Meet Zoe Stella Shapiro, Founder of Boutique Tour Company Stellavision Travel
Issue #17
When it comes to traveling around Italy, Zoe Stella Shapiro is one of the tastemakers you want to know. She moved here from Toronto in 2019 and spent her first six months as a nomad, road tripping around the country with her miniature Australian Shepherd Chutney. Having worked in marketing and hospitality, Zoe initially planned to spend a yearlong sabbatical in Italy, but fate had other plans for her. When the pandemic grounded her, she ended up putting down roots and seizing the chance to create a company, Stellavision Travel, which is shaking up the industry.
Through Stellavision, she organizes boutique small group trips for self-identifying women that focus on the path less taken. She launched with a tour of Secret Southern Italy in 2021, organized a groundbreaking size-inclusive tour last year, and has just announced a slate of new itineraries for this year. I caught up with Zoe last weekend over lunch and am thrilled to share her story as part of my ongoing series of interviews with entrepreneurs and creatives doing amazing things in Italy.
Zoe, thank you so much for agreeing to this interview. I was thinking back to when we first met, July 2020, through Annie Ojile, and a lot has changed since then.
A lot has changed since then, like worlds apart.
I think you were living in Italy for about a year at that point, is that right?
In summer 2020, I would have been between my past and my future. I had intended on returning to Toronto April 2020. That would have been my first year in Italy. But as you know, we were on lockdown in April 2020 and I was actually—I’ll never know, so I chalk it up to fate—I was either pickpocketed or lost my wallet in a very atypical way on March 9, the day before lockdown.
So I entered into lockdown without my ID or driver’s license and when flights were canceled, it also removed the possibility of driving to Paris and getting home via a flight from there. And so I spent lockdown in Italy and then met you not long after we came out of it, at which point I was beginning to think about where my life was gonna go. My initial plan to return after 12 months was null and void at that juncture. It was almost a spontaneous decision about a longtime dream and I thought perhaps I could stay, perhaps I could start my company and I began to work on both things in earnest that summer.
I’ve heard the story about losing your wallet, but I’m curious about what actually made you decide to stay because obviously at a certain point things opened up again, so you could have gone back if you wanted to, right?
Well, the first thought was “I’ve earned another Italian summer goddamit.” Italy was a very scary place to usher in the Covid pandemic and it was also quite difficult to experience that really far from my friends and family. I’m so lucky to have a network in Rome now, but that wasn’t true then, so it was a very lonely, scary experience. The lockdown ended and I was like, fine, I’m staying for another summer. I deserve some sunshine and it truly was the silver lining to pandemic Italy before the tourists were allowed back.
We had Rome to ourselves. We had so many parts of the country devoid of crowds and it was bliss that summer. So I was not in a hurry to leave. And then as the temperature began to drop a little bit, it was time to get my life together and make some decisions. And in a couple different respects, everything was tied together. I couldn’t start my company until I got my residency here officially. 2020 was the last year I could apply for residency as a Brit before Brexit came into effect, so everything was contingent upon each other. So I began to work on my company, applied for my residency. That came through by the end of the year. A business plan was created, and then it was all systems go.
Amazing. And you launched Stellavision in 2021.
I launched it on the anniversary of my arrival in Italy. April 29, 2021.
Tell me a little bit about the impetus behind it because up until then you were still freelance marketing, right?
Yes, most of my marketing career has revolved around hospitality brands, travel brands, certainly lifestyle brands. My life has revolved around female communities. And as a marketer I’m someone who is always very excited about brand development professionally and personally. I dreamt of the day I would create my own. I was almost certain it would be in the travel hospitality space in some format.
You're a travel journalist, you know me now to be a travel entrepreneur, but before that was my profession, it was certainly my passion. I got to a point in my personal life where strangers would email me for a New York itinerary because I sent their friend the ultimate New York itinerary, so even in my personal life there was this passion, flair, talent—whatever you wanna call it—for this world.
And then I moved to Italy and so many people were engaged with my experience and curious and hungry for the kind of travel they saw me doing, which I wanted to make more accessible to more people. At the end of the day, what I say is we’ll find you a great guide, but Stellavision is never gonna offer a tour of the Colosseum. There’s people here that have been doing that since before I arrived, better than I ever will, and that’s their strength. Where Stellavision excels is taking solo travelers, female travelers, niche travelers to experience an authentic behind-the-scenes Italy that is typically inaccessible or just unknowable to your average tourist.
That’s such a great segue to talking about the flagship itinerary, Secret Southern Italy, which brings people to hard-to-access or under-the-radar places like Puglia, Basilicata, and Campania—not the famous part of Campania like Positano, but Caserta.
It just made sense to me that the first tour—our flagship tour—should fulfill the brand promise and take people to my favorite spots in the south. As you know, the south is not connected like the north is. The best, tiniest coves in Puglia—if you don’t rent a car, which is a daunting or expensive idea for plenty of people—you’re not gonna see them.
