5 Executive Retreat Destinations for Strategic Planning in 2025
In today’s fast-paced, hybrid business world, the ability for leadership teams to step back, align, and plan strategically has never been more essential. And while Zoom calls and digital dashboards may keep operations ticking, they don’t replace the clarity and vision that emerge from in-person strategic off-sites.
That’s why CEOs, founders, and heads of operations are turning to curated executive retreat locations for CEOs 2025—environments designed for vision casting, problem-solving, and high-level decision-making. These aren’t just beautiful locations; they’re purpose-built backdrops that combine luxury, privacy, and productivity.
In this guide, we explore five elite destinations that blend environment with impact. Whether you’re planning your next leadership off-site, executive getaway, or innovation sprint, these locations will deliver inspiration and ROI in equal measure.
1. Jackfish at CliffCo – Canada’s Secluded Strategy Sanctuary
Tucked away in the Canadian wilderness but equipped with modern comforts and stunning design, Jackfish by CliffCo has emerged as one of North America’s most sought-after executive retreat locations.
Designed specifically for leadership retreats and C-level gatherings, Jackfish provides a distraction-free setting that prioritizes clarity and creativity. Whether you’re aligning the leadership team or preparing for a product pivot, this location helps decision-makers focus on what matters most.
The setting is wild, the service is world-class, and the architecture intentionally complements deep thinking and breakthrough strategy. From chef-prepared meals to lakeside reflection decks, every detail is intentional. For CEOs seeking a rare combination of luxury, seclusion, and strategic facilitation, this is a top contender for 2025.
To explore the property and its unique offerings, check out the Jackfish visual retreat experience, where inspiration meets execution in the most breathtaking way.
2. Amangiri – Utah, USA
For CEOs who want to combine desert solitude with five-star service, Amangiri offers an otherworldly setting in southern Utah’s canyon country. This ultra-luxury retreat provides panoramic views, world-class spa treatments, and architecture that almost disappears into the landscape.
What makes Amangiri perfect for executive planning is its exclusive privacy. Teams can book entire sections of the resort or the full property, creating a closed-door environment ideal for tackling sensitive topics like mergers, succession planning, or investor strategy.
Amangiri also understands the importance of balancing intensity with recovery. After a day of meetings and whiteboarding, your team can unwind with wellness therapies, guided hikes, and stargazing in one of the quietest regions in the U.S.
As part of Aman Resorts, Amangiri brings with it a reputation for unparalleled hospitality—a critical factor for high-performance executive teams.
3. Blackberry Mountain – Tennessee, USA
Part nature immersion, part innovation lab, Blackberry Mountain is a rising star in the world of leadership retreats. Nestled in the Great Smoky Mountains, it offers an elevated yet grounded environment that encourages strategic thinking and personal reflection.
The retreat blends luxury accommodations with curated leadership workshops, private wellness sessions, and breathtaking views. Blackberry Mountain places emphasis on the whole leader—mental clarity, physical wellness, and emotional intelligence.
This makes it ideal for team off-sites that aim to do more than review KPIs. It’s where personal development meets executive strategy, helping CEOs and teams unlock new levels of performance and cohesion.
Plus, with proximity to Atlanta, it’s a smart pick for Southeast-based executives looking to escape without going far. If you’re organizing Atlanta events or leadership retreats that need a memorable backdrop, this one fits perfectly.
4. Ashford Castle – County Mayo, Ireland
Sometimes, stepping away means stepping into something old, grand, and deeply inspiring. Ashford Castle, a 13th-century estate turned luxury hotel in western Ireland, offers exactly that. With sprawling grounds, private meeting rooms, and curated group experiences, it’s ideal for team planning getaways that double as cultural immersion.
Leadership teams can enjoy fly fishing, falconry, and fine dining—all within a castle that feels like a different era. But behind the historical façade lies state-of-the-art hospitality and event support.
For multinational executive teams or those headquartered in the UK or Europe, Ashford Castle offers both gravity and intimacy—perfect for major milestones, board retreats, or annual strategy sessions.
5. CliffCo Custom Retreats – Global Design, Local Impact
Sometimes, the destination isn’t a specific city or castle—it’s a concept delivered wherever your team needs it. CliffCo’s custom corporate retreats take the guesswork out of planning by curating location, agenda, and facilitation around your business goals.
Whether you’re planning an executive reset in the Pacific Northwest or a coastal innovation sprint in New Zealand, CliffCo builds experiences that fuse luxury, strategy, and culture-building. Their team handles logistics, creative programming, and facilitation—so CEOs and operations heads can focus on what they came for: alignment and breakthroughs.
For leaders who want the impact of a destination retreat without the operational overhead, explore what CliffCo can build through their executive event design service. Their retreats are bespoke, scalable, and built to deliver real outcomes.
What to Consider When Choosing a 2025 Executive Retreat Location
The right retreat destination sets the tone for everything else. Here’s what top-performing companies consider when planning their 2025 off-sites:
- Privacy: Can the location ensure confidential strategy discussions stay confidential?
- Inspiration: Does the setting spark creativity and long-term thinking?
- Accessibility: Is the location easy to access for international or distributed teams?
- Customization: Can the venue or host tailor experiences to your goals?
- Service Level: Will the team be supported so leaders can fully engage?
While all five destinations featured meet these criteria, the best choice depends on your culture, goals, and current business phase.
The Strategic Value of In-Person Planning in 2025
The data is in—companies that physically gather leadership teams are more aligned, resilient, and innovative. Remote collaboration tools are powerful, but they can’t replicate the insight that comes from face-to-face discussion in an inspiring setting.
Executive retreats give leadership teams space to think beyond the day-to-day, align around future goals, and reconnect on a human level. They enable honest reflection, bold visioning, and more cohesive execution.
This is why the question CEOs should be asking isn’t “Can we afford a retreat?” but rather “Can we afford not to have one?”
Final Thoughts: Investing in Vision, Not Just Location
In 2025, executive retreats are more than travel perks. They’re strategic imperatives. They offer leaders the space to step back, think forward, and plan with renewed clarity. Whether it’s the rugged inspiration of Jackfish or the global customization of CliffCo’s experiences, the best retreat destinations don’t just house meetings—they shape outcomes.
For CEOs and operations heads looking to align their teams, refresh their strategy, or prepare for a major shift, choosing the right destination is a powerful first move. These aren’t just trips. They’re transformation platforms.
If your next big decision deserves more than a boardroom, now is the time to reimagine what’s possible—away from the noise, in a setting built for breakthroughs.
Frequently Asked Questions (FAQ)
Q1: What’s the ideal group size for an executive retreat?
Most CEO-level retreats are most effective with 5–20 participants. This allows for rich discussion while keeping the experience intimate and efficient.
Q2: How far in advance should I plan a 2025 retreat?
Start planning 4–6 months in advance, especially for high-demand luxury retreats. CliffCo and similar firms can help accelerate timelines if needed.
Q3: What’s the typical duration of a leadership retreat?
Most effective off-sites run for 2 to 4 days, depending on travel requirements and objectives.
Q4: Do these retreats include facilitation or just location?
It varies. Some destinations are space-only, while others—like Jackfish and CliffCo—offer full retreat design, including facilitators, wellness programming, and executive coaching.
Q5: Are luxury retreats really worth the investment?
Yes. When properly aligned with strategic goals, luxury retreats yield a high ROI through stronger leadership alignment, faster decision-making, and renewed executive clarity.
