This is the story of our Italy and Paris anniversary trip — the one we planned for our 25th, postponed twice, and finally took 27 years into our marriage.
When I was a little girl, I had an earring holder shaped like the Eiffel Tower.
I don’t know exactly when the fascination began — but Paris lived in my imagination long before I had a passport. Shower curtains with the Parisian skyline. Prints on my walls. Little trinkets scattered around my home. The Eiffel Tower wasn’t just a landmark to me. It was a symbol of something I quietly carried for decades — a dream I hadn’t yet dared to call a plan.
Fast forward to August 1995. I marry my person. We build a life together — careers, a home, four kids, the beautiful, ordinary chaos of two people growing up side by side. Twenty-seven years pass in the way years do — quickly, and full of everything.
My husband’s dream was always Italy. Mine was Paris. So for our 25th anniversary, we decided to do both — a grand sweep through Italy followed by a few magical days in Paris. We booked the flights in late 2019. And then 2020 arrived and the world stopped.
We postponed to 2021. Then again. By the time we finally went, it was 2022 — our 27th anniversary year. The trip had grown from a 25th anniversary celebration into something bigger: proof that some dreams survive everything life throws at them.
It wasn’t until October 2022 that we finally stepped off a plane onto European soil — two years late, and 27 years after we said “I do.”
“Some dreams are worth waiting for. Ours survived a pandemic and two years of delays — and it was still the best decision we ever made.”
Why We Almost Didn’t Take Our Anniversary Trip to Italy and Paris
I’ll be honest — after two and a half years of postponing, there were moments I wondered if the trip would ever happen. Life kept moving. The pandemic changed everything. And at some point, a dream deferred starts to feel like a dream abandoned.
But we had waited too long. We had pictured this trip too many times. And so in October 2022, we finally took our Italy and Paris anniversary trip — flying Aer Lingus from Chicago to Dublin — and then onward to Naples, Italy — and just like that, the dream became real.
🌿 Travel Tip: We upgraded our transatlantic flights from Economy to Business Class using points — no extra cash required. The difference on an overnight flight was extraordinary. I’ll never fly economy on a long-haul flight again if I can help it.
The Amalfi Coast: The Moment That Took My Breath Away First
I had dreamed of the Amalfi Coast the way you dream of something you’ve only ever seen in photographs — beautiful in a way that feels slightly unreal, like it couldn’t possibly look like that in person.
It does.
We drove that coastline in a Mercedes van with a skilled driver who navigated those dramatic cliffside curves with an ease that both terrified and thrilled me. I’ve driven California’s Pacific Coast Highway from San Diego to San Francisco — twice. I thought that would prepare me. It didn’t. The Amalfi Coast is something else entirely.
Turquoise water far below. Colorful villages clinging to the cliffs. The scent of lemon trees in the October air. My husband’s hand in mine. I remember thinking — this is exactly what I imagined. And then the road curved, and the view opened up even wider, and I thought — no, it’s even better.
We had arrived in Naples the night before, checking into the Grand Hotel Parker’s — a grand, storied property perched above the city. We made our way up to the rooftop where a row of bronze goddess statues lined the terrace, each one holding a lamp aloft over the Bay of Naples. I ordered some kind of fruity cocktail garnished with a star-shaped slice of pineapple and we toasted to finally being here. It was dark, so we could only make out the city lights and the silhouette of Vesuvius. But the next morning at breakfast, overlooking that same bay in full daylight for the first time — the blue water, the city below, the volcano in the distance — I nearly put down my fork and just stared. That was when the trip truly began.
🌿 Travel Tip: If you’re visiting the Amalfi Coast, book a private driver rather than trying to navigate it yourself. The roads are narrow, steep, and breathtaking — let someone else handle the wheel so you can fully take it in.
“The Amalfi Coast is one of those places that makes you understand why people dedicate their lives to travel.”
Rome, Florence & Venice: Where Italy Stole Our Hearts
Over the following days, Italy wrapped us in the kind of warmth that only comes from a place that has been perfecting the art of living well for thousands of years.
