Your dedicated Tour Captain
Your host throughout the journey—coordinating transitions, orienting you in each destination, offering personal recommendations, and helping solve the practical questions that arise along the way.
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The Original 12-Day Small Group Italy Journey.
Venice → Florence → Tuscany → Rome → Sorrento & the Amalfi Coast
No obligation. No pressure.
Choose your Journey
Italy's Great Cities is available in three thoughtfully crafted small group journeys, each designed around the same Now Journey philosophy of elegant pacing, exceptional hospitality, and unforgettable experiences. Whether you're looking for a focused Venice-to-Rome tour, our flagship journey Venice to the Amalfi Coast, or our most complete Italy tour from Lake Como North to South, simply choose the edition that best fits your time and travel style.
Italy was never meant to be rushed
Italy's Great Cities was created for travelers who want the famous places - Venice, Florence, Tuscany, Rome and the Amalfi Coast - without the big-bus feeling, rushed pacing, or generic group-tour machinery.
This is a hosted, thoughtfully paced journey with boutique hotels, memorable dining, local guides, and enough breathing room for Italy to feel personal.
"Every day, every place, every meal, every experience was amazing." Edward K., Now Journey guest
Your Journey Ahead
From Venice to the Amalfi Coast, one beautifully paced journey.
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Why travelers choose Now Journey
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.
What's included
Your 12-day Journey includes 11 hotel nights, daily breakfast, included dining, expert-guided sightseeing, admissions and planned transportation.
Your host throughout the journey—coordinating transitions, orienting you in each destination, offering personal recommendations, and helping solve the practical questions that arise along the way.
Eleven breakfasts are included; departure-morning breakfast is subject to flight timing.
5 dinners, 1 included winery lunch and 2 Apericena experiences.
All itinerary-listed admissions and guided sightseeing, plus the private Venice arrival water taxi, high-speed rail and planned intercity transportation.
International airfare, optional experiences, and the Naples Airport departure transfer are not included.
Explore the Complete Journey from Venice to the Amalfi Coast
Everything you need to know about this small group itinerary through Italy's Great Cities.
Chapter One
Days 1–2
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 1
Arrive at Venice Marco Polo Airport, where a warm welcome and your included private water-taxi transfer bring you into Venice by water. After reaching the hotel, check in, refresh and let Venice begin gently.
Later, meet your Tour Captain for a Discovery Walk through the St. Mark’s area and the practical rhythms of the Journey. The evening is intentionally unhurried, allowing Venice to set the tone.
Day 2
With an expert local guide, explore the St. Mark’s area and Venice’s layered history, including 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, glide through the city’s quieter canals on the included gondola experience, accompanied by live musicians.
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.
“This is the kind of Venice hotel I love: close enough to wander to St. Mark’s Square, but tucked into a quieter rhythm where the city feels like it belongs to you for the evening.”Hotel Note
Chapter Two
Days 3–4
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 3
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 historic center, including Giotto’s Campanile, the Baptistery, the Duomo and Ponte Vecchio. That evening, gather for a hosted Tuscan dinner.
Day 4
Begin at the Accademia Gallery with 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: time to wander, shop, linger over lunch, visit Santa Croce, choose another gallery or simply look up.
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.
“In Florence, the right hotel should keep the Duomo, the river, the piazzas and the evening streets within easy reach. The city is best when you can step back into it after dinner.”Hotel Note
Chapter Three
Days 5–6
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 life and time that feels less scheduled.
Day 5
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.
Settle into a family-run Tuscan estate for a guided cellar visit, curated tasting and leisurely farm-to-table lunch. Later, continue to Cortona, where your Tour Captain handles check-in before leading a gentle Discovery Walk into the historic center.
Day 6
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. Optional experiences may be available, but none is required, and the evening remains open for an unhurried night in one of Tuscany’s loveliest hill towns.
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.
“Cortona works best when the hotel has a sense of place. It should feel smaller, warmer, and more rooted in the Tuscan hillside than a grand-city hotel ever could.”Hotel Note
Chapter Four
Days 7–9
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 7
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 at street level.
Day 8
Begin with a guided morning in Vatican City, exploring the Vatican Museums and Michelangelo’s Sistine Chapel. When visitor operations and access permit, continue to St. Peter’s Basilica and Square as your guide brings context to the art, ritual and architecture of Vatican City.
The afternoon and evening are intentionally open for independent discovery, with suggestions from your Tour Captain.
Day 9
Set out through Rome’s ancient heart, where ruins and modern life share the same streets. Through the Roman Forum and the surrounding imperial landscape, your guide traces the layers of the ancient city, from Palatine and Capitoline context to triumphal arches and views across the historic center.
Tonight, join your Tour Captain for a Farewell to Rome dinner—a moment to reflect before the Journey turns south toward the coast.
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.
“Rome rewards location. When your hotel sits near the historic heart, the city stays with you between the guided moments: a fountain at night, a piazza after dinner, a short walk that becomes a memory.”Hotel Note
Final Chapter
Days 10–12
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.
Pompeii gives the final chapter its ancient depth; Sorrento gives it sea air, open time and room to let the Journey settle.
Day 10
Leave Rome as the Journey turns south toward 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, and the final coastal chapter begins beside the Bay of Naples.
Day 11
Today is intentionally open for the coast. Stay in Sorrento, follow your Tour Captain’s recommendations, or let the Sorrento Peninsula unfold at your own pace.
Optional experiences are available for travelers who want them, but they are choices rather than requirements, and the day needs no filling.
Day 12
As the Journey closes, your Tour Captain or the Now Journey team can assist with practical departure guidance.
An optional transfer to Naples Airport may be requested separately and is not included in the base Journey. If you would like more time in Southern Italy, ask about extending your stay when appropriate and subject to availability.
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.
“Sorrento should feel like a conclusion, not just a final hotel stop. The views, terraces, pools and sea air help the Journey slow into its last beautiful chapter.”Hotel Note
Guest reviews
Now Journey guests consistently mention the same things: thoughtful planning, seamless logistics, special surprises, beautiful hotels, and the feeling of being genuinely cared for.
"I can't say enough about our recent trip to Italy. It was perfection from beginning to end."Esther P., Now Journey guest
"We all were made to feel special, almost like royalty, with skip-the-line access, personal service by fabulous chefs, and seamless check-ins at our gorgeous hotels."
Teresa C."Our hotel accommodations were all perfect. Now Journey did an exceptional job planning and we even got surprises along the way."
Tammy A.Now Journey Hotels Collections
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.
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.
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.