This was obviously conceived before James Bond added extra eyes to Matera, but you know, Matera has only been engaged in tourism since 2014 in a major way. It is still in its first decade of tourism. So all of these hard-to-reach spots are my favorite pieces of my exploration and it made sense to link them all and give people an amazing time.
I’m really curious what your travelers thought because I think you told me that for some of them, it was their first trip to Italy. What were they expecting? How did they react to being in all these places that are so different from the Colosseum or the Duomo in Florence and all that?
They loved it. I have never received a bad review. It’s not to say that every minute was perfect for eight days straight, but there was no one who wished for a different experience or was disappointed that we were skirting Naples in favor of Caserta or anything like that. I think that when you create a brand and are very transparent in your ideals and what people are gonna experience, there’s always room for surprise and delight, but there’s no bait and switch. Everyone signed up specifically for this experience of Italy. This was what appealed to them. And I get so much joy from the fact that I put something out there and people are responding to it and I think it attracts the kind of tourist that craves that.
Not the kind of people who are just in it for the Instagrams... even if you have an amazing photographer! It’s not the kind of people who just wanna get that one shot of Positano.
No, very much not. And we’ve had mega influencers on our tour who capture and share incredible content or who share our professional photographer’s content, but they’re there for the experience. And that’s how I think of Stellavision—it truly is experiential travel.
I love that you also took it a step further last year, with the size-inclusive trip, which was almost the same itinerary as Secret Southern Italy, right?
With some tweaks.
Aside from my article for AFAR, you got a lot of great press coverage in Condé Nast Traveler and other publications, so you struck a note there obviously. What do you think about that?
It’s a funny one because in a perfect world there would be less need because that community would be better served. And it would be my goal that that community is better served and fat travel and accessibility and communities traveling together is something more and more prevalent moving forward. Without that being the case, I was very proud to be able to offer that experience and hopefully to help shape the directions this group is able to move in collectively, in Italy or beyond, with Stellavision or without. I’m really proud to have put some fingerprints on this concept. And it was such a fulfilling week in so many ways, there was all the joy of the Italian travel and there was another layer of fulfillment both for myself and the travelers, that they were traveling with this group.
So how did it go?
It was wonderful. There was so much bonding that happened, as with any tour. These groups come together quickly. Our second night on the tour is always very special. We do a tasting menu at a female-owned restaurant here in Rome, but specific to that tour, I invited an opera singer who has her own story of being a plus-size woman and not embraced by her operatic community the same way some of our travelers have struggled, and she performed for us. It was a private concert in this restaurant. Everyone was in floods of tears. I don’t mean to make everyone cry, but I certainly joined them. The restaurant owners, the dishwashers, everyone was standing at the door with their iPhones out. It was just electric and magic to have that experience—and that was night two. And then we got on a bus and headed south and began our road trip in earnest.
Wow, that sounds like such a special moment.
It was such a special moment that I absolutely had to invite her back this year, so we’re going to offer the same concert for the 2023 edition of Secret Southern Italy, the size-inclusive version only. She is amazing. Courtney Mills. Such a talent.
And the restaurant was Pianostrada?
It was, yes. In a beautiful garden before any of their other guests arrive. It’s just our group and an opera singer blowing the roof off the place.
I’m getting the chills just thinking about it and I wasn’t even there.
I’m hoping this year to record it and have video footage.
I wanted to also get some insight into the new tour you’re launching, which is focused on another underrepresented community in the travel space, the Queer-inclusive Tuscany trip. That was actually born in a partnership with some of your previous travelers, right? Tell me about that.
Absolutely. We had travelers on our Secret Southern Italy tour last year, a queer couple, and they had such an amazing time that we spoke about what a collab would look like. They expressed a desire to travel in the Stellavision style but with a queer community. I myself am a cis-heterosexual woman and authenticity is so important to me. I don't belong in those spaces without an invitation, without a partner, and so when they expressed an interest, I said, “If you wanna come on board as co-hosts and help lead and shape this trip, I will put all of my Italy itinerary production to support,” and they were excited and that’s how it came about. So we are headed to Florence and through Tuscany with a queer-inclusive group this May.
So tell me about that. What makes it interesting to those travelers?
The heart of these trips really is about community because so often traveling as a marginalized person, traveling in a marginalized body is a daunting thing to do. There's a lot of not just safety but comfort that traveling with your peers offers you, especially when that trip has been vetted by a professional who is looking out for your particular interests.
On the size-inclusive trip, that means that in advance of arriving, I know which chairs have arms and which don’t and I’m swapping out those seats in a restaurant for my travelers who require that. For the queer-inclusive trip, it means that all of our partners are more than understanding—they are hospitable, welcoming, and engaged with who’s about to walk through their doors. So the community is a huge element to it, but beyond that is the itinerary and the programming.
