Should You Host a Trip for Your Newsletter Readers?

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In 2024, I interviewed Vidar Bergum, a Norwegian-born food writer who publishes the newsletter Meze from his home in Turkey. In addition to his food writing, Vidar has curated and hosted trips for groups of his readers to join him on a food and cooking tour in Istanbul.

He admitted that putting these on was exhausting and that it typically took a little time for the travelers to gel, but in the end, the experience was rewarding. “My experience is positive; it brings a different level to the relationship that [readers] have with you,” he said. Plus, “for every group, at least one or two, maybe even three people signed up for [my] paid membership afterwards.” It didn’t hurt that he partnered with a travel agency that did much of the legwork and paid him for his efforts. “The Norwegian tour agents pay me for my participation and then they pay this Turkish guide who organizes everything because I can’t organize all this stuff. I’m the curator of the program, and I participate in the food parts.” 

The idea of putting on excursions for your newsletter audience stuck with me. We’ve published stories about newsletters that host events, from private dinners and book readings to workshops and conferences. In a world where it’s getting harder to tell what’s human and what’s AI, in-person events can be an amazing way to build relationships with readers — and also a revenue stream. 

But inviting your newsletter readers to join you on a trip is more than your typical event. A trip to Istanbul with your family could be an ordeal; now imagine doing it while hosting a group of strangers, all of whom know you and most of whom you’ve probably never met.

So I wanted to understand: How can you create a travel experience that is fun, useful, and worth the money for your readers? Can it be worth the effort, for you and everyone involved? Is there a way to do it and not be the only person on the hook for troubleshooting? And can you actually make money doing this?

I spoke with four newsletter writers — and part-time trip planners — about the decisions they made and the lessons they learned from taking the plunge. Hosting a successful trip like this involves a lot of planning, details, pricing strategy, good chemistry, good luck, and ideally a good partner. Otherwise, do you want to be the only one problem-solving on the fly, like when a speaker backs out at the last minute, or your venue’s chef quits before you get there? (Both really happened to the writers I talked to.)

But on the other hand, it’s an interesting opportunity for a precious offline connection, either for leisure or networking. So if you and your readership have a brave spirit, if you want to forge a connection with them that goes beyond the inbox, and if you’re interested in a new way to possibly monetize your newsletter and connect with your readers, perhaps you’ll be willing to pack your bags and tell readers to pack theirs, too.

Questions to ask before you launch a trip

A trip is a major undertaking — it takes, at minimum, weeks to plan, longer to sell to your audience, and that’s before you get to the travel part. So before you decide to take on all the logistics of an in-real-life newsletter event and add the element of travel to it, it’s worth asking a few questions:

• Does it need to be a trip? — A trip is really just an event with a lot more travel, which means a lot more logistics to sort out and things that can go wrong. Make sure there’s a very good reason for the travel — there’s something that’s best done in a particular place. Otherwise, you might be adding more complications to what could be a more straightforward event.
• Are you comfortable taking the lead and spending time with new people? — When you lead a trip, even if you have a partner who handles logistics, you’re taking on a cruise ship director-type role. You will need to be available to people who may need various things from you, if just face time. That’s a big responsibility, and it’s definitely not for everyone. 
• Do you have a partner you can work with on these? — Many of the organizers we talked to found someone to work with — a trip organizer, a professional organization, or a friend/spouse. Having a partner to share the marketing or planning burden with is a really good idea for a first-time trip organizer.
• Are there signs that your audience might be willing to pay and show up for something like this? — Maybe you’ve already built an audience of paying subscribers or members, and you’ve seen a willingness for readers to pay for your content or insights. Maybe you’ve hosted events before, whether digital or IRL. Or maybe you’ve gotten feedback via surveys that suggests there’s interest. Make sure you have some positive signals around interest before you invest in these.

Once you’ve identified that trips are a good fit for you and your reader, the next step is figuring out what type of trip to run. Here are a few ideas.

