What Goes Into Planning a Cherish Trip (And Why It's Not Just a Tour)
There's a question I get before someone books with us, sometimes asked directly, sometimes just hovering underneath the conversation: Is taking a tour going to feel like a generic travel experience?
I get it. Most of us have been on a version of a trip that just didn’t feel like it catered to our needs but catered to the masses. The type of trip with fancy promises of its itinerary, but it was mostly rushed photo stops at the famous landmarks and stopping points. The "authentic local experience" that turned out to be a restaurant that primarily exists for tour groups. The guide who clearly recites the same speech to every group with a lack of enthusiasm or passion for the story behind the place you’re visiting.
I used to travel like this, and I’ve had a handful of experiences like this with larger tour companies since starting my business. Once you've had that experience, it's hard not to be skeptical.
So let me pull back the curtain on what actually goes into planning a highly curated immersive travel experience for women, because it looks a lot different than what most people assume.
What is a Cherish trip?
Cherish is a small-group travel company for women. We plan immersive, intentional trips built around the people and places that make a destination worth knowing and worth seeing. Every trip is capped at fifteen travelers, planned around women-owned and women-operated businesses, and designed to connect you with the communities you're visiting in a way that actually means something.
We vet before we commit. Every time.
Before any business, maker, or guide is ever included in a Cherish itinerary, I research them extensively. I look for the person behind the company, who owns the business, who represents it, what values they have and bring to their experiences within their communities. Almost always, I also visit to have the experience firsthand before it ever ends up on one of our itineraries for our guests to experience themselves. I want every experience we include to feel intentional and hand-selected.
I'm looking for a few specific things: Does this business/person genuinely love what they do? Are they rooted in the community, not just operating in it? Is this an experience that only exists because of who they are, not just what they offer?
Here's what that distinction looks like in practice. When I was in Colombia recently, everyone told me I had to fit a beach day into my Cartagena experience. I booked one that came highly recommended. It was awful. I felt like I was being herded. I was stuck on a speedboat without water or a bathroom for an hour and a half just to transfer to the beach. We met no locals. It was a big, pretty spectacle, exactly the kind of experience I never want our guests to have.
Contrast that with our Panama trip. Our lodge picks guests up on a private boat; the driver is from the local indigenous community on the island, and he's genuinely invested in making sure every person on that boat has a meaningful experience. He knows those waters better than anyone. That's the difference between an experience that exists to move people through a destination and one that exists because of who's behind it.
That's the filter. It's not just "is this a good business?" It's "Would I personally recommend this to a close friend?"
If the answer isn't a confident yes, it doesn't make the itinerary.
Small groups aren't a logistics choice. They're the point.
People describe small-group travel as a nice perk for their travel experience. It’s an opportunity to be with fewer people, have individualized attention, and make it easier to move around. All of that's true, but it misses the point entirely.
Small groups change what's possible in each destination.
When you're traveling with fifteen people instead of forty, you can sit around an actual dinner table with the winemaker. You can ask the shop owner about the decision that changed their business. You can go off-script when something interesting happens, and something interesting always happens.
Big groups require a rigidity that small groups don't. It requires people to wait for others when they don’t want to, it asks travelers to give up their own personal choice in sacrifice of the group as a whole, it makes guides less able to answer individual questions, and it takes away access to the more intimate experiences of a place you're visiting. These limitations, requirements, and rigidity are exactly what make large group travel feel like a production instead of an experience.
I believe the size of a group is one of the most underrated decisions in travel planning. It determines almost everything else.
Curated with women in mind, including your personal choice.
There's a reason Cherish trips are specifically for women. Women travel differently from the average group. We ask different questions, we linger in different places, we want to know who made the thing we're buying, who owns the restaurant we're eating in, what the story is behind the woman at the counter, and we want to connect with our fellow travelers and the places we visit. We want space to reflect, not just to consume.
This mentality is why I love traveling with women and creating itineraries that they love. I want each and every trip with us to feel like a vacation. In order to create that experience for each of our travelers individually, I build in downtime for personal choice. Because women also want their own time and the ability to opt out of an activity that doesn't feel right and opt into something that does.
