Choosing a retreat company · 2026
The best executive retreat companies, compared.
Eleven firms that run or plan executive and leadership retreats, grouped by what they actually do, with who each one is best for. "Executive retreat company" covers three different businesses, and most bad retreats start with hiring the wrong kind.
Quick picks by what you need
- A leadership team in conflict, or one that needs trust rebuilt: Legendary Retreats, or a custom Outward Bound Professional program.
- A measured change in behavior after the retreat: Legendary Retreats (day-30 report included).
- A large-organization leadership development program, not a single retreat: Center for Creative Leadership.
- A team-building session with a charitable component: Odyssey Teams.
- A strategic plan your team will execute: Leadership Strategies, Building Champions or the Lefko Group.
- Venue, travel and logistics handled, with your own agenda: Offsite, Moniker Partners, Teamland or Simetras.
How we compared them
We judged each firm on what a buyer of an executive retreat actually needs to know, using only public information: the firm's own site and published profiles. Where we could not confirm something, we left it out.
- What they ownLogistics, the sessions in the room, or the whole outcome.
- Who leads the roomA named principal, a staff facilitator, or you.
- FormatExperiential, facilitated working sessions, or event production.
- After the retreatAny follow-through or measurement once the team is home.
Side by side
| Company | Type | Best for | Format | Public pricing |
|---|---|---|---|---|
| Legendary Retreats | Full-service experiential designer | Teams of 5 to 12 that need to work as one | Multi-day experiential, five-star or off-grid | Yes: $35,000 to $500,000+ |
| Outward Bound Professional | Experiential programs (regional) | Collaboration and communication | Outdoor, one day or multi-day | No |
| Center for Creative Leadership | Leadership development institute | Multi-session programs at scale | Custom programs, assessments, coaching | No |
| Odyssey Teams | Team-building programs | Established teams; giving back | Philanthropic build simulations | No |
| Building Champions | Executive coaching firm | Alignment and a 12 to 24 month plan | Two-day coach-led retreats | No |
| Leadership Strategies | Facilitation firm | Strategic planning | Facilitated planning sessions | No |
| The Lefko Group | Facilitator and CEO advisor | Strategic planning retreats | Facilitated retreats | No |
| Offsite | Planner and venue marketplace | Logistics for team offsites | Booking marketplace or full planning | Per-person fee; base rates not listed |
| Moniker Partners | Logistics and event production | Travel and on-site execution | Planned and produced retreats | No |
| Teamland | Offsite and team-building provider | Executive offsites of 4 to 18 | 1 to 5 days, venue or your site | No |
| Simetras | Retreat planner and workshops | Offsites with workshops built in | Executive, outdoor and glamping retreats | No |
Experiential retreats and team development
Firms that use shared experience, rather than a conference room, as the main tool. The right choice when the problem is trust, conflict or a team that is not yet a team.
Legendary Retreats legendary-retreats.com
Best for: executive teams that need to work as one, including teams in conflict
- What they do
- Designs and leads experiential retreats for CEOs and leadership teams of roughly 5 to 12: off-road, winter survival, sailing, wilderness and remote lodges, plus five-star strategic planning retreats. Turnkey: design, facilitation, lodging, meals, activities and transfers.
- Who leads
- James Carter, the founder, on every retreat.
- After
- A 30-day challenge with a written day-30 report against a baseline. How it is measured.
- Pricing
- Published: Focused $35,000 to $50,000, Signature $45,000 to $150,000, Bespoke $75,000 to $500,000+. Written proposal within 72 hours for Focused and Signature.
- Not the right fit
- Groups much larger than 20, logistics-only requests, or a single afternoon of team building.
Outward Bound Professional outwardbound.org
Best for: outdoor team and leadership development with a long track record
- What they do
- The professional arm of Outward Bound runs custom team and leadership programs through regional schools, from a single day to several days. Regional programs list collaboration, communication, problem solving and change management among their focus areas.
- Worth knowing
- Each regional school runs its own programs, so format and venues vary by location. The Chesapeake school cites more than 50 years of work with teams, including executive teams.
- Ask them
- Which regional school would deliver your program, and who would facilitate it.
Center for Creative Leadership ccl.org
Best for: larger organizations building leadership capability over months
- What they do
- A global leadership development institute offering custom programs for organizations, delivered in person and online, often as multi-session journeys with assessments and 360-degree feedback coaching.
- Worth knowing
- Strongest when the goal is a development program across many leaders rather than a single retreat for one team.
Odyssey Teams odysseyteams.com
Best for: established teams that want team building with a charitable outcome
- What they do
- Business-simulation team building with a philanthropic component, such as building bikes for children in need or assembling prosthetic hands. The company says it ran its first bike-building program in 1999, and it also offers virtual programs.
