Italy's Great Cities — 10-Day Essential Italy | Now Journey
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Now Journey Essential Italy

Italy's Great Cities10-Day Italy’s Great Cities

Four Italian chapters. One beautifully focused journey.

The Original 10-Day Small Group Italy Journey.The Original 10-Day Small Group Italy Journey.

Venice → Florence → Tuscany → Rome

Duration10 Days / 9 Nights
Group & HostingGroup Size8–12 Guests · Hosted by a Now Journey Tour Captain8–12 Guests · Maximum 16
Thoughtful PaceNo One-Night Hotel Stops
OvernightsPersonal HostingVenice 2 · Florence 2 · Tuscany 2 · Rome 3Hosted by a Now Journey Tour Captain
Explore Daily Itinerary View Dates & Prices
“Our hotel accommodations were all perfect. Now Journey did an exceptional job planning and we even got surprises along the way.” — Tammy A.

10-Day Italy's Great Cities Tour

The Essential Italy: Venice · Florence · Tuscany · Rome

THE ESSENTIAL 10-DAY ITALY’S GREAT CITIES

The Story Begins with the Italy You’ve Always Imagined.

There are moments in Italy that stay with you forever: Florence’s magnificent Duomo above the terracotta rooftops, that first glimpse of Michelangelo’s David, Venice’s enchanting canals, a leisurely Tuscan winery lunch, and Rome in the golden afternoon light.

This is the Italy we want you to experience—not simply the famous sights, but Renaissance streets, little cafés, artisan shops, and unexpected discoveries that become treasured memories.

There are moments in Italy that stay with you forever — gliding through Venice’s canals by private water taxi, standing before Michelangelo’s David in Florence, sharing a leisurely Tuscan winery lunch, or watching the golden afternoon sun illuminate Rome. Beyond the celebrated landmarks, it’s the character, stories, and unexpected discoveries that make Italy truly unforgettable.

Mark Story with Now Journey guests on a rooftop terrace in Italy
Mark Story, Owner and Managing Director of Now Journey
Meet Our Director Mark Story Owner & Managing Director “My favorite moments in Italy are often the unexpected ones—the conversations, discoveries, and connections that stay with you long after the journey.”

When my team and I created our 10-Day Essential Italy, we wanted every day to count. Beautiful, centrally located hotels, exceptional local guides, your Now Journey Tour Captain, and a very small group are thoughtfully brought together—with the details handled and room for discoveries of your own.

Because in the end, it’s not just about the places you’ll see. It’s about how Italy makes you feel and the memories you’ll carry home.

When my team and I created our 10-Day Essential Italy, we wanted every day to count. Beautiful, centrally located hotels, exceptional local guides, your own Now Journey Tour Captain, and a genuinely small group — thoughtfully brought together with time and freedom to discover Italy in your own way.

Journey at a Glance

ITALY’S GREAT CITIES · ESSENTIAL ITALY · 10 DAYS

Four Italian Chapters. Ten remarkable Days.

Scroll through citiesSwipe through cities

  1. 01 Venice2 nights · Journey beginsWhere 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.
  2. 02 Florence2 nightsRenaissance masterpieces, artisan workshops, and evenings that linger long after sunset. Florence invites you to slow down and savor every beautiful detail.
  3. 03 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.
  4. 04 Rome3 nights · Journey finaleAncient ruins, lively piazzas, hidden neighborhoods, and unforgettable evenings. The journey concludes amid the many layers of the Eternal City.
  • Venice2 Nights
  • Florence2 Nights
  • Cortona & Tuscany2 Nights
  • Rome3 Nights

Why Now Journey

Luxury that Feels Personal.

Small enough to make a difference.

Typically just 8–12 guests, never more than 16. More personal attention, genuine connections, and the freedom to experience Italy without the dynamics of a large group tour.

Typically 8–12 guests, never more than 16. More personal attention, genuine connections, and no large-group crowds.

Personally hosted. Expertly guided.

Your dedicated Now Journey Tour Captain is with you throughout the journey, while expert local guides bring Italy's history, art, and culture to life.

Your Now Journey Tour Captain hosts throughout, while expert local guides bring Italy to life.

Discover Italy without the rush.

No one-night hotel stops. Guided discoveries are balanced with an open afternoon in Florence, a full independent day in Cortona, and time to explore Rome at your own pace.

No one-night stops. Guided discoveries, free time, and leisurely lunches from Tuscany to Rome.

Beautiful stays. Thoughtful details.

