What if the life you’ve always wanted isn’t waiting for you somewhere “out there,” but underneath the habits, fears, and stories you’ve spent a lifetime building? The Enneagram is one of the world’s most powerful tools for understanding why we think, feel, and behave the way we do. Rather than placing people into boxes, it helps us recognize the unconscious patterns that shape our lives and offers a path toward greater freedom, healthier relationships, authentic leadership, and a more meaningful way of living.
This isn’t simply an Enneagram workshop. It’s an immersive, week-long Enneagram retreat that blends personal growth, adventure, reflection, and genuine connection. Together we’ll slow down, ask better questions, laugh often, spend time in nature, enjoy exceptional food and wine, and discover how greater self-awareness can transform the way we lead, love, work, and live. Each morning, we’ll explore the wisdom of the Enneagram through engaging teaching, storytelling, journaling, experiential exercises, and meaningful conversation. Drawing from the work of Brené Brown, Parker Palmer’s Center for Courage & Renewal, Richard Rohr, Russ Hudson, Suzanne Stabile, and other respected teachers, we’ll examine the motivations, fears, strengths, and blind spots that shape each of the nine Enneagram types, while learning practical ways to move beyond our automatic patterns.
Then we’ll close our notebooks.
Because some of the most meaningful learning doesn’t happen during a presentation. It happens on a hiking trail. Over lunch at a winery. Around a fire pit. Our afternoons are intentionally designed to bring the morning’s learning to life. We’ll experience the best of Temecula Wine Country through scenic hikes, award-winning wineries, charming Old Town Temecula, exceptional meals, and unhurried conversations. These shared experiences create the space where insight becomes transformation and strangers often become lifelong friends. Evenings are intentionally unstructured. Relax by the pool, soak in the hot tub, enjoy a glass of wine, or simply linger in conversation with remarkable people. Time and again, participants tell us these moments become some of the most meaningful memories of the week.
Whether you’re brand new to the Enneagram or have spent years studying your type, this retreat will meet you where you are. You’ll return home with greater self-awareness, stronger relationships, practical tools for everyday life, renewed purpose, and a clearer understanding of the person you’ve always been underneath the personality you’ve developed.
Many participants join us to earn 30+ CME/CEU credits while investing in their own wellbeing. Others simply know it’s time to slow down and reconnect with themselves. Whether you’re a physician, nurse, healthcare professional, leader, educator, business owner, or simply someone seeking greater authenticity, you’ll find an unforgettable week of learning, adventure, community, and personal transformation in the heart of Temecula Wine Country.
WHAT’S INCLUDED
WHAT’S NOT INCLUDED
CANCELLATION DETAILS
PLEASE NOTE
This itinerary may change slightly due to accommodation availability, rain, festivals and spontaneous side trips. This is not an endurance race, nor a competition. Please be respectful of all the different paces and walks of life that come together on this group trip.
CONTINUING EDUCATION CREDITS
To claim CME/CEU credits, participants are required to purchase a $50 annual Learner+ membership. This one-time registration provides unlimited access for one year to claim credits through reflective activities—both from this retreat and other eligible experiences. Learner+ is an accredited activity portal designed for busy healthcare professionals, including physicians, nurses, nurse practitioners, physician associates, pharmacists, social workers, athletic trainers, case managers, dietitians, chaplains, and more. It allows you to capture reflections at the point of learning or care and convert them into continuing education credits. Reflections based on session content may be eligible for up to 30+ AMA PRA Category 1 Credits™ per session. Learn more about CME/CEU eligibility for your specialty here.
🌊🌊 Swim Out Experience
You’ve started exploring your inner life—maybe through a book, a podcast, therapy, or a few reflective conversations—and now you’re ready for more. This experience offers grounding tools, mindset shifts, and meaningful dialogue to support your next steps. It’s a great fit for those looking to reconnect with themselves and gain momentum in their growth journey
| 💧 Retreat Depth | Who It’s For | What to Expect |
|---|---|---|
| 💦 Dip Your Toes | Brand new to personal growth or retreat spaces | Gentle, welcoming, and low-pressure. A perfect introduction to self-reflection, connection, and emotional wellbeing—without overwhelm. |
| 🌊 Wade In | You’ve started exploring inner work or want to revisit the basics | Reflective practices, mindset shifts, and tools for resilience. Ideal for folks ready to grow, but not quite ready to cannonball. |
| 🌊🌊 Swim Out | You’ve done some personal work and are ready to go further | More depth, more vulnerability, and more challenge. You’ll explore identity, relationships, and what’s getting in your way. |
| 🌊🌊🌊 Go Deep | You’re experienced in inner work and craving transformation | Brave spaces, soulful inquiry, and a strong container for people navigating transitions, reinvention, or purpose. Designed for the seasoned soul. |
Leadership: Joining Courage & Renewal facilitator, Corey Martin MD is Mary Messina.
Mary Messina
7:00 – 7:30 AM | Breakfast at the hotel.
7:30 AM – 12:00 PM | Inspirational Sessions
Interactive Enneagram education, reflection, journaling, experiential exercises, and group discussion.
12:00 – 5:00 PM | Hiking Stunning Trails
Lunch followed by Temecula adventures: hiking, wineries, Old Town, local experiences, and time to explore the region.
5:00 – 6:00 PM | Personal Renewal Time
Take this time to recharge in your own way: journal, meditate, swim, read, or simply soak in the beauty of the landscape.
6:00 – 8:00 PM | Group Dinner
Share a nourishing meal while reflecting on the day’s insights and experiences.
