Business

Planning a team off-site: How to do it in 11 steps

A guide to planning a team off-site, covering goals, budget, venue, agenda, activities, and a timeline.

Did you know?

A full 85% of US employees who’d attended an off-site in the past year said off-sites strengthened their connection to their organization, according to Emburse’s 2025 State of Corporate Off-sites report.

In this guide, we’ll share 11 steps on planning a team off-site that delivers that kind of result.

And if your team travels abroad for the event, Holafly for Business keeps employees online with secure mobile data.

In this article

Why run a team off-site?

A normal workweek keeps your team busy, but it leaves little room to step back and ask whether you’re working on the right things. An off-site creates that space by taking people out of their usual environment for a few days.

That time away gives your team room to do work that’s hard to fit in between meetings.

It also builds trust, because people trust those they know and have spent time with. This is particularly important for distributed teams, where colleagues may rarely meet in person (see our guide to remote work best practices for the day-to-day side).

When to hold a team off-site, and how often

It’s best to hold off-sites on a regular schedule. Even so, some events make an immediate gathering worthwhile.

Examples of such events include:

Low buy-in for the strategy
Confusion about how decisions get made
Reorgs, waves of new hires, or leadership changes
Broken trust or communication
Start of a new year or quarter, or a major business decision

As for frequency, once a year is a sensible minimum, with a second session halfway through the year if your budget allows. Note that not every off-site needs the whole company, and you might run separate off-sites for:

Leadership team
Sub-teams within the company
Whole company
Board

It’s also worth treating the off-site as working time for those who attend, since it’s where the team does its most strategic work.

How to plan a team off-site in 11 steps

These steps take you from the first “why” to the day people arrive.

1. Set goals and outcomes

Start with “Why are we meeting?” before “Where should we go?”, as the purpose shapes every later choice, from the venue to the agenda. Ask what must be true by the end, then pick two or three outcomes everyone on the team can repeat.

Your outcomes will fall into two groups:

Tangible outcomes: Concrete deliverables (e.g., ranked priorities, an agreed roadmap, documented ways of working)
Intangible outcomes: Shifts in how the team feels and works (e.g., more trust, renewed energy, alignment on direction)

To pin both down, work through these questions with your senior stakeholders:

Why are we meeting in person, and why now?
What are the non-negotiable outputs?
How do we want the team to feel?
What’s getting in the way of the team’s success?
What behavior should change afterward?
What should the team stop doing?
What are the constraints (e.g., time, location, existing commitments)?
How will we know it worked two weeks to a month later?

The answers can change your plans, too. For example, if you want the team to feel relaxed and connected, a rental home may suit you better than a hotel conference room.

Write the answers in a brief and use them at every stage, from the budget to the agenda.

2. Decide who attends and involve the team

Choose attendees based on your goals, and leave out anyone who doesn’t need to be there for the outcomes you’ve chosen. Then, gather input from a cross-section of levels and functions with a short survey or a few conversations.

Ask them:

What they hope to get out of the time together
What’s been difficult lately
What they’d consider a waste of time

That said, involve people in the goals, but keep the planning group small. A few organizers, at least one person who’ll attend, and the final approver are enough. It’s also a good idea to tell the team early that the planning group makes the final calls, so people don’t expect endless changes.

Lastly, ask leaders to join the sessions and activities for the whole event. A leader who gives a keynote and then leaves signals that engagement isn’t a priority.

3. Set a budget

The budget shapes every later decision, from how far you travel to whether you hire a facilitator. Set it in a spreadsheet with a tab per cost category, such as:

Travel and accommodation: Flights, ground transport, and individual rooms for every night (often the largest line item)
Venue and AV: Room hire, breakout spaces, and equipment, which some venues bundle and others charge separately
Catering: Meals, breaks, and dinners, including dietary alternatives
Facilitation: An outside facilitator or consultant, if you hire one
Activities: Team dinners, experiences, and other social programming
Materials and gifts: Flipcharts, sticky notes, printed packs, and any swag or welcome kits

If your plan runs over budget, shorten the event or choose a location closer to the office.

However, it’s best not to pick the cheapest venue or hotel, as a decent room shows people their time and effort are respected.

