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Florence and Brunelleschi's dome across the Renaissance skyline

An Italian Encore

Return to the Great Cities

A new chapter in the places that became part of our story.

The cities you remember. A journey you haven’t experienced.

This is not a repeat of Italy’s Great Cities. It is the next chapter.

Venice → Bologna → Florence → Cortona → Rome → Sorrento & Ischia

  • 12 days / 11 nights
  • Oct 31–Nov 11, 2027 · May 14–25, 2028
  • 8–12 guests
  • Tour Captain hosted
Itinerary Dates & Prices

No obligation. No pressure. Just thoughtful planning.

Your Journey at a Glance

Your Journey Ahead

Five Italian chapters. One beautiful return.

From lagoon light to the Bay of Naples—a return shaped by fresh perspectives, unhurried moments and places that still feel like part of us.

Scroll through citiesSwipe through cities

  1. 01Venice2 nights · Journey beginsBegin where the map becomes water: Bovolo views, the outer lagoon and an evening gondola.
  2. 02Bologna & Florence2 nights in FlorenceTaste first. Then follow the Medici through Florence with a fresh point of view.
  3. 03Cortona2 nights · TuscanyA winery lunch, Cortona at golden hour and a full day with nowhere you have to be.
  4. 04Rome3 nightsLook below the streets—and beyond the center—for Rome’s deeper layers.
  5. 05Sorrento & Ischia2 nights · Journey finaleCoastal light, an included private boat to Ischia or a full day in Sorrento carry the Journey to its farewell evening.

The Journey Story

Returning to Italy with fresh eyes.

Italy has a way of remaining with us—the light on the water, the sound of a piazza at evening, the laughter around a table. Return to the Great Cities brings us back to places that feel familiar while opening completely new doors: a different Venice, a flavorful pause in Bologna, a more personal Florence, time to breathe in Cortona, new layers beneath Rome and a final Mediterranean chapter beside the Bay of Naples.

Mark Story with Now Journey guests overlooking Florence

A personal invitation

For those who have shared Italy with us before.

Some of my favorite memories in Italy have very little to do with monuments. They are the laughter around the dinner table, the unexpected moments during a walk, and the friendships that continued long after we returned home.

I created Return to the Great Cities for guests who have shared those moments with us before. We’ll return to a few traditions we love, but most of this Journey opens completely new doors—new neighborhoods, new stories and new tables.

It is less a return to an itinerary than a return to the feeling we shared there.

— Mark Story

Created with returning guests in mind

You already know how we travel.

You remember the small group, the personal attention and the pleasure of having the details handled without losing the freedom to make the Journey your own. This time, the feeling is familiar—but the experiences are new.

What You’ll Remember

  • A true small group of typically 8–12 guests
  • A dedicated Tour Captain
  • Central, characterful hotels
  • Beautiful evenings around the table
  • Guided experiences balanced with real leisure
  • The feeling of being personally cared for

What Will Feel New

  • Venice from the Bovolo
  • The outer lagoon
  • A culinary pause in Bologna
  • The Medici story from a fresh perspective
  • Cortona as an unhurried Tuscan interlude
  • Underground and imperial Rome
  • Ischia and the Bay of Naples
Now Journey guests raising a glass together around a table

The best part was never only the cities.

Explore the complete Journey

The Complete Itinerary

Twelve days designed around deeper stories, slower moments and a finale on the Bay of Naples. Open one destination at a time, or expand the complete Journey.

Venice Grand Canal in warm evening light

Chapter One

Days 1–2

Venice

A spiral stair above the rooftops, an aperitivo welcome, the outer lagoon and an evening on the canals.

Return by water. Look in a new direction.

Venice opens the Journey gently, with a new vantage point and enough room to remember why this impossible city stays with you.

Day 1

Welcome back to Venice

A beloved tradition

Arrive in Venice and settle into your hotel. Later, meet your Tour Captain and fellow guests for a gentle first discovery centered on the Scala Contarini del Bovolo, where the spiral stair and rooftop outlook offer a fresh introduction to the city.

An aperitivo eases the group into the evening before the included Welcome Dinner sets the tone for the Journey.

Included Today

  • Arrival orientation and Tour Captain welcome
  • Scala Contarini del Bovolo visit
  • Hosted aperitivo
  • Welcome Dinner in Venice

Your stay begins tonight

Venice

2 nights

Deluxe

Hotel Saturnia & International or similar

A historic and warmly Venetian address near La Fenice and St. Mark’s Square.

