Hey Reader, Every other gay man you know is heading to Puerto Vallarta this winter. What if you did something completely different instead? Back in June I told you about the trip I've been dreaming up for years — January 15–24, 2027, ten days across Argentina, Uruguay, and Brazil, timed for the one month a year when it's peak summer south of the equator while everyone back home is freezing. The interest since then has been incredible, and we're down to just a few spots. August 31 is the real...
15 days ago • 2 min read
New Trip Release! Hi Reader, This is one of the biggest announcements I've ever sent. I'm taking a group to Australia — the seventh continent I will have personally led a Pivot Trip on, and the final piece of a goal I've chased since the very first day this company existed: leading a trip on every single continent on Earth. And it goes even deeper than that. Years ago, I sat on a bench on Bondi Beach and made the decision that became Pivot Trip. I didn't know that yet, sitting there — I just...
29 days ago • 3 min read
New Trip Release Hi Reader, It's official — my next big trip of 2027 is here, and it's the one I get asked about more than almost any other destination: New Zealand. I led a group through New Zealand's South Island in January 2025, and it's still the trip my travelers bring up unprompted — the kind of "remember when" that surfaces in random conversations, completely out of nowhere, months later. Today, it's back. New Zealand. 13 days. January 30 – February 13, 2027. A quick note before I go...
about 1 month ago • 3 min read
Hi Reader, Happy Pride! And today I get to make a big announcement. Six months ago I started planning the trip I've wanted to build for a long time — one that came together after traveling through South America myself. Today it's finally here — and I could not be more excited to share it with you. South America. 10 days. 3 countries. January 15–24, 2027. Iguazu Falls South America is one of those destinations that sits on nearly every list — and never quite gets booked. And I get it. Buenos...
3 months ago • 3 min read
Hey Reader, When I sent out my annual survey last month asking where you wanted to travel in 2026-2027, one destination came back louder than any other: Japan. Not just "interested." Not just "maybe someday." But "this is the year I'm finally doing it." So I partnered with a Japan specialist to create something truly exceptional—a trip that goes far beyond what you could experience booking independently or joining a standard tour group. And it's already happening. Four past travelers have...
7 months ago • 5 min read
Hi Reader, I've been waiting to share this with you. My most popular trip is officially open for booking—and I couldn't be more excited to invite you to join me in Indonesia this October. 🌴 BALI + KOMODO • OCTOBER 1-10, 2026 This will be my 6th time leading this journey. There's a reason it's become my signature adventure: no other gay travel company offers anything like this combination. The trip sells out every single year. This year, I only have 6 rooms available. ✨ Why This Trip is...
7 months ago • 3 min read
Hi Reader, I'm beyond excited to finally open this trip to the full list: Ireland, September 4-13, 2026 – and this isn't just any Ireland trip. This is the full island experience most tour operators won't give you. We're covering the entire circuit – from the vibrant streets of Dublin and Galway to the historic heartbeat of Belfast in Northern Ireland. You'll stand at the edge of the legendary Cliffs of Moher, walk among the otherworldly basalt columns of the Giant's Causeway, and step back...
8 months ago • 3 min read