Stellavision is not a seminar, it’s an Italian vacation. The brand’s the brand at its core, but we obviously want to build upon that and speak to who’s coming specifically. So for the size-inclusive tour that meant having a moment with Courtney, not just to experience her talent, but to have her sit down to dinner with us after the show and share her experiences with the group and open up a forum for them to share their experiences if they so choose.
For the queer-inclusive tour, we’ve developed some bespoke programming which I’m really excited about. Another contact of mine here in Rome is the gallerist, historian, and art writer Francesco Dama Zini and he has such a wealth of expertise in his field. He himself is a gay man. And instead of booking a queer tour, we are developing a bespoke experience of the history of Florence through a queer lens, which is so exciting.
Is there a rich queer history in Tuscany? It’s one of those things that we don't talk about so much, but on the other hand, if you think about ancient Rome, it was pretty prevalent, right?
This is part of my learning as well. Because the moment I become fully awakened will be the moment my travelers do, when I experience that tour with them. But it’s more than you would believe. From the story of Hadrian’s lover to the fact that in Napoleonic France, someone gay would be called a Florentine.
I did not know that!
It’s true. This is something I’ve discovered in the course of designing this tour and working with these amazing collaborators, which is why authenticity is so important to me. There’s so much more to be unraveled and learned. I’ve begun my journey. I’m so excited to be able to offer it to the travelers. And when you and I sit down six months from now, I’ll be able to explain so much more about the presence of queer people in all different eras of Italian history.
That’s so fascinating. I also know that by the time this newsletter comes out, you will have announced your new itinerary, right?
Itineraries plural. Yes, that is right, by the time this comes out the Stellavision world and the world at large will know about our new trips and I’m so incredibly excited about them. The first one is in partnership with the Cheeky Chef, otherwise known as Linda Sarris, and we are going to be commandeering two catamarans and cruising the Aeolian Islands.
Gosh, the itinerary is such a dream. It’s a real cultural and culinary exploration of the Aeolian Islands. We are going to be touching down on four different islands in our seven days at sea together. There are days we’ll be sleeping in ports and be able to walk to the nightlife and enjoy more luxurious shower facilities, and there are days when we’ll be dropping anchor in the middle of the Mediterranean in a bay and you will literally be rocked to sleep by mother nature’s gentle breeze. Between that, we’ll be linking up with locals to learn about the volcanic islands, we are gonna be eating at a Michelin-starred chef’s restaurant...
There are Michelin-starred restaurants on the Aeolian Islands?
In 2019, Martina Caruso was named Michelin’s female chef of the year and we are gonna be dining at her restaurant.
I haven’t been—the islands are at the top of my bucket list—but they’re really small, right?
Tiny, tiny, tiny.
Way off the radar.
It’s hard to get to, but Stellavision is gonna make it easy. A Stellavision guide is gonna meet our travelers in Palermo and take them all the way to Lipari, where we are meeting up with our captains, our catamarans, and Linda herself. And apart from all the delicious meals we’re gonna be eating—pane cunzatu, Michelin-star Sicilian hospitality—we have a private chef onboard and we’re gonna be having Sicilian family-style meals onboard everyday. So a lot of culture, a lot of culinary, and then just swims, snorkels, sunbathes, chasing sunsets.
I am so jealous of this trip.
I’m going on this trip.
So what’s the other itinerary you’re launching this summer?
I’m really excited about our other new itinerary because it’s our first short tour. It’s half a week instead of a full week and I would love to keep creating these moments because a lot of our travelers come to Italy, spend their entire week with Stellavision, and then return. We are so grateful and honored to be their Italian vacation and we offer them a real diverse experience, but I think as the company grows it’s going to be really exciting to give people the opportunity to do their own thing for a week, join us for four nights, and then head home. So this itinerary is that. It’s called the Rome Relax Remix.
We are going to be taking some of our favorite pieces of our days here in Rome, such as our feminist tour of the Campidoglio, which we do in collaboration with another female-owned travel business, and then we are headed out of town for 48 hours towards Maremma, towards Capalbio. We are going to be doing some luxury glamping at the only property in Italy that offers thermal springs glamping. The tents and the accommodations are beautiful, the spa facilities and the pools are beautiful, and then in true Stellavision style, we’ll be pairing it with lunch on the beach and a visit to an incredible contemporary art location nearby.
The Tarot Garden, right? Which is one of my favorite under-the-radar places in Italy and I don’t know why more people don’t go.
I know, so many people skip it. It speaks to so many things our travelers adore. Art is a passion of mine. It’s always a part of our itineraries and this is a life-size theme park devoted to a badass female artist’s life work, Niki de Saint Phalle. So it’s gonna be a really amazing moment in the Eternal City and then we have an incredible unwind day spent swimming and sunning and a little bit of exploring.
