Mandy Picchiottino shared their story and experiences with us recently and you can find our conversation below.
Mandy, we’re thrilled to have you with us today. Before we jump into your intro and the heart of the interview, let’s start with a bit of an ice breaker: Would YOU hire you? Why or why not?
I say all the time that I’m not my ideal client. To really appreciate what’s great about Land + See, you need to be the kind of traveler who can let go of the reins and trust the process—something I struggle with. Planning a trip the way I’d want it? Exhausting. For most people, doing a trip justice is a grind. Hours of research, calls, double-checking… and even then, stuff comes up on the trip that needs quick fixes. Most people just don’t have the time for that, and honestly, after putting that much into it, it hardly feels like a relaxing vacation.
That’s exactly why Land + See works. When I’m planning, I’m not on vacation—I’m working hard. But it’s work I love, and I’m good at it, so it ends up being a win for everyone. We all get the experience we are after. The truth is, I’m not the type to fully let go of the reins—I like having my hand in the cookie jar. That’s my toxic trait, and I’m working on it. But it’s also why I can create a trip where people CAN just show up, relax, and enjoy the experience without any of the stress.
Can you briefly introduce yourself and share what makes you or your brand unique?
At Land + See Tours, we create travel experiences that go beyond the usual tourist spots. Our trips are all about getting off the beaten path, connecting with locals, and seeing a place through the eyes of the people who actually live there. We know most people don’t have the time to plan a trip like that, so we take care of all the research and logistics. Whether it’s a custom trip with friends or family, or a guided group adventure with fellow travelers—couples, solo travelers, or anyone in between—we make it easy to relax, explore, and really experience a place.
Great, so let’s dive into your journey a bit more. What did you believe about yourself as a child that you no longer believe?
When I was a kid, I believed travel just wasn’t in the cards for people like me. We didn’t have a lot of extra money growing up, and traveling to places where we didn’t have a free couch to crash on just wasn’t something we did. I thought that seeing the world beyond your backyard was a luxury reserved for the wealthy or the elite.
As I got older, opportunities started opening up—school trips, programs, and experiences made possible through the generosity of friends, family, and a few after-school jobs. Slowly, I realized how limited my thinking had been. Travel wasn’t just for the privileged—it could be for anyone, and that changed everything for me.
That realization shaped Land + See. I know most people can’t just plop down thousands of dollars for a trip, but there are ways to make amazing experiences accessible without breaking the bank. If you can plan ahead and commit, you can travel, and travel comfortably—it just takes a little discipline and saying yes to yourself.
I also used to think investing in travel for myself was selfish, but it’s really the opposite. Travel teaches you patience, empathy, and perspective. It makes you a better friend, partner, and community member. For example, I’ve seen travelers return from immersive trips with new ideas for their work, deeper connections with family, and a fresh sense of confidence that carries into every part of their lives. That’s what I want for everyone who travels with Land + See.
What did suffering teach you that success never could?
A few years ago, my best friend and fellow teacher, Brittany, was tragically killed by a drunk driver. Brittany and I were on such similar paths—both teachers, young moms, wives—and we spent so much time dreaming together about the future: where we’d take our kids, the memories we’d make, the goals we’d reach. Losing her was devastating, but it was also a wake-up call for me.
Her death made me realize how much I’d been putting life on hold—waiting until “the kids are older,” “after a raise,” or “when it’s safe” to pursue things that really mattered. Suffering taught me what success never could: that tomorrow isn’t promised, and if you wait for the perfect moment, you might miss what truly matters.
Since then, I’ve tried to live more deliberately. I make an effort to be present with my family, to make memories—even the small ones—as soon as I can, to say yes to opportunities instead of letting fear hold me back, and to tell people what they mean to me while I can. I travel with my kids even when it’s challenging, and I try to embrace life fully in the moment, because I’ve learned that presence and connection are far more valuable than any measure of success.
Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. What important truth do very few people agree with you on?
I believe people are inherently selfish—not in a malicious way, but just by nature. We can only care so much, especially with the constant stream of news, social media, and information coming at us every day. Unless something feels personal, it’s easy to scroll past or tune out.
That’s why I think it’s so important to expose ourselves to cultures and lifestyles outside our own. When we experience something firsthand—whether through travel, meaningful conversations, or immersion—it suddenly becomes personal. It opens doors to empathy and understanding in a way that news headlines alone never can. We all need more of that. When the world feels closer to us, we care more, and that makes us better people.
Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. When have you had to bet the company?
During COVID-19, we had to cancel countless tours—many of which we lost money on. Airlines and hotels kept our deposits, and insurance companies labeled COVID as an unforeseeable event, so we didn’t get refunds. Back then, we were lucky if we broke even on trips, and profitability felt impossible.
But for us, it was a moment to show up for our travelers. We felt it was necessary to reimburse people for trips that weren’t happening, even if it meant dipping deeply into our savings. We were in the red big time. It could’ve gone sideways really fast.
Thankfully, when travel opened back up, people stuck with us. Several even said it was how we handled COVID that gave them the confidence to travel with us in the future. A few years later, we’re not only back in the black—we’re thriving. That period taught me a lot about integrity, trust, and the long-term payoff of doing the right thing, even when it feels risky.
Contact Info:
- Website: https://www.landandseetours.com
- Instagram: land_and_see_tours
- Linkedin: https://www.linkedin.com/in/mandy-picchiottino-22674113a
- Facebook: https://facebook.com/landandseetours
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