More ways to up your press trip game

It's not too late to fill your trips - here's how I can help

May 08, 2025

Hello friends,

Greetings from sunny (but gonna start raining any minute) New York, where I’m banging out deadlines and wrapping up online consults before heading to Spain next week.

Speaking of….after 10 days in Tenerife, I’ll be spending three days in Madrid on my own. If you represent a cool or interesting property in Madrid, I’d be open to arranging a press stay while I’m in the area.

Have a good weekend!

Cassandra

Press Trip Trends Workshop

WOW! Yesterday’s workshop for paid subscribers was so much fun. Over 30 people registered, and I fielded dozens of questions about press trip dynamics, itinerary design, when to send trip invites, how to frame them, and how small brands and destinations can compete with the big boys and their bigger budgets.

Here’s what I’m hearing from attendees:

“Thank you for organizing such an insightful and candid conversation about press trips in today's media landscape. I left the call with so many ideas/improvements on how to approach future press trips!”
-Sarah Winston, HomeExchange
“I joined the press trip trends call today and wanted to thank you once again for hosting and all the insights. With the media landscape changing constantly, it's always valuable for our clients and team when we're able to hear honest feedback from you about what's working, what's not, and how we can stay up to speed on everything. I enjoyed the intimate format and found your examples super helpful.”
-Sabrina Diaz, CIIC PR
What an incredibly productive and beneficial zoom sesh!! I wasn't sure what to expect with this being my first live-action AMA group chat, but WOW - your Press Trip Trends workshop was awesome. Great turnout. Great questions. Great open candor among industry peers. I can't wait to sign up for the follow-up Pod session. Well done.
Katie Fontana, PR + Hospitality
Thanks, Cassandra, your sessions are always helpful.
Kristen Montag, Meet Minneapolis

Upgrade to Paid

Press Trip Trends Coaching Pods

A few months ago, I sent out a poll to see if there was interest in small group coaching pods where I’d meet with 3-5 people at a time instead of 1:1. The advantage of these small groups is three-fold:

You get much more individualized attention than in large group calls
You benefit from the support and feedback from your peers.
It’s a lot cheaper than 1:1 consults

Given the enormous interest in press trip development and refinement, I’ll be holding my first pod sessions around that theme.

Event Description:

You're spending time, energy, and money crafting and running press trips—so why are your invitations going unanswered?

Join my small group coaching pods to get personalized, targeted feedback about how to improve your press trips.

Whether you're hosting group tours or solo media visits, these pods will help you uncover what journalists really want, how to make your trips stand out in a crowded inbox, and how to design experiences that get booked—and get written about.

This is not a webinar, a lecture, or an Ask Me Anything session. It is an interactive, hands-on workshop that will dig into the essential elements that make or break a press trip and (pitch), tailored to your specific destination and press trips.

You bring your press trip, and I’ll help you figure out what’s working and what’s not. You could bring a current press trip you’re trying to fill, or an idea for a new press trip you are considering.

These small groups will be limited to 3-5 of your peers each, so you can learn and grow in a supportive group of savvy PR practitioners and destination reps, without your questions getting lost in a huge group event.

This 75-minute session is perfect for tourism boards, PR professionals, and tour operators who are tired of ghosted emails and half-filled trips.

Once you join, you’ll be sent a list of potential times the call will take place in late May and early June.

What to Expect:

Learn why it’s harder than ever to get journalists on board—and what to do about it
Learn what experienced writers actually look for in a press trip
Get expert tips for crafting irresistible invitations
Discover how to balance structure and flexibility in your itinerary
Real talk: Learn what makes a trip feel like a waste of time to a journalist
Immediate feedback: Present your trip and learn how it could be improved.
Peer Input: Learn from supportive peers what’s worked and what hasn’t.
Differentiate yourself: Walk away with ways to make your press trip stand out from the crowd.
Live Q&A with Cassandra Brooklyn