Daily breakfasts and select group dinners are included, with time built in to explore independently.

No. This is intentionally designed as a small group touring experience, not a traditional large bus tour.

Now Journey essential journey

Italy's Great Cities

Q: Is the tour fast-paced?

No. The tour is intentionally balanced, allowing time to explore, reflect and enjoy each destination.

Everything that makes Italy unforgettable — thoughtfully distilled into ten remarkable days.

8 to 12 guests
Max 16
Tour Captain hosted
Deluxe hotel collections
50+ five-star reviews

Request a Journey Proposal Itinerary View Dates & Prices

No obligation. No pressure.

10 DaysFocused pace

Venice to RomeCultural route

8–12 GuestsMax 16

Deluxe CollectionsSignature & Elevated

Tour CaptainHosted throughout

Choose your Journey

Three editions. One design philosophy.

Italy's Great Cities is offered in three thoughtfully crafted editions. Each follows the same Now Journey philosophy—small groups, elegant pacing, and thoughtful care from beginning to end. Simply choose the Journey that best fits your time and travel style.

Three ways to experience Italy’s Great Cities. Choose the Journey that best fits your time and travel style.

Essential

Essential Journey

10 Days

Venice → Rome

Ideal for travelers with less time.

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Signature Journey

12 Days

Venice → Amalfi Coast

Our flagship and most popular Journey.

Most Complete

Grand Journey

14 Days

Lake Como → Amalfi Coast

Our most immersive Italian experience.

Scroll through citiesSwipe through cities

01 Venice2 nights · Journey beginsWhere canals replace streets and mornings begin with church bells across the lagoon. Arrive by water, settle in, and let Italy reveal itself at an unhurried pace.
02 Florence2 nightsRenaissance masterpieces, artisan workshops, and evenings that linger long after sunset. Florence invites you to slow down and savor every beautiful detail.
03 Cortona & Tuscany2 nightsWinding vineyard roads, timeless hill towns, and long lunches beneath the Tuscan sun. This is the Italy travelers imagine—and the one they'll remember.
04 Rome3 nights · Journey finaleAncient ruins, lively piazzas, hidden neighborhoods, and unforgettable evenings. The journey concludes amid the many layers of the Eternal City.

Venice → Florence → Cortona → Rome

Italy was never meant to be rushed

The Italy tour people hope exists.

The Essential Journey was created for travelers who want Venice, Florence, Tuscany and Rome in one beautifully focused cultural arc - not hurried, not overfilled, and never made to feel like a compromise.

This is the essential Now Journey Italy experience: hosted with care, shaped around landmark cities and meaningful pauses, and designed so ten days feel complete rather than crowded.

"Every day, every place, every meal, every experience was amazing." Edward K., Now Journey guest

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Why travelers choose Now Journey

Hosted, not herded.

A smaller group changes the entire texture of Italy: easier movement, better meals, better hotels, more personal attention, and far fewer moments spent waiting for a crowd.

Compare Mainstream bus tours...

• 24 to 50 guests moving as one large group
• Fixed touristic and hotel restaurant rotations and rushed meals
• Generic hotels or edge-of-city locations
• Large coach buses and slower logistics
• More optional add-ons and upsell moments

With us: Now Journey True Small Group Tours

• 8 to 12 guests, with a maximum of 16
• Dedicated Tour Captain hosted throughout
• Boutique, heart-of-the-city hotel collections
• More included experiences, premium beverages and local dining
• Thoughtful pacing, fewer hassles, no big buses, no upselling

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What's included

The details are handled. The discoveries still feel yours.

Nine Deluxe hotel nights and 15 included meals—9 full breakfasts, 4 hosted dinners, 1 Italian Apericena and 1 Tuscan winery lunch with tasting—join expert guides, Tour Captain hosting, admissions and thoughtful transportation.

9 nights & 9 breakfasts

Deluxe hotels in Venice, Florence, Cortona and Rome, with a full breakfast each morning.

5 hosted dining events

Four destination dinners and one Italian Apericena, with the page’s established premium-beverage inclusion.

1 Tuscan winery lunch

A family-run estate visit, cellar experience, regional lunch and wine tasting.

Guides, admissions & movement

Tour Captain hosting, local experts, scheduled admissions, high-speed rail, private boat and road transportation.

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The Journey Story

From lagoon light to the Eternal City.

