8-Day Luxury Italy Journey
8 Days | 2 Nights Rome | 2 Nights Florence | 3 Nights Tuscany
Starting from $3,500 per person | Land Only*
The Colosseum, the Duomo, the Cinque Terre & the Tuscan hills
Inquire About This JourneyBegin with two days in Rome. End in the vineyards of Tuscany.
This is the Italy journey travelers dream about: two nights in the Eternal City for the Colosseum, the Vatican and café-lined piazzas—then north to Florence, a day among the Cinque Terre's seaside villages, and three nights of vineyards, cypress lines and hilltop towns in the Tuscan countryside.
Your journey ends where it began, back in Rome for your departure flight, so there is no wasted travel day—just a seamless circle through Italy's greatest hits, designed and booked end to end by Jamie Leigh.
The journey
The Eternal City Welcomes You
Land in Rome and let everything be waiting: your private transfer into the city, your hotel confirmed and ready, your first evening unhurried.
Settle in, then step out for an aperitivo in a quiet piazza as the evening bells ring across the rooftops.
Jamie Leigh plans this arrival around your flight so the very first hours feel effortless, not rushed.
The Icons, Without the Crowds
Your full day in Rome is designed around what you love—the Colosseum, the Vatican, hidden trattorias, elegant boutiques or a little of everything.
Timing matters: Jamie Leigh sequences your visits so you see the icons when the crowds are thinnest and linger where the light is best.
In the evening, choose from a shortlist of restaurants reserved with you in mind, from neighborhood classics to a quietly celebrated chef's table.
Renaissance • Riverside Evenings
Board Italy's high-speed train in Rome and watch the countryside slip by on the way to the cradle of the Renaissance.
Arrive in Florence, where your private driver meets you and delivers you to your Florentine home base, moments from the Duomo and the Arno.
Explore the markets and golden-stone lanes before an evening stroll along the river as the city turns amber.
A Day Trip From Florence
Leave Florence early for the Cinque Terre—five pastel villages stacked above the sea along Italy's most dramatic coastline.
Travel by private transfer or by train with a plan Jamie Leigh has sketched for you: swim, wander the cliffside paths, and linger over a long seafood lunch by the harbor.
Return to Florence in the evening for a relaxed dinner and your second Tuscan night.
Hilltops, Vineyards & Cypresses
Trade the city for the countryside: a private drive into Tuscany, where vineyards, olive groves and hilltop towns unfold outside your window.
Settle into your Tuscan home base—a countryside relais or a town like Siena, chosen with Jamie Leigh for the way you like to travel.
Toast your first Tuscan sunset with a glass from the hills around you.
Wine, Villages & Long Lunches
Your days in Tuscany are shaped around what you love—private wineries and cellars, hilltop villages like San Gimignano, artisan studios or simply slow mornings and long lunches.
Timing matters here too: Jamie Leigh sequences your visits so the famous views belong to you and not to the crowds.
In the evening, dinner in a stone village or at your relais, with the valley lights below.
Cooking, Markets & One Last Sunset
Spend your final full day in the countryside as you wish: a private cooking class, a market morning, a vespa ride through the vines, or an unhurried pool and book afternoon.
This is the day travelers remember most—the one with nothing urgent on it and everything beautiful around it.
Enjoy a special farewell dinner before your journey home.
Arrivederci • Until Next Time, Italy
Your private transfer carries you back to Rome for your flight home—no backtracking, no wasted day.
Or extend: more time in Rome, the Amalfi Coast, Lake Como or Venice one more time can be added to your design.
Until next time, Italy. Jamie Leigh is already ready to plan the next one.
How it works
Your hotels in Rome, Florence and the Tuscan countryside, your high-speed train seats, your private transfers and drivers, your guides at the Colosseum, in Florence and through the wine hills—reserved, confirmed and sequenced before you ever pack a bag.
Jamie Leigh handpicks the hotels, times the visits, and builds in the free afternoons that make a luxury trip feel like a luxury trip rather than a checklist.
And because you are in touch with a real person a phone call away—not a call center—if anything changes while you travel, she is the one who fixes it.
Personally designed
The route is the beginning.
Jamie Leigh designs the experience.
Add a private food tour in Trastevere, a vineyard lunch in Chianti, a cooking class in the countryside, extra days on the Amalfi Coast—or slow the whole journey down a full day.
Whether this is your honeymoon, a couples' escape or a girls' getaway, the journey is tailored to the way you want to travel. No two Follow Your Bliss journeys are exactly alike.
Plan your journey
Selected departures are available April through October 2027.
Starting from $3,500 per person*
8-day journey, 2 nights Rome, 2 nights Florence and 3 nights Tuscany, land arrangements only. Airfare is additional.
*Starting price is per person for land arrangements only; airfare is additional. Final pricing is confirmed in your personalized proposal, based on your dates, your hotels and your experiences, and is subject to availability and change until confirmed. Tell Jamie Leigh when you hope to travel and she will design the journey and its pricing around you.
Start My JourneyFollow Your Bliss Travel
Tell Jamie Leigh when you hope to travel and how you'd like to make Rome, Florence & Tuscany your own. This is an inquiry, not a confirmed reservation.