Deluxe | Elevated

Nolinski Venezia

Superior Room

Optional city upgrade: $700 per night · 2 nights

Planned properties and room categories are subject to availability and confirmation in your personalized Journey Proposal.

A new chapter

Set out by private boat for a flexible half-day exploration of Venice's outer lagoon and one of its less-visited island communities. The exact route is shaped by local conditions and confirmed operationally, keeping the experience intimate and responsive to the day.

The afternoon is completely open. Revisit a favorite corner, choose a museum, linger over lunch or simply wander. This evening, an included gondola experience brings the group back together on the water.

Included Today

  • Private half-day lagoon boat experience
  • Outer-island discovery, route subject to conditions
  • Open afternoon in Venice
  • Evening gondola experience
Florence and its cathedral dome

Chapter Two

Days 3–4

Florence

Bologna's flavors lead into a Florence story shaped by ambition, patronage and the extraordinary Medici family.

One city feeds the Journey. Another changes its point of view.

Bologna is enjoyed without an overnight before Florence and the Arno move to the center of the next chapter.

A new chapter

Depart Venice and pause in Bologna for a half-day tasting experience that introduces Emilia-Romagna through its markets, arcades and celebrated food traditions. Bologna is a flavorful interlude rather than an overnight stop.

Continue to Florence and settle into your hotel. This evening, gather for an included Welcome to Florence Dinner.

Included Today

  • Planned transportation from Venice
  • Half-day Bologna tasting experience
  • Onward transfer to Florence
  • Welcome to Florence Dinner

Your stay begins tonight

Florence

2 nights

Deluxe

Hotel Brunelleschi or similar

A characterful Florentine hotel in the historic center, moments from the Duomo and the city’s Renaissance landmarks.

Deluxe | Elevated

Hotel Brunelleschi

Junior Suite, Executive Level Room

Optional city upgrade: $470 per night · 2 nights

Planned properties and room categories are subject to availability and confirmation in your personalized Journey Proposal.

Follow Florence through the rise, reach and contradictions of the Medici. With an expert local guide, connect palaces, churches, public squares and works of art to the family whose influence helped shape the Renaissance.

The later afternoon and evening remain open for personal discovery from your riverside base.

Included Today

  • Expert-guided Medici story walk
  • Context across Florence's historic center
  • Open afternoon and evening
Cortona in the Tuscan hills at evening

Chapter Three

Days 5–6

Cortona

Vine-covered hills, 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.

The landscape shifts as rolling hills and cypress trees guide you into the Tuscan countryside. Travel directly to 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.

Included Today

  • Family-run wine-estate visit and curated tasting
  • Regional farm-to-table winery lunch
  • Cortona Discovery Walk
  • Cortona Apericena

Your stay begins tonight

Cortona

2 nights

Deluxe

Monastero di Cortona Hotel & Spa

A beautifully restored former monastery offering a quiet, atmospheric retreat within historic Cortona.

Deluxe | Elevated

Monastero di Cortona Hotel & Spa

Junior Suite

Optional city upgrade: $410 per night · 2 nights

Planned properties and room categories are subject to availability and confirmation in your personalized Journey Proposal.

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

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

Included Today

  • Full day of independent time in Cortona
  • Tour Captain recommendations for pacing and local possibilities
Historic Rome and the Pantheon district

Chapter Four

Days 7–9

Rome

Three nights create room for underground archaeology, imperial Rome and a new perspective beyond the center.

Ancient Rome, reconsidered.

The familiar city gains depth when the Journey moves below the streets and into Rome's monumental imperial civic spaces.

A new chapter

Travel from Cortona to Rome and settle into your central hotel. Then join an expert-led exploration beneath the city's present-day surface, where excavated spaces and layered foundations reveal how one Rome was built upon another.

This evening, gather for an included Welcome to Rome Dinner.

Included Today

  • Planned transportation to Rome
  • Expert-guided underground Ancient Rome experience
  • Three-night central hotel stay
  • Welcome to Rome Dinner

Your stay begins tonight

Rome

3 nights

Deluxe

The Pantheon Iconic Rome Hotel or similar

A refined central address near the Pantheon, Piazza Navona and the heart of Rome’s evening life.

Deluxe | Elevated

Orient Express La Minerva

Superior Room

Optional city upgrade: $560 per night · 3 nights

Planned properties and room categories are subject to availability and confirmation in your personalized Journey Proposal.

