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The First Fancy Dinner Alone: How Solo Travel Changed Everything
My first real solo trip didn’t exactly start as a solo trip. I was in Ireland for work—Dublin, to be exact. Technically alone, sure, but let’s be honest: business travel is like solo travel with a safety net. You’ve got a hotel room to yourself, but you’re still going to lunch with coworkers, sitting in meetings, and exchanging Slack messages at midnight. It's solo with strings attached.
But one weekend, I booked a trip—just me, no colleagues, no agenda—from Dublin to Rome. And that’s where it truly began.
Rome was my first true solo adventure. I wasn’t nervous. I was excited. Maybe a little raw—burnt out from an incredibly stressful job—but more than anything, I needed a break. My manager at the time had suggested a few restaurants, so I made reservations at one for my first night. It was fancy, formal, and very... Roman. The kind of place where the table linens are ironed within an inch of their lives and the waiters glide instead of walk.
I showed up, realized no one really spoke English, the menu was fully in Italian, and—yep—I was about to dine alone in a Michelin-recommended restaurant. For the first time ever.
And here’s the thing: I survived. I ordered, ate, and slowly took in my surroundings. And by dessert, I felt this strange sense of joy. A kind of liberation I hadn’t expected. Like I’d cracked open a door I didn’t even know existed. I was out of my comfort zone, sure—but I felt alive.
The next day, I joined a guided tour of the Colosseum—soaking in the history, the stories, the grandeur. And I’ll be honest, a part of me wanted to channel my inner Russell Crowe and shout “Are you not entertained?!” right there in the arena. I didn’t (you’re welcome, fellow tourists), but the moment made me laugh and realize: I was having fun. Real, genuine fun. On my own.
That trip flipped a switch. I went on excursions, talked to strangers, made friends, and just like that, I caught the solo travel bug. Fast forward ten years—almost to the month—and I haven’t looked back.
Since then, I’ve solo traveled to places I never imagined I’d go alone: Tokyo, Florence, Edinburgh, Barcelona, Sydney, Mexico City, Annecy, Bordeaux, Berlin, Valencia, Granada, Zurich, Frankfurt, and so many more. I’ve wandered through Madrid’s bustling neighborhoods, felt the calm of early mornings in Basel, admired art in Milan, soaked up sun in Alicante, explored history in Dubrovnik, and strolled through the lavender fields of Tuscany. Solo. Me, myself, and I.
And here’s the thing: I’ve learned more about myself in those quiet solo moments than in years of performance reviews and life plans.
It’s become such a part of who I am that these stories are now a fixture at family dinners. I have a big, close-knit extended family—lots of aunts, uncles, and cousins—and whenever we’re all gathered around the table, someone always asks, “How was the food in Barcelona?” or “Did you like traveling alone in Tokyo?” or “What was the best thing you ate in Florence?” Sometimes there’s a little envy too—“Ugh, I need to do a solo trip. Sounds like you had a blast.” These moments turn into rich conversations that go beyond small talk—deep dives into culture, food, courage, and self-discovery. It’s storytelling that brings us all a little closer, and maybe even inspires the next person to take that leap.
But solo travel isn’t just about racking up stamps on a passport. It’s about mental clarity. Emotional reset. It’s therapy, really—but with better scenery and (usually) better food.
In today’s world—where we’re constantly overstimulated, overbooked, and under-rested—solo travel provides something radical: silence. Stillness. A reminder that it’s okay to be alone with your own thoughts. That you don’t always need a plan, a partner, or a perfectly curated Instagram moment. Sometimes, all you need is a street corner café in Lyon, a hot cup of coffee, and the space to breathe.
I can honestly say solo travel made me stronger. It helped me handle anxiety better. It reminded me that I can figure things out on my own—language barriers, train strikes, confusing street signs, all of it. Each trip added a layer of confidence, and in some small way, peeled away a layer of stress.
And here’s another truth: travel—especially solo travel—makes you kinder. It makes you more open-minded. You meet people from all over the world. You sit next to strangers on planes, in parks, at museum cafés. You connect. You listen. You share.
You realize very quickly that people everywhere are just trying to live their lives with a little bit of joy and a whole lot of heart. That understanding softens you. It builds compassion. It chips away at bias and fear. It makes it very hard to see the world as “us versus them” when you’ve shared wine with a couple from Berlin or received directions from a kind stranger in Tokyo.
Honestly, I think if more Americans traveled solo—not just for vacation, but with the intent to truly observe—we’d all be a little more grounded. A little more humble. And a lot more compassionate.
