How to Choose the Right Location & Venue for Your Next Team Offsite
A team offsite is no longer just a few PowerPoint sessions in a bland hotel ballroom. For innovative companies, it’s a chance to step away from the day-to-day, spark creativity, and strengthen the human side of work, which can get lost behind a computer screen.
Done well, an offsite can boost morale, increase engagement, and give your entire team a sense of shared purpose.
Done poorly? It feels like an expensive field trip.
The difference starts with where you host it.
So how do you choose the right location and venue for your next team offsite?
It begins with getting clear on your goals — why you’re bringing people together and what success should look like when everyone returns home. From there, you’ll want to consider:
- Travel ease: How simple it is for your team to reach the destination.
- Atmosphere & culture: Does the place match your company’s personality and inspire the mindset you want to cultivate?
- Accommodations & design: Will the venue you choose keep people comfortable, inspired, and connected?
- Technology & support: Strong Wi-Fi, AV, and on-site help can make or break productivity.
- Experiences beyond the boardroom: Activities that build trust, spark ideas, and keep energy high.
After hosting corporate retreats and events for more than 20 years in the heart of Costa Rica, we know what it takes to create off-sites that leave a lasting impression on your team’s connection and on your business’s bottom line.
In this post, we’re sharing our insider tips and expertise for planning the best team offsites.
What’s the most important part of planning team retreats?
A location that will spark creativity, increase engagement, and boost morale.
Step 1: Get clear on your offsite purpose
Before you open Google Maps or RFP a single venue, answer:
- Why are we bringing the team together?
- What do we want people to feel and take away when they return?
- How will we know this offsite was worth the investment?
Your answers will guide every other decision from the vibe of the destination to how much tech infrastructure you’ll need.
Step 2: Weigh the core location factors
The location sets the entire tone and practical foundation for everything that follows.
It’s more than flights and Wi-Fi (while those things are of the utmost importance, too); it’s about what the place signals to your employees and leadership.
| Factor | Key Question to Ask | Why It Matters |
| Travel Ease | Are there direct flights?
How long is the ground transfer? Will the team have jet lag/ cross too many time zones? |
Short, simple travel saves budget and prevents fatigue before you even start. No one wants strategy sessions at the 3AM equivalent their time. |
| Legal & Compliance | Are there visa requirements that are restrictive for some team members?
Are there tax implications or benefits of hosting in a certain destination? |
For global teams, hosting in places like the U.S. is complicated right now with visa challenges. Choose a destination with more flexible visa rules to avoid headaches for international team members. |
| Venue Availability | What kinds of venues are there?
Do these venues have availability? |
Location and venue go hand-in-hand. You may have a dream location, but if they don’t have a hotel, villa, or resort that will work to host your team, it’s not a plausible location. |
| Vibe & Culture | Does the destination align with your company’s personality and offsite goals? | A creative coastal town feels different than a financial district boardroom. |
| Safety & Stability | Is it business-friendly and safe for employees?
Is there reliable healthcare nearby? |
A relaxed, secure team engages more fully. You also don’t want to have your team get special vaccinations just to travel to your meeting locale. |
| Accessibility & ADA Compliance | Are spaces wheelchair-friendly, with ramps, elevators, and accessible rooms? | Ensures inclusivity and compliance with corporate policies. |
| Activities Beyond the Boardroom | Can we layer in adventure, wellness, or cultural experiences and excursions for team-building? | These moments create the bonding Zoom can’t. |
| Climate & Season | Will the weather support outdoor sessions or recreation? | Sunshine = energy. Rain = potential backup plan required (unless you have a venue that’s perfect for rainy season, like Villa Punto de Vista). Snow = delayed flights. |
| Connectivity & Tech | Will Wi-Fi and AV support your work sessions? | Nothing kills momentum like bad tech. While this is sometimes venue-specific, it can also be country or region-specific. |
| Prestige & Perception | Will this impress attendees? | Your offsite also signals company values. |
| Privacy & Discretion | Can your team meet confidentially without risk of outsiders overhearing or photographing? | Important for sensitive strategy, product launches, or legal conversations. |
| Budget | Does the location have venues that are within our budget?
Does the transportation cost fit within budget? |
The cost of a retreat in Bali and a retreat in New York City may end up being similar because of transportation cost, you want to factor in all budget factors before you decide. |
Insider perspective
We’ve watched offsite teams who had only met on Slack become fast friends after a few days together overlooking the Pacific, surfing at dawn, and sharing rooftop dinners. Location matters.
Step 3: Build your destination shortlist
With the above factors in mind, make a list of destinations that would work, and eliminate those that may not fit the bill due to tricky visa requirements, no quality off-site venues, weather concerns, or budget restrictions.
Then, once you have a couple of options, it’s time to move on to venue sourcing, which is typically what helps organizations solidify which spot is going to be the best for their attendees.
Why does a successful offsite start with good venue selection?
Once you have two to three potential destinations, make a shortlist of venues you like in each destination.
You can use tools like Cvent to send out a full RFP or search for those that meet your criteria in Venue Report and make your own list in a Google Sheet that can be shared across your team. Both of these venue sourcing tools cover international destinations, whereas some don’t, so be sure to check if you’re looking to host your team internationally.
