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 grand 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.

The Complete 14-Day North-to-South Italian experience.

8 to 12 guests
Max 16
Tour Captain hosted
Boutique hotels
50+ five-star reviews

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Choose your Journey

Three editions. One design philosophy.

Italy's Great Cities is offered in three thoughtfully crafted small group journeys, each built around the same Now Journey philosophy of elegant pacing, exceptional hospitality, and meaningful experiences. Whether you prefer our Essential Journey from Venice to Rome, our flagship Signature Journey from Venice to the Amalfi Coast, or our Grand Journey from Lake Como to the Amalfi Coast, simply choose the edition that best fits your time and travel style.

heart of italy

Essential Journey

10 Days

Venice → Rome

Ideal for travelers with less time.

Signature Journey

12 Days

Venice → Amalfi Coast

Our flagship and most popular Journey.

Complete North to South

Grand Journey

14 Days

Lake Como → Amalfi Coast

Our most immersive Italian experience.

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14 DaysMost complete

Lake Como to AmalfiNorth to south

8-12 GuestsMax 16

4-5 Star HotelsDeluxe collection

Tour CaptainHosted throughout

From $9,895Per person

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Scroll through citiesSwipe through cities

01 Lake Como2 nights · Journey beginsVilla-lined shores, mountain light, and an unhurried arrival by water. Bellagio opens the journey with quiet beauty and elegant ease.
02 Venice2 nightsWhere 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.
03 Florence2 nightsRenaissance masterpieces, artisan workshops, and evenings that linger long after sunset. Florence invites you to slow down and savor every beautiful detail.
04 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.
05 Rome3 nightsAncient ruins, lively piazzas, hidden neighborhoods, and unforgettable evenings. Every day reveals another layer of the Eternal City.
06 Sorrento & the Amalfi Coast2 nights · Journey finaleHigh above the blue Mediterranean, the journey concludes with dramatic coastal views, relaxed seaside elegance, and one final taste of la dolce vita.

Italy was never meant to be rushed

The Italy tour people hope exists.

Your Journey begins with an elegant Lake Como prologue before the story of Italy's Great Cities unfolds through Venice, Florence, Tuscany, Rome and the Amalfi Coast.

Lake Como is not an added stop. It is the graceful opening note: a quiet arrival into Italy by water, mountain light and villa-lined shores before the great cities begin.

"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, premiuum beverages and local dining
• Thoughtful pacing, fewer hassles, no big buses, no upselling

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The journey by chapters

A Prologue + Five Italian Chapters.

A Prologue. Five Italian Chapters. One unforgettable Journey. Lake Como sets the tone before Venice, Florence, Tuscany, Rome and the Amalfi Coast unfold in the familiar rhythm of Italy's Great Cities.

The Prologue

Lake Como

The Grand Journey opens with a gentler kind of beauty: Bellagio, villa-lined shores, mountain light, a private boat perspective and the feeling that Italy has begun with elegance rather than urgency.

Days 1-22 nightsBellagio

Arrival into the Lake Como region
Tour Captain Discovery Walk
Welcome dinner with Lombardy flavor
Lake Como sightseeing and private boat perspective
Villa Belvedere, Grand Hotel Villa Serbelloni, Grand Hotel Cadenabbia or similar

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Day 1 welcomes you to Lake Como with time to settle in and a warm opening dinner. Day 2 explores Bellagio and the lake by land and water, leaving the afternoon open for the slower rhythm that makes Como such an elegant beginning.

See the complete prologue

Chapter One

Venice

Begin on San Marco Island with a private water-taxi arrival, an opening walk with your Tour Captain, hidden corners, glittering mosaics, Doge's Palace, and a gondola experience before sunset.

Days 3-42 nightsSan Marco

Private water taxi arrival
Discovery Walk through Venice
St. Mark's Basilica and Doge's Palace
Included gondola experience
Hotel Saturnia, Monaco & Grand Canal, Hotel do Pozzi or similar

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Days 3 and 4 bring you into Venice with arrival support, your hotel on or near San Marco, and time for the secrets, treasures and atmosphere of the lagoon city.

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Chapter Two

Florence

Venice fades into the Renaissance as you arrive in Florence by high-speed train, walk into the heart of the city, and settle into evenings of Tuscan flavor and architectural drama.