We’d understand how different countries approach life: how in some places, people work to live—not the other way around. We’d see how cultures prioritize connection, rest, community. And maybe we’d start to question why our schedules are always so packed, our inboxes always so full, our lives always on overdrive.
Solo travel offers a kind of mental reset that I wish more people could experience. It helps clear out mental clutter. And most importantly, it builds empathy. When you’ve walked in another culture’s shoes—even briefly—it becomes harder to hold onto judgment, fear, or hate.
So no, I didn’t become a different person overnight. But I became more of myself. Softer in the right places. Sharper where I needed to be. And better equipped to navigate not just airports, but life.
So, if you’re burnt out, overwhelmed, or just plain curious—book that ticket. Take the trip. Eat the dinner alone.
Because sometimes, the most unforgettable journeys begin with a solo reservation at a fancy restaurant in a city you’ve never seen before.
Here are five key points about the mental health benefits of solo travel, cited from the popular source Forbes:
Reduces Stress and Anxiety
Traveling helps lower cortisol levels, the hormone associated with stress, leading to a calmer and more content state of mind. Solo travel, in particular, allows individuals to disconnect from daily pressures and focus on self-care
Boosts Happiness and Satisfaction
Experiencing new places and cultures rewires the brain, enhancing mood and self-confidence. Solo travelers often report feeling more fulfilled as they step away from routines and embrace personal growth through unique experiencesBuilds Mental Resilience
Navigating unfamiliar environments alone fosters adaptability and emotional strength. Facing challenges during solo travel helps individuals become mentally tougher and more independentEncourages Self-Discovery
Solo travel provides an opportunity for introspection, helping individuals reflect on their goals, interests, and values. This process can lead to greater self-awareness and a stronger sense of purposePromotes Personal Freedom
Traveling alone allows individuals to set their own pace and make decisions independently. This sense of autonomy can be empowering and liberating, contributing to improved mental well-being
Quick Plug: 🏡Catskills, NY Cabin for Rent:
ZenWood Manor
Escape NYC and embrace spring at Zenwood Manor in Livingston Manor. This peaceful 3-bedroom, 2-bath retreat features two cozy living rooms, a washer/dryer, and sits on 5 private acres—perfect for recharging in nature.
Just minutes from Main Street’s vibrant scene, enjoy amazing food and drink at:
• The Walk Inn (@thewalkinn) for brunch vibes
• Stumble Out (@stumbleoutny) for craft cocktails and killer comfort food
• Main Street Farm (@mainstreetfarm) for local market fare
• Kaatskeller (@kaatskeller) for wood-fired pizza under the stars
• Threshold (@thresholdlivingstonmanor) for upscale seasonal dishes
Also nearby: Upward Brewing Company (@upwardbrewing) for mountain views + beer, and The Arnold House (@thearnoldhouse) for classic Catskills charm. Get fresh organic produce from the farm @somewhereintimefarm.
Hike scenic trails, try fly fishing, or just kick back under the trees. Don’t miss spring events like Flower Day (May 17), plus the Livingston Manor Farmers Market starting May 25!
Book your weekend escape now. Click here to book: ZenWood Manor
📩 Interested? Reach out to me @rajp10 or @zenwoodmanor
City Spotlight: London
Visiting London is a feast for the senses—steeped in history, royalty, and endless things to do. After soaking in the sights of Buckingham Palace, the Tower of London, and strolling through Hyde Park, dive into the city's incredible food scene. For top-tier Indian cuisine, Dishoom offers rich, Bombay-inspired flavors in a stylish setting, while Gymkhana delivers an elevated twist on traditional dishes that’s perfect for a special night out. Don’t miss Mayfair Chippers for classic fish and chips done right, and head to Brick Lane for a lively stretch of some of the best curries in town. Foodies will love wandering the Harrods Food Hall, where gourmet options abound, and London's famous food markets like Borough or Camden—especially if you’re hunting down those legendary, pillowy donuts. And of course, pop into a classic pub to enjoy a pint and soak in that cozy London charm. For the perfect stay, the InterContinental Hotel on Park Lane is a dream—offering sleek luxury, top-notch service, and a location that puts you right in the heart of it all.
Big thanks for reading and being part of this ride. Travel is about living big, and I want this newsletter to be just as inspiring. So, what’s on your radar? A five-star retreat? A private island where “crowds” are just seagulls? Insider access to exclusive experiences? Or maybe you just want to indulge in luxury without maxing out your Amex (trust me, it’s doable). Whatever it is, hit me up—I’ll make sure future editions serve up exactly what you’re craving.
Until then, keep chasing epic moments, and I’ll see you out there. Safe and stylish travels!
