correctly – especially if you do things by yourself or with naughty vendors.

The biggest investment you will likely make is in Venue and Accommodation. It’s crucial that you work with a Destination Management Company that can get you a better deal than dealing directly with proprietors.

Your second biggest investment will probably be Transportation. The biggest chunk of this will be for flights – especially for remote teams. Then you’ve got trains, buses, and taxis while you’re on the ground.

Next up, you need to book some quality Activities and Facilitators. There are team buildings to explore, workshops to benefit from, and guest speakers to get your team inspired.

And, of course, you have Food and Beverage to think about. For sustenance, yes – brain food for all these activities. But, you also want to experience local life. What better way to do that than through food? Plus, your team ought to celebrate too!

Putting that into numbers for you, a Sample Budget Breakdown for a 3-Day Corporate Retreat can be seen like this: 

• Venue: 40%
• Food & Beverage: 20%
• Activities: 15%
• Transportation: 15%
• Miscellaneous: 10%

Create a detailed budget and include a contingency fund for unexpected expenses. Remember, a well-planned retreat doesn’t have to break the bank—it’s about maximizing value.

Retreat Planning Advice From an Expert

Now you’ve clued up on the big retreat planning challenges. This means you’re ready for some expert advice on how to smash them! We’re giving you a crash course, taken from How to Plan a Retreat – Masterclass with OnsiteHub co-founder and retreat planning expert, Milana Martinović. So enjoy her retreat planning myth-busting and top Do’s and Dont’s!

Money Myths

Myth: Group rates are always cheaper than individual bookings, just like airline tickets.

Truth: Surprisingly, hotel group rates are often higher than individual rates. Hotels know that groups are less flexible and can charge a premium. However, with the right negotiation skills or a partner like OnsiteHub, you can secure exclusive deals and discounts that actually save you money.

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Myth: Buying out a venue is the best way to ensure privacy and exclusivity.

Truth: While a buyout might sound ideal, it’s not always in the venue’s interest—and it can cost up to 3x more than booking a room block. Instead, consider partial buyouts or off-peak dates to achieve exclusivity without breaking the bank.

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Myth: Hiring an agency is expensive and adds unnecessary costs.

Truth: Agencies like OnsiteHub save you money. They have access to preferential pricing, insider deals, and multiple income streams (like partnerships with venues and vendors) that you wouldn’t get as a one-off group. Plus, they handle the logistics, so you don’t have to pay for costly mistakes.

Do’s and Don’ts: Practical Tips for Overcoming Retreat Planning Challenges

Do!

1. Start Early: Plan at least 6–12 months in advance to secure the best venues and rates.
2. Engage Stakeholders: Involve key decision-makers early to ensure alignment on goals and budget.
3. Leverage Technology: Use event management tools like Trello, Asana, or Eventbrite to streamline logistics and communication.
4. Prioritize Experience: Focus on activities and accommodations that enhance engagement, such as unique team-building exercises, outdoor adventures, or cultural experiences.
5. Allow Ample Travel Time: Account for delays, unexpected situations, and logistical hiccups—it will always take longer than expected.
6. Communicate Clearly and Timely: Provide structured, well-timed updates to keep participants informed.
7. Balance Structure and Flexibility: Include planned activities but allow for sufficient downtime to avoid burnout.
8. Challenge Comfort Zones: Consider individual preferences, but encourage team members to step outside their usual routines.
9. Follow Up and Evaluate: Gather feedback post-retreat to identify areas for improvement and refine future events.

Do Not! 

1. Overambitious Agendas: Cramming too much into a short timeframe leads to exhaustion and disengagement.
2. Ignoring Feedback: Failing to gather input from attendees before planning results in a less effective retreat.
3. Underestimating Costs: Overlooked expenses like transportation, last-minute changes, or incidentals can derail the budget.
4. Unclear Goals: Trying to achieve multiple conflicting objectives in one retreat dilutes the impact.
5. Insufficient Planning Time: Organizing a retreat with less than three months' notice often leads to logistical challenges.
6. Poor Timing Choices: Throwing a party on the first night or having attendees travel back late on Sunday and work on Monday can cause fatigue and disengagement.
7. Trying to Please Everyone: While preferences matter, attempting to meet all individual requests creates unnecessary stress and dilutes the retreat’s purpose.

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‍Ready to take your retreat planning skills to the next level? Subscribe to our newsletter now and get exclusive access to the full How to Plan a Retreat – Masterclass with Milana Martinović. Don’t miss out—your next retreat could be your best one yet!

‍FAQs for Common Retreat Planning Challenges

1. Why are retreats important for organizations?

Retreats help foster team cohesion, boost morale, enhance collaboration, and align organizational goals. They offer a break from routine and provide an opportunity for strategic planning, skill-building, and deeper team connections.

2. What are the biggest challenges of retreat planning?

The main challenges include:

• Defining clear objectives
• Managing budgets effectively
• Choosing the right location
• Handling logistics like transportation, accommodation, and activities
• Ensuring engagement and productivity

3. How do I set the right goal for my retreat?

Start by identifying the primary purpose of your retreat. Whether it's team building, leadership development, or strategic alignment, having one clear goal ensures better planning and execution. Trying to achieve too many objectives can dilute the impact.

4. How do I determine the right number of attendees?

Consider your retreat’s goal, budget, and type—whether it’s a team, department, or all-hands retreat. Groups are usually categorized as:

• Small (10-20 people) – Intimate discussions, focused interactions
• Medium (20-50 people) – Suitable for workshops and team-building
• Large (50+ people) – Requires extensive logistical planning

Also, account for cancellations and whether attendees can bring guests. Tailoring the size to the retreat type ensures the experience aligns with your objectives.

5. When is the best time to plan a retreat?

Start planning 6-12 months in advance for smooth execution. Avoid peak travel seasons to save costs and align with team schedules to ensure maximum participation.

6. How long should a retreat last?

• 1-2 days: Short team-building events
• 3 days: Ideal for corporate retreats
• 4+ days: Suitable for leadership or international retreats

Balance structure with downtime to prevent burnout.

7. Where should I organize my retreat?

Retreat locations fall into three categories:

• Onsite Retreats: Held at the office or virtually; cost-effective but less engaging.
• Off-Site Retreats: Local venues offering a change of scenery.
• International Retreats: Full-immersion experiences, requiring more planning.

Popular destinations include Europe, offering scenic beaches, vibrant cities, and adventure-filled mountains.

8. How do I create a realistic retreat budget?

A typical 3-day retreat budget breakdown looks like this:

• 40% – Venue & accommodation
• 20% – Food & beverage
• 15% – Activities & facilitators
• 15% – Transportation
• 10% – Miscellaneous expenses

Always include a contingency fund for unexpected costs.

9. Are group hotel rates always cheaper?

Not necessarily. Hotels may charge higher group rates due to demand predictability. Working with a retreat planning service can help negotiate better deals.

11. Is hiring a retreat planning service worth it?

Yes! Professional planners handle logistics, secure exclusive deals, and ensure a seamless experience, ultimately saving time and money while maximizing retreat effectiveness.

12. How can I start planning my retreat today?

Contact a retreat planning service like OnsiteHub for expert guidance in organizing a stress-free and successful retreat.