EXPLORE THE COMPLETE JOURNEY

Italy's Great Cities

Every hotel. Every destination. Every included experience. Every thoughtfully designed day. Here you will discover how Italy's Great Cities unfolds - from the moment you arrive until the morning you depart.

Complete Journey Overview

The complete Journey, thoughtfully revealed.

Explore your hotels, included experiences, Discovery Walks, dining, practical travel notes, and the distinctive touches that make traveling with Now Journey feel effortless.

This guide is intentionally transparent. You will see how each day unfolds, what is included, where the Journey leaves room to linger, and how the practical details are handled with care.

Here is how it unfolds.

Chapter One

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 the 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 Italian cooking, wine and premium beverages included.

  • Included arrival support and private water taxi
  • Tour Captain-led Discovery Walk
  • Opening dinner in Venice
  • 2 nights with breakfast

Signature Moment

Venetian Opening Night

Your first evening is not just dinner. It is the moment the group settles in, the Tour Captain begins to shape the rhythm, and Venice becomes the doorway into the Journey.

1

Arrival by water

Meet-and-greet arrival support and private water taxi transfer bring you into Venice the way Venice should be entered.

Day 1

2

Discovery Walk

Your Tour Captain introduces San Marco, the Grand Canal, the Campanile and the first practical rhythms of the Journey.

Day 1

Day 2

Venice: the Story begins

With our expert local guide, explore Venice's hidden corners and layered history as you visit St. Mark's Basilica, the Doge's Palace, the historic prisons, and the Bridge of Sighs. The day is designed to reveal Venice 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 our included gondola experience through the city's quiet canals, accompanied by live musicians.

Afterward, your Tour Captain will invite you to join fellow travelers for an optional dinner at a favorite local restaurant. These informal evenings are a hallmark of the Now Journey experience - always welcoming, always optional, and often where some of the trip's best conversations begin.

Included Today

  • St. Mark's Basilica and Piazza San Marco
  • Doge's Palace, historic prisons and Bridge of Sighs
  • Stories of Casanova, the Winged Lion and Venetian power
  • Gondola experience with live musicians

Where you stay

Venice hotel atmosphere

Venice Hotel Collections

Our Deluxe Hotel collection includes Hotel Saturnia & International, Hotel Monaco & Grand Canal. Our Classic Hotel Collection includes Hotel do Pozzi or similar.

"Saturnia & International is one of my favorite properties in all of Italy - a palace with the texture and mood of old Venice."Mark's Thoughts

Can you picture yourself arriving this way?

If the idea of beginning Italy by water, with your arrival handled and Venice opening slowly around you, feels right, keep reading. The Journey only deepens from here.

Chapter Two

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

After breakfast, Venice gently fades behind you. 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 Florence Discovery Walk through the heart of the city, including Giotto's Campanile, the Baptistery, the Duomo and Ponte Vecchio before ending near the hotel. That evening, gather for a hosted Tuscan dinner with regional specialties, local wines and premium beverages.

Included Today

  • Private Boat Transfer to the Venice Train Station
  • High-Speed Rail to Florence
  • Florence Discovery Walk
  • Welcome to Florence Dinner

Day 4

Florence: birthplace of the Renaissance

Florence comes alive through art, architecture and story. Enjoy skip-the-line entry to the Accademia to see Michelangelo's David, then continue through the historic center with your guide: 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. You may wander, shop, linger over lunch, visit Santa Croce, climb the Duomo, explore the Uffizi, or choose a privately arranged museum experience.

    Included Today

    • Accademia Gallery with Michelangelo's David
    • Florence Historic Center and Renaissance landmarks
    • Guided context in districts many tours miss
    • Free afternoon with optional museum experiences

Signature Moment

David, then Florence at your pace

The morning gives you the masterpieces. The afternoon gives you the city - time for leather markets, churches, cafes, rooftops, galleries or simply looking up.

3

Onward by rail

Private boat transfer to Santa Lucia station, then a comfortable high-speed train into the artistic heart of Italy.

Day 3

4

Florence revealed

Duomo, Baptistery, Giotto's Campanile, Ponte Vecchio and the historic center become your first Florentine orientation.

Day 3

5

Tuscan table

A hosted welcome dinner introduces the regional flavors of Tuscany and Chianti.

Day 3

6

Afternoon at leisure

The Journey leaves room for Santa Croce, Brunelleschi's dome, the Pitti Palace, shopping or a long cafe pause.

Day 4

Optional Florence moments

Uffizi Gallery

Private guided tour from $339 per person, small group guided tour from $179 per person, or admission only from $49 per person.

Duomo Climb

Climb the 463 steps to the cupola for an extraordinary view over Florence. Ticket from $59 per person.

Santa Croce

Visit the basilica known as the resting place of Michelangelo, Galileo, Rossini, Machiavelli and other Italian greats.

