Kalymnos Women in Leadership Retreat

Moderately Challenging Greece

Kalymnos Women in Leadership Retreat

KALYMNOS LEADERSHIP DEVELOPMENT PROGRAM

The Kalymnos Women in Leadership Retreat is an immersive experience designed to strengthen confidence, courage, and authentic connection through real challenge and intentional dialogue. Set on the world class climbing island of Kalymnos, the retreat places women in a supportive environment where self limiting beliefs become visible and new ways of leading can be practised in real time. Outdoor experiences such as guided rock climbing, Aegean sailing, and island exploration create practical conditions where trust, presence, and voice matter. These moments are paired with facilitated circles and workshops inspired by Dare to Lead, helping participants explore vulnerability, boundaries, values, and the armour women often carry in leadership environments.

1

Purpose designed women’s leadership experience focused on confidence, visibility, belonging, and the inner barriers women navigate at work.

2

Courage through real experience using guided rock climbing as an honest environment where fear, voice, and trust surface naturally.

3

Connection at the core through circles, shared meals, peer dialogue, and collective challenge that builds psychological safety quickly.

Trip photographer to capture it all
Small groups and great community vibes only
No hidden costs its all included
Hassle free airport to airport service
Directly led by us and our local experts
Carefully curated to make it all epic

WHAT'S INCLUDED IN THIS TRIP

  • Accommodation in Kalymnos with daily breakfast
  • All group lunches and dinners as outlined in the itinerary at curated local tavernas
  • Professional rock climbing guides and all technical climbing equipment
  • Guided Aegean sailing day including onboard lunch
  • Guided island exploration experience
  • Daily leadership facilitation integrated throughout the retreat
  • Structured circles, reflection sessions, and facilitated peer dialogue
  • Dedicated Life Happens Outdoors Team Leader on the ground throughout
  • All permits, safety planning, and activity logistics
  • Coordinated ferry transfers between Kos and Kalymnos within the program flow

WHAT'S NOT INCLUDED IN THIS TRIP

  • What is not included
  • Entry visas to Greece
  • Travel and health insurance
  • Discretionary tips and gratuities
  • Personal clothing, see gear list

Itinerary

Day 1 Arrival and Women’s Leadership Circle

Participants arrive via Kos and take the short ferry crossing to Kalymnos. After check in, there is time to settle in before the opening Women’s Leadership Circle. This session establishes psychological safety, shared agreements, and personal intentions, introducing self limiting beliefs and the armour women often wear in leadership. Lunch and dinner are hosted at curated family run tavernas.

Day 2 Rock Climbing, Courage, and Trust

A guided rock climbing day on the world class routes of Kalymnos. No prior climbing experience is required. Themes of fear, confidence, boundaries, and voice become visible through real moments on the rock, supported by professional guides and the group. After lunch near the climbing sectors, a short yoga session supports recovery, followed by a facilitated workshop debrief and dinner by the coast.

Day 3 Vespa Island Tour, Perspective, and Freedom

The group explores Kalymnos by Vespa through villages, coastal roads, and panoramic viewpoints. Reflection stops explore identity and authenticity in leadership, including where women adapt, shrink, or over perform. Lunch and dinner are enjoyed across village and coastal settings.

Day 4 Aegean Sailing, Reflection, and Integration

A sailing day along the coastline of Kalymnos and Telendos with time to swim, rest, and reconnect. Facilitated dialogue focuses on values, influence, and courageous leadership, including what to release and what to strengthen moving forward. Lunch is served on board, followed by a celebratory farewell dinner in the evening.

Day 5 Departure

After breakfast, guests take the short ferry back to Kos for onward travel. Departures are coordinated based on individual flight times.

OUR COMMITMENT

OUR COMMITMENT

We are dedicated to ensuring that everyone involved in our services receives a fair living wage in their respective countries. We invest in our team members, fostering upward mobility within the adventure travel industry, expanding educational opportunities, and offering support wherever we can. By joining an LHO adventure you are directly impacting the incredible people and the remote communities that make these life-changing experiences possible.

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HEALTH & SAFETY GUIDELINES

HEALTH & SAFETY GUIDELINES

We do our best to ensure your wellbeing on LHO adventures. That's why the facilities we use throughout our trips are required to meet our health and safety standards. We also follow the laws and protocols of every country that hosts our adventures. This extends to national regulations requiring Covid-19 testing, vaccination certificates, mask wearing or any other local guidelines that may apply. Contact us for the most up to date protocols related to your destination.

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Frequently Asked Questions

Is this a fixed itinerary or can it be tailored?

It can be tailored. We use a proven five day framework, then adapt the pacing, intensity, and emphasis based on your objectives, the participant profile, and the outcomes you want to prioritise.

Who is this retreat designed for?

Women in leadership and emerging leaders who want to strengthen confidence, presence, boundaries, and authentic communication, while building meaningful connection within a cohort.