Remember that the venue becomes the stage for everything: meetings, meals, late-night conversations that change strategy, and ultimately make money in the long term.
You’re finally out of the office, creativity is flowing between rest, relationships are being built, and team morale is high. But if there are issues or discomfort with the venue, that doesn’t happen.
What should I look for when choosing a company offsite venue?
So, as you’re searching for that offsite meeting venue, what should you be looking for to find a spot that will foster meaningful connections, support company culture goals and team bonding, make the planning process simple, and help you save money?
Here’s your venue sourcing checklist:
Logistics & Access
- Distance from the closest airport
- Reliable ground transportation (private transfers, shuttles, or concierge service)
Venue Fit & Experience
- Sufficient space for the entire group (sleeping rooms and meeting rooms)
- Meeting rooms with natural light, flexible layouts, and pro AV/Wi-Fi
- Private or semi-private spaces for sensitive discussions
- Comfortable sleeping arrangements (single occupancy where needed)
- Wellness, adventure, or cultural activities nearby or on-site
- Inclusive & ADA-friendly design (ramps, elevators, accessible rooms)
Budget & Contracts
- Transparent pricing with minimal hidden fees
- Clear F&B policies (corkage, buyouts, bespoke dining)
- Simple attrition/cancellation clauses
- Predictable cost per head (or clear buyout model)
Brand & Culture
- Venue vibe aligns with company personality and offsite goals
- Branding opportunities (signage, lighting, takeovers)
- Balance of prestige and comfort (signal company values, reward team)
Safety & Stability
- Secure, friendly destination like Costa Rica
- Reliable healthcare nearby
- Low political or environmental risk during your chosen season
Tech & Productivity
- Strong, enterprise-grade Wi-Fi
- Backup internet or IT support available
- AV support and on-site tech help
Staffing
- Sufficient staff dedicated solely to your group
- Trusted service levels (as indicated in reviews, or a contract clause)
Food & Beverage
- Ability to cater to diverse dietary restrictions
- Healthy, fueling cuisine for ultimate creativity and brainpower
Planning Ease
- On-site concierge or event coordinator
- Trusted vendor network for excursions, team-building, and transport
- Responsive, experienced sales/event team
How do retreat venues vary in terms of services and amenities?
We get this question a lot from startups and companies looking to host a team retreat or offsite meeting for the first time.
How is hosting at a private luxury villa different from a typical hotel or all-inclusive? Let’s break it down:
| Criteria | Standard Hotel / Conference Center | All-Inclusive Resort | Private Villa (Fully-Staffed Estate) | Airbnb Rental (1+ Homes) |
| Privacy / Exclusivity | Shared property; difficult to secure full privacy | Shared; guest density high | Exclusive-use; full buyout for ultimate privacy | Neighbors, shared spaces |
| Meeting Spaces (AV, Breakouts) | Built-in ballrooms/AV; many breakouts, standard design | Decent AV; tourist-oriented | Custom pro AV brought in; flexible room layouts and creative venues | Inconsistent; usually DIY |
| Staffing & Service | Banquets, AV techs, sales mgr. | Large staff; service varies | Concierge, private chef, butler, driver; one team just for you | Host only, no service provided in many cases |
| F&B Quality / Flexibility | Package menus; corkage, many additional fees | Buffet-heavy; limited bespoke | Bespoke menus, wine pairings, brandable dinners | Cook or outsource; inconsistent |
| Agenda Customization | Moderate; venue rules/curfews | Low–moderate; fixed programming | High; timelines, spaces, and experiences tailored | DIY; limited by house rules |
| Branding / Takeovers | Limited; hotel branding prominent and subject to property restrictions | Limited; hotel branding prominent and subject to property restrictions | Full brand canvas (signage, lighting, menus, gifts) | Full brand canvas but all DIY, no support |
| Team-Building Access | Vendor list; off-property shuttles | On-site activities; touristy | Curated adventures for your team specifically by a concierge in many cases (national park, catamaran, beach BBQ, spa) | Must source vendors on own; transport gaps |
| Security / Discretion | Standard hotel security | Standard; crowded | On-site security; discreet events; NDAs optional | Minimal |
| Noise / Curfew | Strict event windows | Entertainment zones but rules | Manageable, within local regs; no other guests | Strict; neighbors/HOAs |
| Sleeping Rooms (Single Occupancy) | Many rooms; easy splits | Many rooms | Suites; fewer total keys—great for exec teams | Few beds; odd layouts |
| Group Size Sweet Spot | 30–500+ | 50–500+ | 8–40 in one villa; 50+ with estate/overflow | 6–20 across homes |
| Cost Predictability | Room blocks + banquet minimums + fees | Per-person predictable | Clear buyout + curated add-ons; high value at HNW level | Variable; add-on creep |
| Hidden Fees / Contracts | Attrition, service charges, resort fees | Service charges, upsells | Transparent; fewer line items | Cleaning, extra guests, event bans, no protection from cancellation by host |
| Booking Lead Time | Moderate | Moderate | 9–12+ months for prime dates | Short if flexible |
| Accessibility (ADA) | Strong | Strong | Elevators/ramps vary by property | Rare |
| Connectivity (Wi-Fi/IT) | Enterprise-grade | Good enough | Strong Wi-Fi; enterprise gear rentable in many cases | Unreliable with no support |
| Transportation / Logistics | Easy; central | Easy; shuttles | Private transfers; concierge-managed | DIY cars/rideshares |
| Risk / Compliance | Proven processes; rigid terms | Proven; tourist focus | High-touch management; bespoke docs | Event restrictions; neighbor risk |
| Standout Advantage | Scale, infrastructure | One price, lots of amenities | Total privacy, bespoke luxury, unforgettable setting | Cheap(-ish) + casual |
| Best For | Large, agenda-heavy meetings and conferences | Incentives, large mixed groups | C-suite/board offsites, leadership retreats, high-trust work | Budget teams, informal meetups |
Insider Tip
For C-suite or board offsites, leadership retreats, and high-impact strategy sessions, a fully staffed private estate strikes the balance between discretion, customization, and white-glove service without the distractions of a resort or the DIY headaches or cancellation risk of an Airbnb.
