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Now Journey | Private Italy Collection
The Italian Journey
Italy.
Beautifully Yours.
From Lake Como to Positano, a private journey through six remarkable Italian destinations—personally planned and thoughtfully arranged for the way you want to travel.
- Journey
- 14 Days / 13 Nights
- Travel Style
- Private for Two
- Departures
- Daily March–October
- From
- $18,649 per guest
Opening scene
A Personal Welcome
Some journeys deserve to be entirely your own.
There’s something special about experiencing Italy on your own terms. The freedom to linger a little longer, discover a beautiful place without a crowd, or enjoy an extraordinary evening simply because the moment feels right.
That’s what inspired The Italian Journey. We’ve brought together some of Italy’s most remarkable places, exceptional local expertise, and the thoughtful attention that makes travel feel effortless.
The itinerary is our starting point. The experience becomes yours.
Journey at a Glance
Six chapters.
One beautiful progression.
From the lakes and peaks of the north, The Italian Journey moves through Venice, Renaissance Florence and Tuscany before reaching Rome and the vertical beauty of Positano on the Amalfi Coast.
Daily Private Departures · March through October · Your requested dates
- 01Lake ComoDays 1–2 · 2 Nights
- 02VeniceDays 3–4 · 2 Nights
- 03FlorenceDays 5–6 · 2 Nights
- 04Cortona & TuscanyDays 7–8 · 2 Nights
- 05RomeDays 9–11 · 3 Nights
- 06Positano & CapriDays 12–14 · 2 Nights
Lake Como→Venice→Florence→Cortona→Rome→Positano
14 days · 13 nights · Day 14 is departure day
Signature Experiences
Moments Worth Traveling For
Five included experiences that give the journey its rhythm—private, deeply local and memorable for all the right reasons.
Included · Day 2
Lake Como by private boat
See villas, gardens and mountain villages from the perspective that reveals the lake best.
Included · Day 4
Venice with musicians
Glide through the city by gondola as live music carries across the water, weather permitting.
Included · Day 6
Michelangelo’s Florence
Stand before David, then follow the city’s art and civic ambition into its historic streets.
Included · Day 7
A long lunch in wine country
Pause at a Tuscan estate for a cellar visit, tasting and an included winery lunch.
Capri, privately yours
Leave Positano by privately arranged boat for dramatic coastline, island time and the open Mediterranean.
The Freedom of Traveling Privately
Italy moves at a more personal rhythm.
Your journey begins with personal planning around a proven six-destination route. Requested dates, hotels, rooming and optional experiences are checked and confirmed in your proposal; private transport and expert local guides are arranged where the itinerary specifies them.
Personal planning
A Now Journey specialist shapes the proposal around your dates, hotel collection, rooming and priorities.
Private arrangements
Private vehicles, water transport and other services are arranged where they are specified day by day.
Expert local guides
Private guided visits bring informed local perspective to the art, history and places on the itinerary.
Considered freedom
Guided experiences are balanced with independent time, while additions remain subject to availability and confirmation.
Personally Planned
Make This Italian Journey Yours
Tell us what you would like more of. Choose any interests that feel right—or none at all—and we’ll use them as a starting point for a personal conversation.
The Journey in Motion
Follow Italy as the story unfolds.
Move through six destination chapters. The map follows the chapter in view; every day can be opened independently.
Chapter 01 · Days 1–2 · 2 Nights
Lake Como
Bellagio, the lake and an unhurried northern beginning.Lake Como opens the journey with mountain air, elegant villas and villages that seem to rise directly from the water. The pace is deliberately unhurried.
Day 1Arrive on Lake ComoOpen day
Your included arrival transportation brings you to the Lake Como area, where the lake and surrounding peaks set an immediate sense of place. After time to settle in, an orientation-style Discovery Walk introduces your surroundings before an included welcome dinner.
- Included transport: Arrival transportation to Lake Como
- Included experience: Arrival welcome and Discovery Walk
- Included dining: Welcome dinner
Day 2The Lake from BellagioOpen day
Discover Bellagio on foot, then meet a local captain for a private boat journey past storied villas, lake gardens and changing mountain silhouettes. Return with the afternoon and evening free to follow the rhythm of the waterfront.