What outcomes can we expect?

Participants leave with stronger self trust, clearer personal values, practical tools for courageous leadership, and a shared language that supports ongoing accountability and connection back at work.

What makes this different from a typical corporate retreat?

This is experiential. The outdoor environment makes patterns visible in real time, then facilitation turns those moments into insight and action. It is designed around women’s lived leadership barriers, not generic leadership theory.

What leadership approach do you use?

The retreat includes facilitated circles and workshops inspired by Dare to Lead, with themes such as vulnerability, values, boundaries, and the armour women often carry in leadership environments.

Who is Emile Woolf and what is their role?

Emile Woolf is our leadership and behavioural training partner. They support the design and facilitation of the leadership elements, helping translate what happens outdoors into practical leadership behaviours and real workplace application.

Do participants need rock climbing experience?

No. No prior climbing experience is required. Professional climbing guides lead the sessions and all technical equipment is provided.

How physically demanding is it?

Moderate. Expect several hours outdoors most days with breaks. The climbing day is guided and paced, the Vespa island day is light but active, and the sailing day is restorative.

Is it suitable for mixed fitness levels?

Yes. We adjust the climbing sectors, time on the rock, and the day flow to match the group, while keeping everyone included and supported.

What happens if someone does not want to climb?

We can adapt. Climbing is a powerful component, but the retreat can be shaped for different comfort levels and objectives, including more emphasis on facilitation, reflection, and alternative island activities.

What safety standards do you follow?

Safety is central. Technical activities are delivered by professional guides with appropriate equipment, briefings, and conservative decision making based on conditions and group readiness.

What happens if weather is poor?

We adapt the plan. Kalymnos offers flexibility across locations and activity types, so we can adjust timing, choose sheltered areas, or replace elements while protecting the integrity of the retreat.

What is the accommodation like?

Comfortable and well located accommodation that supports rest and connection. Kalymnos is intentionally grounded rather than ultra luxury, creating space for presence, simplicity, and group cohesion.

How do we get there?

You travel via Kos International Airport, then take a short ferry crossing to Kalymnos. Ferry transfers are coordinated within the program flow.

Do you accommodate dietary requirements?

Yes. We collect dietary requirements in advance and coordinate with the local restaurants and venues included in the program.

Do participants need travel insurance?

Yes. Each participant should have appropriate travel insurance that covers the destination and the planned activities.

What is the ideal group size?

It works best with small to mid sized cohorts where trust and honest dialogue can build quickly. We can scale delivery with additional guides and facilitation if required.

Can we customise the retreat for our company values and culture goals?

Yes. We can tailor sessions and prompts around your culture themes, leadership behaviours, and inclusion priorities, while keeping the retreat grounded in lived experience and real connection.

How does booking work if dates are custom?

You submit an enquiry with your preferred date window, cohort size, and outcomes. We then shape the itinerary and logistics into a proposal with deposit terms to secure delivery.

Can we pay by company invoice and bank transfer?

Yes. We can invoice the company and support bank transfer payments, subject to the agreed booking terms.

What is your cancellation and change policy?

Because accommodation, guides, and logistics are secured specifically for your group, cancellation and change terms depend on lead time and supplier commitments. We provide clear terms in the proposal before any payment is taken.

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PAYMENT PLANS AVAILABLE

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TELL YOUR FRIENDS
An adventure holiday for anyone with a pulse. No fitness requirements or prerequisites. Come as you are. Great for those who already train 1-2 times per week or would like to use this upcoming adventure as an opportunity to kickstart a fitness journey. Joiners should be comfortable with their physical fitness and regularly train at least 2-3 times a week in the lead up to this adventure. Joiners should be comfortable with their physical fitness and regularly train at least 2-3 times a week in the lead up to this adventure.Joiners should be comfortable with their physical fitness and regularly train at least 2-3 times a week in the lead up to this adventure. Need we explain further? No prior experience is required. Basic skills may be taught during this adventure. The skills necessary to safely complete this adventure will be taught as a part of this experience. This adventure requires prior experience, pre-requisite skills or certifications. See below for details. We aim to strike a balance between unique local experiences and international standards of comfort and hygiene. Hostels are dorm-style accommodation used during certain legs of our trips and expeditions. They can be quite trendy with common areas, restaurants and cafes. Expect rooms to include a bed and a mattress as well as a common dining area with chairs and tables. You’ll need to bring a sleeping bag and an optional pillow. When the experience includes camping we provide the tents, sleeping mats, common dining tents, camping chairs and camping tables. The only thing you’ll need to get is a sleeping bag and an optional camping pillow. Please refer to the LHO gear list for more information specific to the trip you’re on. Mountain Lodges are usually well equipped, providing beds with duvets and pillows. They also include a common restaurant area. Some lodges require a sleeping liner.

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