Vacations by Jillian
Italy

Italy

Rome's ancient streets, the art cities of Tuscany, the canals of Venice, and the cliffs above the Bay of Naples — woven into one journey.

← Featured Destinations
The Whole of Italy

Italy isn't one trip — it's several, done right.

When people tell me they want Italy, they usually mean all of it — and that's exactly how I love to design it. We start where the country starts: Rome, with the Vatican and the Sistine Chapel one morning and the Colosseum and the Roman Forum the next, then a slow evening eating your way through Trastevere. From there the journey opens up — north to Florence and the Tuscan hill towns, on to Venice and its canals, or south to Sorrento and the Amalfi Coast.

What ties it together is the way it's run. I work with a team on the ground in Italy — their own guides and drivers and small family suppliers, the kind you don't find on a search engine. Private transfers meet every train and flight, the museum lines are skipped, and there's a real person on call in Italy around the clock. We design the days around how you actually like to travel, and handle the rest.

A Few of the Moments

What We'd Weave In

The Vatican & Ancient Rome

A private guide takes you through the Vatican Museums and Sistine Chapel to stand under Michelangelo's ceiling — then, another day, into the arena of the Colosseum, the Roman Forum, and Palatine Hill where the city began.

A Tuscan Art-City Day

The most complete day in Florence: a walk into the Accademia to meet Michelangelo's David, then the Uffizi and Botticelli's Birth of Venus — with day trips out to Siena, San Gimignano, and the Carrara marble quarries.

Venice & the Grand Canal

St. Mark's Square and the Doge's Palace, a gondola through the back canals, and a cicchetti-and-spritz crawl through the little bàcari where Venetians actually eat.

The Amalfi Drive & Capri by Boat

A private driver winds you along the cliffs to Positano, Amalfi, and Ravello, with no fixed itinerary — stop where you like. Another day, a boat traces the Sorrento coast past the Faraglioni rocks to Capri.

Pompeii & Mount Vesuvius

Walk the excavated streets of Pompeii with a guide who brings them back to life, then lunch and a Lacryma Christi wine tasting at a working winery on the slopes of the volcano that buried it.

Eat & Drink the Real Italy

A Trastevere food stroll past the tourist traps to hidden Roman trattorias, and a lemon-grove cooking class in the Sorrento hills — the long, unhurried meals that are the whole point.

Kind Words

She listened to us very carefully to create the trip of a lifetime to Italy. We enjoyed an incredible adventure, and she was always available for questions.

Mary Weathers · Italy
Travel Thoughts

Learn More

Your Journey Begins

Let's design your Italy.

Tell us how you love to travel — we'll take it from there.

Book a Consultation
Proud Member
Rainbow Getaways Travel Network Ensemble Travel Group ASTA — American Society of Travel Advisors Certified Travel Associate