We head to Key West to explore one of the most iconic LGBTQ+ destinations in the world and the legendary Island House Key West. 

Jeff Smead, Director and General Manager of Island House, talks to us about his journey in hospitality and what it takes to run a resort that has become a global favorite for queer men. As Island House celebrates its 50th anniversary, Jeff shares how the resort has evolved since 1976 while staying true to its roots as a clothing optional, community-driven space where guests can fully be themselves.

We dive into what makes Island House so unique, from its famous daily happy hour and social atmosphere to its balance of relaxation and connection. Plus, we zoom out to talk about Key West as an LGBTQ+ travel hotspot, including tips for first-time visitors, the local vibe, and why this island continues to attract queer travelers from around the world.

SPONSORS:

Island House Key West

islandhousekeywest.com

Provincetown Office of Tourism 

ptowntourism.com/lgbtq

Looking for the ultimate LGBTQ+ summer getaway in the US? In today’s episode, we’re diving into Provincetown (aka PTown) America’s queer summer capital.

Located at the tip of Cape Cod, Provincetown transforms each year into a vibrant LGBTQ+ haven filled with iconic events, beach days, unforgettable nightlife, and a powerful sense of community. But beyond the parties, this historic seaside town has deep roots as one of the oldest art colonies in the country and one of the most welcoming queer destinations in the world.

We break down everything you need to know before you go, including the biggest LGBTQ+ events like Pride, Bear Week, Carnival, and more. We’ll also cover where to stay, from social guesthouses to waterfront resorts, as well as the legendary Tea Dance and Provincetown nightlife scene, and must-do activities like beaches, dunes, and whale watching. Plus, we’ll go over the history that shaped Provincetown into a queer cultural hub.

Whether you’re planning your first trip or heading back for another summer, this episode will help you experience Provincetown to the fullest.

SPONSORS: 

Provincetown Office of Tourism 

ptowntourism.com/lgbtq

Whale, Hello There – Why Provincetown Is America’s Queer Summer Capital

wobadtourists.com/whale-hello-there-why-provincetown-is-americas-queer-summer-capital

Detours 
detourstravel.com

In this micro-episode, we share all the details about our upcoming LGBTQ+ Danube River Cruise group trip happening August 22-29, 2027.

We’ll be cruising through some of Europe’s most beautiful and historic destinations including Budapest, Bratislava, Dürnstein, Melk, Salzburg, Linz, and Vienna — all while enjoying the comfort of a five-star river ship with full-board dining, included guided excursions, and an all-inclusive drinks package.

We tell you all about the incredible destinations we’ll visit along the route, what’s included on the cruise and onboard experiences, and important booking deadlines and early booking saving. If you’ve ever dreamed of cruising through central Europe’s castles, medieval towns, and iconic cities, this is the perfect opportunity to join our community and travel with us.

⚠️ Important:

Book by April 2, 2026 to save $150 per person.All bookings close April 27, 2026 and availability is limited.

Learn more & reserve your cabin: twobadtourists.com/st_tour/7-days-in-austria-slovakia-hungary-river-cruise

SPECIAL OFFER: Get $300 off any retreat between April & August 2026 with promo code TBT300

We are joined by Shelby Clark, founder of Qasa, a queer-owned retreat sanctuary nestled in the Costa Rican jungle. Shelby is a certified yoga instructor, meditation guide, and somatic facilitator devoted to helping queer people unlearn performance, heal shame, and return to authenticity.

Together, we explore why shame often disguises itself as success, sex, and self-control; what cruising, risky sex, and substance use may really be seeking; and how queer people can meet those longings in ways that are more satisfying, embodied, and affirming. Shelby shares how Qasa’s immersive retreats, nature-rooted practices, and community-centered care create powerful spaces for transformation.

We also talk about Qasa’s groundbreaking 2024 research study on plant medicine and LGBTQ+ healing, the documentary capturing retreat experiences, and what it truly means to move from fitting in, to being desired, to deeply belonging.

SPONSOR:

Qasa

https://qasa.house

Queer Medicine: Research & Film

https://qasa.house/queer-medicine

Is Namibia safe for LGBTQ+ travelers? And what does a luxury gay safari there look like? To answer these questions, we are joined by Heiko Dörgeloh, founder of OUT Namibia, the country’s first LGBTQ+ travel concierge. Together, we explore why Namibia is quietly becoming one of Africa’s most welcoming and transformative destinations.

Heiko shares how Namibian culture’s deep respect for privacy and discretion creates a surprisingly comfortable environment for LGBTQ+ visitors, and how OUT Namibia curates bespoke luxury safaris where travelers can fully be themselves. From vast desert landscapes and wildlife encounters to champagne dune breakfasts and conservation-minded luxury lodges, he reveals a side of African travel many queer travelers haven’t imagined.