We stood in the ruins of Pompeii in 80-degree October heat, and I watched Jim go quiet in a way I hadn’t seen before. He loves history — always has — but there’s something different about actually walking the same streets that people walked two thousand years ago, looking into the rooms where they lived and worked. We even stumbled upon what the guide told us was an ancient brothel. Jim was absolutely mesmerized the whole time. Seeing him experience something he had dreamed of for years is a memory I’ll always carry.
One of our first nights in Rome, we did a food tour through Trastevere that I still consider one of the best evenings of the entire trip — and honestly, one of the best food tours I have ever taken anywhere. Our host was a wonderful woman named Kopal who led a small group of just four or five couples through the neighborhood with warmth and genuine passion. We hit a deli, then a spot for supplì — those incredible Roman fried rice balls — then a pizzeria, then a place with pasta that made me understand why Italians take their pasta so seriously. We ended at a restaurant serving a rich, soul-warming stew paired with one of the best glasses of wine I had on the entire trip. And we finished with gelato, where Kopal taught us exactly how to spot authentic, homemade gelato versus the tourist trap stuff. I use this knowledge every time I’m in Italy now.
But the moment that stopped me in my tracks was at that last restaurant. They took us down into an underground cellar beneath the building — and inside were ancient artifacts. The kind of ancient that predates the Colosseum. We were standing in a neighborhood that had been continuously inhabited for over two thousand years, and the evidence was literally beneath our feet. Rome does that to you — it layers history on top of history until your mind can barely hold it all. I now book this exact tour for every client I send to Rome. It is the perfect introduction to the city.
We discovered an entire archaeological site beneath the Trevi Fountain that most tourists walk right past. We upgraded mid-trip to the Waldorf Astoria, and one evening after a long day of exploring, we had dinner and cocktails and I ended up just wandering slowly through the hotel corridors. It felt like walking through a museum — antique furniture, centuries-old paintings lining the marble hallways. I was completely enchanted. And their bathroom was one of the most beautiful I have ever seen in my life.
But the moment I keep coming back to happened just outside. We walked about fifteen minutes down the street until we found a hilltop with an open view of all of Rome. The rooftops, the domes, and there in the distance — the Vatican. Jim and I just sat there together and looked. There are moments in travel that become core memories the instant they’re happening, and that was one of them.
In Florence, we went to a Tuscan farmhouse for a cooking class that I still talk about. A sweet woman taught us to make gelato from scratch — genuinely fun, genuinely delicious. Then two Italian guys took over to teach us how to make pizza. They were absolutely hilarious, kept us laughing all night, and every person made their own personal pizza with whatever toppings they wanted. We even made the dough and got to toss it in the air. At one point we stepped outside and stood on a hill on the property and looked out over Florence below us. I didn’t want to leave. We also stood in front of Michelangelo’s David that day, and I bought my first real leather bag from a craftsman in San Gimignano who had been making them the same way for generations.
In Venice, we stayed at the Ca’ Sagredo — a historic palazzo on the Grand Canal that has hosted guests for centuries, and which happened to be the filming location for the movie The Tourist. Our room was the one where the famous window scene was filmed — the one where Johnny Depp (or more likely his stunt double) jumps into the canal. The room was filled with antiques. The bathroom, again, was extraordinary. We watched a glassblower on Murano turn molten glass into something impossibly delicate. We took a 45-minute gondola ride through canals so narrow you could reach out and touch the walls. Our gondolier pointed out the history of the buildings as we drifted past. No singing — but we did pass gondolas where other gondoliers were singing, and it floated through the evening air like something out of a movie.
Through all of it — the mishaps included (a taxi scam in Naples, a missed ferry in Sorrento, a lost luggage tag on Capri) — we moved through the world as a team. We problem-solved. We laughed. We held hands on train platforms and shared plates of pasta and reminded each other, again and again, that the adventure was the point.
I haven’t even mentioned the Sistine Chapel — because that moment deserves its own post entirely. Standing beneath Michelangelo’s ceiling, finally understanding why people weep in that room, is something I am still not sure I have the words for. That’s coming in Part 2 of this Italy and Paris anniversary trip series.
🌿 Travel Tip: Italy’s train system is efficient and affordable. Book intercity trains a month or so in advance for the best prices. It’s one of the most enjoyable ways to travel between cities.