Pitti Palace & Boboli

Private guided experience from $339 per person, or admission-only options for the palace, gardens or combination.

Where you stay

Florence hotel atmosphere

Our Boutique Florence Hotels

Our Deluxe Hotel Collection includes Grand Hotel Cavour, Hotel Bernini Palace, Hotel Savoy, Hotel L'Orologio, Hotel Santa Maria Novella, Hotel Brunelleschi or similar. Our Classic Hotel Collection includes Hotel Renaissance or similar.

"Florence hotels should feel like part of the city - elegant, historic, close enough that the city is still with you when the day ends."Mark's Thoughts

Already imagining the slower middle of Italy?

Florence and Tuscany are where many guests begin to feel the Journey becoming personal: art, wine, hill towns, open time, and the relief of having the details beautifully handled.

Then Italy softens.

The great cities make way for vineyards, stone towns, long lunches and the slower pleasures that make Tuscany feel less visited than lived.

Chapter Three

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 meals and time that feels less scheduled.

Day 5

Tuscany: a day of flavor and tradition

The landscape shifts as rolling hills and cypress trees guide you into the Tuscan countryside. Begin in San Gimignano, famed for its medieval skyline and artisan streets, with a toast of Vernaccia, the town's signature white wine.

Then settle into a family-run Tuscan estate for a guided cellar visit, curated tasting and leisurely farm-to-table lunch paired with Chianti and Super Tuscan wines. Later, continue to Cortona, where your Tour Captain handles check-in before leading a gentle Discovery Walk into the historic center.

  • San Gimignano visit and Vernaccia toast
  • Winery visit, tasting and countryside lunch
  • Scenic drive through Tuscany
  • Cortona Discovery Walk and Apericena

Day 6

Cortona: slow moments and simple pleasures

Enjoy a full day at leisure in Cortona. The day can be as quiet or as active as you wish: a long piazza morning, a walk through vineyards, a cooking class, horseback riding, a Siena day trip, a monastery visit, or time exploring Cortona's upper streets and Etruscan layers.

Your Tour Captain will help shape the day around your style. The evening remains open for a final Cortona dinner or an unhurried night in one of Tuscany's loveliest hill towns.

  • Full free day in Cortona
  • Optional cooking class, Siena, Assisi or guided local walks
  • Tour Captain recommendations for dining and pacing
  • 2 nights in the Cortona hotel collection

Signature Moment

Tuscan Winery Lunch

This is the day Italy softens: wine country, a family estate, regional cooking, long-table conversation and the feeling that time has finally stopped hurrying.

"Tuscany has a way of slowing people down. I have watched guests arrive eager to see everything - and leave realizing their favorite memories were often the quietest ones: lunch overlooking vineyards, conversations in Cortona's piazza, or simply watching the light change across the hills."Mark's Thoughts
7

San Gimignano

Wander the medieval hill town of towers and toast Tuscany with Vernaccia, its signature white wine.

Day 5

8

Wine country lunch

A cellar visit, curated tasting and farm-to-table lunch pair Chianti and Super Tuscan wines with regional cooking.

Day 5

9

Cortona Discovery Walk

Your Tour Captain introduces Etruscan, Roman and modern stories as Cortona opens into evening.

Day 5

10

Apericena

A relaxed Tuscan evening with the spirit of aperitivo and dinner woven together.

Day 5

Optional Cortona moments

Cooking class

Learn to prepare a multi-course Tuscan meal just outside Cortona, then enjoy what you have made. From $280 per person.

Countryside ride

Horseback riding options can be arranged for beginner or experienced riders. From $99 per person for the first two hours.

Siena day trip

Round-trip transfer and guided Siena walking tour, with free time in the afternoon. From $465 per person.

Cortona & Le Celle

A private guided walk through Cortona with a visit to the Franciscan Monastery of Le Celle. From $190 per person.

Ancient Cortona walk

A steeper walk through fortresses, convents, churches and panoramic upper Cortona for stronger walkers. From $190 per person.

Assisi

Privately guided visit to the hometown of Saint Francis with round-trip transportation. From $279 per person.

Where you stay

Cortona hotel atmosphere

Our Tuscan Hotels in Cortona

Our Deluxe Hotel Collection includes Villa Marsili, Monastero di Cortona Hotel & Spa, or similar. Our Classic Hotel Collection includes Hotel San Luca or similar.

"In Cortona, the best hotels are often rustic, centuries-old Tuscan manor houses, villas, restored convents and monasteries."Mark's Thoughts

Chapter Four

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 three days of layers: the Pantheon and 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 continues south toward the Eternal City. After arrival and check-in near the Pantheon, your Tour Captain leads a Discovery Walk through the heart of Old Rome.

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

  • Comfortable 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 privileged access

With privileged entry, explore the Vatican Museums, stand beneath Michelangelo's Sistine Chapel, and continue into St. Peter's Basilica and Square. Your guide brings context to the art, ritual, architecture and living pageantry of Vatican City.

The afternoon and evening are open. You may explore Trastevere, Campo de' Fiori, a hidden wine bar or a quieter Roman corner with suggestions from your Tour Captain.

  • Vatican Museums guided experience
  • Sistine Chapel
  • St. Peter's Basilica and Square
  • Afternoon and evening at leisure

Day 9

Imperial Rome

Set out through Rome's ancient heart, where ruins and modern life share the same streets. Visit the Colosseum and Roman Forum with admission and guiding included, then trace the shape of empire through Palatine Hill, Capitoline Hill, triumphal arches and views toward Trajan's Market.

Tonight, join your Tour Captain for a special Farewell to Rome dinner - a moment to reflect before the Journey turns south toward the coast.

  • Colosseum guided experience
  • Roman Forum and ancient city context
  • Capitoline Hill and imperial landmarks
  • Farewell to Rome dinner

Now Journey Exclusive

Farewell to Rome

After the Vatican, the Forum and the evening streets around the Pantheon, we've created a dinner that becomes a hinge in the Journey: one last amazing Roman night before the road turns toward Pompeii and the sea.

11

Old Rome arrival

Settle near the Pantheon before walking through Piazza Navona, Campo de' Fiori and Largo di Torre Argentina.

Day 7

12

Vatican City

Privileged access to the Vatican Museums, Sistine Chapel, St. Peter's Basilica and St. Peter's Square.

Day 8

13

Imperial Rome

Walk through the Roman Forum and ancient city, where modern life and empire still share the same stones.

Day 9

14

Farewell to Rome

A special hosted evening lets the Journey pause before turning south toward the coast.

Day 9

Optional Rome moments

Trastevere

Cross the river for a moodier, local-feeling Roman evening.

Baths of Caracalla

Privately guided visit with admissions and round-trip taxi transfer from the hotel. From $250 per person, minimum two guests.

Hidden wine bars

Your Tour Captain can recommend intimate places for an unhurried Roman night.

Ostia Antica

An evocative ancient Roman port city option for travelers who want more archaeological depth outside central Rome.

If Rome is the chapter you have been waiting for...

The Journey gives Rome time to breathe: sacred spaces, imperial stones, piazzas, evening walks and the rare pleasure of staying close to the city's historic heart.

Where you stay

Palazzo Navona hotel atmosphere

Our Hotels in the Heart of Rome

Our Deluxe Hotel Collection includes Palazzo Navona, The Pantheon Iconic Rome Hotel, Orient Express La Minerva, L'Orologio or similar. Our Classic Hotels Collection includes Hotel Navona or similar.

"There is simply no place like Rome. Staying near the Pantheon lets the city remain with you long after sightseeing ends."Mark's Thoughts

Chapter Five

Sorrento & Amalfi Coast

The final chapter turns toward the sea: Pompeii, lemon groves, coastal light, Sorrento evenings and the sense of arrival that only Southern Italy can give.

The coast becomes the finale.

After Rome, the Journey descends south: ancient Pompeii, the Sorrento Peninsula, the Amalfi Coast and a final stretch of Mediterranean light.

Day 10

Pompeii, Sorrento and the coast

Say goodbye to Rome as the Journey turns south. Arrive near Naples and continue to Pompeii, the ancient Roman city lost for nearly 1,700 years before its rediscovery. With an expert local guide, explore the site and hear the human story behind its dramatic history.

After Pompeii, continue to Sorrento. Following check-in and time to relax, your Tour Captain leads a Discovery Walk into the heart of town. That evening, gather for a hosted Sorrento dinner filled with local hospitality and coastal flavor.

  • Travel from Rome to Pompeii and Sorrento
  • Guided Pompeii ancient site experience
  • Sorrento Discovery Walk
  • Hosted welcome dinner in Sorrento

Day 11

Exploring the Amalfi Coast at leisure

Today is intentionally open for the coast. Stay in Sorrento, follow your Tour Captain's suggestions, or choose the highly recommended Isle of Capri experience when available.

In the evening, gather once more for a final walk and traditional farewell Apericena - a relaxed celebration of the places, meals, discoveries and friendships gathered along the way.

  • Free day on the Sorrento Peninsula and Amalfi Coast
  • Optional Isle of Capri experience
  • Final passeggiata with your Tour Captain
  • Farewell Apericena

Day 12

Arrivederci Italy

Breakfast is included this morning if your departure timing allows. Guests ending in Sorrento may request an optional transfer to Naples Airport, and extra nights can often be arranged when available.

Signature Moment

Sorrento Finale

The Journey closes with sea air, an evening walk, farewell Apericena and the particular feeling of Southern Italy: warm, generous, and hard to leave.

15

Pompeii

Explore the ancient Roman city with an expert guide before continuing to the coast.

Day 10

16

Sorrento

Arrive into the Sorrento Peninsula, where the rhythm changes to sea air and evening walks.

Day 10

17

Coastal day

Enjoy time along the coast, with Tour Captain guidance and room for unhurried discovery.

Day 11

18

Arrivederci

Departure support from the Naples area closes the Journey with grace.

Day 12

Optional coastal moments

Isle of Capri

Highly recommended private boat experience when available, with island time, refreshments, towel service and coastal cruising. From $579 per person.

Capri & Anacapri

Explore the island towns with Tour Captain guidance and island transportation when part of the confirmed experience.

Monte Solaro

Ride the chairlift for panoramic views when timing, weather and the day's plan allow.

Capri and private boat details are confirmed closer to departure and are subject to weather, sea conditions and supplier availability. If the exact boat experience is not available, Now Journey will advise on the best alternative.

Where you stay

Grand Hotel Capodimonte view

Sorrento hotel collection

Examples may include Grand Hotel Capodimonte, Hotel Continental, Bellevue Syrene, Hilton Sorrento Palace or similar.

"Sorrento hotels should capture coastal beauty, classic Italian comfort and the feeling that the Journey has reached its sunlit conclusion."Mark's Thoughts

Your Italian story does not end here.

By now you have wandered Venice's canals, admired Florence's masterpieces, lingered over lunch in Tuscany, explored the Eternal City, and watched the evening light settle over the Amalfi Coast.

What began as an itinerary has become something much more personal. That is exactly how we hope every Now Journey feels.

Decision reassurance

Why guests tell us they choose Now Journey

"I wanted Italy without feeling lost in the crowd."

Small-group travel, personal hosting and a more intimate pace help the famous places feel less overwhelming and more human.

"I wanted the details handled beautifully."

Hotels, guides, transfers, meals, sightseeing and transitions are thoughtfully coordinated before you arrive.

"I wanted a Journey, not just a tour."

Now Journey blends structure with discovery, hospitality and meaningful local connection so Italy feels personal.

"Our goal is not simply to take you through Italy's great cities. It is to help you feel cared for in each one - with enough structure to relax, enough freedom to explore, and enough local connection to make the Journey feel personal."Mark's Thoughts

A thoughtful match

Is this the right Journey for you?

This section is not about rules. It is about recognition. The right traveler usually reads this and thinks, "Yes, that sounds like me."

  • You want Italy thoughtfully planned without feeling over-scheduled.
  • You prefer small-group travel where guests are known by name.
  • You appreciate boutique and deluxe hotels with character and strong locations.
  • You value local guides who tell stories, not scripts.
  • You want meaningful sightseeing balanced with time to linger.
  • You would rather experience Italy with care, context and hospitality than rush from place to place.

Thoughtful guidance

Let's Plan Your Journey

Requesting a proposal is not booking your trip. It is simply the beginning of a thoughtful planning conversation with experienced Journey Specialists who know this itinerary exceptionally well.

No obligation. No pressure. Just personalized guidance.

Your Personalized Journey Proposal Includes

  • Available departures
  • Current pricing
  • Hotel Collection recommendations
  • Room category suggestions
  • Extension possibilities
  • Air travel guidance, if desired
  • Recommendations based on your travel style
  • Answers to your questions
"The itinerary was meticulously crafted, with every detail seamlessly planned - and filled with unforgettable experiences."
Mikki, Northern Italy Bella Adventure

Perhaps you have already begun imagining yourself there

Is this the Italy you have been hoping to experience?

If you have made it this far, you have done more than browse a vacation. You have walked through each chapter, explored where you will stay, discovered the experiences you will enjoy, and seen how thoughtfully every day has been designed.

If the answer might be yes, we would be honored to prepare your personalized Journey Proposal. No obligation. No pressure. Just thoughtful guidance from people who know this Journey intimately.

Reference notes

Practical information, whenever you want it.

If you would like to keep exploring the practical side, these notes gather the essentials in one quiet place.

Hotel collections

Deluxe hotels feature 4- and 5-star properties. Classic hotels are well-located 3-star-plus properties with private bathrooms, air conditioning and breakfast.

Meals and dining

Daily breakfasts and select lunches and dinners are included, with independent dining time built into the flow.

Walking pace

Expect moderate walking in historic centers, often on cobblestones and stairs, at a pace designed to feel thoughtful rather than rushed.

Transfers

Official tour-day transfers and local movement are thoughtfully coordinated, with arrival and departure guidance provided before travel.

Optional experiences

Optional moments enrich free time. They are suggestions, not pressure to fill every hour.

Solo travelers

Many guests travel solo. The small group setting makes connection easy while preserving personal space.