- Included experience: Bellagio walk and private lake boat tour
- At leisure: Afternoon and evening
- Optional: Dinner suggestions and reservations
Your stay: Lake Como / Bellagio area · 2 nights · View hotel examples
Chapter 02 · Days 3–4 · 2 Nights
Venice
Arrival by water, San Marco and the city’s quieter passages.In Venice, water becomes the road. Grand palaces and quiet passages share the same lagoon light, and even an arrival feels like part of the experience.
Day 3Across Northern Italy to VeniceOpen day
Leave Lake Como for Milan and continue by high-speed rail, or by private vehicle when that arrangement is specified in your proposal. In Venice, a private water taxi carries you into the city, where a Discovery Walk introduces the San Marco area before an included welcome dinner.
- Included transport: Planned transfer, rail or private vehicle, and Venice water taxi
- Included experience: Venice Discovery Walk
- Included dining: Welcome dinner
Day 4Venice, Secrets & TreasuresOpen day
With an expert local guide, trace the power and pageantry of St. Mark’s Square, the Doge’s Palace, the historic prisons and the Bridge of Sighs. St. Mark’s Basilica and listed museum admissions are included when operations permit. Later, glide through Venice by gondola with live musicians, weather permitting.
- Included sightseeing: Doge’s Palace, historic prisons, Bridge of Sighs and San Marco area
- Included experience: Gondola with musicians, subject to weather
- At leisure: Balance of the afternoon and evening
Your stay: Venice · 2 nights · View hotel examples
Chapter 03 · Days 5–6 · 2 Nights
Florence
Renaissance masterpieces, market streets and time of your own.Florence rewards a closer look: carved stone, ambitious domes and masterpieces encountered in a historic center that remains intimate enough to explore on foot.
Day 5Venice to Renaissance FlorenceOpen day
Travel by water to Santa Lucia station and continue by high-speed rail to Florence. A Discovery Walk follows the Duomo complex, Giotto’s Campanile, the Baptistery and the streets of the historic center before an included Tuscan welcome dinner.
- Included transport: Boat transfer and high-speed rail
- Included experience: Florence Discovery Walk
- Included dining: Welcome dinner
Day 6Florence, Art & Living HistoryOpen day
Meet an expert guide at the Accademia for Michelangelo’s David, then continue through the city to Piazza della Signoria, the Duomo complex and Ponte Vecchio. The afternoon and evening are open for a favorite museum, a market or simply another walk across the Arno.
- Included sightseeing: Accademia admission and guided historic-center walk
- At leisure: Afternoon and evening
- Optional: Additional museums, the Duomo, markets or dinner
Your stay: Florence · 2 nights · View hotel examples
Chapter 04 · Days 7–8 · 2 Nights
Cortona & Tuscany
Hill towns, a winery lunch and the pleasure of slowing down.The landscape widens into vineyards, cypress roads and hill towns held within old stone walls. Here, a long lunch and an unscheduled afternoon are part of the point.
Day 7San Gimignano, Wine Country & CortonaOpen day
Pause among the towers of San Gimignano, then continue to a Tuscan wine estate for a cellar visit, tasting and included lunch. In Cortona, a Discovery Walk leads into an included apericena—the relaxed Italian meeting point between aperitivo and dinner.
- Included sightseeing: San Gimignano and wine-estate visit
- Included dining: Winery lunch with tasting and Cortona apericena
- Included experience: Cortona Discovery Walk
Day 8A Day Entirely Your OwnOpen day
Enjoy a full independent day in Cortona. Optional possibilities include a cooking experience, horseback riding, Siena, the Le Celle hermitage or a more active exploration of Cortona’s upper town.
- At leisure: Full day and evening
- Optional at additional cost: Cooking, Siena, riding and private local touring
- Planning: Current pricing and operating details are confirmed before booking.
Your stay: Cortona · 2 nights · View hotel examples
Chapter 05 · Days 9–11 · 3 Nights
Rome
Three nights among ancient streets, Vatican art and imperial history.Rome unfolds in layers: ancient stone beneath Renaissance streets, neighborhood piazzas beside world-changing monuments, and daily life moving confidently through it all.
