Wholly Designed Team Retreats
Lead with clarity.
Align with purpose.
Move forward together.
Teams don’t need another offsite filled with generic activities. They need space, intention, and guidance to pause, reflect, and realign.
Wholly Designed Team Retreats are fully customized, in-person experiences created to meet your team exactly where they are — whether that’s leadership development, culture building, vision alignment, or simply reconnecting after a season of growth or change.
Our Team Retreat Framework
A Wholly Designed Team Retreat is a 4-day, immersive, in-person experience designed specifically for your team.There is no pre-packaged agenda. No one-size-fits-all curriculum. Instead, Lisa and Jaime work closely with you to design a retreat that addresses the exact topics, challenges, and opportunities your team is facing right now.
These Retreats are Ideal For…
Leadership teams
Business owners and their teams
Organizations navigating growth or transition
Teams seeking stronger culture and communication
Groups needing clarity around vision, roles, or direction
Teams ready to slow down in order to move forward well
If you have a group of people who work, lead, or serve together — this experience can be shaped for you.
What We Can Cover
Each retreat is intentionally designed around your team’s needs. Topics may include Leadership development, Team culture and values, Purpose, direction, and alignment, Communication and trust building, Vision and strategic planning, Wellness, rest, and sustainable leadership, Team dynamics and collaboration, Reflection, reset, and future planning
You don’t need to come with all the answers — part of the process is helping uncover what your team actually needs most.
The Retreat Experience
Duration
4 days / 3 nights (Thursday–Sunday)
Location
Hosted in beautiful Siesta Key, with the option to explore other locations upon request.
Format
In-person only
Structured sessions paired with margin for rest, reflection, and connection
Thoughtful pacing to allow insight to turn into real alignment
Optional Add-On
Teams may add additional days for 1:1 mentorship or leadership sessions with Lisa and Jaime if deeper individual support is needed.
Our Approach
Lisa and Jaime bring years of hands-on business and leadership experience, guiding teams through real decisions, real growth, and real complexity.
Rather than facilitation for facilitation’s sake, their role is to:
- Ask the right questions
- Create space for honest conversation
- Help teams name what matters most
- Guide clarity, alignment, and forward movement
The goal is not perfection — it’s shared understanding and intentional next steps.
FAQs
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Every retreat is fully customized. Before the retreat, Lisa and Jaime work closely with your leadership to understand your team, your goals, and your current challenges. From there, a curriculum is designed to cover the topics that matter most — whether that’s leadership development, culture, vision, communication, or alignment.
There is no pre-set agenda. The experience is shaped around what your team needs right now.
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Team Retreats are typically four days and three nights, running from Thursday through Sunday. This pacing allows enough space for meaningful work, rest, reflection, and connection without feeling rushed.
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Most Wholly Designed Team Retreats are hosted in Siesta Key, offering a calm, distraction-free environment that supports both clarity and connection.
If your team prefers a different location, alternative destinations can be discussed and arranged.
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Team Retreats are in-person only.
The depth of conversation, alignment, and connection we aim for is best supported when everyone is fully present in the same space. -
Yes. Teams have the option to add additional days before or after the retreat for 1:1 mentorship or leadership sessions with Lisa and Jaime. This is especially helpful for leaders who want deeper personal clarity or strategic support.
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Wholly Designed retreats are:
Fully customized — no templates or pre-written curriculum
Guided by real business and leadership experience
Intentionally paced with space for rest and reflection
Focused on clarity, alignment, and sustainable next steps
The goal isn’t to overwhelm your team with content, but to help them walk away aligned, grounded, and clear.
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Team Retreats are custom-priced based on:
Team size
Location
Length of stay
Scope of preparation and facilitation
Optional add-on mentorship days
Pricing is discussed after an initial conversation to ensure the experience is designed well for your team.
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The first step is simply a conversation.
We’ll talk through your team, your season, and what you’re hoping to gain from a retreat. From there, we’ll determine whether a Wholly Designed Team Retreat is the right fit and outline next steps together.Inquire Below