The Essential Journey distills Italy’s great cultural arc into four distinct chapters. It begins on the water in Venice, awakens among the Renaissance streets of Florence, softens into the Tuscan countryside and gathers all of its scale, history and energy in Rome. Four places. Four different rhythms. One complete Italian story.

01The Opening

Venice

The Journey begins on water.

The mainland begins to disappear and Venice approaches the way it has for centuries—from the lagoon. Boats replace cars, canals replace streets and the ordinary rhythms of arrival suddenly feel very far away. San Marco glows, narrow passages pull you deeper into the city and the Essential Journey begins somewhere unlike anywhere else.

02The Awakening

Florence

From water to Renaissance stone.

Venice slowly recedes behind you and Florence changes the texture of the Journey. Bells, stone, artisan windows, river light and Brunelleschi’s dome replace the lagoon. The masterpieces matter, but so does what happens afterward—time to wander, shop, sit in a piazza or simply look up and absorb the city that helped change the world.

Tuscan vineyards and farmhouses across warm green hills

03The Pause

Tuscany

Then Italy softens.

The great cities give way to vineyard roads, medieval hill towns, long tables and the slower pleasures of the countryside. San Gimignano, regional wine, a Tuscan lunch and Cortona bring a deliberate change of pace. This is the chapter where doing a little less becomes part of experiencing considerably more.

04The Finale

Rome

All roads lead here.

Rome gathers the Journey into something larger: empire beneath modern streets, church domes over neighborhood cafés, fountains opening suddenly into piazzas and ancient stones woven into everyday Roman life. Vatican City, Old Rome and Imperial Rome bring history into extraordinary scale—and the Journey closes exactly where so much of the Western story seems to converge.

Essential Journey · Venice to Rome

The Complete Itinerary

Ten beautifully paced days through Venice, Florence, Tuscany and Rome.

Venice's Grand Canal in golden evening light

Chapter One

Days 1–2

Venice

The Journey begins on water: a private arrival, San Marco light, hidden passages, music on the canals and the strange, impossible beauty of a city that should not exist.

Gondolas glide as Venice whispers its secrets.

Venice is less an introduction than a spell. The first days are designed to orient you gently—not by rushing from site to site, but by letting the city reveal its rhythm.

Day 1

Welcome to Beautiful Venice

Begin in signature Now Journey style with a warm arrival welcome and included private water-taxi transfer from Venice Marco Polo Airport to your hotel in the heart of San Marco. Check in, refresh and let Venice begin gently.

Later, meet your Tour Captain for a Discovery Walk through Piazza San Marco, the Campanile, the Grand Canal and the practical rhythms of the Journey. That evening, gather for a Venetian opening dinner with regional cooking, wine and premium beverages included.

Included Today

Arrival support at Venice Marco Polo Airport
Private water-taxi arrival transfer
Tour Captain-led Discovery Walk
Opening dinner in Venice

Day 2

Venice: The Story Begins

With an expert local guide, explore Venice’s hidden corners and layered history through St. Mark’s Basilica, the Doge’s Palace, the historic prisons and the Bridge of Sighs. Venice emerges not as a postcard, but as a republic shaped by power, intrigue, faith and extraordinary beauty.

Later, as Venice begins to glow in the evening light, enjoy an included gondola experience through quieter canals, accompanied by live musicians.

Included Today

St. Mark’s Basilica and Piazza San Marco
Doge’s Palace, historic prisons and Bridge of Sighs
Expert-guided Venetian history and context
Gondola experience with live musicians

This evening, your Tour Captain may invite you to join the group for an optional dinner, or the evening is entirely yours.

Where You Stay

Your Home in Venice

Hotel Saturnia & International or similar keeps you within easy reach of St. Mark’s and the quieter Venice that appears after the day visitors drift away.

Other Deluxe hotels we sometimes use: Monaco & Grand Canal or similar.

“Close enough to wander to St. Mark’s Square, but tucked into a quieter rhythm where Venice begins to feel like yours.”HOW WE CHOOSE

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Travelers overlooking Florence and its cathedral dome

Chapter Two

Days 3–4

Florence

Venice fades behind you. Florence arrives with bells, stone, Renaissance proportion, river light, artisan windows and the quiet confidence of a city that changed the world.

David’s city, Florence of the Renaissance.

Florence is approached with elegance: by water, rail and then on foot. The days balance guided discovery with space to wander, shop, sit, sip and look up.

