Luxury Travel to Italy, Designed Around You
Italy is personal around here.
I studied Italian in college, spent five formative months living in Florence, and have been finding reasons to return ever since.
But knowing Italy isn't just about knowing where to go. It's knowing which places will feel right for you.
Lake Como or Lake Garda? A grand hotel on the Amalfi Coast or a tiny hideaway on Ischia? Three nights in Florence—or five in Tuscany with nowhere particularly important to be?
At Viviamo Travel Co., I design custom luxury trips to Italy that are thoughtful, deeply personal and intentionally paced. Trips with extraordinary hotels and memorable experiences, yes—but also enough space to actually enjoy being there.
Because the best trip to Italy isn't the one that checks the most boxes.
It's the one that feels like yours.
Meet Your Italy Travel Advisor
I'm Alexandra Shea, founder of Viviamo Travel Co., a Chicago-based luxury travel advisor specializing in custom travel to Italy and beyond.
My relationship with Italy began long before Viviamo. I studied International Communications with a minor in Italian, lived and studied in Florence, and speak Italian. In the years since, I've returned again and again—exploring the country as a traveler, a hotel obsessive, and eventually as a travel advisor.
Today, I combine that firsthand knowledge with relationships throughout Italy to design trips that go beyond the obvious itinerary.
That might mean pairing Florence with a few quiet days in the Tuscan countryside. Choosing Lake Garda because it actually suits you better than Lake Como. Building an Amalfi Coast trip that doesn't leave you exhausted. Or finding the hotel that becomes the place you talk about long after you've forgotten which museum you visited on Tuesday.
I don't want to show you everything Italy has to offer. I want to show you the parts you'll love most.
How We Travel Italy
There are a thousand ways to do Italy.
Viviamo trips tend to favor fewer places, better hotels, exceptional food and experiences worth leaving the hotel for.
We'll absolutely see the things you've dreamed of seeing. But I'm just as interested in what happens between them.
The long lunch.
The afternoon at the pool when you decide not to go anywhere.
The tiny restaurant you still talk about three years later.
The morning you wander out for coffee without an agenda.
Those aren't the empty spaces in an itinerary.
They're often the trip.
Where We Go
Italy rewards slowing down. The question usually isn't whether a place is worth visiting—it's which combination of places makes sense for this trip.
Part of my job is helping you resist the temptation to do all of Italy at once.
Northern Italy + The Lakes
Lake Como · Lake Garda · Milan · Piedmont
Northern Italy can mean grand lakefront hotels and wooden Rivas, a few stylish days in Milan or lingering over Barolo in Piedmont.
The Italian Lakes are particular favorites of mine—and while Lake Como deserves its reputation, it isn't automatically the right choice. Lake Garda has its own kind of magic, with beautiful hotels, charming towns and a little more room to exhale.
We'll choose based on the experience you actually want, not simply the destination you've heard the most about.
Rome
There is nowhere quite like Rome.
The history is extraordinary, of course, but Rome is at its best when you leave some room for the city happening around it.
We'll balance the Colosseum, Vatican and ancient sites with neighborhood walks, aperitivo, excellent pasta and time to wander—so Rome feels like somewhere you experienced rather than somewhere you successfully completed.
Venice + The Dolomites
Venice · Cortina d'Ampezzo · South Tyrol · The Dolomites
Venice is one of those places that can feel completely magical or completely overwhelming. The difference is often in how you do it: where you stay, when you explore and whether you give yourself enough time to wander away from the crowds.
From there, the Dolomites offer an entirely different version of Italy—dramatic mountains, beautiful design-forward hotels, incredible hiking and some of the country's best wellness experiences.
Together, they make a pretty spectacular pairing.
Puglia
Valle d'Itria · Ostuni · Lecce · Salento
Puglia feels wonderfully different from Italy's classic first-trip circuit.
Think whitewashed towns, ancient olive groves, masserie turned beautiful hotels, long dinners outside and miles of Adriatic coastline.
It's particularly lovely for travelers who want to settle into a place rather than sightsee their way through it. Rent a car, choose a beautiful home base and give yourself permission to follow the day where it takes you.