Day 9Into the Heart of RomeOpen day
Travel south from Cortona and settle into Rome’s historic center. A Discovery Walk links the Pantheon, Piazza Navona, Campo de’ Fiori and Largo di Torre Argentina, revealing how many centuries coexist within a few streets, before an included welcome dinner.
- Included experience: Old Rome Discovery Walk and Pantheon admission when available
- Included dining: Welcome dinner
- Stay: Three nights in Rome
Day 10Vatican CityOpen day
Explore the Vatican Museums with an expert local guide, including the Sistine Chapel. Continue to St. Peter’s Basilica and Square when Vatican operations and access permit. The afternoon and evening are open.
- Included sightseeing: Guided Vatican Museums and Sistine Chapel visit
- When access permits: St. Peter’s Basilica and Square
- Access note: No after-hours or exact early-entry time is promised.
Day 11Imperial RomeOpen day
Walk through the Colosseum and Roman Forum with an expert guide, tracing the civic, political and ceremonial center of the ancient city. Views toward the Capitoline and Palatine hills place the ruins within the larger story of Rome before an included farewell-to-Rome dinner.
- Included sightseeing: Colosseum and Roman Forum admissions and guided touring
- Included dining: Farewell-to-Rome dinner
- Access note: Entry sequence and areas depend on current venue operations.
Your stay: Rome · 3 nights · View hotel examples
Chapter 06 · Days 12–14 · 2 Nights
Positano & Capri
Ancient Pompeii, a vertical coastal village and the Mediterranean by private boat.The road turns toward the sea, pausing at Pompeii before two nights among Positano’s pastel buildings, steep lanes and extraordinary coastal light.
Day 12From Ancient Pompeii to PositanoOpen day
Travel south from Rome through the landscapes of Campania to Pompeii, where an expert local guide reveals the streets, homes and daily life of the ancient Roman city. Continue to the Amalfi Coast as Positano rises in a cascade above the Mediterranean. Settle into your hotel, enjoy time to discover the town and gather for an included coastal welcome dinner.
- Included sightseeing: Pompeii admission and private expert-guided visit
- Included transport: Private journey transportation to Positano
- Included dining: Positano welcome dinner
Day 13Capri, Privately YoursOpen day
From Positano, set out for the Isle of Capri aboard your privately arranged boat. Discover dramatic coastline, hidden coves and striking rock formations, with time ashore in Capri and Anacapri according to the confirmed itinerary before returning to Positano.
- Included excursion: Private Capri boat and island day, with hotel-to-boarding-point logistics and island transportation
- Weather dependent: Boat routing, swimming, grotto visits and coastal stops
- Evening: At leisure in Positano unless a hosted dinner is expressly confirmed
Day 14Arrivederci, PositanoOpen day
Enjoy a final morning on the Amalfi Coast before your included departure transportation from Positano to Naples International Airport, scheduled according to the confirmed arrangements. Or, ask us to extend your time on the coast.
- Included dining: Breakfast, subject to flight timing
- Included transport: Departure transportation to Naples International Airport
- By request: Additional nights on the Amalfi Coast
Your stay: Positano · 2 nights · View preferred hotel examples
Personalize or extend: When feasible, add a separately quoted private Amalfi Coast outing to Ravello, Amalfi or Praiano without crowding the included Capri day.
Hotel Collections
Exceptional Places to Call Your Own.
From the shores of Lake Como to the heart of Rome and the cliffs of Positano, the places you stay are part of the story. Choose the collection that suits your travel style, and we’ll thoughtfully arrange accommodations that bring each destination to life.
Deluxe Curated 4- and 5-star stays with the established Now Journey room standards.
Lotus Distinctive luxury properties and elevated room categories where available.
Classic Comfortable, thoughtfully selected 3-star-plus hotels; examples confirmed in your proposal.
Examples, not guarantees. Featured hotels are examples and subject to availability at the time of booking. Sea-view accommodations are based on availability at booking and are not guaranteed unless specifically confirmed in your proposal.
Lake Como / Bellagio · 2 Nights
The lake at your doorstep.