Well-located hotels, coordinated transportation, and local guide and driver gratuities included. No on-tour upselling—just more time to enjoy the journey.

Well-located hotels, seamless transportation, and guide and driver gratuities included. No on-tour upselling.

The Journey, through our guests' eyes

“The level of detail is remarkable, every hotel, every experience, every meal feels like it was handpicked just for you. These are the kind of “remember forever” moments that truly elevate travel.”
Rich H. — Now Journey Guest

Why travelers choose Now Journey

50+ five-star TripAdvisor reviews

A true small group of 8–12 guests, with a maximum of 16. Hotels in the heart of each destination, thoughtfully arranged transportation and sightseeing, priority admissions where available—and no unnecessary upselling while you are on tour.

Read Our TripAdvisor Reviews

10 Days from Venice to Rome

The Complete Itinerary

See exactly how each day unfolds—from your arrival by private water taxi in Venice to a final hosted evening among the layers of Rome.

Venice's Grand Canal in golden evening light

Chapter One

Days 1–2

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 your 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 cooking, wine and premium beverages included.

Included Today

  • Arrival support at Venice Marco Polo Airport
  • Private water-taxi arrival transfer
  • Tour Captain-led Discovery Walk
  • Opening dinner in Venice

Day 2

Venice: The Story Begins

With an expert local guide, explore Venice’s hidden corners and layered history through St. Mark’s Basilica, the Doge’s Palace, the historic prisons and the Bridge of Sighs, with the story of Casanova adding another layer of intrigue. Venice emerges not as a postcard, but as a republic shaped by power, faith and extraordinary beauty.

Skip-the-Long-Line Special Access Admissions Included: Enjoy reserved priority admission to St. Mark’s Basilica and the Doge’s Palace, allowing more time to discover Venice’s extraordinary history and beauty. Standard security procedures and attraction access requirements still apply.

Included Today

  • Skip-the-line entry to the Doge’s Palace and historic prisons
  • The Bridge of Sighs and its powerful symbolism
  • St. Mark’s Basilica, with time to quietly absorb its Byzantine splendor
  • Piazza San Marco and its hidden details, from the Clock Tower to Caffè Florian
  • Stories of emperors, empires, and the Winged Lion of Venice

This evening, your Tour Captain will invite you to join the group for an optional dinner, or the evening is entirely yours.

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Travelers overlooking Florence and its cathedral dome

Chapter Two

Days 3–4

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

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.

Discovery Walk: Florence

On our Discovery Walk, explore the heart of historic Florence, passing major landmarks including Giotto’s Campanile, the Baptistery and the Duomo. Discover Orsanmichele and the historic streets near Santa Margherita dei Cerchi, once home to prominent Florentine families. Conclude at the Ponte Vecchio, the city’s only bridge to survive World War II.

Enjoy the balance of the afternoon at leisure until our welcome dinner tonight.

Included Today

  • Private boat transfer to Venezia Santa Lucia
  • High-speed rail to Florence
  • Florence Discovery Walk
  • Welcome to Florence dinner

Day 4

Florence: Secrets & Treasures

Following our included special-access visit to the Accademia to stand before Michelangelo’s extraordinary David, continue with your expert local guide through Florence’s Renaissance heart. Discover the exterior landmarks of Santa Maria del Fiore, Giotto’s Bell Tower, the Baptistery and its Gates of Paradise, then continue through Piazza della Signoria and Piazza della Repubblica.

The afternoon is intentionally open. Wander, shop, linger over lunch, visit Santa Croce or choose an art and architecture experience shaped around your interests.

Included Today

  • Skip-the-line entry to the Galleria dell’Accademia, home to Michelangelo’s David
  • Exploration of Florence’s historic center, including Santa Maria del Fiore, Giotto’s Bell Tower, and the Baptistery
  • Admiring the legendary Gates of Paradise, as your guide shares the story behind Ghiberti’s masterpiece
  • A leisurely stroll through Piazza della Signoria and Piazza della Repubblica, where Florence’s past and present meet

This evening, your Tour Captain will invite you to join the group for an optional dinner, or the evening is entirely yours.

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Rolling green hills and a cypress-lined farmhouse in Tuscany

Chapter Three

Days 5–6

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 life and time that feels less scheduled.

Day 5

Tuscany: A Day of Flavor & Tradition

Rolling hills and cypress trees guide you into the 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 estate for a guided cellar visit, curated tasting and leisurely Tuscan lunch.

