The Summary

Here, at Conversations in the Vineyard, we believe the vineyard has much to teach us about life and leadership.  Pull up a chair.  We’ll pour some wine.  Let’s talk!

During a Conversations in the Vineyard retreat, we immerse ourselves for a day and a half in the metaphor of the vineyard to gain valuable insights for our personal leadership journeys and organizations.  As we consider each season, the vineyard provides a framework for life principles and key insights into practicing sustainable leadership.

Conversations in the Vineyard brings together leadership growth with soul refreshment.  During a retreat, important leadership and life conversations occur while we walk in the vineyard or drink a great glass of wine.  Imagine discussing hard leadership decisions while considering the pruning process in winter.  The natural rhythm of the vineyard and the joyful conviviality over wine refreshes the soul in ways that nothing else can.  

We’d love for you to join us!  Be refreshed. Cultivate your leadership.

Here’s a little more information:

The Experience

We welcome you to the quintessential wine-country town of Healdsburg, California, with a wine reception and dinner where we begin the first of many rich conversations.  After dinner, Session One focuses on Summer in the vineyard, applying principles of growth to our lives and contexts.

After a comfortable night’s rest in a beautiful hotel, inn or estate home, we gather for an excursion in a vineyard and winery, followed by a picnic.

Session Two reveals the work of harvest and the abundance of Fall. Then we offer free time in the afternoon for rest and reflection, allowing space to process and engage more intentionally with the topics presented.  In the evening, we enjoy great wine and seasonal food, which eases us into Session Three—Winter. Here we explore the particular gifts of dormancy. Finally, the next morning, we come full circle to Spring and Session Four, while enjoying brunch and a final conversation.

Each session includes a short lecture, learning activities, and group discussion. Conversations center on the metaphor of seasons in the vineyard with application to leadership in our personal lives, relationships, and organizational contexts, depending on the focus of your retreat.   Through Conversations, you gain a deeper understanding of each season you will traverse as a leader and leave with a framework through which to understand sustainable leadership practices.

Sample Schedule



Wine Reception


Session One:  Summer


Day 2

Vineyard and Winery Experience

Session Two:  Fall

Wine-country picnic

Free Time


Session Three:  Winter


Day 3

Session Four:  Spring


Dismiss at noon

Types of Retreats


Teams and Groups

Bring a group such as a Board or an Executive Leadership Team.  We work with you to incorporate time for your agenda, as well as the Conversations experience.  We also tailor our content to address your group’s current opportunities and maximize team learning and growth.

Old Vines

Friends and Family

Bring a group of your favorite people or have a family retreat (all participants must be 21+).  Imagine enjoying the beauty of wine-country with your besties!  Add the bonus of learning and growing together as you each influence the world in unique ways.  It’s a powerful opportunity to consider your life journey together.


A Blend of Like-Minded People

Come on your own, with a spouse / partner, or a couple of friends and meet other, like-minded people.  Share your journey and learn from others’ leadership.  Confidentiality is paramount, as we create a safe space together.  Leave with a renewed vision for your leadership and a trusted group of friends.  You may choose to continue the journey by coming back every year in a different season or meet four times in one year for a deeper understanding of the metaphors and principles associated with the vineyard.

*Note: Except for intact teams, retreats must have at least six and no more than twelve attendees for an ideal experience. 



We love to customize our retreats!  Take a look…

Spiritual -- Contemplate the spiritual aspects of the vineyard metaphor.  We weave rich, spiritual insights from the vineyard throughout the retreat.  Our spirituality flows from the Bible and the Christian tradition, which is full of images and stories from the vineyard.  

Extended -- An extended retreat offers one more night, two more sessions and another vineyard and winery experience.  Because of the extended time, the group can enjoy more depth, more conversation, more processing, more free time, more wine… basically, more of everything! 

Elsewhere -- Want to meet in France?  Italy?  Argentina?  Texas?  Napa?  Wherever there are vineyards, we can take the retreat on the road.  Just let us know.  We love to travel!  



We choose accommodation according to the needs of the group.  Some of the places we like in and around Healdsburg are listed here:

Directions to Healdsburg

Closest Airport:  Santa Rosa (STS) is a regional airport just 15 minutes from Healdsburg

San Francisco (SFO) or Oakland (OAK) are each about 1.5 hours away by car.  There is also a shuttle bus that will take you from either of the larger airports to STS.

Driving:  Healdsburg is one hour directly north of the Golden Gate Bridge just off the 101.