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THE MASCULINE JOURNEY

AN INVITATION, NOT AN OPEN REGISTRATION

An island exists for men
who built the life and 
lost parts
of themselves building it.

You're reading this because someone who knows you thought you belonged here.

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WHO THIS IS FOR

Surrounded by people. Known by no one.

You're surrounded by people. A team, a family, a calendar full of names. And there's still no one who gets the real version of you.
 

The part that numbs out on your phone after everyone's asleep. The part that dives back into work to feel worth something. The part that learned a long time ago that being loved meant performing well enough to earn it.
 

Not because you're broken. Because you've never had a room where that could be said out loud without it changing how people see you.

Men leave Pine Island different.
More present at home. Clearer about what matters.
Lighter than when they arrived.

Not because we promised it, but because four days off the grid
with the right men does that.

THE JOURNEY

Every man's journey here is his own.

No two men walk onto this island carrying the same thing. One man's work is a marriage he's stopped showing up for. Another's is a business he built that swallowed him whole. You won't be handed someone else's process and told to make it fit. What gets challenged in you is specific to you, and so is what you'll walk away with.
 

But you won't be alone in it. Every man in that circle can relate. He's there right now, he's been there, or he will be. Whatever you're carrying, someone next to you already knows the weight of it.

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THE SETTING

​​There is no road in. That's the point.

Pine Island is private. You reach it only by boat, seaplane, or water taxi. Over a thousand feet of shoreline, loons and eagles overhead, and a constant breeze that keeps it mosquito-free. There are Tentsile hammocks strung in the pines, a lagoon and a grotto, and a place the island calls Whale Rock.
 

Getting here means leaving the easy way behind. By the time the boat pulls away from the mainland, you've already started.

Pine Island Intro
Alex Boylan

Pine Island Intro

THE ARC OF THE DAYS

Out of your head. Into your body.

Most of what's keeping you stuck isn't in your head. It's in your body. Years of performing, achieving, and holding it together live as tension you've stopped noticing.
 

Each day moves through structured work to unlock it. Dynamic meditation and movement to work loose what your nervous system has been holding tight against your own programming. Breath work to teach your body how to actually downshift instead of gritting through. Grounded practice that brings you back into yourself instead of just your head. This isn't talk therapy. It's what happens underneath the talking.
 

There's structure, but not a packed one. A lot of what happens here isn't scheduled. It's the island itself. The water, the quiet, the unplanned hour that turns into the conversation you didn't know you needed. We give space so the environment can do more.

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THE EXPERIENCE

HEART OPENING EXERCISES

Engaging sessions on personal growth, relationships,
and self-discovery, with powerful activities designed to unlock your emotional potential.

HEALTH EXPLORATION

Dynamic meditations, outdoor adventures, and bonding experiences, plus new ways to prioritize your physical and mental well-being.

RELATIONSHIP MASTERY

Cultivate deep, meaningful connections with
others and yourself.

WEALTH OF WISDOM

Personal time for introspection and integrating your experiences, with insights on achieving abundance in all areas of your life.

THE RETREAT

Four days on Pine Island.

A small group of accomplished men, one island on Long Lake, and the space to do the work that actually matters. Guided practice, real brotherhood, and time away from the version of you that performs — with room for the version of you that's ready.

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DAY 1 - THURSDAY

Arrival & Opening Circle

Dinner

Evening Breathwork

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DAY 3 - SATURDAY

Morning Movement

Breakfast

Morning Workshop

Lunch

Afternoon Workshops

The Feast

Sound Bath

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DAY 2 - FRIDAY

Sunrise Meditation

Breakfast

Morning Workshop

Lunch

Afternoon Workshops

Dinner

Kundalini Meditation

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DAY 4 - SUNDAY

Breakfast

Closing Ceremony

Journey Home

WHO'S GUIDING THIS

I’m a paragraph. Double click me or click Edit Text, it's easy.

Randy Bernard

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Josh Lanphear

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Mark Carey

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Brandon Hawk

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Andrew Carter

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Not theorists. Every man guiding this has stood exactly where you are, between the life they built and the person they lost building it.

Men who've lived the gap you're
standing in.

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I’m a paragraph. Double click me or click Edit Text, it's easy.

I’m a paragraph. Double click me or click Edit Text, it's easy.

I’m a paragraph. Double click me or click Edit Text, it's easy.

IN THEIR WORDS

From men who've been in the circle.

Chris' Testimonial

What you're actually asking.

FREQUENTLY ASKED QUESTIONS

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THE INVESTMENT

What it costs, and what's held inside it. 

$3,500

October 8 -11, 2026  ·  Pine Island  ·  Naples, Maine

Lodging on the island

All guided sessions, movement, and breath work

Meals

Transport from Ricker's Resort to the island

A few surprises along the way we're not giving away yet

APPLY

This isn't a checkout. It's a conversation.

Tell me a little about where you are. If it feels like a fit, the next step is a call with me directly. No forms after that, just a real conversation about whether this is your October.

Can you commit to October 8–11 in full?
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