Grand Hotel Cadenabbia is in Cadenabbia, not Bellagio. March requests may require a suitable seasonal alternative.Deluxe exampleGrand Hotel Cadenabbia
An appropriate 4-star lakefront property or similar.
Lotus exampleGrand Hotel Villa Serbelloni
A luxury Bellagio property or similar, with elevated room selection subject to confirmation.
Classic A comfortable, thoughtfully selected 3-star-plus Lake Como-area hotel, confirmed for your dates. Ask about these stays
Venice · 2 Nights
Palace atmosphere near San Marco.
Historic character, a central setting and easy access to the waterways that define the city.Deluxe exampleMonaco & Grand Canal
A 4-star luxury Venice property or similar.
Lotus exampleNolinski Venezia
A distinctive luxury hotel or similar; exact room category confirmed in proposal.
Classic A comfortable, thoughtfully selected 3-star-plus Venice hotel, confirmed for your dates. Ask about these stays
Florence · 2 Nights
In the Renaissance heart.
A central base for early museum visits, evening walks and independent discoveries.Deluxe exampleGrand Hotel Cavour
A verified 4-star property in Florence’s historic center, or similar.
Lotus exampleRocco Forte Hotel Savoy
A refined luxury Florence stay or similar, with room selection confirmed by proposal.
Classic A comfortable, thoughtfully selected 3-star-plus Florence hotel, confirmed for your dates. Ask about these stays
Cortona / Tuscany · 2 Nights
History held within stone walls.
A restorative hill-town stay at the midpoint of the journey.Deluxe exampleMonastero di Cortona Hotel & Spa
The named Cortona property or a similar hotel.
Lotus exampleMonastero di Cortona Hotel & Spa
An elevated room or suite category, or an equivalent higher-tier property.
Classic A comfortable, thoughtfully selected 3-star-plus Cortona hotel, confirmed for your dates. Ask about these stays
Rome · 3 Nights
The Eternal City outside your door.
Three nights within reach of Rome’s historic core, neighborhood restaurants and evening passeggiate.Deluxe exampleThe Pantheon Iconic Rome Hotel
A verified 5-star luxury property near the Pantheon, or similar.
Lotus exampleOrient Express La Minerva
A luxury hotel at Piazza della Minerva, or similar, with category confirmed in proposal.
Classic A comfortable, thoughtfully selected 3-star-plus Rome hotel, confirmed for your dates. Ask about these stays
Positano / Amalfi Coast · 2 Nights
A beautiful address on a vertical coast.
Four preferred examples offer distinctly different perspectives on Positano. The confirmed property will align with your selected collection, dates and practical access needs.Hotel Buca di Bacco
A four-star stay beside Spiaggia Grande in Positano’s pedestrian center. Reaching the hotel from the road or parking area requires a short walk; luggage transport is arranged separately when confirmed.
Add to my preferencesHVF Villa Franca
An official five-star hotel on the hill above Positano, combining a secluded outlook with access to the town. Exact arrival and transfer arrangements are confirmed for each stay.
Add to my preferencesHotel Miramare
A family-run four-star hotel with a long Positano history. It sits below the road and parking level, reached by approximately 130 steps, with no lift; porter timing must be confirmed.
Add to my preferencesVilla Magia
A boutique resort evolved from an eighteenth-century watchtower, with terraces and two panoramic pools. Road approach, steps and luggage assistance will be reviewed for the confirmed arrangements.
Add to my preferencesFeatured hotels are examples and subject to availability at the time of booking. Sea-view accommodations are based on availability at booking and are not guaranteed unless specifically confirmed in your proposal. The image shows Positano scenery, not a named hotel.
Dates & Pricing
Your Dates. Your Italian Journey.
This journey is thoughtfully designed for two guests, with the flexibility to tailor your dates, hotel collection and select experiences. Families and private parties are warmly welcomed.
Daily private departure requests · March 1–October 31
Classic
$18,649per guestThoughtfully selected 3-star-plus hotels; property examples confirmed in your personalized proposal.Choose ClassicDeluxe
$21,579per guestCurated 4- and 5-star properties with Now Journey’s established room standards.Choose DeluxeLotus Hotel Collection
$26,979per guestDistinctive luxury properties and elevated room categories, confirmed for your dates.Choose LotusPublished starting prices are in U.S. dollars, per person, based on exactly two guests traveling together and sharing one room. Final proposals reflect requested dates and confirmed arrangements. Parties larger than two receive custom pricing. No hotel, view, suite or room category is guaranteed until confirmed.
