What Is a Sailing Retreat and Why Should Your Team Try One?

Team offsites are evolving. More companies are moving away from hotel conference rooms and toward immersive, experience-rich retreats that help their people reconnect, recharge, and refocus. One of the most powerful formats to emerge in recent years? Sailing retreats.

This article breaks down what sailing retreats are, who they’re best suited for, and why they’re an incredible option for teams looking to combine strategy, wellness, and adventure — all in one unforgettable journey.

What Is a Sailing Retreat?

A sailing retreat is a multi-day offsite experience held aboard a yacht or catamaran. These retreats take your team out of traditional settings and onto the open sea — offering a mix of exploration, team bonding, and purposeful downtime. Each day combines elements of group work, wellness, and shared adventure, with the ocean as your meeting space and the islands as your agenda.

At Get Lost, we specialize in planning curated sailing retreats across Greece. From setting your route through the Cyclades or Ionian Islands to organizing onboard chefs, workshops, and wellness sessions — we handle all the details so you can focus on your team’s growth.

Who Should Consider a Sailing Retreat?

Sailing retreats are a great fit for:

• Remote teams reconnecting in person

• Executive leadership teams planning strategy in a distraction-free setting

• Startups looking to align post-funding or post-launch

• Creative and wellness-driven companies that value clarity, balance, and connection
  

They’re especially powerful for teams that thrive in dynamic environments, value trust and communication, and are open to stepping outside the norm.

Why Your Team Should Try One

1. Strengthens Team Bonding

Working and living together on a boat naturally brings people closer. Whether it’s docking at a harbor, preparing a group meal, or navigating a windy stretch, the shared challenges and wins create stronger connections.

2. Builds Leadership and Problem-Solving Skills

A sailing retreat isn't just relaxing — it's hands-on. Teams take turns steering, navigating, and solving real-time challenges, which brings out leadership potential in unexpected ways.

3. Offers a True Digital Detox

Out at sea, there’s no pressure to be online 24/7. It’s an opportunity to unplug as a group, giving your team the mental space to be more present and creative.

4. Sparks Creative Thinking

The combination of movement, nature, and novelty breaks the usual thinking patterns. Many teams report major breakthroughs during sailing retreats — the kind that don’t happen in typical boardrooms.

5. Combines Wellness with Adventure

With daily swimming, healthy meals, fresh air, and optional wellness sessions (like yoga or guided reflection), sailing retreats naturally support both physical and mental health.

Top Destinations for a Sailing Retreat

Some of the most sought-after sailing retreat routes in Europe include:

• Greece – A perfect balance of rich history, calm waters, and charming island villages. Get Lost operates extensively in Greece, planning bespoke sailing routes from the Cyclades to the Ionian Islands.
  

• Croatia – Ideal for coastal exploration and island hopping with medieval towns and crystal-clear coves.
  

• Italy – The Amalfi Coast or Sicily offer food-forward itineraries with spectacular coastal scenery.
  

Each destination offers something unique, and we tailor your experience based on your team’s goals, preferences, and energy level.

What’s Included in a Sailing Retreat

Every retreat is customized, but here’s what’s typically included:

• A private yacht or catamaran with professional skipper and crew

• Comfortable private cabins and shared onboard spaces

• All logistics and route planning

• Onboard meals or private chef services

• Access to water sports like paddleboarding or snorkeling

• Cultural stops, coastal hikes, and downtime in picturesque towns

• Optional facilitation, coaching, or wellness programming
  

You can explore a sample of our offerings on the Sailing Adventures page.

Is a Sailing Retreat Right for Your Team?

If your team is looking for something that goes beyond the typical retreat format — something that fosters deeper trust, energizes collaboration, and creates lasting memories — a sailing retreat is worth considering.

It’s not just about where you go, but how you get there. And for teams who are ready to grow together, sailing offers both the journey and the destination.

Plan Your Sailing Retreat with Get Lost

At Get Lost, we specialize in creating tailor-made sailing retreats across Greece and other iconic sailing regions in Europe. From logistics to onboard experiences, we ensure every element supports your goals for connection, creativity, and clarity.

👉 Start Planning Your Sailing Retreat

Let’s take your team off course — in the best possible way.