Northern Cyclades Reset
Next Expedition

Northern Cyclades Reset

Sat. 13 June – Sat. 20 June, 2026
7 Days Sailing
Cyclades, Greece

A sailing journey through elegant island towns, wild anchorages, and the quiet power of the Aegean. From neoclassical harbors to untouched beaches — this is where sea time becomes real time.

Scroll

Sailing? Network? What to Expect

Beyond the Deck: Learning & Connections

Evening talk on yacht deck at sunset
🎤

Public Talks & Workshops

Each evening, a participant shares their biggest lesson. Peer-led sessions on fundraising, hiring, GTM, and product strategy. Real stories, real problems, immediate feedback.

Topics from Last Time

"How I Failed My First Startup and What I Learned" Most Attendance

Ex-Founder, now VP Product at a Series B fintech

"Raising €2M in 6 Weeks: The Cold Email Strategy"

2x Founder, angel investor in 12 startups

"Building a Remote Team Across 5 Time Zones"

CEO of a 40-person fully remote SaaS company

"From Side Project to €50K MRR in 18 Months"

Solo founder, bootstrapped to profitability

"Why I Turned Down a VC Term Sheet"

Founder of a €5M ARR B2B platform

"The Burnout Nobody Talks About"

Serial entrepreneur, executive coach

Our Sailors

Founders

Company builders and product creators in active growth. They come for straight talk, insight shaped by real pressure, and relationships that last beyond the regatta.

Executive Professionals

Senior leaders with genuine decision authority. Leadership, judgment, and trust emerge through shared challenge, not staged dialogue.

Investors

Capital partners who focus on people before metrics. A space to observe leaders in motion and build long term alignment in real conditions.

The Journey

7 days. Cyclades, Greece. Click waypoints to navigate.

ARRIVAL
ARRIVAL
Saturday

ARRIVAL

Arrival & check-in, welcome dinner

Lavrio → Kythnos
1
Sunday

Lavrio → Kythnos

~18 NM
Highlight: Turquoise wild anchorage

A short and easy first leg designed to shift from land mode to sea mode. Calm waters, a protected anchorage, first swims, and a sunset dinner onboard.

Turquoise anchorage Easy first sail Swimming & sunset Quiet night at anchor
Kythnos → Syros
2
Monday

Kythnos → Syros

~32 NM
Highlight: Former capital of the Cyclades

A steady open-sea passage leading into the most elegant harbor of the Cyclades. The approach to Ermoupolis reveals layered neoclassical architecture rising above the port. Evening walks, cafés, and a refined urban atmosphere.

Cultural stop Elegant town
Syros → Tinos
3
Tuesday

Syros → Tinos

~12 NM
Highlight: Marble-built island town

A short morning crossing to an island shaped by marble craft and pilgrimage traditions. Whitewashed alleys, marble stairways, and quiet cultural depth.

Pilgrimage sanctuary Marble architecture Authentic island town Wind-washed alleys
Tinos → Andros
4
Wednesday

Tinos → Andros

~25 NM
Highlight: Green landscapes & freshwater springs

A downwind open-sea sail toward the greenest island of the Cyclades. Arrival in a relaxed coastal village with beachside tavernas.

Nature contrast Local life
Andros → Kea
5
Thursday

Andros → Kea

~28 NM
Highlight: Elegant closing harbor

A comfortable crossing following the Meltemi flow. The journey closes in a refined harbor village with waterfront dining and warm evening light.

Farewell evening Soft landing
Kea → Lavrio
6
Friday

Kea → Lavrio

~14 NM
Highlight: Final crossing

A short final sail back to base. Calm waters, relaxed deck time, and a gentle return to land.

Return base Journey closure

The Investment

Choose the option that fits your style. All prices include accommodation and full program access.

Most Popular
Shared Cabin

Shared Cabin

A double cabin shared with another guest

Early Bird
€3,300
Regular €3,600
Private Cabin

Private Cabin

Your own private double cabin — for one or two guests

Early Bird
€6,200
Regular €6,800
Whole Catamaran

Whole Catamaran

Bring your own crew

Early Bird
€22,000
Regular €24,000
Early Bird Ends In
-- Days
-- Hours
-- Minutes

What's Included

Yacht
Skipper
Workshops
Welcome Dinner
Merch
Gas
Insurance
Marina
The Cook

The Cook

If everyone on board agrees, a dedicated cook can be added to your catamaran for +€200 per person per week. Fresh meals, local ingredients, zero cooking duty for you.

Monohull

Monohull

If sailing itself is the point, a monohull offers a more direct, hands-on experience. You are closer to the elements, more involved in trim, balance, and motion, and more connected to the act of sailing itself. The trade-off is clear: less space and comfort than a catamaran, but significantly more feel and authenticity underway.


If this is your preference, mention it to us. We will organize a monohull with a like-minded crew to match that intent.

Next Expeditions

2 destinations. Twenty-one builders each. Choose your adventure.

Applications close when we have the right mix, not when we're full.

Luxury sailing yacht at golden hour
Venture Sailing

Sailing, Networking, Ideas building

Conferences give you 7 minutes. Retreats give you a room to hide in. The sea gives you nowhere to go — except deeper.

FAQ