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A Complete Guide to Planning a Successful Offsite

Written by Chris (Minwoo) Nam:

Chris (Minwoo) Nam host blogger at driftawave workations and company offsite retreats

5 Benefits of Company Offsites and How to Plan a Successful Offsite:


In today's dynamic corporate landscape, the importance of offsite meetings and retreats cannot be overstated.

Picture this: you’re sitting at the cafe of a ski resort in the middle of the Austrian Alps, sipping a hot chocolate with your favorite coworker talking about how far you’ve come in your career while the rest of your team is out skiing and snowboarding. In an ideal scenario, you’d have your family there, and taking a trip with your team at your dream company - all expenses paid for.

So what exactly does an offsite do and why is this concept of “workation” thriving in recent times? Offsites spark innovation, prevent burnouts, maximize productivity, and allow everyone to get away from the norm and take a much needed break. With the rise of digital nomads, more and more employees are seeking a way to enjoy a life/work harmony - and what better way to provide the perfect harmony between work and life than to take a trip together?

As we dive deeper, this article provides a comprehensive roadmap for effectively planning and executing these events, ensuring optimal productivity and engagement. Whether aiming to rejuvenate team morale or tackling strategic challenges, harnessing the power of offsites can propel organizations toward significant growth and success.

Remote workers having fun at offsite company retreat

5 Benefits of an Offsite:

1. Set the culture:

Offsites provide an opportunity for team members to interact in a relaxed and informal setting, fostering stronger relationships and camaraderie. Without the stress and weight of work on our shoulders, we’re more inclined to start talking about our personal lives, what’s going on behind our work-related minds and open up opportunities for coworkers to become friends. This is a chance for everyone to pick up on the gossip they started in the break room at the office, to start a new conversation about life that they never had before, and to bring more friendly chats about life that they would not have in work settings - some times even clear the air with that one coworker that we don’t get along with.

By enhancing team cohesion and bonding, offsites can help break down barriers and build trust among colleagues, leading to improved collaboration and teamwork. If you’re a small team, this could also break down hierarchical barriers with your boss, or your colleague that you directly manage.

2. A much needed break:

Investing in offsite retreats improves morale and motivation while demonstrating a commitment to employee well-being and development. That pizza party that they threw for your 1 year anniversary? It makes you think “was the pizza good?”, “did I deserve more than a pizza?”. You deserve more than a pizza party for any accomplishments you’ve made at work, whether it was an anniversary or a record revenue month.

Offsites are a huge investment for employees to feel like they belong and appreciated. It offers a chance for everyone to take a break, breath, relax, and have an opportunity for organizational growth.

If this is not something that your company or team has tried before, it may be time to put in the extra investment and take a break with your coworkers. Statistically, team members return from offsites feeling rejuvenated, energized, and more engaged in their work.

Surfing waves during offsite company retreat team bounding and group cohesion

3. Increased creativity & innovation:

Stepping outside the confines of the regular work environment can stimulate fresh thinking and creativity. It’s the same as taking PTO and going on a vacation with your friends. Why do you do it? What do you get out of it? Most times, taking a trip allows you to come back with new ideas, new motivation, and new goals. Much so, offsites will allow coworkers to get innovative together, build better systems in their workflow, and find a new vision for life.

Offsites offer a change of scenery and perspective, inspiring new ideas, brainstorming sessions, and strategic discussions. By encouraging participants to think outside the box and explore different approaches, offsites can ignite innovation and problem-solving skills.

4. Strategic planning and goal alignment:

As a result of the above mentioned benefits, offsites allow coworkers to discuss strategic goals and shared success. It provides dedicated time and space for organizations to focus on strategic planning, goal setting, and vision alignment. Away from day-to-day distractions, leaders and teams can engage in focused discussions, assess priorities, and develop actionable plans for achieving objectives. We’ll dive deeper into how to plan a strategic session later in the article.

Offsites facilitate strategic thinking and decision-making. There may be a crucial decision the team needed to make: this may be the best time to do it as there’s no better way to do a strategic session than at an offsite. All this leads to ensuring alignment across departments and fostering a shared sense of purpose.

Strategic planning and goal alignment during offsite company retreat

5. Productivity and performance boost: 

Lastly, offsites can provide a valuable break from routine tasks and inspire individuals to approach their work with renewed focus and enthusiasm. Let’s put all the above benefits together. The culture is set, we took a break, discussed some innovative plans, set the strategy for the new growth plan. Ultimately, coworkers will return feeling a productivity boost.

By addressing challenges, refining processes, and setting clear objectives, offsites enable teams to work more efficiently and collaboratively. Cheers to much greater success.

Riding waves during the company offsite increasing productivity and engagement

We discussed the benefits: now what?

How do I plan a successful offsite?

Planning a successful offsite retreat or meeting requires careful consideration and attention to detail. Here are five recommended steps with examples to guide you through the planning process:

1. Decide and define clear objectives and outcomes:

Begin by clearly defining the objectives and desired outcomes for the offsite. What specific goals do you want to achieve? Is this more of a team building trip or is it to enhance performance? Whether it's fostering team cohesion, developing strategic plans, or enhancing creativity, having a clear understanding of the purpose of the offsite will guide all subsequent planning decisions.


2024 Offsite Objectives:

  1. Allow team members to become friends or at least open up more.

  2. Give team time and space away from their typical work environment.

  3. Special recognition for breaking sales record or performance enhancement in the last quarter.

  4. Maximize creativity and prevent burnouts.

  5. You need a break too.

Offsite company retreat workation abroad

2. Choose a location:

Selecting the right location and venue is crucial to the success of the offsite. Consider factors such as distance and travel time for all of your team members, facilities and amenities available, and the overall atmosphere and ambiance of the venue. Whether it's a secluded resort, a conference hotel, or a coworking space, choose a venue that aligns with the objectives of the offsite and provides a conducive environment for collaboration and engagement. Take note of what your employees have said in the past; where did Madison from Marketing want to go for vacation when you talked to her last week…?