Day 3

Onward to Florence

A private boat transfer brings you to Venezia Santa Lucia, where you board a comfortable high-speed train bound for Florence—a seamless transition from lagoon light to Renaissance stone.

Upon arrival, your Tour Captain leads a Discovery Walk through Giotto’s Campanile, the Baptistery, the Duomo and Ponte Vecchio. That evening, gather for a hosted Tuscan dinner with regional specialties and local wine.

Included Today

Private boat transfer to Venezia Santa Lucia
High-speed rail to Florence
Florence Discovery Walk
Welcome to Florence dinner

Day 4

Florence: Secrets & Treasures

Enjoy skip-the-line entry to the Accademia to see Michelangelo’s David, then continue with your expert guide through Santa Maria del Fiore, Giotto’s Bell Tower, the Baptistery, the Gates of Paradise, Piazza della Signoria and Piazza della Repubblica.

The afternoon is intentionally open. Wander, shop, linger over lunch, visit Santa Croce or choose an art and architecture experience shaped around your interests.

Included Today

Accademia Gallery and Michelangelo’s David
Expert-guided Florence experience
Renaissance landmarks and historic center
Intentionally open afternoon

This evening, your Tour Captain may invite you to join the group for an optional dinner, or the evening is entirely yours.

Where You Stay

Grand Hotel Cavour rooftop overlooking Florence's historic towers

Your Home in Florence

Grand Hotel Cavour or similar places the Renaissance chapter close to Florence’s treasures, with rooftop views and a central setting that keeps the city present between guided moments.

Other Deluxe hotels we sometimes use: Bernini Palace, Hotel L’Orologio or similar.

“Florence is best when the Duomo, the river, the piazzas and the evening streets stay within easy reach.”HOW WE CHOOSE

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Cortona's hill-town rooftops glowing at sunset

Chapter Three

Days 5–6

Tuscany

Vine-covered hills, a white wine toast in San Gimignano, a family-run estate, Cortona at golden hour and the permission to slow down.

Vineyards, hill towns and the art of lingering.

Tuscany is the hinge of the Journey: a shift from major-city wonder into countryside texture, regional life and time that feels less scheduled.

Day 5

Tuscany: A Day of Flavor & Tradition

Rolling hills and cypress trees guide you into the countryside. Begin in San Gimignano, famed for its medieval skyline and artisan streets, with a toast of Vernaccia, the town’s signature white wine.

Settle into a family-run estate for a guided cellar visit, curated tasting and leisurely Tuscan lunch. Later, continue to Cortona, where your Tour Captain leads a gentle Discovery Walk before an included Apericena.

Included Today

San Gimignano and Vernaccia toast
Family-run wine-estate visit and tasting
Regional Tuscan lunch
Cortona Discovery Walk and Apericena

Day 6

Cortona at Leisure

Enjoy a full day at leisure in Cortona. The day can be as quiet or active as you wish: a long piazza morning, a countryside walk or time exploring Cortona’s upper streets and Etruscan layers.

Your Tour Captain can help shape the day around your style. The evening remains open for an unhurried night in one of Tuscany’s loveliest hill towns.

Included Today

Full day of independent time in Cortona
Tour Captain recommendations for pacing and local possibilities

This evening, your Tour Captain may invite you to join the group for an optional dinner, or the evening is entirely yours.

Where You Stay

Cortona overlooking the Tuscan countryside

Your Home in Tuscany

Villa Marsili or similar suits the slower rhythm of this chapter, keeping you close to Cortona’s old town while giving the Journey a warmer, more rooted sense of place.

Other Deluxe hotels we sometimes use: Hotel San Michele, Monastero di Cortona or similar.

“Cortona works best when the hotel feels smaller, warmer and rooted in the Tuscan hillside.”HOW WE CHOOSE

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The Pantheon and its columned portico in Rome

Chapter Four · The Finale

Days 7–10

Rome

The Eternal City does not arrive quietly. It appears in domes, ruins, fountains, piazzas, empire, faith, dinner tables and the hum of modern Roman life.

There once was a dream that was Rome.

Rome is the climax in layers: Old Rome and its piazzas, Vatican City, imperial stones and the everyday beauty of a city that never stopped being alive.

Day 7

The Road to Rome

The Journey leaves Tuscany and continues south toward the Eternal City. After arriving and checking in near the historic center, join your Tour Captain for a Discovery Walk through Old Rome.

