Planning a trip to Italy can evoke a mix of emotions. Being such a popular destination makes some people underestimate the complexity of putting together an itinerary that goes beyond the cookie-cutter packages found online. Any assumptions about it being simple to craft a trip often fade after a quick browse. On the other hand, there are people who are intimidated from the start, simply because the sheer volume of choice leaves them feeling as though coordinating it all is an impossible feat. The truth is that it’s not a matter of being easy or hard; it’s about having the right tools to make a dream Italian trip come to fruition. This is where custom travel design companies like Olive & Atlas come into the picture, representing a sector of tourism often overlooked and unknown to most.
Founded by Angela Isherwood, an Italian-American and extensive traveler, Olive & Atlas was born out of what she describes as a “lifelong passion for travel and a conviction that [she] could help people travel ‘better’.” It’s not your ‘run-of-the-mill’ travel agency; it’s a company that specializes in creating bespoke itineraries, stemming from Angela’s personal travel mindset of embracing culture shock and immersing herself in the cultural fabric of a destination. And while Olive & Atlas arranges itineraries for any destination, their core focus is Italy. This is undoubtedly rooted in Angela’s deep connection to Italy. The daughter of a Sicilian father and an Italian-American mother, she first visited Italy at 13 years old and recounts being overcome with a sense of returning home, despite never having visited. It would serve as the beginning of a love affair with Italy and a desire to connect travelers with the country’s people and places through experiential authenticity.
The Olive & Atlas Ethos
What makes Olive & Atlas stand out from other boutique travel companies is the way it views luxury. In an era where it feels like luxury has become a buzzword, it’s incredibly refreshing to discover brands that are taking a calibrated approach to this niche. Angela shares, “Luxury, at its best, is less about gold taps and more about access. Access to the real, the local, the irreplaceable. That’s what Olive & Atlas is built to deliver, in Italy and everywhere else we go.” This philosophy leans into a more mature understanding of luxury, one that recognizes that experiences are the true marker of wealth. Angela and her team are able to deliver this to their clients because they’ve worked hard to build relationships with people on the ground. It allows them to get their clients exclusive access to sights and accommodations that are simply not available when purchasing from other providers.
Another aspect of the Olive & Atlas ethos that sets the company apart is their relatability. With Angela and her team, you needn’t fear being frowned upon for desiring to visit Italy’s highlights, something that isn’t always the case with other luxury travel designers. Instead, they recognize that the main landmarks and attractions are popular for a reason and have a place in some people’s itineraries. But how they approach incorporating these highlights into the picture is what gives these “mainstream” sights an elevated twist. Each itinerary is meticulously crafted to reflect the individuality of the client, making no two itineraries alike. The common thread is a philosophy that rejects the tendency to treat Italy like a product, or as Angela puts it, “like a Disney World built for ‘oohs’ and ‘ahhs’.” If you’re a regular Live in Italy reader, you know how much this treasured value unites our digital community.
Angela Isherwood leads guests through an exclusive winery visit and tasting in Italy, offering an authentic experience beyond typical group tours. Courtesy Image.
The Olive & Atlas Client
The Olive & Atlas client can’t be defined by a specific age group or income bracket, nor by travel experience. Angela’s team works with a variety of clients, but most fall into two categories: the highly knowledgeable and seasoned traveler seeking someone to execute their vision, or the first-time visitor who feels a pull to visit Italy, but needs someone to take the reins. Despite these differing needs, the Olive & Atlas approach is to always ensure their clients feel like they’ve been seen and heard instead of being processed. This level of personalization is a hallmark of exceptional custom travel design, and Olive & Atlas delivers it seamlessly.
Experience Italy with Angela
Each year, Olive & Atlas hosts an intimate small group journey led by Angela. These travel experiences take place in destinations near and dear to her, and are limited to no more than 10 guests. This year’s journey to Sicily is already sold out, but Angela offered us a sneak peek into what’s in store for 2027. The destination: the Dolomites.
Angela recently visited the Dolomites for the first time and remarked on how stunning it was, describing the beauty of its scenery as almost impossibly real. But the area offers more than breathtaking vistas. The harmonious fusion of Italian and Alpine culture – especially its cuisine – inspired her to select it as next year’s destination. Remaining true to the slow travel ethos of Olive & Atlas, the tour will focus solely on this area. These hosted travel experiences go beyond sightseeing and exceptional dining; they’re designed to create connections. Reflecting on past journeys, Angela says: “There is something that happens when a group of like-minded people experience a place together in that kind of environment that simply cannot be replicated any other way. Conversations that start over dinner and continue for years. Friendships formed in the back of a van on a mountain road. Moments that belong only to the people who were there.”
The upcoming small group journey will take place in June of 2027. Additional details will be made available soon, so stay tuned!
Begin Your Olive & Atlas Journey
Travel should enrich one’s life, but the planning that goes into it is often exhausting. Working with a custom travel designer can simplify the whole process by handling all the heavy lifting. Whether you’ve been to Italy more times than you can count or have been longing to visit, but don’t know where to start, Olive & Atlas can help begin your journey. After interacting with Angela, my takeaway was that this is more than a career for her (and her team), it’s a genuine vocation rooted in love for travel and changing people’s lives. In a world with an endless selection of pre-packaged itineraries, there’s a real sense of luxury in a trip carefully curated to reflect your individuality.
For more information, be sure to visit the Olive & Atlas website and follow them on Instagram and Facebook.
