Planning a Corporate Retreat? Read This First!

Planning and executing a flawless corporate retreat is a monumental task. The worst part, most people internally at your company don’t quite understand how time consuming and stressful the process can be.

We’re here to make your life easier with this Step by Step Corporate Retreat and Offsite Planning Guide. Follow this guide to streamline and simplify the planning process and set yourself up for a smooth and amazing retreat for your team. You can also download our 2019 Ultimate Retreat Planning Guide.

If you have any questions or need venue or team building ideas for your retreat, don’t hesitate to book a call with our founder today. We typically respond within the hour!

corporate retreat planning

Step 1: Understanding The Why

It’s important to understand the reason and purpose your leadership team is investing in the retreat. We’re talking about diving deeper with your team to extract what the KPI’s and ROI looks like seven days, one month, six months and more following the retreat.

The goal here is to have a clear understanding among the leadership of the purpose of getting away with the team.

Step 2: Identifying Existing Problems

As fun as this company retreat is going to be, we want to be realistic about issues that might be festering inside of the company before going into the planning phase of the retreat. Talk to your leadership team or share with them the issues you have seen arising on the people or culture side of the business.

A couple common issues we see are as follows:

-Rapid headcount growth and many colleagues don’t know each other yet.

-There is a communication disconnect between the leaderships vision for the future of the company and every employee understanding their role within that vision.

-Employees, top to bottom, need a break. They need to get away and celebrate the wins and deconstruct the losses over the past year.


Great company with a great mission. The Offsite Co. team goes above and beyond to make each of our team offsites meaningful and fun! Also love how their approach to the retreats are environmentally friendly. Highly recommend giving them a call for your next retreat.
— ALYSSA | OFFICE MANAGER

Step 3: Outline The Goals, The Vision & The Budget

This is going to be the foundation of any successful retreat. While we’re working on 10+ company retreats and offsites per month with our clients, it’s vital to have a clear understanding of these elements before really diving into any project.

We always recommend working in a collaborative environment when trying to define the goals and the vision. Most often, the budget is assembled along the way but it is important to have a rough idea from finance or leadership on what they are ok with spending on the retreat.

Identifying The Goals: Is this all work, all play or a mix between the two? Are there specific work sessions you want to tackle while away on the retreat? Do you want to see increased communication among new team members? Do you want people to create new connections and have a better understanding of how each role is essential within the growth and sustainability of the business? These are some of the questions we dig into while trying to identify the goals of the retreat with our clients.

Identifying the Vision: We like to ask our clients to describe a rough itinerary outline of the retreat at this point. If you build a rough itinerary on paper, this can give you a really good starting-off point in the next phases of the retreat planning process. For starters, we use blocks of time with key elements from the goals section to fill in a rough itinerary. Some key elements are typically as follows: Transportation, Meals and Drinks, Team Building, Local Experiences, Work Sessions and Downtime.

Identifying The Budget: Work with your leadership to identify a targeted price per person for your retreat. Once you have a target number here, we can reverse engineer the experience based on your goals and vision as described above.

Step 4: Identify Ideal Dates

We use forms for much our planning process with our clients. Start with your leadership team and find a window of dates that work the absolute “must attend” people. Typically, we will walk away with 3-4 ideal date windows that work for the company from here.

Step 5: Finding The Perfect Venue

corporate retreat planning guide

This is where we see a lot of our first-time clients engage our services. Don’t get overwhelmed but also know that if you’re really looking for that perfect venue, it can become a time consuming process.

Here’s a roundup of our top destinations and venues for Bay Area Corporate Retreats.

For venue research, you have to have a good idea of about how many people will be attending. Don’t get to hung-up on the number but make sure have a good realistic estimate.

Take your budget per person and multiple it by 35%. This is your rough venue/lodging cost target for your company retreat. If you have $1,000/person for a 2 night retreat. You should target for $175/night/person for the venue/lodging, maximum. If your team is sharing rooms and you’re looking at a typical hotel stay, your are looking at hotels up-to $350/night/room.

Let your vision and goals help direct the region you start looking in first. We always try to get a sense of destination style from a client. We break it down as follows: coastal/beach, Mountain, River/Lake, Glamping/Camping, or City/Urban.

Retreat Planning Pro-Tip: Always negotiate with the venue for inclusions once you have decided where you want to go.

Retreat Planning Pro-Tip: Ask the venue for a rooming list template. They will typically provide a sample rooming list you can easily fill-out and return to them to simplify the check-in process.

Venue Roundup: Best Corporate Retreat Venues Bay Area

Step 6: Send Save The Dates

The earlier you can get the Save The Date out for your next company retreat, the better. Use an internal calendar or use a site like Paperless Post.

Step 7: Planning for Transportation

Transportation can open up a whole new can of worms if you try to approach the subject too early in the game.

Remember, our goal here is to simplify and streamline the retreat planning process.


What we know about your next company retreat: The approximate number of people attending, where you’re going, the dates of the retreat and the targeted budget allocation.

First off, if you are already tight on budget, our first recommendation is going to be to look at arranging carpool options for your team. Make sure the venue has enough parking spaces for your group and, if they do charge for parking, you’re going to need to negotiate to get that comp’d.

Most often, for our clients, we’re looking at booking private transportation. This is executed in one of two ways.

