Reground & Rise Retreat
Arrive feeling overwhelmed.
Leave feeling clear.
Growth doesn’t always require more effort.
Sometimes it requires space. Perspective. Breath.
Reground & Rise is a strategic entrepreneur retreat on the coast of Portugal, designed for leaders who want to step away from the noise long enough to hear their own thinking again.
Begin your days with intention, quiet reflection, guided strategy sessions, and space to clarify what truly matters in this season of your business. Afternoons open into thoughtful dialogue, planning, and integration. Evenings are for rest, connection, and letting your mind fully recharge.
This isn’t about escaping your business.
It’s about returning to it differently.
You’ll come back with clearer priorities, stronger boundaries, a steadier leadership presence, and a strategy aligned with the life you’re building.
Join us November 16-20, 2026.
Reground & Rise Retreat
If you’ve been leading in survival mode, this is your reset.
From clarity comes confident action.
Reground & Rise is a strategic pause designed to help you reconnect with your vision, refine your priorities, and build a more sustainable path forward. It is an in-person business retreat in the beautiful countryside of Portugal for entrepreneurs ready to step back from the day-to-day and reset their leadership from the inside out.
This working leadership retreat is grounded in strategic business consulting, nervous system regulation, and intentional growth planning.
November 16-20, 2026
What’s Included:
Five-day retreat experience (Monday - Friday)
Facilitated strategic business consulting sessions
Guided leadership reflection and vision work
Structured planning for sustainable growth
Daily active morning yoga and evening yin sessions
Private one-on-one coaching sessions during the retreat with Jaime
Curated peer conversations and high-trust community
An intimate coastal home stay with three shared bedrooms and a separate mini house
Nourishing daily breakfasts, lunches, and dinners including fresh vegetarian selection
One-hour sauna session (massage is available at an extra cost)
Limited to 8 participants
Investment:
Shared Room €1500
Private Room €2000 (one single room available)
Prices include VAT, flight not included
A Sample Day at Reground & Rise
7:00–8:00 AM Breakfast
Slow conversation and a gentle start to the day.
9:00 AM Active Morning Yoga
Energizing movement to awaken your body and clear your mind before we move into strategic work.
11:00 AM Group Coaching Session
Facilitated leadership and strategy work. Clarify priorities, simplify decisions, and reconnect with your long-term vision.
12:30 PM Buffet Lunch
Nourishing food with unhurried connection.
1:30–4:30 PM Open Space & 1:1 Coaching
Free time to rest, walk the coast, journal, or reflect. Sign up in the morning for your private one-on-one coaching session.
5:00–6:00 PM Gentle Yin Yoga
Slower movement and breathwork to release the day and settle your nervous system.
6:30 PM Dinner
A shared meal and fresh air. Evenings designed for integration and rest.
Leadership Consulting
Facilitated sessions to refine your priorities, strengthen decision-making, and clarify your next stage of growth.
Daily Yoga and Meditation
Gentle movement and guided breathwork to regulate your nervous system and create the internal steadiness strong leadership requires.
Focused Growth Labs
Dedicated working time to simplify offers, strengthen revenue strategy, and map an actionable 90-day plan.
Intentional Community
Small-group dialogue with thoughtful entrepreneurs, real connection, honest conversation, and perspective that expands your thinking.
Meet Jaime Bancroft Gennaro
Jaime is a Strategic Business Consultant and Advisor with over 20 years of experience growing and leading companies. She has scaled and sold startups, served as a COO, and coached leadership teams through pivotal stages of growth and transition.
Known for her ability to quickly see what’s underneath the surface in both businesses and leaders, Jaime helps entrepreneurs clarify direction, strengthen decision-making, and build sustainable strategies that align with the life they want to lead.
She is also a trained yoga instructor, bringing an integrated approach to leadership that blends strategic clarity with nervous system regulation and embodied presence.