An excursion curated around shared interests

Elizabeth Holmes runs the royal fashion newsletter So Many Thoughts, which builds on the sartorial coverage she did for her 2020 bestselling book “HRH: So Many Thoughts on Royal Style.”

Based in California, Holmes had already enjoyed good experiences meeting up with her readers at events, so inviting them to join her on a trip was not out of the question. When she was in the U.K. covering King Charles’ coronation in 2022, Holmes met a representative from Atlas Adventures, a luxury travel team whom Holmes was already familiar with — they, in turn, knew and admired her work as a contributing editor at Town & Country magazine and as a senior style reporter and columnist.

Atlas Adventures reps ran a presentation by her to co-lead a curated women’s trip to the U.K.. It was the best opportunity, as she saw it, to do right by her followers. Other travel agencies had offered her sponsored trips, but none of them felt like the right fit until then. “Atlas gave me several examples, several testimonials and their policies for all of it,” she said. She was also impressed by their inclusive language, “and making sure that everybody is onboard with this idea of group travel, because it is different than solo travel,” Holmes said. “I would highly recommend it if you have a company that can be your buddy in this.” 

In 2024, Holmes led her first trip of about 15 readers to tour London and the Cotswolds. By pairing with Atlas, Holmes could offload not just the logistics that come with international group travel but many of the social concerns that come with bringing together a group of strangers.

Atlas served as Holmes’ planner, question-answerer, and go-between for her and her readers, running a WhatsApp group for anyone with questions and who wanted to chat ahead of time. They drafted contracts for participants to sign and hosted a pre-trip Zoom to gauge expectations and obtain permission from guests willing to be photographed for Holmes’ trip coverage. They also served as “matchmakers” for pairing up hotel roommates. (Atlas also covered Holmes’ trip cost and paid her a day rate, although she paid for a professional photographer’s services out of her own pocket.)

Traveling for several days with a group of women she didn’t know was a leap of faith, which Holmes mitigated through a vetting process. She sent a Google Form to prospective attendees asking for applicants’ social media handles and to answer questions on their travel philosophy and their feelings about the royal family writ large. “It’s not a straightforward thing, and it can lead to a lot of heated discussions,” she explained. 

Holmes did not take on the role of tour guide; that was the role of her partner. “I was able to show up and get to know people. I was very nervous, but it turns out most of the people were very nervous.” At the initial welcome drinks event, the anxiety melted away. “I realized, once I got talking to a number of the women, ‘Oh, they’re fans. They’re here to do these fun things with me.’ It’s a very flattering thing, to be honest.” The group felt more comfortable together as the trip went on. Just to be safe, Holmes consulted with her therapist in advance to get advice on navigating or exiting tough conversations — which she never needed to use. “There was this one woman on our first trip who had never left her kid before,” Holmes said. “I was like, ‘It is so much harder for these women to be here than for me to be here.’ It was this real point of human connection for me that made my anxiety wash away.”

The first trip did not sell out — 16 women signed up — but after Holmes posted about her experiences, interviewing the guests about their experiences and sharing photos, readers felt more comfortable signing up for a proven concept, and a second trip in 2025 did sell out, with 21 people who agreed to “press pause on their busy professional and personal lives, cross an ocean, and spend six days together” as she wrote in a recap. 

Holmes says the trips did not drive new subscriptions — in fact, she believes the price point for the trip may have even alienated some readers. (The 2025 trip cost $6,500 for one week, which included accommodations, some meals, entry to exhibits and theater events. Airfare was not included.)

With that said, Holmes believes the experience deepened her engagement with her readers. “These trips are another way to show that I’m a person. ‘Here I am doing these fun things with these other people and we’ve just come together.’ I do think that the world is craving those connections in a way that the big, messy internet does not offer.” Would she do it again? She doesn’t see why not. Maybe Scotland next time, she said — based on an idea from someone who joined her on both U.K. trips.