8:00 – 9:30 PM | Evening Social & Reflection
Optional social time to unwind with fellow travelers around the hot tub, pool, or during a casual social hour, deepening connections and integrating the day’s lessons.
Welcome to Southern California! Arrive in San Diego at your leisure and settle into our conveniently located airport hotel. Spend the afternoon exploring the waterfront, visiting Balboa Park, relaxing by the pool, or simply unwinding after your travels. This evening is yours to enjoy before we begin our week together. Tomorrow morning, our journey into the Enneagram, and into ourselves, begins. Tonight we stay near the San Diego Airport.
Following breakfast, we’ll gather for our first morning of educational sessions as we begin exploring the Enneagram and discovering the core motivations, fears, and patterns that shape each of the nine personality types. Through engaging teaching, reflection, storytelling, and discussion, you’ll begin identifying your own type and understanding the unique lens through which you experience the world. Following lunch, we’ll travel together by comfortable passenger van to our home for the week—the beautiful Embassy Suites in Temecula Wine Country. After settling in, we’ll have a few more educational sessions and then enjoy our first evening together over dinner, creating space to get to know one another and begin building the supportive community that will accompany us throughout the week. Tonight we stay at the Embassy Suites Temecula. Breakfast included.
Today’s educational sessions move beyond discovering your Enneagram type to exploring the deeper motivations that drive it. Together we’ll examine the childhood messages, core longings, and unconscious patterns that shape how we think, relate, and respond to the world. As our awareness grows, so does our freedom to choose new responses instead of repeating old patterns. This afternoon we’ll begin with a leisurely lunch and optional wine tasting at Ponte Winery, one of Temecula Wine Country’s most beloved vineyards. Afterwards, we’ll explore one of Southern California’s hidden gems—the Santa Rosa Plateau Ecological Preserve. Surrounded by majestic oak trees, rolling meadows, historic adobe buildings, and peaceful trails, we’ll enjoy an easy-to-moderate hike designed for both reflection and conversation while experiencing one of Temecula’s most beautiful natural landscapes. We’ll then return to the hotel to relax and recharge before dinner. Tonight we stay at the Embassy Suites Temecula. Breakfast included.
The Enneagram becomes especially powerful when we begin understanding not only ourselves, but also the people we love, live with, and work beside. This morning we’ll explore how each Enneagram type communicates, experiences conflict, gives and receives love, and shows up in relationships. You’ll leave with practical tools for healthier conversations, deeper empathy, and stronger connections—both personally and professionally. Following our morning sessions, we’ll enjoy lunch and optional wine tasting at Monserate Winery, one of Temecula’s newest and most picturesque vineyards. We’ll then head to the nearby Santa Margarita River Trail Preserve, where towering sycamore trees, gentle river crossings, and shaded trails create a peaceful setting for an easy hike and meaningful conversation. Often described as feeling more like the Midwest than Southern California, this hidden gem invites us to slow down, connect with nature, and continue reflecting on the day’s themes. We’ll return to the hotel in time to relax before gathering for another memorable dinner and an evening of conversation around the patio or hot tub. Tonight we stay at the Embassy Suites Temecula. Breakfast included.
Today’s educational sessions explore what happens when life becomes stressful and how each Enneagram type has a unique pathway toward growth. Rather than remaining trapped in automatic reactions, you’ll discover practical tools to become more grounded, resilient, compassionate, and authentic. This afternoon invites you to slow down. We’ll begin with a peaceful stroll through Rose Haven Heritage Garden, one of Temecula’s hidden gems, where thousands of blooming roses provide the perfect setting for reflection. From there, you’ll have free time to experience Temecula at your own pace. Explore Historic Old Town Temecula, browse local boutiques, enjoy an optional wine tasting, schedule a spa treatment, relax by the hotel pool, or simply journal and reflect on everything you’ve experienced throughout the week. We’ll gather again in the evening for dinner and another opportunity to enjoy the meaningful conversations and friendships that have become the heart of our retreat. Tonight we stay at the Embassy Suites Temecula. Breakfast and Dinner included.
Our final full day focuses on integration. How do we take everything we’ve learned home? What practices will help us continue growing long after the retreat ends? Through reflection, experiential exercises, and group dialogue, you’ll develop a personal roadmap for living with greater authenticity, courage, joy, and intention. This afternoon we’ll slow the pace and spend time at South Coast Winery Resort & Spa. Following lunch and an optional wine tasting, we’ll take a leisurely walk through the vineyards, allowing space to reflect on the week’s experiences while enjoying the beauty of Temecula Wine Country. We’ll then gather for our closing dinner at The Vineyard Rose Restaurant, celebrating the friendships formed, the insights gained, and the journey that still lies ahead. As the sun sets over Wine Country, we’ll raise one final glass—not simply to the week we’ve shared, but to the life each of us is creating beyond it. Tonight we stay at the Embassy Suites Temecula. Breakfast included.
Our final morning together is devoted to bringing the week’s experiences into everyday life. We’ll reflect on what we’ve learned, celebrate the journey we’ve shared, and identify the practices and commitments that will help sustain this work long after we return home. Following our closing session, we’ll travel together by passenger van back to San Diego International Airport, arriving by approximately 12:00 PM. We recommend scheduling return flights after 2:00 PM. Breakfast included.
Please confirm you want to block this member.
You will no longer be able to:
Please note: This action will also remove this member from your connections and send a report to the site admin. Please allow a few minutes for this process to complete.