Choose one of two included guided experiences: the monumental Baths of Caracalla or the extraordinary remains associated with the Baths of Diocletian. The operating selection, access and timing are confirmed in advance for your departure.

The balance of the day is open. Your Tour Captain may invite the group to an optional dinner, or the evening is entirely yours. This dinner is not counted among the six included dinners.

Included Today

  • Choice of one included imperial bath experience
  • Expert context and applicable admission
  • Open afternoon in Rome
  • Optional, guest-paid dinner opportunity

A new chapter

The third Rome day looks beyond the historic center to Hadrian’s Villa, where architecture, landscape and imperial ambition reveal another dimension of the ancient world. The exact access and timing are confirmed for each departure.

Planned Today

  • Hadrian’s Villa experience
  • Expert historical context
  • Third night in Rome
The blue coast near Sorrento

Chapter Five

Days 10–12

Sorrento

Two nights allow time for Ischia, a full leisure day, the Farewell Dinner and an included transfer to Naples Airport.

The Journey exhales beside the sea.

Sorrento and Ischia bring Mediterranean time, coastal light and a finale with an entirely different rhythm.

We travel from Rome to the Bay of Naples

Leave Rome for the Bay of Naples and the Journey’s Mediterranean chapter.

Included Today

  • Transportation from Rome to the Bay of Naples
  • First of two nights in Sorrento
  • Welcome to Sorrento Dinner

Your stay begins tonight

Sorrento

2 nights

Deluxe

Grand Hotel Capodimonte or similar

A classic Sorrento hotel with terraced gardens and broad views across the town and Bay of Naples.

Deluxe | Elevated

Grand Hotel Capodimonte or similar

Suite

Optional city upgrade: $880 per night · 2 nights

Planned properties and room categories are subject to availability and confirmation in your personalized Journey Proposal.

Your final full day is entirely at leisure. Sleep late, linger over breakfast, explore Sorrento independently or follow a personal recommendation from your Tour Captain.

This evening, gather for the included Farewell Dinner and celebrate the Journey together.

Included Today

  • Full day at leisure in Sorrento
  • Tour Captain recommendations and support
  • Farewell Dinner in Sorrento

Breakfast is included as flight timing allows. A planned group transfer to Naples International Airport is included, with timing coordinated around the departure framework provided for your Journey.

Included Today

  • Breakfast, subject to departure timing
  • Included group transfer to Naples Airport (NAP)
  • Departure support from your Tour Captain
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What's included

The details are handled. The discoveries still feel yours.

The core Journey includes 11 hotel nights, daily breakfast, six hosted dinners, the listed guided experiences, admissions and planned transportation—including the departure transfer to Naples Airport.

Your dedicated Tour Captain

Your host throughout the Journey, coordinating transitions, orienting you in each destination and helping with the practical details along the way.

11 hotel nights & daily breakfast

Two nights Venice, two Florence, two Cortona, three Rome and two Sorrento. Departure-morning breakfast remains subject to flight timing.

Six included dinners

Venice Welcome, Florence Welcome, Cortona Apericena, Rome Welcome, Sorrento Welcome and Sorrento Farewell Dinner.

Guiding, admissions & transportation

All itinerary-listed guided sightseeing and admissions, planned intercity transportation, Venice lagoon boat experience, the private boat to Ischia and the included group transfer to NAP.

International airfare, lunches unless specifically added to a final proposal, personal expenses, the optional Lake Como pre-tour and the optional Day 8 dinner are not included. Final operating details are confirmed in departure documents.

First: Choose your Journey

Begin in Venice—or beside Lake Como.

Return to the Great Cities is the complete 12-day, 11-night Journey. The existing Lake Como Prelude may be added before Venice; its hotel, price and transfer details are confirmed in your personalized proposal.

Primary Journey

Return to the Great Cities

12 Days / 11 Nights

Venice → Sorrento

Five beautifully paced Italian chapters created with returning guests in mind.

Optional Prelude

Begin Beside Lake Como

Add the existing Lake Como Prelude

Lake Como → Venice → Sorrento

Arrive early and begin the main Journey refreshed. Final hotel, price and transfer details are confirmed in your proposal.

Dates & prices

Choose your departure.

Prices are per guest based on double occupancy. Every departure offers the complete itinerary in both the Deluxe and Deluxe | Elevated hotel collections.