The B2B networking trip

Hamburg-based Lennart Schneider advises newsletter brands, media companies and non-profits on newsletter and subscription strategies. He also publishes best practices and conversations in his newsletter and podcast under his brand, Subscribe Now. (For an English-language comparison: Imagine his business as part Inbox Collective and part The Rebooting.)

His readers work in German-language media, and they look to him to learn about best practices and opportunities that they can bring back to their orgs. Subscription Tours are like a traveling conference, all curated by Schneider.

On these trips, readers join him to listen to presentations from and network with other leaders in the media world. Schneider partners with the German Association of Business Media (Deutsche Fachpresse), who have been running similar professional tours for years. He presented at one of their events shortly after the pandemic. “Afterwards, they asked me whether or not I would like to join forces and host these events together,” he said.  

In 2025, Schneider expanded his tours. Instead of just doing them within Germany, he brought a group to London. With larger commitments and higher costs than his domestic trips, the group size was winnowed — from 35 to 45 attendees to just 18 guests — and the trip lasted three days instead of one. At one London event, they invited people from the U.K. media industry to join. “We had 20 guests from the Economist, from the Financial Times, the Independent, and many more British publishers,” he said.

The London trip took longer to sell out than the German due to it costing 2,190 Euros (about $3,500 in U.S. dollars), or twice as expensive as the German trips, which typically sell out two to three months in advance. He says that it was also harder to book the London trip’s speakers since he has a smaller network there. “I tried cold outreach on LinkedIn, which sometimes worked, but in many cases I didn’t even get a reply,” he said. “I had to switch my strategy and asked some people, like Madeleine White from The Audiencers, for help.”

For Schneider, the tours pay in two ways: through his share of ticket sales revenue and through paid partnerships with sponsors like the companies Piano and Frisbii. Networking with speakers and guests opens additional doors. “My main job is as a consultant, so it’s a great way to stay in touch with my potential customers and with my podcast and newsletter community,” he said. “It’s great for visibility in this space.” 

Unlike Holmes’ trips, which were more about sightseeing, shopping, and community, professional access is what Subscription Tour guests pay for. In this world, readers want to network, and the intimacy of these trips makes it easier to make new connections, Schneider said.

The London trip was the fifth trip Schneider has hosted; he’s learned several lessons from past experiences. For instance, he used to host a sit-down dinner as the introductory event, but realized it wasn’t a good fit for his audience. “You only have the opportunity to speak to the people around you,” he said. “Sometimes, you discover the next morning that there were amazing guests that you didn’t have a chance to talk to.” Instead, he now kicks things off with a mixer with appetizers to maximize networking possibilities.

He advises those thinking about leading their own similar networking trip to build in enough time to troubleshoot, even if you’re working with a partner. “It usually takes us half a year,” he said, of the planning time for an event. “This time, we had to change big parts of the schedule the week before because we had one cancellation of a speaker of a company we wanted to visit. So that was a very busy week the week before. Quite stressful.”

There can be advantages to testing out different types of trips, he’s learned. On the London trip, he said, “We were having lunches, dinners, travel time together, so [attendees] built quite a strong bond over those days, which I hope will last even after the event.”

Whether it’s domestic or abroad, he says he knows the trip went well when guests tell him that  “they get a lot of inspiration, that they got to know new people, and that they enjoyed the hospitality. It’s very important to me that they are happy not only on a professional level, but that they have had a great time, had some laughs, and had an entertaining time as well as an inspirational time.”

The indie writers retreat

Journalists and friends Ann Friedman and Jade Chang hosted a few in-person writers’ retreats in 2023. “We both used to be magazine editors, and we missed sitting around the table talking about ideas,” said Friedman, author, podcaster and creator of the newsletter The Ann Friedman Weekly. Over 45,000 people, many of them aspiring writers and journalists, subscribe to her newsletter, launched in 2013, which covers a wide-ranging blend of pop culture, gender, work and relationship issues, and more. She and Chang co-hosted a small pitching workshop at Friedman’s California home, which they decided to scale up after she saw how popular a colleague’s event was that she spoke at and promoted in her newsletter. “I was like, ‘I could just do this myself,’” she says. 