It’s also important to decide what the company covers. In the Emburse report above, 65% of the US employees surveyed said attending an off-site had some impact on their personal finances, with costs such as travel incidentals, childcare, and delayed reimbursements adding up. So, pay for bookings up front or reimburse quickly.

Pro tip: Set aside a ~10% contingency for unexpected costs.

4. Get leadership approval

Turn your brief and budget into a short proposal for the people who sign off.

It should cover:

Purpose and desired outcomes
Benefits for the company and for participants
Draft attendee list
Venue options
Suggested dates and duration
Outline of the main sessions
Budget and approximate costs

It’s good practice to work your key stakeholders’ constraints (e.g., dates, budget limits) into the proposal from the start, so the decisions stick once approved.

5. Choose the right venue and location

It’s key to match the venue to your goal.

A resort with plenty of amenities can work for building relationships, but it can distract a team that needs to focus on a few issues, and a relaxed, casual setting suits a team recovering from an intense period of change.

Still, you may want to avoid defaulting to a hotel conference room unless your goals are meeting-heavy. A space that feels different from the office, such as a large house or a venue with access to nature, helps people step out of the day-to-day.

Then, check the venue offers these non-negotiables:

Transport links: Within ~60 minutes of a well-connected airport or major transport hub
Working space: At least a main room for everyone, a breakout room, and an informal lounge for a group under 20
Natural light: Daylight in the main room, as windowless rooms drain energy by mid-afternoon
Comfortable temperature: Working heating or air conditioning, which is worth checking at a villa or smaller rental
Own rooms: Individual rooms, so people have space to rest
WiFi: A connection that holds up for the whole group

Nice-to-haves include outdoor space for walks, a bar or lounge for evenings, rooms you can rearrange, and on-site food.

For off-sites longer than a day, keep everyone on the same property, with shared meals and a communal area, or at least within walking distance of the workspace. It’s also best to keep the location practical for the team, as a far-off destination can rule out parents of young children, people caring for older relatives, and anyone with pressing local commitments.

For a distributed team, pick a place that doesn’t leave one or two people with a much longer journey than everyone else.

6. Decide how long it should run, and when

A one-day or even half-day off-site can work, but people often need time to warm up.

That’s why two days is ideal, with dinner together on the first night, as the second day is often when the biggest insights come.

As for dates, involve the team, so you pick a time that works for them, and announce the dates early so they can plan around family commitments.

7. Build the agenda

Go back to your brief and list what has to happen to reach your outcomes.

Start with must-haves before any nice-to-haves, since an agenda packed with every good idea leaves no room for the work.

Each day can be split into four working blocks of about 90 minutes: two before lunch and two after, each pair split by a break. Place your non-negotiables and biggest topics first, then let the rest of the schedule flow around them. Next, put the hard thinking in the morning and leave relationship-building and reflection for the afternoon and evening.

Another approach for a two-day off-site is to spend the first day on the business (e.g., results, goals, and plans) and the second on the people (i.e., how the team works together and what would help it work better).

Then, build in breathing room:

Buffer of 5–10 minutes around sessions
Morning and afternoon coffee breaks
Lunch of at least an hour
One to two hours of personal time between the last session and the evening program

It’s also a good idea to plan an opening session (i.e., welcome, goals, expectations) and a closing session.

8. Choose formats and activities

A day of back-to-back group discussions tires people and leaves quieter voices unheard. That’s why it’s best to mix formats and favor interactive work over slide decks.

A few formats work well at off-sites:

Guided journaling: People write responses to a series of prompts before sharing, so everyone can form their thoughts first.
Partner walks: Pairs walk for ~20 minutes, with one person speaking on the way out and the other on the way back.
Small group huddles: Groups discuss a prompt or work on a task, then report back to the room.
Affinity diagramming: Everyone writes ideas on sticky notes, then the group sorts them into themes before discussing them.
Around-the-circle discussion: Each person speaks in turn, so every voice is heard.
Silent brainstorming: People generate ideas alone before a group session, which gives a break from intense group work.

For social time, choose activities that need collaboration and keep the stakes low, such as:

Cooking classes or culinary challenges
Escape rooms or scavenger hunts
Volunteering (e.g., environmental cleanups)
Pottery or art classes
Game nights
Outdoor activities (e.g., hikes, a picnic)
City tours

Whichever you choose, connect it to a goal and follow it with a debrief on what it means for the team’s work.