This afternoon, we take a scenic drive to the charming hill town of Cortona, nestled in the heart of Tuscany. Upon arrival at our charming Cortona hotel, your Tour Captain handles check-in, giving you time to relax before gathering for our Cortona Welcome Dinner—a perfect start to our stay.

Included Today

  • San Gimignano and Vernaccia toast
  • Family-run wine-estate visit and tasting
  • Regional Tuscan lunch
  • Cortona Welcome Dinner

Day 6

Cortona at Leisure

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. The evening remains open for an unhurried night in one of Tuscany’s loveliest hill towns.

Included Today

  • Full day of independent time in Cortona
  • Tour Captain recommendations for pacing and local possibilities

This evening, your Tour Captain will invite you to join the group for an optional dinner, or the evening is entirely yours.

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The Pantheon and its columned portico in Rome

Chapter Four · The Finale

Days 7–10

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 the climax in layers: Old Rome and its piazzas, Vatican City, imperial stones and the everyday beauty of a city that never stopped being alive.

Day 7

Discovery Walk: Rome

The Journey leaves Tuscany and continues south toward the Eternal City. After checking into our centrally located hotel, we join our Tour Captain for a Discovery Walk through the very heart of Old Rome.

Our exploration begins with a curious elephant—and from there, more than 2,000 years of Roman history begin to unfold before us.

We enter the extraordinary Pantheon and discover its remarkable story before continuing to Piazza Navona, one of Rome’s most beautiful public spaces and once the setting for ancient athletic competitions and later spectacular celebrations.

Our Discovery Walk continues through Campo de’ Fiori—the Field of Flowers. Do you know whose likeness stands in the famous statue at its center?

We also pass Largo di Torre Argentina and discover the dramatic story of Julius Caesar’s fate. Along the way, we may even spot some of Rome’s famous resident cats.

Tonight, we’ll gather for our hosted Welcome to Rome Dinner, featuring the wonderful flavors of Lazio.

Included Today

  • Journey from Cortona to Rome
  • Old Rome Discovery Walk with your Tour Captain
  • Pantheon admission and historic context
  • Piazza Navona, Campo de’ Fiori and Largo di Torre Argentina
  • Welcome to Rome dinner

Day 8

Vatican City

With Privileged Entry, explore the Vatican Museums, marvel at the Sistine Chapel, and discover St. Peter’s Basilica and Square when access permits.

As we enter St. Peter’s Square, watch for the Swiss Guard in their colorful uniforms. After our visit, Now Journey transportation will be arranged to return us toward our hotels.

Special Sightseeing Includes

Skip-the-Long-Line Special Access

Vatican Museums

Included admission and expert-guided touring of the Vatican Museums, home to some of the world’s most remarkable tapestries, paintings, sculptures and historic collections.

Sistine Chapel

Your expert guide prepares us for one of the world’s great artistic experiences before we enter the Sistine Chapel. Inside, discover Michelangelo’s breathtaking ceiling frescoes and his monumental Last Judgment, which spans the altar wall. A moment of quiet admiration in this sacred space is an unforgettable highlight of our Journey.

St. Peter’s Basilica and Square

Guided exploration of St. Peter’s Basilica and Square, including their history, magnificent architecture and extraordinary artwork. Special access arrangements are used where available and permitted by Vatican operations.

Priority and reserved-entry arrangements are subject to Vatican operations and do not bypass mandatory security screening or guarantee unrestricted access.

The afternoon and evening are intentionally open for independent discovery, with suggestions from your Tour Captain.

Included Today

  • Expert-guided Vatican City experience with privileged entry arrangements
  • Vatican Museums and Sistine Chapel admission
  • St. Peter’s Basilica and Square when access permits
  • Transportation back toward the hotels
  • Open afternoon and evening

This evening, your Tour Captain will invite you to join the group for an optional dinner, or the evening is entirely yours.

Day 9

Today’s Adventure: Imperial Rome

Today, we set out on a captivating stroll through Rome, where ancient ruins and modern life blend seamlessly.

As we wander, witness history woven into the city’s vibrant present, revealing a timeless narrative that continues to shape Roman life today.

Skip-the-Long-Line Special Access Admissions

The Colosseum & Roman Forum

Step into the heart of Ancient Rome with our expert local guide and enjoy included, advance-reserved admission to the legendary Colosseum and Roman Forum. Our special access arrangements help minimize time spent waiting in general admission lines, leaving more time to discover the extraordinary stories of emperors, gladiators and daily life in the Roman Empire. Mandatory security screening and official attraction procedures still apply.