The pair scheduled a small in-person writing retreat in Taos, New Mexico, in 2023, where Chang knew someone who had recently purchased a historic hotel they could use as a venue. “It’s really hard to find the right place at the right price point for us, and this was one that fell in our laps,” Friedman said. Not every newsletter trip needs an ambitious itinerary: provide the right destination, experts, goals and schedule, and a single destination is all you need. 

They created sliding price points from about $2,000 to $4,500 for the week, depending on the accommodations, which Friedman says in retrospect should have been higher, given the work coordinating 37 guests. “I think we were nervous about providing a lot of bang for their buck,” she said. “If we were to do it again, we would charge more, and not just because of inflation, but for the level of energy required to be the center of a group of people who don’t know each other.” She says she would avoid strategizing in the vein of “How little could we get away with charging? How can we cover our expenses plus a little?”

With a subsequent L.A. retreat, held shortly after Taos, they gave themselves a mere six weeks to plan, from announcement to the event. “Six weeks is wild,” she said in retrospect. “I can’t overstate how ridiculous it is to try to sell something like this in six weeks.” But Friedman was pregnant and knew she wouldn’t be able to organize another one for a while. The tight turnaround time meant they only sold 28 tickets — fewer than they would have liked. “For most writers, this is not an impulse buy or a last-minute buy,” Friedman reflected. “It’s something that they really have to consider and decide to invest in.” Even with a newsletter list as large and as engaged as Friedman’s, building in enough time to sell tickets is a must.

For any other publisher considering hosting a long-distance gathering with readers, she’d advise having a collaborator as she did with Chang. “Externalizing the pricing conversation is so important, and it should be someone who knows your world. I love my spouse, but he doesn’t understand the economics of the creative world in the same way that Jade does,” she said. “So our conversations about pricing can be just more detailed and sophisticated because we both come from the same world that we’re trying to sell to.”

A small group on a big adventure

In late 2025, Swedish-American author Linda McGurk, who writes the newsletter The Open-Air Life, which encourages families to live sustainably and find new ways to connect with nature, decided to pilot two 2026 women-only weeklong hiking trips in the Swedish highlands as she launched a new outdoor adventure business.

The idea came from one of her loyal readers who commented on some photos she’d posted of a hiking trip, asking, “Do you know of a company that organizes hiking trips for people in Sweden?” McGurk told her, “Give me a couple of weeks. I’ll put together an itinerary.” She quickly realized that she wanted to lead her own trip. “I just love it up here, and I’ve just felt pretty passionate about wanting to share the place with others ” It seemed like the universe’s way of telling her to go for it.

She said, “I usually go on feeling. There’s usually no firm business plan in place. I find something that I’m passionate about and I figure out a way to make it work and a way to make it a viable business.” Plus, she said, she knows her readers want to get away from their desks and connect IRL. “With AI and everything, there’s a need for authentic meetings,” she said. “The time is ripe.”

Like Friedman, she is piloting the trip without an official sponsor or partner, which is why she decided to keep the group small: only four women. She is informally relying on her own network to organize the trip. “I’m partnering with people in the community, but it’s more like, ‘I’m going to take my guests to this restaurant because I know they got good food.’” 

McGurk set the trip price at $2,690, which includes accommodations, local transfers and most food. To set the cost, she relied on help from her entrepreneur husband, measuring costs against comparable trips in locations like Iceland, Norway, and Finland, with the aim of making a small profit. “Of course, this is the kind of endeavor where you don’t really get paid for all the hours that you put in; it’s a passion project,” she said. “I looked at the actual costs and what kind of margin I would need on that to make it worth my while,” and set the seven-day length based on the length of the hike and time to adjust. With these being her first trips, she’s aware they may not be a huge moneymaker and has already learned a few lessons. “A couple things that I hadn’t figured in were the decreasing value of the dollar as well as some of the bank fees, which could affect my pricing going forward,” she said. But, she said, “the trips are also a way for me to get to know people from my community in real life. And for me to get to do more of what I love  — spending time in nature.”

