Opulent Explorer: Executive Luxury Travel
At Pennyworth Projects, we’ve been fortunate to work with executives across industries and individuals who are constantly on the go. For these high-level leaders, travel is a critical part of both their business and personal well-being. However, planning a seamless luxury travel experience can be overwhelming.
In this feature, we sit down with Stuart Marra, a leading luxury travel expert whose reputation for curating unforgettable experiences precedes him. He has worked with high-profile individuals and business leaders for over two decades, helping them experience the world in the most bespoke and extraordinary ways. Stuart, with his expertise through Opulent Explorer, shares how assistants can collaborate with a luxury travel expert like himself to ensure that every trip exceeds expectations!
What do you suggest an assistant should initially do when they're tasked with organizing a luxury trip for their principal?
Stuart: I'd ask you to take the approach a doctor would take and diagnose the request. Is this a relaxation trip? Is this one where you want cultural immersion or active experiences? How did the principal choose the destination? The "why" is what you're looking for in all of this.
If the reason is that we want to plan a family biking trip, we can now present them with all the available options—not just the ones they've heard about casually from friends. This is the beginning of the planning process. It is where the principal will see the value in having a luxury travel expert to consult, and the EA will pass along work to an expert who can vet the choices.
When it comes to working with a travel expert, how can assistants best streamline the planning process and ensure everything goes smoothly?
Stuart: Some principals might ask, "Why hire a travel advisor when I already have an executive assistant?" Here's why: you're bringing in an expert who's not only been where you're headed but was an executive himself. After 20 years in New York as an Equity Derivatives and Risk Arbitrage expert, I retired at 42 and have sailed the world, visiting 71 countries and all seven continents. I help mitigate travel volatility, elevate the experience through my global relationships, and take the workload off the EA's plate. I've been where you're going next and design executive travel every day—that's the difference I bring to the table.
Last summer, a banking executive was referred to us. She is an art enthusiast, and her dream was to visit the Louvre in Paris and be guided by a local expert. She and her assistant hired a guide off the internet, right away it was apparent something was wrong. The guide was clearly not up to the task, and when pressed by the principal, the guide admitted to being an Uber Eats driver trying to make some extra money. In contrast, we have on-site partners who we have used for years. Their guides are vetted, and when I took my family to the Louvre this summer, our guide had an art history graduate degree and brought fun games that made a treasure hunt out of the Louvre, which captivated our eight-year-old son. The presentation style is essential, but we really want you to be empowered through our guidance to answer any questions upfront.
What are some unique challenges that assistants should be mindful of when planning luxury travel, especially when working with executives who often have unpredictable schedules?
Stuart: Once we've had a few conversations, filled out some forms, and have a clear understanding of the principal's needs, I'll put together a proposal in a video format. I'll walk you through images, hotels, and how everything ties together. Since it's recorded, both you and the principal can watch it at your convenience without distractions. This way, the EA can take notes on the principal's reactions and provide feedback.
It's much more effective than trying to fit into a packed schedule. After that, I'll create a similar presentation for our in-country supplier, ensuring everything is preserved in translation. We'll fine-tune the details to match everyone's preferences, and the EA can access everything whenever needed.
As travel has evolved post-pandemic, many executives now travel with a blend of remote work and vacation in mind. How can assistants ensure that these hybrid trips are successful?
Stuart: We've had executives bring friends on trips—like a couple renting a yacht in the Maldives. They wanted to stick to their morning workouts, so we had an extra room converted into a private gym with a Peloton and weights. We arranged a satellite phone for reliable communication in remote locations where cell service and WiFi can be spotty. My background in finance and travel means I understand your needs and can manage expectations seamlessly.
We exclusively handle ultra-high-net-worth clients, which means you get fast, personalized responses—unlike an AmEx call center, you wait 15 minutes, never speak to the same person, and deal with agents who haven't been there. We're fully invested in you and your principal, and our high-end services reflect that.
What are specific trends in travel that assistants should be aware of when looking to elevate their executive's travel experience in the coming year?
Stuart: I recently wrote an article called "10 Things to Consider When Traveling in 2024 and Beyond," which gives a solid overview of our services and the latest travel trends. With more people working from home, they're looking to go further and explore more remote destinations. Instead of having a quick weekend in Paris, I see clients heading to places like the outskirts of Marrakesh or Istanbul. South America is becoming the new go-to for natural escapes, similar to how Europe is for city breaks—Patagonia, for example, is now rivaling Switzerland.
I specialize in curating these off-the-beaten-path trips, and as a professional travel photographer, my work gives you a glimpse into how I see these unique destinations. I've traveled to Central and South America (not counting Mexico) 20 times! So when I say we don't need to Google hotels or experiences in remote places, it's an understatement.
How about potential pitfalls? Is there anything assistants should avoid when planning luxury travel?
Stuart: Don't follow your friends' itineraries! To truly elevate your experience, you need a professional who's been where you're headed. My success comes from 20 years as a New York executive and a deep passion for travel. That passion is the key to success in anything. I am never more alive than on a trip with a camera around my neck. When you talk to your principal, find out why they want to go to this place. Before they decide on the place, let's talk about the experience that they want to achieve well before we decide where we're going to go. I take 8+ international trips a year just for fun, so trust me, we've got the experience to back it up. On top of that, we design countless bespoke adventures. We've learned the art of traveling right—something you won't get from someone who isn't living and breathing this every day.
What final piece of advice would you give to assistants tasked with planning luxury travel for their executives?
Stuart: While booking travel is within everyone's reach, optimizing the experience takes a professional who has been where you are going next. Travelers don't want more choices; they want confidence in their choices!
Whether you end up working with me or not, I encourage you to reach out and have a chat about your executive's travel needs. I can share insights that will arm you with the right questions for that moment. Think of it as a dry run—you might even guide the principal towards: 'I know someone extraordinary at this, and for X cost, they can handle all the details, smooth out the volatility, and elevate the entire experience. Doesn't that make sense?'
For an executive assistant, this is a no-brainer. We take the workload off your plate and optimize the travel experience thanks to our firsthand travel expertise and exclusive relationships. And here's the thing—I sat in the principal seat and have been on the kind of trip they have in mind. So, explore my site, check out the photos, browse the sample itineraries, and get a feel for what we do. Let's hop on a call, and I'm confident you'll see how we can be the 'easy button' that helps you effortlessly optimize your principal's travel.
PHOTOGRAPHY | ITINERARIES | ARTICLE: "10 Things to Consider When Traveling in 2024 and Beyond"
We’ve seen firsthand how a well-planned trip can positively impact an executive’s life, both personally and professionally. Working with experts like Stuart Marra ensures even the most complex itineraries are planned and executed flawlessly.
Stuart - thank you so much for sharing your invaluable insights and tips on luxury travel planning. It’s clear that through collaboration, we can help executives make the most of their time, wherever their journey may take them!