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

Elegant city hotels such as our Deluxe Grand Hotel Cavour, Bernini Palace, L'Orologio, or our Classic Hotel Renaissance or similar.

Rustic Tuscan manor houses, villas and hill-town properties including our Deluxe Villa Marsili, or our Classic Hotel San Luca or similar.

Perfectly placed hotels near the Pantheon, including our Deluxe Palazzo Navona, Pantheon Iconic, La Minerva, or our Classic Hotel Navona or similar.

Coastal stays such as our Deluxe Grand Hotel Capodimonte, Bellevue Syrene, Hilton Sorrento Palace or similar, or our Classic Hotel Rivage Sorrento or similar.
Dates & prices
Prices are per person based on double occupancy. Deluxe hotels feature 4+ to 5-star properties. Classic hotels feature 3-star-plus properties. Deluxe supplement for a double room for solo use: $3,790. Classic: $3,300.
If you are comparing options, start here. These departures represent the most compelling seasonal choices - spring ease, early summer energy, harvest season, and October value.
Summer in Italy - warm days, long evenings, and a festive city energy.
September brings Tuscany's harvest mood, softer light, and high-season demand.
Warm days often linger, while crowds begin to soften and the cities feel a bit more relaxed.
One of the best times to be in Italy: moderate temperatures, fewer crowds, and spring atmosphere.
Near-perfect weather, flowers, sunshine, and la dolce vita.
A classic Italy window with warm days and high-demand departures.
Fresh, hot Italian summer days and long golden evenings.
September brings Tuscany's harvest, late-summer warmth, and some of the year's most requested weeks.
Autumn atmosphere, softer crowds, and warm days that often linger into the month.
Explore the complete Journey before requesting your proposal, or tell us your preferred season, travel style, and hotel collection. We will help you compare dates without pressure.
Plan & Prepare
A few useful details help you arrive prepared, while your Tour Captain and the Now Journey team take care of the Journey’s rhythm and transitions.
Expect moderate walking in historic centers, often on cobblestones and stairs, at a pace designed to feel thoughtful rather than rushed.
Guided discovery is balanced with intentional open time. Your Tour Captain helps with orientation, recommendations and the practical questions that arise along the way.
Room sizes and layouts can vary in historic European properties. Upgrade requests may be considered when available and are confirmed individually.
Groups travel in appropriately sized private vehicles or luxury micro-coaches, with Italian rail on selected segments. Planned tour-day transportation is coordinated for the group.
The private water-taxi arrival transfer in Venice is included. A Naples Airport departure transfer may be requested separately; it is optional and not included in the base Journey.
Optional moments enrich free time. They are suggestions, not pressure to fill every hour. Solo travelers may ask the Now Journey team about current room arrangements and guidance before reserving.
Frequently asked questions
The essence of this Journey: Premium small-group travel with carefully chosen hotels, authentic experiences, personal support every step of the way, and the freedom to enjoy each destination — not just see it.
Small groups typically range from 8 to 12 guests, with a maximum of 16. It's large enough to enjoy the camaraderie of shared travel, yet small enough to remain personal, flexible, and remarkably effortless.
No. Guided discovery is balanced with open time. Guests should still be ready for moderate walking in historic centers, including cobblestones and stairs, but the pace is designed to leave room to linger and enjoy each destination.
Select meals are included as shown in the day-by-day itinerary, with open time built in for independent dining as well.
No. Depending on group size and route, the Journey uses appropriately sized private vehicles or luxury micro-coaches, plus Italian rail and boat transfers where noted.
Yes. It is one of Now Journey's strongest choices for first-time visitors who want the classics with polish and ease.
Deluxe features carefully selected 4- and 5-star hotels, while Classic features well-located 3-star-plus properties. Exact properties are subject to availability and comparable substitution.
Your Journey Begins Here
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.
No obligation. No pressure. Just a thoughtful conversation about your Italy.