She initially announced the first trip in August 2025, for a trip to take place in July 2026, and the response from her 3,000 subscribers was so robust that she opened up a second trip.

Even though it’s her first time inviting readers to join her on a trip like this, McGurk has experience leading groups, from friends and family to visitors to groups of children. “I’ve been a scout leader,” she said. “I figured that if I can hike with 20 kids aged 8 to 13, then I can hike with adults too.” She knows first aid, is taking a wilderness first aid course, and the attendees will sign waivers.

In terms of group chemistry, she’s hosting Zoom meetings with both groups but otherwise assumes that the women who sign up for the trip self-select into a certain kind of mindset. “I think only women with a certain personality would do something like that,” she said. “You have to be pretty open-minded, pretty adventurous, and also, I think, be flexible in a group setting.” She’s planned a blend of socializing icebreakers to get the group acclimated first; her experience as an outdoor guide has given her a background in team-building and encouraging quiet time to enjoy nature. “I think the setting requires people to work together, but also, I will make sure that people feel that they don’t have to constantly socialize either.”

What kind of person would sign up to hike in remote Sweden with a handful of strangers? Truth be told, I was not familiar with Linda’s newsletter before researching this piece, but the way Linda described the trip and laid out the itinerary spoke to a part of me that wants to get away on an adventure and take a pause from caring for my kids and parents. Interviewing her, I learned more about the expectations for the trip and her background.

I bought my ticket to join her in Sweden this summer.

Five takeaways for hosting a trip

1.) Be generous with your sales timeline — You want to give your readers time to weigh whether they can afford the time and money to take the trip and to plan their logistics (not just transportation and accommodation, but days off, babysitters, pet sitters!). Plus, you want to leave enough time to find an ideal venue. “The venue challenge is real,” Ann Friedman said. “It’s hard to find something that suits our vibe. We are not yoga teachers. We are not a business conference. Finding something that is the right just physical configuration for a group of writers being together, and then do all the rooms have desks? There’s a lot of constraints that come into a physical space.” In fact, she said, “Maybe wait til you have a venue, and then decide whether you want to do this.”

2.) Charge enough to make it worth your energy and stress — Think about the price point in relation to the newsletter itself. “Your newsletter is the accessibly-priced option,” Friedman said. “The workshop or the retreat is a premium item. You don’t need to price it for everyone who gets your newsletter. You are already offering multiple products for people with different incomes, and not everything can be for everyone.”

3.) Find the right partner — Even if you’re not partnering with a sponsor or paid partner like Holmes or Schneider, you’ll want someone like-minded to help you problem-solve, to brainstorm with, even to complain with, like Friedman and Chang do. Plus, if there are last-minute issues like a speaker falling through or someone (even yourself) getting ill, you’ll want some support. 

4.) IRL connection can remind you of the value of your newsletter — When you meet your readers and talk with them, you’re often reminded that others love your work, even if they don’t write back after every newsletter to tell you so. “Usually. I don’t get a lot of feedback on my newsletters,” Schneider said. “I see the opening rates and the clicks and sometimes I see comments on LinkedIn, but it’s not a big interactivity in my case. It’s sometimes a bit lonely. That’s why I totally love to see the people who are reading it.” 

5.) Collect feedback after the trip — You may be so tired after spearheading a trip that you can’t imagine doing it again, or you may be so invigorated that you’ll be tempted to plan the next one right away. Whatever you do, a post-trip survey is a must. Make sure to ask your guests about what they like or what they would change in the future. That’s how Schneider decided to swap an opening-night dinner with a mixer instead, and how Friedman learned that despite her concerns about how she lined up the programming in Taos, guests enjoyed a locally-themed sound bath. The more you learn, the better you can make future events.