Every Detail Considered
What the journey is designed to include.
Included in the published framework
- 13 hotel nights in the selected collection
- Breakfast daily, with departure-morning breakfast subject to flight timing
- Arrival transportation to Lake Como and departure transportation from Positano to Naples International Airport
- Planned journey transportation and selected Italian rail
- Private water transport in Venice as shown
- Expert local guides, admissions and visits shown as included day by day
- Now Journey personal planning and hosting as specified in the confirmed proposal
- Winery visit, tasting and lunch in Tuscany
- Private Capri boat and island excursion with boarding-point logistics and island transportation, weather permitting
- Hosted dinners specifically described in the itinerary
- Local guide and driver gratuities for included services
Not included
- International airfare
- Optional, separately quoted Amalfi Coast outings to Ravello, Amalfi or Praiano
- Additional customizations
- Meals not identified as included
- Gratuity for any Now Journey host assigned in the proposal
- Travel insurance and personal expenses
- Specific hotels, rooms, views or suites before confirmation
Plan & Prepare
A private journey, clearly explained.
Every proposal is personally reviewed. That is where requested dates, accommodations, rooming and operational details become confirmed arrangements.
When can The Italian Journey begin?
You may request any start date from March 1 through October 31. Your date remains a request until hotels and services are checked and confirmed in a personalized proposal. Some featured Lake Como properties operate seasonally, so March stays may use a suitable confirmed alternative.
Is this journey always for two guests?
The published prices are designed for exactly two guests traveling together and sharing one room. Families, multigenerational travelers and other private parties are welcome; their rooming and pricing are prepared individually.
Are the featured hotels guaranteed?
Featured hotels are examples and subject to availability at the time of booking. Sea-view accommodations are based on availability at booking and are not guaranteed unless specifically confirmed in your proposal.
How do Classic, Deluxe and Lotus differ?
The core journey remains consistent. Classic uses comfortable, thoughtfully selected 3-star-plus hotels. Deluxe uses curated 4- and 5-star hotels with established room standards. Lotus emphasizes distinctive luxury properties and elevated room categories where available.
Is the Isle of Capri excursion included?
Yes. The private Capri boat and island excursion from Positano is included on Day 13, with boarding-point logistics, island transportation, time in Capri and Anacapri, and coastal cruising when sea conditions permit. Exact routes, swimming and grotto visits remain weather dependent.
Are airport transfers included?
Yes. Arrival transportation to Lake Como and departure transportation from Positano to Naples International Airport are included, scheduled according to the confirmed arrangements.
What should I know about hotel access in Positano?
Positano is steep, and many hotels require walking along pedestrian lanes or using stairs. Vehicle access, walking distance, porter and luggage assistance, and boat-boarding logistics are reviewed for the confirmed hotel and itinerary. Please share mobility considerations before booking.
Can I add another Amalfi Coast outing?
When feasible, a private outing to Ravello, Amalfi or Praiano can be added as a separately quoted experience. We protect time for the included Capri day and for relaxation during the two-night stay.
Does the Vatican visit include after-hours access?
No after-hours access or exact early-entry time is promised here. The guided visit includes the Vatican Museums and Sistine Chapel, with St. Peter’s Basilica and Square when Vatican operations and access permit.
How active is the journey?
Historic centers involve cobblestones, uneven pavement, stairs, boarding boats and trains, and periods of standing. The pace is considered, but travelers should be comfortable walking for guided visits. Please share mobility considerations in the proposal request.
Begin Your Private Journey
Your Italy. Your Dates. Your Story.
Share a few details. We’ll personally prepare your private journey proposal. No commitment required.
- Personally reviewed by a Now Journey specialist
- No booking commitment or payment
- Availability confirmed in your proposal
The Italian Journey
Italy, arranged around you.
Fourteen days. Six destinations. One private story from Lake Como to Positano.
Request Your Private Journey Proposal