Imagine Italy not as a destination, but as a feeling—effortless, elegant, and entirely yours.
This April 2026, I invite you to join me on a thoughtfully curated escape through Italy’s most iconic and indulgent landscapes. Over the course of two luxurious weeks, we’ll trace the golden thread of la dolce vita—from the grandeur of Rome, to the sun-drenched vineyards and villas of Tuscany, and along the breathtaking coastlines of the Cinque Terre, where charm clings to every cliffside.
Together, we’ll immerse ourselves in beauty, soak in rich layers of culture, and share moments of meaningful connection—over long lunches, hidden art, and unforgettable landscapes.
For those who wish to continue the reverie, the journey extends—north to the timeless allure of Lake Como, where silk, still waters, and aperitivo reign, or south to the understated elegance of Puglia, where olive groves meet the Adriatic in sun-warmed serenity.
This is not just a trip. It's a celebration of the good life—La Dolca Vita—lived fully, shared joyfully.
Rome to Tuscany
Morning
Breakfast included. It will be an early start for the tour of the vatican
Afternoon
We'll travel by mini bus to Tuscany. Enjoying the countryside. And stopping to find some food for the evening at the local town Greve.
Evening
St Peters Basilica
Drive from Rome to Tuscany
Casual Dinner
Food bought from Greve.
Lodgings
Vitticio Wine Estate
Tuesday Apr 7
Travel Time:
3.5 hours drive
Tuscany
Morning
Breakast - do your own thing. Depart at 9am for San Gimignano
Afternoon
Transfer to Tenuta for Wine tasting & Lunch in the Vines
Evening
Private guided tour of San Gimignano
Lunch in the Vines
Casual Dinner
If we need any food, hoping there's something in the fridge
Lodgings
Vitticio Wine Estate
Thursday Apr 9
Travel Time:
1 hour each way
Florence
Morning
Breakfast - do your own thing. Check out David - and of course the San Lorenzo Market (leather and food!)
Afternoon
Saunter around Florence - get lost in its streets.
Evening
Florence Ideas - 1
Florence Ideas - 2
Casual Dinner
Private Transfer back to the Villa, and eat what you've bought in the morning at the Food Market
Lodgings
Vitticio Wine Estate
Saturday Apr 11
Travel Time:
50 min - 1hr
Florence - continues
Morning
Breakfast - do your own thing. We'll travel back to Florence, Uffizi Gallery, the Duomo, Pitti Palace and the Boboli Gardens.
Afternoon
So much to see - so little time
Evening
Florence Ideas - 3
Florence Ideas - 4
Casual Dinner
Casual Dinner
Lodgings
Vitticio Wine Estate
Sunday Apr 12
Travel Time:
50min - 1hr
Cinque Terra via Pisa
Morning
Breakfast - do your own thing. Journey from Tuscany to the Cinque Terre, with a stop in Pisa to admire its iconic Leaning Tower.
Afternoon
Travel to Levanto & the Cinque Terre with a private driver
Evening
Self-exploration of Pisa
Explore Levanto
Casual Dinner
Could buy train tickets for Cinque Terre Express
Lodgings
Hotel Palazzo Vannoni - Levanto
Tuesday Apr 14
Travel Time:
3 hours - stop in Pisa
Cinque Terre - More
Morning
After breakfast explore more of the Cinque Terre
Afternoon
If you want a more challenging walk - try Corniglia to Vernazza
Evening
Cinque Terre Ideas - 3
Cinque Terre Ideas - 4
Casual Dinner
Maybe dinner in Vernazza
Lodgings
Hotel Palazzo Vannoni - Levanto
Thursday Apr 16
Travel Time:
short trips via train
Jacoba leaves Rome
Morning
Afternoon
Evening
Lodgings
Friday May 1
Travel Time:
Il Commentario