Around the Pantheon, continue through Piazza Navona, Campo de’ Fiori and Largo di Torre Argentina, where stories of emperors, markets, fountains and modern Roman life overlap. That evening, gather for a hosted welcome dinner featuring the flavors of Lazio.

Included Today

Journey from Cortona to Rome
Old Rome Discovery Walk
Pantheon, Piazza Navona and Campo de’ Fiori context
Welcome to Rome dinner

Day 8

Vatican City

Explore the Vatican Museums and stand beneath Michelangelo’s Sistine Chapel. When visitor operations and access permit, continue into St. Peter’s Basilica and Square as your guide brings context to Vatican art, ritual and architecture.

The afternoon and evening are intentionally open for independent discovery, with suggestions from your Tour Captain.

Included Today

Guided Vatican City experience
Vatican Museums and Sistine Chapel
St. Peter’s Basilica and Square when access permits
Open afternoon and evening

This evening, your Tour Captain may invite you to join the group for an optional dinner, or the evening is entirely yours.

Day 9

Imperial Rome & Farewell

Set out through Rome’s ancient heart, where ruins and modern life share the same streets. Explore the Colosseum and Roman Forum with admission and expert guiding, then trace the shape of empire through Palatine and Capitoline perspectives, triumphal arches and views across the ancient city.

Tonight, join your Tour Captain for a special Farewell to Rome dinner—a final hosted evening to reflect on the canals, masterpieces, Tuscan tables and ancient stones gathered along the way.

Included Today

Colosseum guided experience
Roman Forum and ancient-city context
Palatine and Capitoline perspectives
Farewell to Rome dinner

Day 10

Arrivederci, Italy

Breakfast is included this morning when departure timing allows. Guests ending in Rome may request guidance for Rome Fiumicino or Ciampino Airport, and extra nights can often be arranged when available.

Rome is the complete finale: a final espresso near the Pantheon, one more walk through ancient streets and the feeling that the essential Italian story has come full circle.

Included Today

Breakfast, schedule permitting
Rome departure guidance

Where You Stay

The contemporary lounge at Palazzo Navona in Rome

Your Home in Rome

Palazzo Navona or similar keeps the Eternal City close: the Piazza Navona neighborhood, rooftop moments, evening strolls and easy walks toward many of Rome’s great sights.

Other Deluxe hotels we sometimes use: Pantheon Iconic, La Minerva, Hotel L’Orologio or similar.

“Rome rewards location: a fountain at night, a piazza after dinner, a short walk that becomes a memory.”HOW WE CHOOSE

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Now Journey Hotels Collections

Stay Where the Journey Lives

At Now Journey, we believe where you stay should be every bit as memorable as where you go. Our Hotels Collections are curated for location, atmosphere, service and the authentic sense of place each property brings to the Journey.

Signature Collection

DELUXE

The signature Now Journey experience, featuring a thoughtfully curated collection of 4- and 5-star hotels chosen for location, character and comfort. Our 4-star stays feature rooms one category above entry level or higher whenever available; at our 5-star properties, accommodations begin with the hotel’s refined entry-level rooms and extend upward.

Elevated Accommodations

DELUXE | ELEVATED

Our signature journey, enhanced with our most elevated hotel accommodations — preferred upper room categories across our 4- and 5-star collection, while the itinerary and experiences remain unchanged.

Curated for character. Chosen for location. Selected for comfort.

Venice

Historic palace-style Deluxe stays near San Marco, including Saturnia & International, Monaco & Grand Canal or similar.

Florence

Elegant, centrally located Deluxe stays such as Grand Hotel Cavour, Bernini Palace, L'Orologio or similar.

Cortona

Rustic Tuscan manor houses, villas and hill-town Deluxe properties including Villa Marsili, Hotel San Michele, Monastero di Cortona or similar.

Rome

Perfectly placed Deluxe stays near the historic heart, including Palazzo Navona, Pantheon Iconic, La Minerva or similar.

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Dates & prices

Choose your season.

Prices are per person based on double occupancy. The Essential Journey is the focused Venice-to-Rome edition of Italy's Great Cities. Solo supplement: $2,990. Deluxe | Elevated is subject to preferred-room and accommodation availability.

DELUXESignature Collection

DELUXE | ELEVATEDPreferred upper-room categories

Best dates to consider first

If you are comparing options, start here. These departures highlight selected Essential Journey dates and current availability.

Sep 8-17, 2026