FAQs for Team Offsite Meeting Planning
Q: How far in advance should I book my offsite venue?
A: For popular destinations and private luxury villa estates, plan 12+ months ahead as these types of accommodations have limited availability. Hotels or resorts may offer more flexibility simply due to size, but prime dates still book early.
Q: What’s the ideal group size for a private villa vs. hotel for a team retreat?
A: Villas shine for 8–50 people, depending on the size of the villa. Hotels/resorts fit 100–500+ and work well for larger, agenda-heavy conferences.
However, with Villa Punto de Vista, we can also help you book overflow accommodations for your group, so if you want to host a large group retreat for closer to 100, we can do that with special attention to logistics and overflow sourcing.
Q: How do I decide between a hotel, resort, or villa for our company offsite?
A: Hotels = infrastructure & scale; Resorts = predictable pricing & on-site fun; Villas = privacy, customization, and high-touch service for exec or leadership retreats.
Q: Do I need an event planner or can my internal team manage a company offsite?
A: If you want a seamless experience, especially internationally, consider a planner or a venue with built-in concierge/event support.
When you book with Villa Punto de Vista, our villa staff becomes your support staff from the moment you book to the moment you depart. It’s helpful to have this level of support so your team can focus on the big picture with tasks like people operations and agendas that will spark new ideas, while our team handles on-site troubleshooting and problem solving, which even the best planned meetings will always require.
Q: How do I justify the cost of a luxury meeting venue to leadership?
A: Connect spend to outcomes: retention, innovation, faster strategy alignment, and relationship building. A productive offsite can pay for itself in engagement and speed to decision.
Key Takeaways
- Start with clarity: Define why you’re bringing the team together and what success should look like when everyone returns home.
- Choose a destination that works: Prioritize easy travel, minimal visa hurdles, safety, and a vibe that aligns with your company’s culture and goals, as well as access to fun team-building activities.
- Your venue sets the tone: Pick a space that inspires creativity, fosters connection, and supports productivity with strong Wi-Fi, AV, and flexible layouts.
- Comfort and inclusivity matter: Look for thoughtful design, private or semi-private spaces, ADA accessibility, and food options for all dietary needs.
- Budget beyond room rates: Factor in transportation, F&B flexibility, hidden fees, and contract terms to avoid surprises.
- Match venue type to your event: Private estates excel for intimate leadership and C-suite offsites; hotels and resorts are best for large, agenda-heavy gatherings.
- Invest in experience: The right location and venue can spark innovation, strengthen company culture, and boost long-term engagement far beyond the offsite itself.
A company offsite isn’t your average corporate event.
Treat your remote teams to their next offsite at Villa Punto de Vista Estate.
Your next offsite can be more than an obligation. It can be a catalyst for innovation, culture, and employee engagement that helps you achieve your company’s goals and bring colleagues together for years to come.
If you’re ready to move beyond generic hotel ballrooms and create an offsite meeting or team retreat that challenges the status quo and sets an example for company standards, we’re here to help you get started and craft a seamless experience for your offsite from start to finish.
Check villa availability and start planning your next team offsite in Manuel Antonio, Costa Rica.
Christien Johnson is the Co-Founder and Managing Partner of Villa Punto de Vista Estate, an award-winning private resort in Manuel Antonio, Costa Rica. With nearly 20 years in luxury hospitality, he has helped make the estate a benchmark for private villa experiences, earning 700+ five-star reviews, 13 consecutive WeddingWire Couples’ Choice Awards (an achievement only secured by the top 3% of venues worldwide) and a vote as the #1 wedding venue in Costa Rica, as well as recognition from Architectural Digest, Condé Nast Johansens, and the Global Choice Awards as the Best Villa in Central America.
Christien also founded and manages Vista Destinations Luxury Travel Agency, Costa Rica Weddings, and Costa Rica Chefs, and advises brands worldwide on automation and AI in luxury hospitality, shaping the next era of high-touch, personalized travel as a trusted voice in private-estate and transformational travel.
