What is Beautiful Masculinity?
Most of us have inherited countless messages about what masculinity is supposed to look like: Be strong. Be confident. Be desirable. Don't be too emotional. Don't be too feminine. Don't need too much. Don't show too much.
As gay/queer men, our relationship with masculinity can be even more complicated. We may have spent years trying to fit into it, rebelling against it, eroticizing it, performing it—or wondering whether we belong within it at all.
Beautiful Masculinity invites another possibility. What if masculinity isn't something we have to prove, perform, or get right—but something we can practice, explore, and embody? Here, there is no single expression we're working toward. Your masculinity might be strong or soft, bold or quiet, rugged or feminine, playful or tender. It may hold contradictions. It may change from moment to moment. What matters is that it belongs to you.
Rather than defining masculinity for you, we'll create space to become curious about your own experience of it. What have you inherited? What have you performed? What have you rejected? And what might you now choose to claim as your own?
Explore — Become curious about the many expressions your masculinity might take.
Practice — Give yourself permission to try something without needing to get it right.
Embody — Notice what actually feels authentic when you experience it in your body.
There is no right answer. There is only an invitation to discover more of yourself.
Fire Island is Part of the Experience
This isn't a workshop that simply happens to be on Fire Island. Fire Island is one of our teachers.
For generations, Fire Island has been a queer sanctuary—a place to gather, explore, celebrate, desire, play, and experience freedoms that weren't always available elsewhere. It has offered generations of queer people space to experiment with identity and expression, deepen connection, and simply be more fully themselves.
Beautiful Masculinity draws upon that legacy. For a weekend, the Pines becomes a place to practice—to explore different expressions of your masculinity, notice what feels authentic in your body, and experience yourself in community with other gay and queer men doing the same.
We'll move between facilitated experiences and the world around us: the beach, the ocean, sunsets, shared meals, bare feet, pleasure, rest, laughter, conversation, and community.
Some of the most meaningful moments may happen during an exercise. Others may happen sitting beside the pool or walking back from the beach with someone who was a stranger two days earlier.
What You'll Experience
Beautiful Masculinity is an embodied experience. We can talk about masculinity—where we learned it, how we've performed it, what we've resisted—but something different happens when we have the opportunity to practice it in our bodies and in relationship with one another.
Throughout the weekend, you'll be invited to explore what your beautiful masculinity feels like when you move with it, express it, connect through it, give and receive from it, experience pleasure within it, and allow yourself to be seen in it.
Through movement, connection, conscious touch, pleasure, conversation, ritual, and embodied practice, we'll create opportunities to try things on—not to find the “right” way to be masculine, but to notice what feels authentic, alive, and yours.
Practice doesn't require perfection. It invites possibility.
Embodiment
Practice moving out of your head and into your body—using movement, breath, sensation, and awareness to explore what masculinity feels like when you inhabit it rather than simply think about it.
Masculinity
Exploring what we've inherited, performed, rejected—and what we might now choose to claim for ourselves. Try on different expressions of masculinity without needing to perform or get it right. Explore what you've inherited, what you've resisted, and what feels authentic when you give yourself permission to make masculinity your own.
Intimacy
Practice being with others in ways that invite greater presence and authenticity—asking for what you want, expressing boundaries, giving and receiving, allowing yourself to be seen, and discovering how you want to meet another person.
Desire & Eros
Explore desire and Eros through pleasure, conscious touch, and embodied connection. Notice what happens when you allow your erotic self to be part of your masculinity—not something separate from it.
Strength & Tenderness
Discovering what becomes possible when strength doesn't require armor and vulnerability doesn't mean weakness. Practice allowing seemingly opposite qualities to coexist. Strength and softness. Confidence and uncertainty. Masculine and feminine. Giving and receiving. Discover what becomes possible when you don't have to choose one at the expense of another.
Play & Freedom
Give yourself permission to experiment. Move, make sound, laugh, flirt, connect, take up space, soften, be bold, be quiet, or try something unexpected. Practice doesn't require perfection—it invites possibility.
Throughout the weekend, these practices may take the form of movement and dance, breathwork, conscious touch, pleasure, ritual, reflective conversation, nature, water, and time together in community.
Everything offered is an invitation. Choice, consent, and personal agency are foundational to the experience. Practicing Beautiful Masculinity includes the freedom to say yes, no, maybe, more, less—or something entirely different.
Come as you are.
Leave with more of yourself.
The Weekend
Friday — Arrive
Arrive in Fire Island Pines, settle into our home for the weekend, meet the men who will share this experience with you, and begin creating our community. We'll share dinner and open our exploration together Friday evening.
Saturday — Explore
We'll move deeper into the body, masculinity, connection, and the stories we carry—moving between facilitated experiences and the natural environment around us. There will also be room for pleasure, meals, conversation, the beach, sunset, and simply being together.