- Worth knowing
- A team-building program you add to an event, rather than a full retreat with venue and logistics.
Strategic planning facilitators and coaches
Firms that lead the working sessions. The right choice when the team is healthy and the job is a plan, and you are able to handle venue and logistics yourself or through a planner.
Building Champions buildingchampions.com
Best for: aligning an executive team on mission, strategy and priorities
- What they do
- An executive coaching firm that runs customized executive retreats, each led by one of its executive coaches. It describes two-day retreats aimed at a clear direction and an actionable 12 to 24 month plan.
- Worth knowing
- The firm says it has been coaching leaders for nearly 30 years. A natural fit if you also want ongoing executive coaching.
Leadership Strategies (LeadStrat) leadstrat.com
Best for: a structured strategic planning session
- What they do
- A facilitation firm offering strategic planning facilitation built on its Drivers Model, plus meeting facilitation and executive and team coaching.
- Worth knowing
- Planning methodology is the core product. Venue, travel and on-site logistics are typically separate.
The Lefko Group (Mark Lefko) marklefko.com
Best for: a CEO who wants an experienced peer-advisor to facilitate planning
- What they do
- Mark Lefko facilitates corporate and strategic planning retreats and CEO peer groups. His published bio says he has coached and mentored more than 100 CEOs, and he previously served as a group chair with Vistage Worldwide.
- Worth knowing
- Principal-led facilitation. Confirm what is included beyond the sessions themselves.
Logistics planners
Firms that source venues, handle contracts and travel, and run the event. The right choice when the agenda is already set and you, or a facilitator you hire, will lead the room.
Offsite offsite.com
Best for: team offsites where venue and logistics are the main job
- What they do
- A venue and vendor marketplace with negotiated rates, plus done-for-you planning: venue contracts, agendas, budgets, vendors and travel. Planning is priced as per-person fees across several plan tiers.
- Worth knowing
- Founded in 2020 and based in New York; raised $3 million in 2023 and reports hundreds of retreats in more than 15 countries. Not to be confused with similarly named firms.
Moniker Partners monikerpartners.com
Best for: travel logistics and on-site production for a company retreat
- What they do
- Combines travel logistics, experience design and on-site event execution, with a free proposal after an introductory call and a stated budget guarantee.
- Ask them
- Whether facilitation of the working sessions is included or needs a separate provider.
Teamland teamland.com
Best for: a packaged leadership offsite with optional coaching add-ons
- What they do
- Offers leadership offsites of 1 to 5 days for groups of 4 to 18, at a retreat venue or your location, with optional executive coaching, team assessments and quarterly alignment sessions. Also runs larger team offsites and team-building events.
- Worth knowing
- Handles vendor onboarding and procurement; asks for more lead time for retreats than for smaller events.
Simetras simetras.co
Best for: an offsite with leadership workshops built in
- What they do
- A Miami-based firm planning executive retreats, company offsites and outdoor or glamping retreats, with leadership workshops on trust, coaching and decision-making. Handles venue sourcing, travel and attendee management.
Who we left out, and why
Venues and resorts with in-house event teams, because they plan events at their own property rather than retreats. Large team-building marketplaces focused on activities rather than executive teams. And several firms we could not verify from public information. For what each type of company owns, see executive retreat planners: who does what, and for the facilitation side, how to choose an offsite facilitator.
Questions buyers ask
What is the best executive retreat company?
It depends on what the retreat has to do. For an experiential retreat that rebuilds trust or resolves conflict on a leadership team of 5 to 12, a full-service designer such as Legendary Retreats or a custom Outward Bound Professional program fits. For a strategic plan, a planning facilitator such as Leadership Strategies or a coaching firm such as Building Champions fits. If you only need venues, travel and logistics handled, a planner such as Offsite, Moniker Partners or Teamland fits.
What is the difference between a retreat planner and a retreat facilitator?
A planner owns logistics: venue, contracts, travel and schedule. A facilitator owns the sessions in the room. A full-service retreat designer owns both, plus the outcome. If the retreat has to change how a team works, someone has to be accountable for that outcome, not only for the event running on time.
How much does an executive retreat company cost?
Few firms publish prices. Legendary Retreats publishes turnkey ranges from $35,000 to $50,000 for a Focused retreat, $45,000 to $150,000 for Signature, and $75,000 to $500,000+ for Bespoke, for teams of roughly 5 to 12, with airfare usually excluded. Logistics planners such as Offsite charge per-person planning fees on top of venue and travel. Facilitators usually quote a fee for design and facilitation only. For a range for your team, try the retreat cost estimator.
Think your team needs the experiential kind?
Three answers and you get a written proposal within 72 hours for Focused and Signature retreats. If we are not the right fit, we will tell you who is.