The Colosseum

Explore the Flavian Amphitheatre with included admission and expert guiding as the stories of gladiators, emperors and public spectacles come into focus.

The Roman Forum

Walk through the ancient center of civic, political and religious life, with the Curia, Temple of Vesta, House of the Vestals and monumental triumphal arches placing Rome’s public history in context.

Palatine and Capitoline Perspectives

Discover how imperial residences, public monuments and Rome’s hills shaped the ancient city’s extraordinary urban story.

Imperial Rome Landmarks

Enjoy views and historical context surrounding Trajan’s Market, the imperial palace complexes, the Vittorio Emanuele II National Monument and other landmarks encountered along the route.

As evening falls, one final Roman celebration awaits.

Included Today

  • Colosseum admission with advance-reserved timed entry
  • Roman Forum admission and expert-guided exploration
  • Palatine and Capitoline perspectives
  • Imperial Rome sightseeing with expert local guide
  • Farewell to Rome Dinner

Day 10

Arrivederci, Italy

Breakfast is included this morning when departure timing allows. Guests ending in Rome may request guidance for Rome Fiumicino or Ciampino Airport, and extra nights can often be arranged when available.

Rome is the complete finale: a final espresso near the Pantheon, one more walk through ancient streets and the feeling that the essential Italian story has come full circle.

Included Today

  • Breakfast, schedule permitting
  • Rome departure guidance
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What's included

The details are handled. The discoveries still feel yours.

Nine hotel nights and 15 included meals—9 full breakfasts, 5 hosted dinners and 1 Tuscan winery lunch with tasting—join expert guides, Tour Captain hosting, admissions and thoughtful transportation.

9 nights & 9 breakfasts

Hotels in Venice, Florence, Cortona and Rome, with a full breakfast each morning.

5 hosted dining events

Five destination dinners, with the page’s established premium-beverage inclusion.

1 Tuscan winery lunch

A family-run estate visit, cellar experience, regional lunch and wine tasting.

Guides, admissions & movement

Tour Captain hosting, local experts, scheduled admissions, high-speed rail, private boat and road transportation.

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Hotel Collections

Same extraordinary journey. Your preferred level of accommodations.

Choose among three thoughtfully curated Hotel Collections. The itinerary, Tour Captain services, sightseeing, transportation and included dining remain exactly the same.

Illustrative refined Italian Deluxe hotel room with warm historic-city character
A Sense of the Deluxe Style

Signature Collection

DELUXE

Hand-selected 4- to 5-star properties emphasizing location, service, comfort and thoughtful room selection.

Your accommodations

At 4-star properties, Now Journey selects accommodations one category above the hotel’s entry-level room; at 5-star properties, accommodations begin with the standard category or better.

Illustrative Italian upper-category junior suite with a sitting area, terrace and city view
The Art of Staying Well

Lotus Hotel Collection

LOTUS

The Lotus Hotel Collection brings an elevated level of comfort and distinction to your Italian Journey.

The Lotus Difference

Thoughtfully selected premium accommodations, spacious rooms, Junior Suites, Suites, and preferred views or terraces where available. You may also ask to upgrade only selected hotels rather than every stay.

Representative compact Classic Collection Italian hotel room with a neatly made bed, simple wood furnishings, writing desk and luggage rack
Thoughtful Value

Classic Hotel Collection

CLASSIC

Our Classic Hotel Collection features thoughtfully selected, comfortable 3-star-plus hotels chosen for their location, character and convenience. Enjoy the very same Now Journey experiences, personalized Tour Captain service, included dining and unforgettable discoveries—with a more approachable level of accommodations.

Representative Classic accommodation. Exact properties and room categories are confirmed in your personalized Journey proposal.

All three collections enjoy the same itinerary, Tour Captain, expert local guides, sightseeing, transportation, admissions and included dining.

The collection images illustrate the Deluxe, Lotus and Classic accommodation styles; the destination hotel photographs below are examples of our Deluxe Collection. Exact properties, room categories and Lotus availability are confirmed in your personalized Journey proposal.

Compare Dates & Prices
Hotel Saturnia Venice

Venice

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

Florence hotel

Florence

Elegant, centrally located Deluxe stays such as Grand Hotel Cavour, Bernini Palace, L'Orologio or similar.

Hotel San Michele Tuscany

Cortona

Rustic Tuscan manor houses, villas and hill-town Deluxe properties including Villa Marsili, Hotel San Michele, Monastero di Cortona or similar.

