La Dolce Vita Sicily
Sicily Adventure
Ragusa, Noto, Siracusa, Ortigia, Modica, Mount Etna, and Taormina.
True small group Italy tours
Italy, without the big bus.
Travel with just 8 to 12 guests, stay in boutique hotels in the heart of each city, and experience Italy in a way that feels personal, immersive, and beautifully paced.
8 to 12 guestsTrue small group travel
Boutique hotelsCentral, characterful stays
Tour CaptainsWarm personal hosting
50+ reviewsFive-star guest stories
Start here
A more elegant way to choose Italy.
New to Now Journey? Our Italy collection begins with the classics - Venice, Florence, Tuscany, Rome, the Amalfi Coast, Sicily, Puglia, and the Italian north - then shapes them into journeys that feel polished, intimate, and unhurried.
Five-star guest review
"Everything about this trip was first class from the accommodations and restaurants to the transportation between cities to the local guides chosen in each city."
Read Tripadvisor reviewsThe table matters
Dinners are not filler. They are part of the story.
No rushed group meals. No preset tourist menus. Instead, Now Journey gathers in distinctive local restaurants where evenings feel unhurried, generous, and genuinely Italian.
Choose your Italy
Journeys with a point of view.
Each itinerary is designed around a distinct feeling: classic first Italy, coastal glamour, villa life, hidden southern towns, seasonal magic, or a slower pair of great cities.
Hidden treasures
Puglia and Basilicata
Alberobello, Polignano a Mare, Matera, Lecce, and Otranto.
Villa experience
Treasures of Tuscany
Florence, a Tuscan villa week, Siena, Montepulciano, and Pienza.
A shorter classic
Week in Italy
Venice, Florence, and Rome by premium rail, designed for travelers with one beautiful week.
Mark Story Adventure
Tuscan Villa
Discover the Tuscan countryside with a slower, more personal villa-based experience.
Seasonal Italy
Italy at Christmas
Venice, Florence, Tuscany, and a festive finale in Rome.
Family adventure
Venice to Rome
Rooftop experiences, guided mornings, and relaxed afternoons for families traveling together.
Italian pairs
Venice and Rome
A slower 7-day pairing of two great Italian cities.
Italian pairs
Florence and Tuscany
7 days designed for a slower, more intimate pace through Florence and the countryside.
Italian pairs
Florence and Rome
7 days linking Renaissance Florence with the grandeur and street life of Rome.
Italian pairs
Rome and Amalfi Coast
A relaxed two-destination flow through ancient Rome and the villages of the Amalfi Coast.
Italian pairs
Cinque Terre and Lake Como
Colorful coastal villages paired with the refined beauty of the Italian lakes.
Italian pairs
Amalfi Coast and Sicily
Mediterranean beauty, southern Italian flavor, and two very different versions of coastal Italy.
Island Italy
Sardinia to Sicily
A Mediterranean island adventure through Sardinia and Sicily.
Mediterranean pairing
Greece and Italy
Athens, Santorini, Mykonos, the Sorrento Peninsula, and the Isle of Capri.
Not your average tour of Italy
Small groups change everything.
Now Journey's true small group tours of Italy are designed for travelers who want a more personal, elegant, and memorable way to travel - without the crowds, the bus-heavy feel, or the rushed pace of larger tours.
Better flow
Small groups move more easily through historic centers, restaurants, museums, hotels, and moments that large groups simply cannot handle gracefully.
Hotels with character
Instead of generic stays outside the center, the experience leans toward boutique, well-located hotels that keep you close to the life of each destination.
Hosted, not herded
A great Tour Captain handles transitions and timing while leaving space for discovery, spontaneity, and the feeling that Italy is still yours.
Italy tours 101
First time to Italy? Start with how you want it to feel.
The right Italy trip is not only about the cities on the map. It is about pace, hotel style, group size, dining, and how much support you want along the way.
Classic Italy, thoughtfully paced
Italy's Great Cities is the natural first choice for Venice, Florence, Tuscany, and Rome without trying to cram all of Italy into one rushed experience.
Coasts, villas, and hidden regions
Choose Amalfi for glamour, Tuscany for villa life, Sicily for atmosphere, Puglia for the road less traveled, or Northern Italy for elegance beyond the obvious.
Support without losing the magic
Transfers, timing, guides, and details are handled carefully, but the journey still leaves room for discovery and unplanned moments.
Begin your Now Journey
Tell us the Italy you are imagining.
Share what you know now. A real travel specialist will help shape the dates, details, and travel style with you - no obligation and no pressure.
+1 (720) 464-3248 | American owned & operated