Transportation Planning A: Full-time transportation throughout the retreat

Transportation Planning B: Two-way transportation. This means that the bus will pick your group up at specific locations and drop everyone off at the venue. On check-out day, the bus will be back and take everyone home. Typically, we like to keep it to 2 total stops per bus but certain cities provide various options in this regard.

All-in-all, the venue, the number of people and the itinerary will be the best indicator of the transportation option you will need. If your group is more than 50 people and you’re investing in multiple off-venue experiences, we’re going to recommend hiring transportation for the entire duration of your company retreat.

Retreat Planning Pro-Tip: The Offsite Co. has a partnership with a U.S. transportation company serving 33 cities throughout the country. Our pricing is typically 30% below group quoted rates.

Retreat Planning Pro-Tip: The venue you’re working with might have a great resource for transportation.

Retreat Planning Pro-Tip: If you’re looking at 50+ person charter buses, make sure to confirm with the venue that a large bus can easily access the front-door or check-in area of the property.

Step 8: Managing Meals and Drinks

The food and drink on a company retreat, when handled correctly, can really be presented as a highlight experience for all. We focus on designing at least one meal as an elevated time for people to connect over food. Here’s our process for organizing the food and drink of a company retreat:

  1. Send a survey to your team to collect food allergies and preferences. This will show your team that you’re thinking about everyone in the retreat planning process.

  2. Go back to your outlined itinerary from the previous steps and decide which meals you want to be group/shared meals and which you want your people to take care of on their own.

  3. Most likely, a couple of the meals will be taken care of at the venue you have chosen. Use your venue contact to get pricing on various menu options for the various meals you plan to offer on-site.

  4. We always start with the first meal offered and work forward through the retreat from there.

  5. Once you have a good idea of how you envision each meal, you can share your allergies and preferences with the various providers you are using to execute the meals.

Step 9: Organizing Work Sessions

Depending on your goals, this will be an action item on your list or you can skip it. Most times though, we want to have at least one area where people can get together to get work done. If you’re like us, we want that workspace to be an inspiring place for people to meet.

Work with your venue to negotiate inclusion for a workspace inside of your quote. For smaller teams looking to get more work done, we use sites like Breather and Splacer.

Step 10: Exploring Local Experiences

Kayaking the Russian River

Kayaking the Russian River

Now we’re onto the most exciting and, in our opinion, the most crucial element of any company retreat or team offsite; The Experience! Going back to your goals, vision, sample itinerary budget; you can create a good idea of what the activities and experiences look like for your team. Planning activities for your group doesn’t have to be a stressful job and you just have to remember that know one knows your company, your culture and your people like you do.

Company Retreat Group Activities: For team building activities, we always recommend running a specific event focused around getting people to connect in new ways. Most of our clients opt for us to design a team olympics, fun run or a scavenge hunt. There is no boiler plate itinerary inside of these activities and each can be highly customized to pull unique things from your company culture to drive better engagement among colleagues.

Company Retreat A-La-Carte Activities: For any size company retreat, we typically offer some time for people to choose what kind of experience they are excited about in the specific destination you have chosen. These include things like white water rafting, kayak tours, hiking, bike tours, survival workshops, crafting, poker tournaments and much much more.

Planning for experiences and activities on a company retreat is where our process extends beyond any event planner or hotelier. The magic is in the process of truly identifying and understand your leadership goals and vision for the retreat. If you’re stuck here, go back to that first itinerary you built and think about the high-level goals you set out. If everyone walked away with one highlight feeling from this retreat, what would it be?

Retreat Planning Pro-Tip: Giving your people a window of time to pick their own experience, from a list provided by you, is a great way to show them that the retreat is truly meant for them. To be able to express and explore their own fit inside of the company and the culture.

Step 11: Planning for Team Building

Team building can be such a scary thing to approach. A healthy and diverse company will see colleagues from all different paths in life, different skill sets, different goals and different interests. Your goal in designing the team building experience is to connect people in new ways. So that when they are back in the office next week, they might have an inside joke or an inspiring moment between them to talk about.

We believe this can happen at various levels and times throughout even a single day retreat and that is why we separate team building time on company retreats into two categories; Structure vs Unstructured.

Structure Company Retreat Team Building:

The Team Olympics: We’ve been running these for years. 40-90 minute event where you will organize everyone into random teams. We do the team organization as an ice breaker event so that off-the-bat, people are connecting in a new way. Once you have team, ask each team to name their team and design a flag. Now we go into a series of 10-20 highly customized events. Each team member has to choose an event to take part in.

Scavenger Hunt: Not your granny’s scavenger hunt here. 90+ minute event that is specific to the destination and venue of your choosing. Split people into teams in the same way as the team olympics. Work with the local area and inside of the vibe of your culture to design various stops for your team collect things. We like the end the scavenger hunt at one location for happy hour or party.

Step 12: Create a Master Timeline

Going back to that initial itinerary you created, we can now fill in each item with a specific Name, Description, Time and Location. We build out these itineraries in a google spreadsheet with our clients. We also color code experiences differently based on the following: Transportation, Meals, Activities, Workspace, Downtime.

Step 13: HAVE FUN!

Trust us when we tell you that we know what you’re trying to tackle here. If you follow the steps above, we hope your planning process will be much more streamlined. The more you can solidify before the retreat starts, the more you will be able to enjoy the retreat.

LatestMat MacDonell