Rome hotel

Rome

Perfectly placed Deluxe stays near the historic heart, including Palazzo Navona, Pantheon Iconic, La Minerva or similar.

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Dates & prices

Choose your season.

Explore our upcoming departures and find the dates that work best for you. Prices are in U.S. dollars, per person, based on two guests sharing a room. Included dining: 9 breakfasts, 5 hosted dinners and 1 Tuscan winery lunch with tasting.

Featured Departures

If you are comparing options, start here. These spring 2027 departures are our recommended Essential Italy dates.

Apr 27-May 6, 2027
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
Limited SpaceRequest this date
May 4-13, 2027
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
Limited SpaceRequest this date
May 25-Jun 3, 2027
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
Limited SpaceRequest this date

The journey is always the same. Every Hotel Collection includes the same itinerary, Tour Captain, expert local guides, and included experiences. Only your accommodations change.

Traveling solo? The published Deluxe Collection supplement is $2,990, and the Lotus Hotel Collection supplement is $4,900. Classic solo pricing will be confirmed in your personalized proposal.

All 2027 departures 10-day Venice to Rome

Spring

One of the best times to be in Italy: moderate temperatures, fewer crowds and spring atmosphere.

Mar 16-25
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date
Apr 6-15
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date
Apr 13-22
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date
Apr 20-29
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date
Apr 27-May 6
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
Limited SpaceRequest this date

May

Near-perfect weather, flowers, sunshine and la dolce vita.

May 4-13
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
Limited SpaceRequest this date
May 11-20
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
Limited SpaceRequest this date
May 18-27
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
Limited SpaceRequest this date
May 25-Jun 3
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
Limited SpaceRequest this date

June

A classic Italy window with warm days and high-demand departures.

Jun 8-17
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date
Jun 15-24
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date
Jun 22-Jul 1
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date

July & August

Fresh, hot Italian summer days and long golden evenings.

Jun 29-Jul 8
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date
Jul 13-22
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date
Aug 10-19
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date

Harvest Season

September brings Tuscany's harvest, late-summer warmth and some of the year's most requested weeks.

Aug 31-Sep 9
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date
Sep 7-16
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date
Sep 14-23
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
Limited SpaceRequest this date
Sep 21-30
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
Limited SpaceRequest this date

October

Autumn atmosphere, softer crowds and warm days that often linger into the month.

Sep 28-Oct 7
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
Limited SpaceRequest this date
Oct 5-14
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date
Oct 12-21
CLASSIC$7,979per personDELUXE$8,779per personLOTUS$11,579per person
AvailableRequest this date

Traveling solo? The published Deluxe Collection supplement is $2,990, and the Lotus Hotel Collection supplement is $4,900. Classic solo pricing will be confirmed in your personalized proposal.

All 2028 departures 10-day Venice to Rome

Spring

One of the best times to be in Italy: moderate temperatures, fewer crowds and spring atmosphere.

May

Near-perfect weather, flowers, sunshine and la dolce vita.

June

A classic Italy window with warm days and high-demand departures.

July & August

Fresh, hot Italian summer days and long golden evenings.

Harvest Season

September brings Tuscany's harvest, late-summer warmth and some of the year's most requested weeks.

October

Autumn atmosphere, softer crowds and warm days that often linger into the month.

Late Autumn & Holiday Season

Cooler days and festive city atmosphere make these late-season departures especially memorable.

Traveling solo? The published Deluxe Collection supplement is $2,990, and the Lotus Hotel Collection supplement is $4,900. Classic solo pricing will be confirmed in your personalized proposal.

Not sure which departure is best?

Tell us your preferred season, travel style and hotel collection. We will help you compare Essential Italy dates without pressure.

Ask for guidanceCompare the Three Journeys
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YOUR NEXT STEP

A Personal Proposal. No Pressure.

A thoughtful next step, with no booking commitment.

You’ve explored the Journey. Now let us help you make it yours. Requesting a proposal begins a personal conversation—not a booking commitment.

  1. 01Tell Us What You’re Considering

    Choose a departure and Hotel Collection, or tell us when you’d like to travel. Your existing selections carry into your proposal request.

  2. 02Personally Reviewed by Our Team

    A Now Journey specialist reviews your preferences, checks availability and prepares a personalized proposal with the options that suit your plans.

  3. 03Decide When You’re Ready

    Review the proposal, ask questions and consider the details without pressure. Requesting a proposal does not reserve space or require payment.

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Make the Journey Your Own

Open time is part of the Journey.