Sardinia
Costa Smeralda · Porto Cervo · Northern Sardinia · Southern Sardinia
The water really is that color.
Sardinia is where I send travelers who want the beauty and glamour of the Mediterranean with plenty of room to actually vacation.
Come for extraordinary beaches, long lunches, boat days and some seriously special hotels. Stay long enough that you don't feel compelled to do very much at all.
And yes, an Aperol Spritz overlooking that impossible blue water absolutely counts as an afternoon plan.
Florence + Tuscany
Florence · Chianti · Val d'Orcia · Lucca · Forte dei Marmi
Florence was my first Italian home, and it remains one of my favorite cities in the world.
We'll make time for the art and architecture you came to see, but also for wandering, shopping, an excellent meal and the simple pleasure of sitting in a piazza with nowhere else to be.
Then head into Tuscany for a completely different rhythm: a villa in the hills, a wine estate, a long lunch in a tiny town or an afternoon by the pool when you decide that today's plans can wait until tomorrow.
The Amalfi Coast + Capri + Ischia
Positano · Ravello · Amalfi · Capri · Ischia · Sorrento
Yes, the Amalfi Coast really is that beautiful.
It's also one of those destinations where thoughtful planning makes an enormous difference. Where you stay, how you get around, which experiences are worth doing and how much you try to squeeze into each day can completely change the trip.
Sometimes Positano is exactly what you've been dreaming about. Sometimes I'd rather put you above it all in Ravello. Sometimes Capri is worth the splurge—and sometimes Ischia is the island you didn't know you were looking for.
We'll figure out which version is yours.
Sicily
Taormina · Noto · Palermo · Mount Etna · Aeolian Islands
Sicily could easily be an entire trip of its own—and I usually think it should be.
There is so much here: Greek and Roman history, Baroque towns, volcanic landscapes, incredible food, beautiful beaches and a culture that feels distinctly Sicilian.
The key is not trying to cover the whole island just because you can. Choose a few places, stay awhile and let Sicily unfold a little more slowly.
Italy Honeymoons
Italy and honeymoons belong together for a reason.
But romantic doesn't have to mean predictable.
We can pair a few glamorous days on the coast with the countryside, build in a city you can actually explore together, find a hotel you'll struggle to leave, and make sure your honeymoon doesn't require recovering from your honeymoon.
The goal isn't to create the most impressive itinerary.
It's to give you two weeks you'll want to relive forever.
Italy With Kids
Italy is one of my favorite destinations for families because you don't have to choose between a trip that's wonderful for the adults and one that's fun for the kids.
Gelato helps.
So do boats, beaches, pasta, pools, castles and piazzas where nobody minds if a child isn't sitting perfectly still.
The trick is pacing it correctly.
For families, I pay particular attention to room configurations, transfers, how much touring is realistic, strategically placed downtime and hotels that genuinely welcome children—not merely tolerate them.
What Does a Luxury Trip to Italy Cost?
There isn't one useful answer to this question—but there are realistic starting points.
For a thoughtfully designed custom trip to Italy, Viviamo's full-service itineraries typically begin around $12,000 per week for two travelers, excluding international airfare.
From there, the investment varies significantly based on season, destination, hotel category, room selection, private touring, transportation and how you want to experience the country.
Italy can also be surprisingly nuanced. A beautiful trip doesn't require choosing the most expensive hotel in every destination. I'd much rather help you decide where the splurge will matter to you—and where it won't.
A Few Italy Favorites
For the lake lover: Lake Garda
For pure romance: Ravello
For the hotel obsessive: Italy is frankly unfair
For food: Piedmont, Emilia-Romagna + Sicily
For families: Tuscany + the lakes
For a return trip: Puglia or Sicily
For doing absolutely nothing beautifully: Find me a pool in Tuscany
For my forever city: Florence
Start Planning Your Italy Trip
Maybe you already know exactly where you want to go.
Maybe you've saved 147 hotels and somehow feel less certain than when you started.
Or maybe all you know is that you want to go to Italy and you want it to be incredible.
That's enough.
We'll start with how you want the trip to feel, then build from there.
Trips that match your vibe, not copy-paste itineraries.
Andiamo?
