The Weekly Passport

Issue #55

THE WEEKLY PASSPORT

We set goals this year, and we accomplished every single one. The latest—an interview with a celebrity visiting our city where we talked about travel and culture.

This is not our end-of-the-year newsletter, but dammit if it couldn’t be. After last week, we’re excited for what we’ll accomplish in 2026… and we still have Amsterdam for our fashion show left this year!

Let’s see what legendary comedian Sheryl Underwood wanted to do on her visit to San Antonio…

CULTURE
SHERLY UNDERWOOD X THE LAYOVER PODCAST 

In 2025, we wanted to interview one celebrity on The Layover Podcast who was visiting San Antonio for their show or event. On this show, we talk about the biggest topics in travel and culture with the biggest names you know, and those you should.

For San Antonio, it’s our way of connecting visiting artists to the community through conversation, culture, and fun.

Check out our interview with Sheryl. Oh, and join the conversation online when Sheryl asked who has the BEST soul food restaurant in San Antonio. There were LOTS of opinions. 

Instagram Post

TRAVEL 
AMSTERDAM…WITH STYLE!

Leroy’s New Years Eve outfit

We recently wrapped up production on our fashion travel show! Check out some pics from the set below.

Chilaeya’s elegant dinner outfit option

Chilaeya’s New Years Eve outfit option

Leroy and Carmen review the show script

Next, we head to Amsterdam, where Chilaeya and I will wear each outfit that Carmen, our stylist, has curated for us. Watch one video from behind the scenes.