What a 17-Day Anniversary Trip Did for Our Marriage
There’s something that happens when you travel with your person — really travel, the kind where you’re navigating a foreign country together, making decisions, getting lost, finding your way back. The ordinary rhythms of home fall away. You see each other differently.
I saw Jim light up at Pompeii the way I hadn’t seen him in years. I watched him stand at the edge of the Colosseum and just look. He loves history — that’s always been part of who he is — and watching him actually walk through it, experience it in three dimensions after a lifetime of reading about it, reminded me of something I already knew but had maybe forgotten to notice: I married someone who gets genuinely excited about the world. That’s not a small thing.
And for me, it was Italy itself. I hadn’t expected to fall in love with it the way I did. But somewhere between Pompeii and the Tuscan farmhouse and the gondola and the food — the food above all else — Italy worked its way into my bones. Twenty-seven years of marriage, and we were still capable of surprising each other.
“Travel doesn’t just show you the world. It shows you who you are — and who you are with the person beside you.”
I Planned This Italy and Paris Trip for Paris. Italy Stole My Heart Instead..
Here’s the thing I didn’t expect: I went on this trip thinking Paris was the grand finale. The dream destination. The whole point.
And Paris was everything I imagined. It truly was.
But Italy? Italy absolutely stole my heart.
My husband had always been the one who dreamed of Italy. I was along for the ride, honestly. And somewhere between the Amalfi cliffs and a Tuscan farmhouse at sunset and a gondola in Venice and the best food I have ever eaten in my life — Italy became my favorite country in the world. It still is.
We loved it so much that we went back the very next year — October 2023 — this time bringing our youngest son Aaron along for the Amalfi Coast and Sicily. Because some places deserve a second chapter. And a third.
“I went for Paris. I stayed for Italy. And I’ve never been the same since.”
Paris for an Anniversary: Finally Standing Beneath the Eiffel Tower
We took the Bernina Express through Switzerland, past Lake Como and alpine meadows and scenery so beautiful it felt staged. We spent a night in Zurich. And then, on October 28th, we took the train to Paris.
I have to pause here for a moment.
Because Paris — Paris was always the dream. Not just a destination. The destination. The one I had been carrying since I was a little girl with an Eiffel Tower earring holder, since the first shower curtain, since every print and postcard and passing daydream.
We checked into the Park Hyatt Paris and booked something I had been looking forward to almost as much as the tower itself — a photo shoot with Panos, a Greek filmmaker and photographer who shoots couples all over Europe. I normally hate having my picture taken. Genuinely. But Panos was different from the first moment. He’s a filmmaker, so he sees scenes and moments rather than just poses. He moved us through Paris like we were characters in a story — a café, the Seine, the Pont de Bir-Hakeim with the city glowing behind us and the tower rising in the distance.
He was supposed to be with us for an hour. He stayed for double that, at least. He said he just loved us and wanted to keep shooting. We walked all over the city that evening, and somehow I forgot I was being photographed. I was just in Paris, with Jim, finally. The photos from that night are some of my most treasured possessions.
The next day we took the train to Versailles — and if you think you know what to expect, you don’t. The Hall of Mirrors, the gardens stretching further than your eye can follow, the sheer scale of it — Versailles stopped me in my tracks in a way I genuinely didn’t anticipate. I’ll be dedicating all of Part 3 to the final days in Paris, and Versailles will get the space it deserves there. We also saw the Louvre and went up inside the Eiffel Tower.
And I stood there — at the top of the tower I had stared at on earring holders and shower curtains for three decades — and I cried. Happy tears. The kind that come when something you’ve held in your heart for a very long time finally becomes real.
We flew home on Halloween — October 31st — arriving back in Chicago with full hearts, tired feet, and a camera roll that would take weeks to go through.
Paris has since given me a different kind of story to tell — but that’s for another post. This one belongs to the dream. Check out that story here.
“I stood at the top of the Eiffel Tower and cried. Not because I was sad — but because some dreams really do come true.”
Why This Anniversary Trip Made Me a Better Travel Advisor
We came home from our Italy and Paris anniversary trip different. Fuller, somehow. More us.
But something else happened on that journey too. Through every taxi mix-up, every missed connection, every moment of “we didn’t plan for this” — I kept thinking: I want to figure out how to do this better. Not just for us. For everyone who has a dream trip living quietly in the back of their mind.
That trip — with all its magic and all its mishaps — is a big part of why I became a travel advisor. I wanted to learn everything. To plan the kind of trip where the surprises are wonderful ones. Where every detail is thought through, every transfer is arranged, every moment is designed to be savored rather than survived.
I wanted to help other people feel what I felt standing at the top of that tower.
Your Dream Trip Is Waiting
Your Dream Trip Is Waiting
Maybe you have your own version of my Eiffel Tower earring holder. A destination you’ve carried for years. An anniversary coming up. A milestone worth marking with something extraordinary.
The best is yet to come — and I would love to help you plan it.
Whether you dream of an Italy or Paris anniversary trip like ours, or Ireland, Scotland, Alaska, or somewhere entirely your own — I’ll handle every detail so you can simply show up and let the story unfold.
Every Journey Writes a Story.
What will yours say?
— Karla Tugan, Owner & Travel Designer, Whispering Willow Travel
Frequently Asked Questions: Planning an Anniversary Trip to Italy and Paris
How long should an Italy and Paris trip be?
For a meaningful Italy and Paris anniversary trip, I recommend a minimum of 14–17 days. Our trip was 17 days and covered Naples, the Amalfi Coast, Sorrento, Capri, Rome, Florence, Tuscany, Venice, Zurich, and Paris — and we still could have used more time in each place. If you only have 10 days, I would focus on either Italy or Paris rather than rushing both. Quality over quantity always wins on an anniversary trip.
What is the best time of year to visit Italy and Paris for an anniversary?
October is my personal favorite — and I recommend it to nearly all my clients. The summer crowds have thinned, the weather is warm but not brutal (we had 80°F in Pompeii in late October), and the light is beautiful. Shoulder season also means better hotel availability and often better pricing. Spring (April–May) is a close second. July and August are the most crowded and most expensive months, especially on the Amalfi Coast.
Is the Amalfi Coast worth it for an anniversary trip?
Absolutely — and without hesitation. The Amalfi Coast is one of the most breathtaking places I have ever seen in my life, and I have traveled extensively. I would put it in my top three destinations in the world for couples. The key is to do it right: book a private driver rather than renting a car, stay in Sorrento or Positano as your base, and give yourself at least two full days. We returned to the Amalfi Coast the following year — that’s how much we loved it.
What are the best hotels in Italy for an anniversary trip?
We stayed in some truly exceptional properties on our trip. The Grand Hotel Parker’s in Naples is a historic hilltop hotel with a rooftop terrace overlooking the Bay of Naples — an incredible first night in Italy. The Waldorf Astoria Rome is a museum-quality hotel with antique-filled corridors and one of the most beautiful bathrooms I have ever seen. In Venice, the Ca’ Sagredo on the Grand Canal is a magnificent historic palazzo — and was the filming location for The Tourist. Splurging on hotels for an anniversary trip is worth every penny. The accommodations become part of the memory.
Should I book a photo shoot for my Paris anniversary trip?
Yes — and I say this as someone who normally hates having her picture taken. A professional photo shoot in Paris is one of the best investments you can make on an anniversary trip. Look for a photographer who is also a filmmaker or videographer, as they tend to capture more natural, cinematic moments rather than posed portraits. Our photographer Panos was Greek, shot all over Europe, and extended our session to double the time because he loved the experience. The photos from that evening are among my most treasured possessions. Book it for the evening so you get the golden light and the tower lit up behind you.
How do I plan an Italy and Paris anniversary trip without the stress?
Work with a travel advisor who has personally been there. I have been to Italy multiple times and to Paris, and I handle every detail for my clients — flights, hotels, transfers, tours, restaurant recommendations, and backup plans for when things go sideways (because sometimes they do, and it’s much easier when someone is handling it). The trips I design for clients are far smoother than the one my husband and I navigated ourselves. That’s the whole point. You should show up and experience it — not manage it. Reach out at WhisperingWillowTravel.com to start planning yours.
COMING NEXT IN THIS SERIES:
Part 1: Naples, Amalfi & the Art of Slowing Down in Southern Italy
Part 2: Rome, Florence & the Soul of Italy
Part 3: Venice, the Bernina Express & the Magic of Paris
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