I just went on the best press trip ever - Here's why it was great and how to improve your trips

Hi friends,

Greetings from Milwaukee, Wisconsin. I flew here directly from Spain a few days ago (pic above from a cycling trip there). Here, I’m spending mornings hiking in search of migrating Baltimore orioles, afternoons with my mom at her nursing home, and evenings helping my niece ride her bike.

Wherever you are, I hope you’re enjoying some lovely late spring weather.

Cassandra

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Sponsored Summer Travel Articles

Instead of waiting around for publications to increase freelancer budgets (which may never happen), sponsored posts are a great way to guarantee coverage.

I’m partnering with PressHook on several sponsored summer travel articles for Yahoo, where some of my articles have ranked #2 on Google and gotten hundreds of thousands of views.

For this piece, I’m seeking the best summer travel, skincare, and picnic products. PressHook will be coordinating the products and payments, which cost $350 per product. Here’s more on that.

What is PressHook?

If you haven’t heard of PressHook, well, it’s a platform that connects publicists with journalists in a streamlined, non-spammy way. Basically, publicists create and manage brand profiles and press kits, and the AI-driven platform then connects them with journalists in a streamlined way. Writers can also post pitch calls (referred to as “Source Requests”) on there and have brands apply directly, which is the way these sponsored articles are working.

For instance, when I posted a Mother’s Day Source Request on there, brands and PR managers were able to respond to me directly about it, but the AI algorithm also auto-suggested some relevant profiles on PressHook for me to consider.

PressHook offers a suite of workflow tools that benefit both publicists and journalists, like allowing us to search for potential products by category and also flag certain categories in our pitch calls. As such, it’s a win-win for everyone involved.

My summer travel stories pitch call is open on PressHook for a few more days, and guess what? I have a code for you to test out PressHook FREE for two weeks. Deal, right?

So, if you’re interested, test it out for free for two weeks, apply to some pitch calls, and let me know what you think of the platform!

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Press Trip Trends Coaching Pods

Want to learn how to plan the perfect press trip? Yes, you do, so I released a few more dates for upcoming press trip coaching pods (June 3, 5, and 12 for now).

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 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

“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

Discount for Paid Subscribers

Substack paid subscribers will get 20% off with the code below:

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The BEST Press Trip Ever

I just got back from 10 days in Tenerife, Spain, and I have to say that it was one of the best press trips I’ve ever taken. I had such a wonderful time and got so much out of it that I already wrote a piece on Cycling in Tenerife, Spain this Summer.

Here are 8 reasons why I loved this press trip:

1. They sent one of the best trip itineraries I’ve ever seen. The itinerary was highly detailed, including all the cycling routes, distances, and elevation profiles, plus detailed descriptions of the bikes available, as well as info on the hotels and all non-cycling activities (like snorkeling). I knew within 2 minutes of looking at it that I wanted to join this trip because it looked fun and very well-organized. More importantly, the actual trip lived up to the hype in the itinerary proposed.

2. This was a cycling-focused trip, so I got to do 5 days of lengthy, scenic rides. This is rare because most trips only include a day of cycling.

3. They offered an e-bike, which allowed me to cover even more distance since I don’t ride as much as I used to. This was extra important because…SURPRISE…Tenerife is a bunch of volcanoes, and the elevation was out of control.

4. They let me extend the trip by adding on 3 days of hiking and diving. This made the trip more enjoyable for me and broadened my firsthand experience, allowing me to write authoritatively about the topics I encountered.

5. They flew me on my preferred airline (where I earn miles and sometimes get free upgrades), and included an extra domestic leg back to Milwaukee so I could check on my mom. I know this cost them more money, but I need to visit my mom every month, and this is the only way to make it happen.

6. My flights connected through Madrid, so they got me a 3-day layover there. They didn’t pay for that layover, but just having that worked into the flights was a big bonus to me, and I covered the rest since I’d never been there.

7. They had an awesome group of people on the trip. Not only was it a treat to travel primarily with Europeans (there were 2 other Americans and one Canadian), but they had a good mix of writers, travel operators, and influencers. Normally, I don’t like traveling with influencers, but these were all pro- and semi-pro athletes-turned-influencers, so they were there to ride, not just take pretty pics.

8. Not only were the people on the trip cool and interesting, but none of the writers covered the same outlets. This is key because it’s so hard to find coverage for a destination when everyone else on the trip writes for the same outlets.

Want to learn more about planning the perfect press trip?

Substack paid subscribers will get 20% off with the code below: