Journey Guide • Grand Edition • 14 Days
The complete companion guide to your Journey through Lake Como, Venice, Florence, Tuscany, Rome, and the Amalfi Coast, including the pacing, hotels, experiences, itinerary, and details that help you picture exactly how the Journey unfolds.
Private Journey Companion
The main tour page gives you the invitation. This guide gives you the full story — the chapters, pacing, hotels, itinerary, and details that help you understand what the Journey actually feels like from arrival to farewell.
Move through it chapter by chapter. Each section is meant to clarify the rhythm of the Journey, show where you will stay, and reassure you about the practical details without turning the guide into another sales page.
Now Journey Hotels Collections
At Now Journey, we believe the hotel is not an afterthought. It shapes the rhythm of each day, the ease of exploring, and the feeling you carry with you when you return from dinner, a guided walk, or an evening on your own.
That is why our Hotels Collections are curated with intention. We consider location, walkability, comfort, service, atmosphere, breakfast, room quality, cleanliness, character and the way each property supports the story and pacing of the Journey.
Curated for character. Chosen for location. Selected for comfort.
We do not simply select hotels by star rating. A grand lobby means little if the location pulls you away from the life of the city. Each property is chosen for how it supports the Journey: easy arrivals, walkable evenings, warm service, a strong sense of place and a level of comfort that lets the day unfold beautifully.
Our Deluxe Hotels Collection features carefully selected 4- and 5-Star hotels. Deluxe itineraries include entry-level room categories at 5-Star properties and one category above entry-level at 4-Star properties whenever available, with more refined amenities and a more elevated stay.
Our Classic Hotels Collection features quality 3-Star+ properties with private bathrooms, air conditioning and continental breakfast. Classic is not a budget substitute. It is a value-conscious, well-located and comfortable collection that preserves the Now Journey experience with simpler amenities.
Italy's great cities are best when they remain close. We favor hotels that keep you near historic centers, evening streets, piazzas, restaurants, waterfronts and guided meeting points, so your independent time feels natural and the Journey keeps its graceful pace.
Historic city-center hotels in Europe may have smaller rooms than many American hotels, and room sizes and layouts can vary even within the same property. Location, charm and sense of place are often prioritized over large standardized rooms. Upgraded room categories may be available upon request, and a Journey Designer can help compare room options before you choose your departure.
Printable Itinerary
Download the printer-friendly 14-Day Grand itinerary for easy sharing, planning notes or offline review.
Prologue
Italy begins with lake light, Bellagio, villa-lined shores and a gentler arrival before the great cities unfold.
Lake Como is not an add-on tacked to the front. It is the graceful prologue: a place to arrive, settle, breathe and let Italy begin at a more elegant rhythm.
Day 1
The adventure begins on the breathtaking shores of Lake Como. Whether arriving from a pre-tour stay in Milan or stepping directly into the Journey today, settle into the village, the lake views and the slower rhythm that makes Como such a graceful opening.
Meet your Tour Captain, begin to get oriented, and gather for a welcome dinner featuring Lake Como regional cuisine.
Included Today
Day 2
After breakfast, join your Tour Captain for a morning on Lake Como. Stroll through Bellagio, uncover local history, then see the lake by water, taking in villas, villages and the alpine setting from a private boat perspective when conditions allow.
The afternoon is intentionally open. Linger over lunch, enjoy the waterfront, return to the hotel or simply let the lake set the tone before Venice, Florence, Tuscany and Rome begin.
Included Today
After Lake Como, the Journey continues toward Venice. The pace changes from lakeside calm to water taxis, bridges, marble, mosaics and the theatrical beauty of San Marco.
Lake Como: Hotel Belvedere or similar. This lakeside stay gives the Grand Journey a peaceful beginning: lake views, gardens, a hillside setting and the relaxed luxury of arriving before the great cities gather momentum.
Other Deluxe hotels we sometimes use: Grand Hotel Villa Serbelloni, Grand Hotel Cadenabbia or similar.
Chapter One
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.
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 3
This morning, say arrivederci to Lake Como and travel toward Venice. Depending on the departure, the journey may be by fast train from Milano Centrale, micro-coach or sedan.
Upon arrival, a private water taxi takes you toward your San Marco-area hotel. After check-in and a little time to relax, enjoy a Discovery Walk through Venice's iconic first impressions: Piazza San Marco, the Campanile, the Grand Canal and the maze of lanes and bridges. That evening, gather for a Venetian opening dinner with regional Italian cooking, wine and premium beverages included.
Included Today
Signature Moment
Your first evening is the threshold: the group settles in, Venice begins to glow, and the Journey finds its rhythm.
After the Lake Como prologue, a private water taxi brings you into Venice the way Venice should be entered.
Day 3
Your Tour Captain introduces San Marco, the Grand Canal, the Campanile and the first practical rhythms of the Journey.
Day 3
Day 4
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 can point you toward a favorite local restaurant for an optional dinner with fellow travelers.
Included Today
Venice: Hotel Saturnia & International or similar. This refined, family-owned stay keeps you within easy reach of St. Mark's while supporting the best kind of Venice evening: a quiet wander after the day visitors have drifted away.
Other Deluxe hotels we sometimes use: Monaco & Grand Canal or similar.
After Venice has worked its quiet spell, the Journey turns inland. The next chapter trades canals and reflected light for Florence's domes, workshops, river bridges and Renaissance proportion.
Chapter Two
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.
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 5
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
Day 6
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
Signature Moment
The morning gives you the masterpieces. The afternoon gives you the city - time for leather markets, churches, cafes, rooftops, galleries or simply looking up.
Private boat transfer to Santa Lucia station, then a comfortable high-speed train into the artistic heart of Italy.
Day 5
Duomo, Baptistery, Giotto's Campanile, Ponte Vecchio and the historic center become your first Florentine orientation.
Day 5
A hosted welcome dinner introduces the regional flavors of Tuscany and Chianti.
Day 5
The Journey leaves room for Santa Croce, Brunelleschi's dome, the Pitti Palace, shopping or a long cafe pause.
Day 6
Florence: Grand Hotel Cavour or similar. This historic city stay places the Renaissance chapter close to Florence's treasures, with rooftop views and a central setting that keep the city present even between guided moments.
Other Deluxe hotels we sometimes use: Bernini Palace, Hotel L'Orologio or similar.
Florence gives the Journey its artistic center. Tuscany changes the tempo, making room for hill towns, vineyard light, a longer lunch and the pleasure of letting Italy slow down around you.
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
Vine-covered hills, a white wine toast in San Gimignano, a family-run estate, Cortona at golden hour and the permission to slow down.
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 7
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.
Included Today
Signature Moment
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.
Day 8
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.
Included Today
Wander the medieval hill town of towers and toast Tuscany with Vernaccia, its signature white wine.
Day 7
A cellar visit, curated tasting and farm-to-table lunch pair Chianti and Super Tuscan wines with regional cooking.
Day 7
Your Tour Captain introduces Etruscan, Roman and modern stories as Cortona opens into evening.
Day 7
A relaxed Tuscan evening with the spirit of aperitivo and dinner woven together.
Day 7
A free Tuscan day gives you time for a slow piazza morning, a countryside walk, or one of the optional Cortona experiences below.
Day 8
Cortona: Villa Marsili or similar. This intimate hillside stay suits the slower rhythm of the Tuscan chapter, keeping you close to the 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.
Chapter Four
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.
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 9
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.
Included Today
Day 10
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.
Included Today
Day 11
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.
Included Today
Now Journey Exclusive
After the Vatican, the Forum and the evening streets around the Pantheon, this dinner becomes a hinge in the Journey: one last Roman night before the road turns toward Pompeii and the sea.
Settle near the Pantheon, walk through Piazza Navona, Campo de' Fiori and Largo di Torre Argentina, then gather for the included welcome dinner in Rome.
Day 9
Privileged access to the Vatican Museums, Sistine Chapel, St. Peter's Basilica and St. Peter's Square.
Day 10
Walk through the Roman Forum and ancient city, where modern life and empire still share the same stones.
Day 11
A special hosted evening lets the Journey pause before turning south toward the coast.
Day 11
The Grand Edition gives the Eternal City time to unfold: arrival in Old Rome, sacred art at the Vatican, imperial stones, and a hosted evening that lets the Roman chapter settle before the Journey continues south.
Rome: Palazzo Navona or similar. This central Rome stay 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.
Final Chapter
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.
After Rome, the Journey descends south: ancient Pompeii, the Sorrento Peninsula, the Amalfi Coast and a final stretch of Mediterranean light.
Day 12
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.
Included Today
Day 13
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.
Included Today
Day 14
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.
Included Today
Signature Moment
The Journey closes with sea air, an evening walk, farewell Apericena and the particular feeling of Southern Italy: warm, generous, and hard to leave.
Explore the ancient Roman city with an expert guide before continuing to the coast.
Day 12
Arrive into the Sorrento Peninsula, where the rhythm changes to sea air and evening walks.
Day 12
Enjoy time along the coast, with Tour Captain guidance and room for unhurried discovery.
Day 13
Departure support from the Naples area closes the Journey with grace.
Day 14
Sorrento: Grand Hotel Capodimonte or similar. This coastal stay lets the final chapter soften into the Bay of Naples: sea-view terraces, cascading multi-level pools and the pleasure of ending somewhere made for lingering.
Other Deluxe hotels we sometimes use: Bellevue Syrene, Hilton Sorrento Palace or similar.
By now you have watched Lake Como begin the story, 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 now has shape: chapters, meals, hotels, walks, pauses, and the particular light of each place.
Guide Notes
Each chapter shows how guided time, hosted moments and open time fit together.
Hotels, meals, transfers and optional moments are gathered in one calm reference.
The daily notes help you picture arrivals, walks, meals, open time and transitions.
How to Use This Guide
Some guests read straight through. Others begin with hotels, pacing, or the final coastal days. Use the guide in the way that helps you see the Journey clearly.
Choose Your Next Step
Use this guide as long as you like. When you want dates, pricing or room guidance, a Journey Designer can help you compare the practical details.
Clear guidance, whenever you are ready.
A Journey Designer Can Help With
Your Journey Begins Here
You've now walked the Journey in your imagination: Lake Como at the beginning, Venice by water, Florence in Renaissance light, Tuscany at a slower pace, Rome in all its layers, and the Bay of Naples as the coastal finale.
The only thing left is deciding whether you'd like to experience it yourself. If this feels like the Italy you've been hoping for, we'd be honored to help you begin.
Reference notes
These notes keep the practical details close at hand.
Deluxe hotels feature 4- and 5-star properties. Classic hotels are well-located 3-star-plus properties with private bathrooms, air conditioning and breakfast.
Daily breakfasts and select lunches and dinners are included, with independent dining time built into the flow.
Expect moderate walking in historic centers, often on cobblestones and stairs, at a pace designed to feel thoughtful rather than rushed.
Tour-day transfers and local movement are coordinated, with arrival and departure guidance provided before travel.
Optional moments enrich free time. They are suggestions, not pressure to fill every hour.
Solo room options and pre-travel guidance can be reviewed before you choose a date.