Days 5-62 nightsRenaissance city

High-speed rail to Florence
Duomo, Baptistery, Ponte Vecchio and historic center
Florence Secrets & Treasures guided walk
Warm Tuscan welcome dinner
Grand Hotel Cavour, Bernini Palace, Hotel Renaissance or similar

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Days 5 and 6 bring the transition to Florence, an introductory Discovery Walk, deeper exploration of the historic center and time to wander, linger, shop or simply savor the city.

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Chapter Three

Tuscany

The pace softens in Tuscany: San Gimignano, vineyard roads, a family-run estate, wine tasting, a farm-to-table lunch, and two nights in Cortona.

Days 7-82 nightsCortona

San Gimignano and Vernaccia wine country
Curated wine tasting and Tuscan lunch
Cortona Discovery Walk
Apericena in Cortona
Villa Marsili, Hotel San Michele, Monastero di Cortona, Hotel San Luca or similar

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Days 7 and 8 move through Tuscany's hill towns and wine country before settling into Cortona for a slower Tuscan chapter with room for wandering, cooking, wine, countryside views or simply doing less.

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Chapter Four

Rome

Rome arrives with grandeur: the Pantheon, Piazza Navona, Campo de' Fiori, Vatican City, Imperial Rome, and a farewell evening that feels worthy of the Eternal City.

Days 9-113 nightsOld Rome

Discovery Walk through the heart of Rome
Vatican Museums, Sistine Chapel and St. Peter's
Roman Forum and Imperial Rome
Farewell to Rome dinner
Palazzo Navona, Pantheon Iconic, L'Orologio, Hotel Navona or similar

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Days 9 through 11 enter Rome through the historic center, Vatican City and Imperial Rome before the Journey turns south toward Pompeii and the coast.

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Chapter Five

Amalfi Coast

The finale brings Pompeii, the Sorrento Peninsula, coastal light, sea air, and the kind of ending that lets the whole story settle in.

Days 12-142 nightsCoastal finale

Naples and Pompeii ancient site
Sorrento and the Amalfi Coast
Time for coastal wandering and sea views
Grand Hotel Capodimonte, Hotel Continental, Bellevue Syrene or similar
Departure from Naples area

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Day 12 travels south with Pompeii and arrival in Sorrento. Day 13 gives the coast its moment. Day 14 closes the journey with transfers and an Italian story you will carry home.

See the complete chapter

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Explore at your pace

Want to See Every Detail?

You've just experienced the story of this Journey. Now choose how you'd like to explore the details — from continuing through the highlights on this page to opening the complete Journey Guide & Itinerary or downloading a printable PDF to review at your own pace.

Continue Exploring

Stay on this page for the hotels, experiences, dates, pricing, and planning details.

Keep Reading

Complete Journey Guide & Itinerary

Open the full interactive guide with day-by-day details, included experiences, dining, practical notes, and how the Journey unfolds.

Open Journey Guide & Itinerary

Printable PDF

Download a beautifully formatted guide to read offline, print, or share with your travel companion.

Download PDF

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What's included

The details are handled. The discoveries still feel yours.

Boutique hotels, expert guides, Tour Captain hosting, breakfasts, select dining, skip-the-line sightseeing, memorable experiences, and thoughtful transitions are woven into the journey.

Tour Captain hosting

A warm, capable presence throughout the journey.

Local experts

Guides who bring Venice, Florence, Rome and Pompeii to life.

Curated dining

Select dinners and food moments that feel genuinely Italian.

Seamless movement

Thoughtful transfers, rail, vans, water taxis and logistics.

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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.

Deluxe Hotels Collection

Carefully selected 4- and 5-Star hotels, with entry-level room categories at 5-Star properties and one category above entry-level at 4-Star properties whenever available. Upgraded room categories may be available upon request.

Classic Hotels Collection

Quality 3-Star+ properties with private bathrooms, air conditioning and continental breakfast, also selected for excellent locations in the hearts of the destinations we visit. Amenities are simpler than our Deluxe Collection, but the experience remains unmistakably Now Journey.

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

Explore Our Hotel Collections in the Journey Guide & Itinerary