That's why every Cherish itinerary is built with personal choice embedded in it. There are always options. There is always room to say "I'd rather spend this afternoon at the market" or "can I skip the morning excursion and meet you at dinner?" A curated trip doesn't mean your schedule is locked. It means someone has done the thinking, so you don't have to then you can make it your own from there.
The itinerary isn't just a schedule. It has a point of view.
The women we partner with in each destination are also part of our itinerary’s intentionality. When women earn income, they reinvest a disproportionate share back into their families and communities. Choosing to spend your travel budget with women-owned businesses isn't just a nice idea; it has a measurable impact on the places you visit. That's a thread that runs through every Cherish trip.
Our itineraries are shaped around the women who make each destination worth visiting. These aren't stops on a highlight reel. They're relationships.
In Sonoma, our trip is built around women like Doralice Handal, who owns Locals Tasting Room in Geyserville and was my first real introduction to the wine community there. She's the one who opened the door to every other connection — Kelly Comstock Ferris at Comstock Wines, Domenica Catelli at her family's restaurant Catelli's, Brenda Bullington at Stuhlmuller Vineyards, Jade Hufford at Maison Healdsburg. These women didn't end up on our itinerary because they run good businesses. They ended up there because Doralice trusted them, and I trust Doralice.
In Costa Rica, I’ve built intentional relationships with amazing local women for over 6 years. Women like Ann-Elin, who runs a cacao farm with her husband and is making a direct impact on her local community by providing farmers with access to ethical, higher-paid jobs. She is doing this work through tourism by offering a direct look and education into the chocolate industry. She is a highlight of our Costa Rica trips and our women travelers always walk away with a higher level of understanding and respect for chocolate.
In Tanzania, I was directly impacted by the relationships one woman shared with me. I originally intended on our safari to be offered in Kenya, which is a beautiful country but I didn’t have the relationships there that truly matter in making a meaningful experience possible. I was introduced to an amazing woman named Anty, who was born and raised in Tanzania and is now the project manager for a non-profit that is directly changing the lives of Tanzanian students and their families. When she suggested a partnership between Cherish and United the World with Africa Foundation, it was an immediate yes. Now our safari directly sponsors young women to attend secondary school.
When you travel with Cherish, you're not just visiting a destination. You're being introduced to the women who shape it.
Questions worth asking before you book any curated trip
Whether you're looking at Cherish or any other travel company, here are the questions I'd ask before I booked:
Who specifically are we meeting, and what's your relationship with them? Generic answers here are a red flag. If they can't name people, they haven't done the vetting or don’t have the personal relationships that make an itinerary unique.
How many people will be in the group? If the answer is more than 20 travelers, expect a fundamentally different kind of experience.
Where is the money going? Are your dollars actually reaching the communities and businesses you're visiting?
Does the cost of this trip reflect the quality of the experiences included? Ask what's covered and what isn't, and who benefits from what you're spending.
How do I get to spend my free time? A well-curated trip has built-in flexibility. If every hour is accounted for without any room for personal choice, that's worth knowing.
Have you done this trip yourself? Not "has someone from the team" — has the person who built this itinerary actually been there, had these experiences, met these people?
What happens if something in the itinerary changes? How they answer tells you whether they're running a script or genuinely responding to you.
You deserve a real answer to all of these. If a company can't give you one, that's information too.
If you want to experience the kind of meaningful travel that leaves you with memories for a lifetime without doing all of this research yourself, our upcoming Cherish trips are small, intentional, and built around people and places I've personally vetted.
Check out our upcoming trips
Have you ever taken a trip that completely exceeded your expectations or one that fell flat, and you knew immediately why? I'd genuinely love to hear about it. Drop a comment below or reach out directly.
About Cherish: Cherish Tours is a women-focused small-group travel company built around meaningful, immersive experiences. We believe that how you travel matters and directly impacts many people around the world. Learn more at gocherishtours.com.