The Journeys

• Leave the details to us. From arrival to departure, accommodations, dining, and experiences are thoughtfully designed so you can focus on the journey.

• Travel your way. Come solo, with friends, or as a couple. Our small groups make it easy to meet others and share experiences naturally.

• Connect without the forced socializing. This isn’t a traditional group tour. There’s room to engage, explore, and enjoy time on your own.

• Feel welcomed wherever you go. We choose destinations and experiences where gay men can feel comfortable, welcomed, and a genuine sense of belonging.

February 11-15, 2027 | 4 Nights/5 Days

Palm Springs Pickleball Escape: The Modernism Week Edition

Limited to 32 Guests | From $3,650 per person

Palm Springs, CA: Experience Palm Springs' celebrated Modernism Week and enjoy three days of open play and round-robin pickleball for intermediate (DUPR 3.0–3.9) and advanced (4.0+) players, plus a private modernism tour, the Palm Springs Aerial Tramway, and time to relax and connect.

April 8-April 12, 2027 | 4 Nights/5 Days

Miami Beach Pride Pickleball Escape and Tournament

Limited to 32 Guests | $TBD per person

Miami Beach, FL: Celebrate Pride in Miami Beach with a getaway that combines community, sport, and the city's vibrant energy. Enjoy the festival and parade, and compete in the inaugural Miami Beach Pride Pickleball Tournament for intermediate and advanced (DUPR 3.0+) players.

Coming Soon
We are putting the finishing touches on this journey. Be the first to know when registration opens.

May 27-31, 2027 | 4 Nights/5 Days

Pacific Coast Pickleball Escape & Puerto Vallarta Pride

Limited to 32 Guests | $TBD per person

Nuevo Nayarit, Nayarit, Mexico: Celebrate Puerto Vallarta Pride with a getaway that blends pickleball, community, and celebration in one of the world’s top LGBTQ+ destinations. Enjoy open play and round-robin competition with intermediate and advanced players (DUPR 3.0+), experience the Pride festivities, then retreat to the resort for refined all-inclusive hospitality, relaxation, and time to connect.

Coming Soon
We are putting the finishing touches on this journey. Be the first to know when registration opens.

October 2027 | 3 Nights/4 Days

Breathe & Reflect:

The Purpose Retreat

Limited to 14 Guests | $TBD per person

Retreat for a restorative journey centered on wellness, reflection, and purpose. Guided by a renowned spiritual teacher and transformation coach, explore the practice and power of breathwork while creating space for deeper inquiry, meaningful connection, and a renewed understanding of what matters most.

Coming Soon
We are putting the finishing touches on this journey. Be the first to know when registration opens.

Your Journey.

Designed Together.

Bring together the men who matter to you for a journey shaped by shared interests, meaningful experiences, and time well spent. Whether celebrating a milestone, exploring somewhere new, or simply reconnecting, we invite you to begin a conversation about a custom-designed group journey

My Story

The Journey That Led Me Here

A Crossroads and a Different Question

At 50, I found myself at an unexpected crossroads. I had been laid off from a senior nonprofit role, leaving behind a good salary and the security that came with it. But I knew I didn’t want to simply find another job and return to the same path. I wanted my next chapter to feel different.

Years earlier, a mentor introduced me to personal development and lessons about resilience, perspective, responsibility, and possibility. Those lessons stayed with me. So rather than asking, “What job should I find next?” I asked:

“What are the criteria for the life I want to create now?”

My answer was surprisingly simple: fun and joy.

Rediscovering What Brings Me Alive

I find joy in helping people grow and discover what is possible in their lives. I also find it in movement like lifting weights, practicing yoga, and especially playing pickleball.

What began as a game with family eventually led me to help organize an LGBTQ+ pickleball league in Washington, D.C. Along the way, I rediscovered something important: the power of play to create community.

Travel has shown me something similar.

The Transformative Power of Travel

One of the first journeys I organized as a travel advisor was a culinary exploration of Oaxaca during Día de los Muertos. Through food, history, and culture, I was reminded that meaningful travel does more than introduce us to a destination. It invites us to understand a place, and sometimes ourselves more deeply.

After more than two decades working alongside LGBTQ+ leaders and organizations, I have seen how powerful it can be when we come together. Around a dinner table, on a pickleball court, atop a mountain, or halfway around the world, we create space for connection, discovery, and joy.

The Beginning of Fellow Travelers

That idea became the foundation for Fellow Travelers.

I wanted to bring together what has given my own life meaning: personal growth, physical well-being, extraordinary travel, cultural discovery, and genuine human connection.

I deeply admire the resilience of the LGBTQ+ community. But I believe we deserve more than resilience. We deserve opportunities to thrive, to breathe freely, to belong fully, to challenge ourselves, to discover something new, and to experience joy.

That is why I created Fellow Travelers: to explore the world together, invest in our well-being, and build the connections that make a rich life even richer.

Orlando Gonzales, Founder

New York City, NY

Virgin Voyages, Brilliant Lady, Québec City, Canada

Virgin Voyages, Peggy's Cove, Nova Scotia, Canada

The Great Elephant Migration, art installation, Miami Art Week and Art Basel, Miami, FL

Travel Well. Leave Something Behind.

At Fellow Travelers, we believe meaningful travel should leave something behind. Community investment is woven into every journey we create, with a portion of each experience supporting a nonprofit organization connected to the destination or community we visit, or a U.S.-based 501(c)(3) organization whose work reflects our values.

It is our way of ensuring that travel is not only about what we discover, but also what we give back.

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