Some of the most memorable travel moments happen when the schedule opens up. Enjoy that time completely at leisure, follow your Tour Captain’s suggestions, or choose from curated experiences we can help arrange.

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Guest reviews

The proof is in the way guests talk about it.

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.
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Plan & prepare

Is this your kind of Italy?

Expect moderate walking in historic centers, including cobblestones, stairs and time standing during guided visits, alongside independent time and travel between destinations.

Included: 9 hotel nights, daily breakfast, 5 hosted dinners, a Tuscan winery lunch with tasting, itinerary-listed guided visits and admissions, the Venice arrival water taxi and planned tour transportation. Not included: international airfare, optional experiences, other meals and your Rome airport departure transfer.

Walking & Activity: What to Expect

Our journeys are thoughtfully paced, but exploring Italy’s historic centers means walking on cobblestones, uneven pavement, stairs and occasionally uphill streets. These operational estimates are provided to help you plan comfortably.

Day 1 · Venice

Approximately 2 miles for the orientation Walkabout, canal-side routes and walking to the welcome dinner. Expect bridges, cobblestones and stairs.

Day 2 · Venice

Approximately 1.4 miles during the included guided sightseeing, with historic lanes, bridges and periods of standing.

Day 3 · Florence

Approximately 3 miles for the orientation Walkabout and walking to the included Florence dinner.

Day 4 · Florence

Approximately 4 miles for included Renaissance sightseeing, museum visits and associated historic-center walking. Independent-afternoon activity varies by guest.

Day 5 · San Gimignano & Cortona

Approximately 3 miles across hill-town streets, inclines and stairs during San Gimignano sightseeing, Cortona orientation and walking to dinner.

Day 6 · Cortona

This is an independent day, so walking varies according to your plans and is not required as a scheduled group activity.

Day 7 · Rome

Approximately 3–4 miles for the Old Rome orientation and welcome dinner, including cobblestones and busy historic-center streets.

Day 8 · Vatican City

Approximately 4–5 miles for Vatican sightseeing and associated walking, with extended standing and stairs possible at major sites.

Day 9 · Imperial Rome

Approximately 3 miles for the Colosseum and Imperial Rome sightseeing, including ancient paving, uneven surfaces, stairs and inclines.

Day 10 · Departure

No scheduled guided walking activity. Your departure arrangements determine the day’s practical activity.

Guided tours may involve extended standing and outdoor walking in varying temperatures. Comfortable walking shoes are important. Guests should be comfortable moving independently through historic centers; travelers with mobility concerns should speak with Now Journey before booking.

Walking distances are estimates and may vary with hotel locations, sightseeing arrangements, weather and operational conditions. Your Tour Captain coordinates the daily activities. Optional excursions and independent exploration may involve additional walking.

Included dining and sightseeing

The day-by-day “Included Today” lists show the included visits and services. Nine breakfasts are included; departure-morning breakfast depends on flight timing. Dining includes 5 hosted dinners and 1 Tuscan winery lunch with tasting. Other meals and optional experiences are extra. Included admissions do not eliminate security procedures or every queue.

Transportation and luggage

Planned transportation uses appropriately sized private vehicles or luxury micro-coaches, with high-speed Italian rail between Venice and Florence. Ask the team about luggage arrangements and limits for your departure before booking.

How do the Hotel Collections differ?

All three collections share the same itinerary and included experiences. CLASSIC offers thoughtfully selected 3-star-plus accommodations; DELUXE features the curated 4- and 5-star collection; the Lotus Hotel Collection offers preferred upper room categories. See the authoritative Hotel Collections details and hotel examples.

Solo travel and pricing

Prices are per person, double occupancy. The supplements for a double room for solo use are $2,990 for DELUXE and $4,900 for the Lotus Hotel Collection. Request a Journey Proposal for your selected departure and room preference; Classic solo pricing is confirmed by proposal.

Arrival and departure transfers

The private water-taxi arrival transfer from Venice Marco Polo Airport is included. Your Rome airport departure transfer is arranged separately; your proposal specialist can help with the planning.

Independent time and optional activities

An independent afternoon is planned in Florence, Day 6 is open in Cortona, and Rome includes time for discoveries of your own. Optional experiences cost extra and are clearly identified.

Booking and payment terms

Our team reviews your preferences, confirms availability and prepares a personalized proposal. Sending an inquiry is not a confirmed booking or reservation hold. Review the existing booking and payment terms before reserving.

Can I choose a different journey length?
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