Sunday — Embody
Sunday invites us further into expression, desire, intimacy, connection, and Eros. What might you allow yourself to experience when you don't have to perform who you're supposed to be? We'll close our final evening by celebrating what we've discovered—and one another.
Monday — Integrate
Monday morning gives us time to harvest the learnings from the weekend and consider what we want to carry with us beyond Fire Island. We'll collect the data, share our discoveries and have lunch one last time before saying goodbye.
Our Home in Fire Island Pines
For three nights, we'll make our home in two neighboring houses in the heart of Fire Island Pines, giving us space to gather as a community as well as room to relax and recharge.
Accommodations are separate from retreat tuition, giving you the freedom to choose where you'd like to stay during the weekend.
We have eight spaces available in two neighboring homes near our retreat space. Together, the properties offer two pools, 2 hot tubs, a sundeck, and some of the most beautiful water views on Fire Island—a wonderful setting for relaxing and connecting between our time together.
Once these spaces are filled—or if you simply prefer something different—you're welcome to arrange your own accommodations elsewhere on Fire Island. Staying in Fire Island Pines is recommended for ease of getting to and from our time together.
Who is this for?
Beautiful Masculinity is for gay, bi, and queer men—including trans men—as well as non-binary people who feel drawn to an exploration of masculinity, embodiment, intimacy, and Eros.
You’re a great fit for this retreat if…
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You’re ok going to a naked yoga class
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You’re interested in sacred sexuality or conscious sexuality
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You’re excited to build a close knit community with the other participants that long weekend
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You’re intrigued about using pleasure and eros as a healing medicine in community
This is NOT the right retreat for you if…
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You’re looking to party in the Pines
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You’re unwilling to engage in intimate touch with other men (all touch will require consent)
You don't need to feel particularly masculine.
You don't need to reject masculinity.
You don't need to know what masculinity means to you.
You may be confident in your body or deeply uncertain about it. You may feel sexually liberated or still be discovering what you want. You may love being seen as masculine—or have spent much of your life questioning what the word means.
Curiosity is enough.
Come as you are.
Your Facilitators
Win Chesson
(With Officer Keegan, Head of Security)
Win Chesson is a leadership coach, Stanford educator, and devoted student of embodiment, intimacy, pleasure, and connection. He has taught leadership at Harvard and currently facilitates training groups at Stanford focused on emotional literacy and interpersonal influence.
A gay man, passionate Fire Islander, lifelong swimmer, and daily journaler, Win loves creating spaces where queer men can practice beautiful masculinity, vulnerability, pleasure, and authentic connection—with themselves, one another, and nature.
Don Shine
Don is a facilitator, intimacy coach, and sacred intimate whose work explores embodiment, pleasure, connection, intimacy, and Eros.
A facilitator with the Body Electric School since 2022, Don leads workshops and retreats throughout the United States and internationally. His work draws from Body Electric, Tantra, Taoism, the Wheel of Consent, conscious touch, and embodied practices centered on choice, curiosity, and authentic expression.
Donnie Parton and Winnifred Sweetcheeks express their beautiful masculinity.
The Details
Dates:
October 9–12, 2026
Location:
Fire Island Pines, New York
Begins: Friday evening at 5pm
Ends: Monday after lunch
Retreat Tuition:
Suggested tuition: $1,600 (Sliding scale based on your financial capacity)
We invite you to choose the amount within this range that feels appropriate for your financial circumstances. No application or explanation is required.
Tuition includes the complete retreat experience and all meals throughout the weekend, including breakfast, lunch, dinner, and snacks.
Accommodations
Lodging is separate from retreat tuition. Participants may stay with us in one of two neighboring homes or arrange their own accommodations elsewhere in Fire Island Pines.
Shared room / double occupancy: $875 per person
Private room / single occupancy: $1,750
Group Size
Intentionally limited to preserve the intimacy of the experience. Roughly 15 participants
Transportation
Transportation to and from Fire Island Pines is not included. Detailed travel information, including ferry and public transportation options, will be provided to participants.
How to Register:
Because Beautiful Masculinity is an intimate, experiential retreat, registration includes a brief phone conversation with Win and/or Don. This gives us an opportunity to connect, answer any questions you may have, and make sure the retreat feels like a good fit for you.
To begin the registration process, contact Win by clicking here [Link to Win's E-Mail]
Make It Yours
There is no single way to be masculine.
Your masculinity can be strong and tender. Bold and vulnerable. Playful, sensual, quiet, expressive, fluid, grounded—or something entirely your own.
Beautiful Masculinity is an invitation to practice. To try things on. To discover what feels alive and authentic in your body. To express parts of yourself that may not always have had room to be seen.
For one long weekend, surrounded by queer community and the freedom of Fire Island, give yourself permission to explore what’s possible.
Bring your curiosity.
Bring your desire.
Bring your tenderness.
Bring your strength.
Bring all of you.
Come to Fire Island
Explore it. Express it. Embody it.