Cornerstone’s 2027 Leadership Retreat
STRONGER TOGETHER
Hacienda Pinilla, Guanacaste, Costa Rica • February 28–March 5, 2027
Five nights for Cornerstone member owners, CEOs, and executive leaders to step away from daily demands, learn together, and return with renewed perspective.
*Airfare not included
WHY WE GATHER
Leadership is stronger when it is not carried alone.
Leading an organization can be deeply rewarding, but it can also be incredibly isolating. Cornerstone created our members-only Leadership Retreat around a simple belief: organizational leaders should have a trusted community where they can speak candidly, learn from one another, and step away from daily demands to unwind, reconnect, and gain perspective.
We’re excited to host our third retreat in beautiful Guanacaste, Costa Rica in partnership with our member, Offbeat Travel!
Cornerstone’s Leadership Retreat gives unparalleled opportunities to network and grow in a relaxing and soothing environment. And this year, the experience will be intentionally less programmed so members have more influence over the agenda and more time to connect.
Pulling from feedback we gained after our last two retreats, we’re building in more flexibility and less structured agendas. Cornerstone will provide the framework, facilitation, and two guest presenters, but we will not overfill the week. Members will help shape the agenda before arrival and continue adapting it as new questions and opportunities emerge onsite.
BEFORE WE ARRIVE
Share What Matters Now
The enrollment process will invite members to identify current questions, challenges, and opportunities they want the community to explore.
THE 2027 APPROACH
More room for the conversations members need.
DURING THE RETREAT
Keep shaping the agenda
An evolving topic board will make room for timely conversations, small-group discussions, and the issues members most want to address together.
FROM OUR COMMUNITY
Share what works
Optional peer-led sessions will give members a way to share a useful system, successful practice, hard-earned lesson, or idea that could benefit others.
A setting designed for time together and room to unwind.
Our group will stay across three private villas in the Hacienda Pinilla community of Guanacaste. The beautiful 10-bedroom, 11.5-bath main house will serve as the center of the retreat and the location for all scheduled events and meals.
Two additional homes are reserved offering equal comfort, private rooms, and open floor plans. We’ll have golf carts available to transport ourselves between villas.
ADDITIONAL ACCOMMODATIONS
PRIMARY HOUSE
Photo from the 2025 Leadership retreat
Morning: Gather & Learn
Guest perspectives, member-selected topics, and guided conversations while the group is fresh.
THE RETREAT RHYTHM
Enough structure to create momentum. Enough space to be present.
Expect focused learning without an overfilled schedule. Each day will balance facilitated conversation with room to rest, connect, and enjoy where we are.
Afternoon: Choose Your Pace
Small group conversations, peer-led sessions, local exploration, quiet reflection, or unstructured connection.
Evening: Reconnect Naturally
Shared meals and relaxed time together.
Photo from the 2025 Leadership retreat
SHARED LEARNING
Two guest presenters. More learning from within the room.
We are intentionally limiting the formal presenter lineup so there is more time to explore what members bring with them. The two invited presenters will introduce meaningful ideas and practical tools selected to support the questions leaders want to examine together.
Cornerstone will help connect those ideas to the needs in the room, while optional peer-led sessions give members an easy way to contribute their own expertise. Presenter details and the first round of member-selected topics will be shared as the retreat approaches.
TIME TO RELAX
A Mid-Retreat Day to Recharge
Midway through the retreat, we’ll set aside a day to experience Costa Rica at your own pace. Relax on the beach, join a surf lesson, explore Hacienda Pinilla, or simply choose whatever helps you recharge and enjoy the pura vida lifestyle.
During the evening, we’ll enjoy a private sunset catamaran experience - one of the retreat highlights! Swim, snorkel, and relax among the beautiful scenery while enjoying food and an open bar.
A Cornerstone retreat, strengthened by local partnership.
We are incredibly pleased to partner with our good friends at Offbeat Travel for this retreat!
Offbeat has been a Cornerstone member for 5 years and will be supporting the experience with local knowledge, logistics, and in-country staff. Ricardo Romero, their CEO, will be joining us the retreat, too!
Join us in Costa Rica to see first-hand why Offbeat Travel is one of the most trusted operators in Latin America.
Retreat Package Inclusions
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Five nights of villa accommodations
All meals prepared by a private chef
Nonalcoholic drinks, beer, and wine
Scheduled group airport-transfer windows
Golf carts for local transportation within the retreat area
Private, sunset catamaran tour
Two guest presenters and Cornerstone-led facilitation
Offbeat Travel’s local logistics and onsite support
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Airfare to and from Liberia International Airport, Costa Rica.
Transportation outside the scheduled group transfers
Optional personal activities or pre- and post-retreat travel
Personal emergency medical, repatriation, and trip-cancellation or interruption insurance coverage
Welcome to Hacienda Pinilla
Attendees will arrive into Liberia International Airport and be transferred to our retreat location at Hacienda Pinilla in Guanacaste, along Costa Rica’s northwestern Pacific coast. Set across 4,500 gated acres on the Nicoya Peninsula, the community blends historic ranchland, tropical dry forest, and three miles of coastline.
Hacienda Pinilla’s coastline includes Playa Avellanas, Playa Langosta, and Playa Mansita. Visitors enjoy surfing, peaceful walks, Pacific sunsets, and the Hacienda Pinilla Beach Club overlooking Playa Avellanas.
Throughout the retreat, we’ll embrace Costa Rica’s pura vida lifestyle. More than a familiar expression, pura vida represents joy, balance, gratitude, and a deeper connection with nature, other people, and oneself - a fitting spirit for our time together.
Pricing and Registration
Register and pay the $500 deposit by November 15, 2026, to qualify for “early bird” savings! Both private and shared-room options are available from the opening of registration, subject to room availability and Cornerstone confirmation.
PRIVATE ROOM
Early Bird Price: USD $3,895
Standard Price: USD $4,095
$500 deposit due at registration. Balance due January 8th.
Specific bedrooms and villa location remain subject to registration priority and availability.
SHARED ROOM
Early Bird Price: USD $3,395
Standard Price: USD $3,595
$500 deposit due at registration. Balance due January 8th.
Name a preferred roommate or request contact about a possible match. Each attendee registers separately.
FAQs
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The 2027 “Stronger Together” retreat is designed for Cornerstone member owners, CEOs, and executive leaders. Space is intentionally limited to protect the small-group experience.
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Cornerstone will provide a flexible framework and two guest presenters. Members will suggest topics before the retreat, add timely topics onsite, and may volunteer to lead optional peer-learning sessions.
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The 2027 retreat will be less structured than prior retreats. There will be purposeful gathering times, along with meaningful space for rest, informal conversation, optional sessions, and local exploration.
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We will collect dietary, mobility, and other accommodation needs during enrollment and work with Offbeat Travel and the villa team to plan appropriately.
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Offbeat Travel is a Cornerstone member and our local host. They will support logistics, destination expertise, transportation coordination, and onsite staffing. This remains a Cornerstone event designed and led by Cornerstone.
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Roommate preferences and compatibility considerations will be collected during enrollment. Cornerstone will work with attendees to create appropriate assignments before the retreat.
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Airfare and travel insurance are not included. Members should consider purchasing emergency medical, repatriation, and trip interruption coverages.
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A $500 deposit is required. Early-bird pricing requires registration and deposit by November 15, 2026; the balance is due January 8, 2027. The deposit is non-refundable if the attendee cancels and refundable if Cornerstone cancels.