SPONSOR:

OUT Namibia

outnamibia.com 

twobadtourists.com/out-namibia-luxury-travel-concierge

We head to Puerto Rico (virtually) to chat with Chris and Wil, the couple behind Freedom House Retreat, an all-male nudist guesthouse nestled in the foothills of El Yunque Rainforest. 

They share what nudism means to them and how they created a welcoming, clothes-free space rooted in freedom, connection, and community. They also tell us what guests can expect at Freedom House Retreat and why nudist travel can be a positive experience for queer men.

We also zoom out to talk about Puerto Rico as an gay travel destination with queer-friendly beaches, welcoming culture, nature adventures, and why the island continues to capture the attention of LGBTQ+ travelers.

SPONSORS:

Freedom House Retreat

instagram.com/freedomhousepr

We chat with writer, journalist, and cultural organizer Paul Burston for a wide-ranging conversation about queer culture, intentional travel, and the power of gathering.

Paul shares his journey from LGBTQ+ journalism and activism in the UK to founding cultural platforms like the Polari Salon and Polari Prize. We then explore his role as a lead voice for Glainne, an international queer-centered project creating intimate salons and immersive residencies focused on conversation, shared meals, and moments of cultural exchange.

We discuss the upcoming Lisbon Salon, unpacking what salons are, who they’re for, and why this format resonates so deeply in today’s fast-paced world. We also talk about Lisbon itself, from fun facts about the city to why it’s a compelling destination for LGBTQ+ travelers seeking depth, culture, and connection.

SPONSOR:

Glainne - Lisbon Salon

November 13-15, 2026

glainne.com/lisbon-26

Colombia is one of the most biodiverse and culturally rich countries on Earth, and it’s quickly becoming a favorite destination for LGBTQ+ travelers. We welcome back Sam Holdren, founder of OUT in Colombia and the new LGBTQ+ experience brand Queer Scout, to talk more about gay-friendly Colombia. 

We kick things off with fun facts about Colombia, from pink river dolphins and ancient lost cities older than Machu Picchu to why Medellín is known as the “City of Eternal Spring.” Then Sam shares what’s changed in Colombia since his last appearance on the podcast, why the country continues to surprise queer travelers, and how LGBTQ+ tourism can positively support local communities. We also learn about Queer Scout, Sam’s new venture offering immersive queer experiences like bar crawls, dance nights, food adventures, and cultural tours in Medellín. 

Whether you’re curious about Colombia for the first time or already planning your next adventure, this episode offers insight, inspiration, and practical tips for traveling confidently as an LGBTQ+ traveler.

SPONSORS: 

OUT in Colombia

outincolombia.com 

Queer Scout

thequeerscout.com 

Greater Miami & Miami Beach
VisitMiamiLGBTQ.com

We talk with Miles Mitchinson, founder of Detours Travel, and Daniel Naughton, the company’s new owner, to explore a decade of gay adventure travel and where it’s heading. Born from backpacking journeys, spontaneous exploration, and a belief that travel should feel like discovering the world with friends, Detours has grown into one of the most recognized LGBTQ+ group travel companies worldwide. Miles shares the story behind building Detours from scratch, while Daniel reveals what inspired him to take the reins and lead the brand into its next chapter.

Together, they discuss what makes Detours trips different from traditional tours, how queer community forms on the road, why adventure travel still matters for LGBTQ+ travelers, and how they’re designing experiences that balance freedom, connection, and unforgettable destinations. 

SPONSOR: 

Detours Travel

detourstravel.com

We chat with Danni Ponter, Co-Founder and Senior Travel Expert at Sikeleli Travel & Expeditions, about luxury LGBTQ+ travel in Africa with a special spotlight on WorldPride 2028 in Cape Town.

Danni shares how Sikeleli creates white-glove, tailor-made journeys across Africa, Asia & Europe, what makes Cape Town one of the world’s most exciting queer travel destinations, and how their team designs Pride experiences that go far beyond the parade. We also talk about safety for LGBTQ+ travelers, conservation-minded tourism, and what guests can expect from a truly personalized adventure.

Plus, fun facts about Africa, travel stories, and insider tips for anyone dreaming of their next adventure.

SPONSOR:

Sikeleli Travel & Expeditions

sikelelitravel.com

World Pride Cape Town 2028 - Curated Pride Packages

sikelelitravel.com/discover-the-ultimate-lgbtq-adventure-at-world-pride-2028