Pro tip: Keep evening events optional and give everyone one free night, so people who need time alone can recharge.

9. Manage logistics

Logistics determine whether people can focus once they arrive. Collect what you need with a survey one to three months in advance and work through each area:

Travel: Arrival and departure times, ground transport, and a backup plan for delays
Catering: Breakfast before the first session, coffee breaks, a lunch of at least an hour, dinners, and water and snacks throughout the day
Dietary needs: Allergies, intolerances, and preferences, sent to the venue three to four weeks in advance, with more than one vegetarian option
Materials: Flipcharts, markers, sticky notes, paper, pens, and a screen with a confirmed HDMI or wireless connection
Rooms: Room preferences and accessibility needs, gathered before you book
Safety: Safe transport and accommodation, with one go-to person for on-the-day problem.

Pro tip: Keep everything in one master spreadsheet, including backup activities in case the weather ruins outdoor plans.

10. Make the off-site inclusive and accessible

An off-site only works if everyone can take part. So plan for these needs from the start:

Varied activities: A mix of physical, creative, and intellectual options for different ages, abilities, and interests
Food requirements: Dietary, religious, and allergy needs collected early and locked in with the caterer
Accessibility: A venue where people of all abilities can move around, and adaptable activities (e.g., a paved, wheelchair-accessible trail option on a hike)
Alcohol-free options: Social events that don’t center on drinking
Caregiver needs: Time to check in with family and, where needed, a private room for nursing parents
Downtime: Quiet time and privacy for people with different energy levels

11. Communicate early and set expectations

Announce the dates and purpose as soon as they’re confirmed, and share details as early as possible so people can arrange to attend.

Once confirmed, send everyone the:

Goals and agenda
Travel and hotel details
Dress code
Split between work sessions and free time
Times to check email

Tell people the topics in advance, too, so no one feels ambushed and everyone can come prepared.

As for pre-work, ask a few people to prepare the materials the sessions will need (e.g., results summaries, financial forecasts, key questions) and give everyone time to read them in the room.

Keep all of this on a single shared page or channel (e.g., Notion, Slack) so people can find details without having to ask the organizer (see our guide to remote team communication tools).

Team off-site planning timeline

For a larger off-site, start three to six months in advance and work through the tasks in this order.

Here’s how it looks:

When	What to do
Three to six months before	Set goals, form the planning group, set the budget, get approval, and shortlist venues
Two to three months before	Book the venue, rooms, facilitator, and activities, and send the pre-event survey
Three to four weeks before	Finalize the agenda, send dietary needs to the venue, and share details and pre-work
One to two weeks before	Confirm materials, room setup, and what the venue provides
Right after	Send a feedback survey and share a recap

For a full list of tasks, see our corporate event planning checklist.

Keep traveling employees connected with Holafly for Business

When your team flies in for an off-site abroad, secure mobile data is key.

Holafly for Business is a business eSIM provider available in 160+ destinations that activates on your team’s devices, so they don’t have to worry about local SIM cards or roaming charges. You also get access to our centralized management platform, the Holafly Business Center, where you can manage individual eSIMs, invoices, and data usage.

Holafly Plans for Business come in four tiers, all featuring hotspot, 4G/5G, and 24/7 multilingual support:

Daily: Unlimited data with pay-per-day flexibility, built for short business trips under 16 days a month.
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Annual: Unlimited data for ultra-frequent travelers, suited to long-term global operations and predictable annual budgets.
Enterprise: Bespoke plans for companies managing travel for 20+ employees a year, with volume discounts, a dedicated account manager, priority support, and custom integrations, built to optimize costs, streamline operations, and ensure seamless global connectivity across teams.

Not sure which plan is right for your team? Book a demo.

Max Woolf

Writer

I’m a writer with over eight years of experience in digital content. My work has appeared in publications such as The New York Times, Forbes, Business Insider, and the BBC. At Holafly, I write clear, practical guides to help travelers stay connected with eSIM technology. In my spare time, I enjoy car detailing, biking around Warsaw, and capturing portraits.

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