Team of 25 | Ages 24-58 | Globally distributed in Europe, North & South America, and South Asia | Mostly introverted

Step 1: Decide on 4 places you want to take everyone - Switzerland, Thailand, Canada, Argentina.

Step 2: Run an informal survey - you can have one or two members hear your plan and have them secretly ask where everyone wants to go on vacation.

Step 3: Decide based on the feedback you get from Step 2, keeping in mind that most are introverts and probably don’t want to do too much team building activities, but are all at physically active ages, but from different cultures and backgrounds.

Step 4: Announce the offsite with the location, without disclosing the agenda yet to get feedback. You may and absolutely can change the destination if needed.

3. Develop a meaningful agenda and schedule:

A meeting without an agenda doesn’t go very far. The same goes for an offsite. Building a meaningful agenda and itinerary will allow for the objectives to be met, optimized desired outcomes, and and allow the team members to only focus on having a good time while attending meetings in between. Break down the agenda into specific sessions, activities, and breaks, ensuring a balance between structured sessions and informal networking opportunities. Communicate the agenda and schedule to participants well in advance to allow for adequate preparation and participation.


3 Day Offsite in Banff, Canada

Day 1: Arrival and Team Bonding


  • 9:00 AM - Arrival at Banff, Canada.

  • 10:00 AM - Welcome Breakfast at the hotel or a nearby café.

  • 11:00 AM - Icebreaker activities to facilitate introductions and team bonding.


  • 1:00 PM - Lunch at a local restaurant.

  • 2:00 PM - Scenic hike in Banff National Park, allowing for informal discussions and team building amidst nature.

  • 5:00 PM - Return to the hotel for relaxation and downtime.


  • 7:00 PM - Group dinner at a traditional Canadian restaurant.

  • 9:00 PM - Informal team games or movie night at the hotel lounge.

Day 2: Team Development and Exploration


  • 8:00 AM - Breakfast at the hotel.

  • 9:00 AM - Team building workshop or training session focused on communication, collaboration, or leadership skills.


  • 12:00 PM - Lunch break.

  • 1:00 PM - Group activity such as canoeing on Lake Louise or exploring Johnston Canyon.

  • 4:00 PM - Free time for personal exploration or relaxation.


  • 7:00 PM - Dinner at a cozy restaurant in Banff town.

  • 8:30 PM - Optional stargazing session or visit to Banff Upper Hot Springs for relaxation.

Day 3: Reflection and Departure


  • 8:30 AM - Breakfast and check-out from the hotel.

  • 9:30 AM - Reflection: Each team member shares key takeaways from the offsite and goals for applying them in their work.

Late Morning:

  • 11:00 AM - Adventure activity such as a guided snowshoeing tour or a visit to the Banff Gondola for stunning views of the Rockies.


  • 1:00 PM - Farewell lunch at a local café or restaurant.

  • 2:30 PM - Departure from Banff. Airport transfers or individual departures based on travel plans.

Nature hike during company offsite retreat

4. Facilitate engagement and participation:

Without engagement and participation, an offsite is essentially useless. Design interactive and engaging activities and sessions that encourage participation and collaboration among participants. These could include a mix of team-building exercises, brainstorming sessions, group discussions, and hands-on workshops to stimulate creativity, foster teamwork, and achieve the desired outcomes. Do consider incorporating icebreakers and energizers to create a positive and inclusive atmosphere and keep participants engaged throughout the offsite.


  • Icebreaker: Share a fun fact about yourself that others may not know.

  • Team dynamic: How would you describe our team's strengths and weaknesses?

  • Goal Setting: Are there any challenges or obstacles hindering our progress, and how can we overcome them?

  • Feedback and Improvement: Are there any areas where you feel we could be more efficient or effective?

  • Personal and Professional Development: What skills or knowledge do you want to develop further in your role?

  • Reflection and Appreciation: Is there anyone on the team whose contributions you'd like to acknowledge or appreciate?

  • Vision and Future Planning: Where do you see our team in the next 6 months/1 year/5 years?

5. Evaluate, enhance, and engage:

Let’s say you went on an offsite, planned new strategies, set new goals, and made new friends - but you come back and nothing changed. Not an ideal scenario. As a leader, your role is to evaluate the result of the offsite, enhance workflow and systems that were discussed, and engage in feedback and setting the example and culture.

While the offsite is still fresh on the team’s minds, listen to what the employees are saying, how they’re performing and acting at work, and take note. As you and the leadership team makes changes to allow for better productivity and optimize the work environment, make sure to change what the employees are wanting: just like how we change our products and services to match customer demand - your employees are your #1 customer. In the end, you set the culture. Engage with your #1 customer, make changes to fit the demand, and be the first to see a need then fill a need.

Yacht trip company offsite retreat for incredible team bounding

Driftawave workation and company offsite booking

Are you ready? Then buckle up, soar beyond limits, embark on an unforgettable journey with Driftawave. Our mission is to provide travel experiences that go beyond the ordinary, offering you the opportunity to thrive on both personal and professional levels. Whether you are representing a company to go on an offsite or an individual traveler who is ready to unlock your inner adventurer with like-minded future friends, get in touch with us and let’s journey together.

surfing on company offsite retreat

driftawave workation and company offsite partner

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