Are all of these itineraries happening this summer?
Oh yes. And the Rome Relax Remix is going to be offered four different times this summer, so if you’re traveling to Italy in July, August, September, or even October, you can join us on that one.
That is a lot! And you’re doing personal travel planning now.
Yes, I am. The tours will always be the center point to what we offer at Stellavision because these curated itineraries and community are so powerful, but I completely understand that it doesn’t fit with everyone’s budget or travel plans, or they’re coming to Italy and they can’t leave their husband behind—that’s okay too.
So in the world of private travel planning, there are three different price points, three different levels of collaboration. You can book a call with me and that is really about finessing your trip. Some of my travelers are super independent. I spoke to a mother and daughter who are doing a hell of a road trip, but they really needed assistance figuring out the ferries and learning about some great restaurants and things like that. For another couple I'm working with right now, they’re celebrating a tenth anniversary and they want it to be special. They want to do the cornerstone sights and experiences in Rome and Florence, but how are we changing it up for them? So that was a quick call followed by a bespoke email with links and tips and introductions.
I also offer a travel concierge service, where we’ll design your dream itinerary together based on your goals, your travel preferences, and your budget and then I'll hand it over to you and you’ll do all the bookings yourself. There are many people who want to collect the points on their own credit card and I totally respect that. And then the third level is the tried and true travel agent idea where you are completely hands-off. We’ll plan your trip based on your goals, we’ll take care of all your bookings and coordinate everything for you. For our private travel clients, they’re dealing with a Rome-based expert and that expert is me.
I did want to talk also for a moment about the real real of living here because you plan incredible vacations for people in Italy, but you also live here and I feel like I get a lot of comments from people back home who either have this romanticized vision of Italy or they’re like, “Oh I love going to Italy on vacation, but it must be so hard to live there.” Do you get that?
I do. At the end of the day, I am a guest in this country. I was not born here and I feel privileged to be here and I think it would be flat-out wrong to superimpose my North American ideals and expectations on my adopted country. It’s not like home here. That’s why I came here and it would be small-minded to wish that it was.
That being said, are there days that Italy drives me absolutely crazy? Of course there are. There are things that make me frustrated, there are things that are more difficult than necessary, and there are days that are really hard as a result of it, but the balance to me is so worth it. There’s so much privilege to living here.
It is good for me to be able to live in my beautiful apartment in my beautiful neighborhood, stroll to the market, eat the best produce I’ve ever eaten in my life, and enjoy this affordable, more mellow life. It’s good for me and I’m so happy here.
Before I wrap up this interview, since you are a foodie and an art lover, would you share a few of your top picks for where to eat and where to see art here in Rome?
Absolutely. My two favorite restaurants time and time again, hands-down the best carbonaras in Rome, are Roscioli, which is not a secret. It’s a staple of the center and they recently announced a New York opening, but at the end of the day they are a family-run business.
And then the other one is SantoPalato, where there’s a badass female chef that happens to be small in stature and big in flavor who has taken the centuries old history of cucina povera and is both honoring it and updating it at the same time. That’s Sara Cicolini and she’s doing incredible things. So when I personally have guests in town, we’re at one of those two spots and when I do bookings for my private travelers, those are some of the first two places.
What about art? Where are your favorite places to see art here?
In Rome, I would say that the most exciting places to see art are the small installations, for me. There are great exhibits at MAXXI and things like that, but I loved when you and I went to the apartment of Giacomo Balla. And across the cobblestones from Da Enzo is Sant’Andrea de Scaphis, where it’s a broken down church that’s been converted into a gallery, so they’ll show a very interesting contemporary show every couple of weeks. Near the Arco dei Banchi is Le Finestre run by a contemporary gallerist and there’s always an interesting installation popping up there. So it’s moments like those that I really love in Rome.
And beyond Rome?
Beyond Rome, you should stay tuned for Stellavision’s tour to the Biennale in Venice because that is an enormous and intimidating art fair to navigate by yourself, but that is the world’s fair of contemporary art and if you’re an art lover, you should experience the majesty of Venice Biennale every other year.
I will definitely stay tuned for that. Thank you so much.
Thank you so much!
This interview has been edited for length and clarity.
Further Reading
You can read the article I wrote for AFAR about Stellavision’s size-inclusive trips here.
My colleague Erika Rae Owen wrote this lovely article about Stellavision’s size-inclusive trips for Condé Nast Traveler that I mentioned in the interview.
Zoe wrote this thoughtful op-ed for the Globe & Mail about how Italy helped her make peace with her weight and shape and how it inspired her to launch size-inclusive trips.
She was also interviewed about the topic in a segment for TVO Today.
This article in the Toronto Star tells the story of how Zoe moved to Italy and launched Stellavision.
I want to go on all of these trips!