DELUXECharacterful four- and five-star hotels
DELUXE | ELEVATEDLandmark hotels and enhanced room categories

Scheduled departures

Choose the late-autumn atmosphere of 2027 or the spring light of 2028. Both are complete 12-day, 11-night Journeys from Venice to Sorrento.

Oct 31–Nov 11, 2027

12 days / 11 nights · Venice to Sorrento

DELUXE$11,579per guestDELUXE | ELEVATED$18,579per guest
AvailableRequest a Journey Proposal

May 14–25, 2028

12 days / 11 nights · Venice to Sorrento

DELUXE$11,579per guestDELUXE | ELEVATED$18,579per guest
AvailableRequest a Journey Proposal
Prefer to elevate only part of your Journey? Explore individual city upgrades.
Individual hotel upgrades may be requested by city and remain subject to availability. The listed supplements apply only when requested with the Deluxe collection; they are not added to the complete $18,579 Deluxe | Elevated price. Request an individual city upgrade and name the city or cities in the request form.

Prices are quoted per guest in U.S. dollars, based on double occupancy, and are land-only unless your proposal states otherwise. International airfare is separate. Solo pricing, room categories, deposit terms and the final hotel plan are confirmed in your personalized Journey Proposal. The Deluxe | Elevated package price is fixed and already includes its Elevated accommodations; individual city supplements are not added to $18,579.

Hotel collections

One Journey. Two ways to stay.

The hotel for each destination now appears on the first night of that itinerary chapter, exactly where it becomes part of the Journey. Here is the simple distinction between the two collections.

Deluxe

Characterful four- and five-star hotels

Thoughtfully selected, centrally located properties with a strong sense of place, comfortable rooms and the personal service expected on every Now Journey.

Deluxe | Elevated

Landmark hotels and enhanced room categories

The same complete itinerary, Tour Captain service, sightseeing, transportation and dining, paired with the listed elevated properties, suites or enhanced room categories.

Hotels shown in the itinerary are the planned collections, not a guarantee of a particular room, category or property. Now Journey may substitute a comparable hotel when availability or operating conditions require it. All selections and requested upgrades are confirmed in the personalized Journey Proposal.

Guest reviews

Why guests travel with us again.

Now Journey guests consistently mention thoughtful planning, seamless logistics, personal service, 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.

Frequently asked questions

The practical details.

If your question is not answered here, request a proposal and a Journey specialist will help shape the right departure.

No. The first Journey introduced the landmarks. This one reveals the layers between them, with a different Venice, Bologna, the Medici story, Cortona, underground and imperial Rome, Hadrian’s Villa, Ischia and generous leisure time.

No. It was created with returning guests in mind, but any traveler drawn to a deeper, thoughtfully paced Italian Journey is welcome.

Fresh experiences include the Bovolo and outer lagoon in Venice, a Bologna tasting, the Medici story in Florence, an unhurried Cortona interlude, underground and imperial Rome, Hadrian’s Villa and Ischia.

Days 6 and 11 are completely at leisure, with additional open time in Venice, Florence and Rome. The Journey is intentionally paced to make independent discovery feel possible.

It is the existing optional pre-tour addition before the 12-day Journey. Availability, hotel, price and transfer details are confirmed in your personalized proposal.

Both collections include the same complete Journey and personal Now Journey service. Deluxe features characterful four- and five-star hotels; Deluxe | Elevated adds the listed landmark properties and enhanced room categories.

Yes, individual city upgrades may be requested with the Deluxe collection, subject to availability. The applicable nightly supplement is confirmed in your proposal and is not added to the complete Deluxe | Elevated price.

Groups typically include 8 to 12 guests, with a maximum of 16, and are hosted by a dedicated Now Journey Tour Captain.

Six dinners are included: Venice Welcome, Florence Welcome, Cortona Apericena, Rome Welcome, Sorrento Welcome and the Sorrento Farewell Dinner. The possible group dinners on Days 6 and 8 are optional and guest-paid.

The named hotels are the planned collections. Exact assignments and room categories are subject to availability and confirmed before departure; comparable substitutions may be made when necessary.

Boat experiences depend on safe local operating conditions. Now Journey will adapt routing or provide an appropriate alternative when conditions require it.

Your personalized proposal will confirm the appropriate arrival framework for Venice. On Day 12, the confirmed itinerary includes a planned group transfer to Naples International Airport, coordinated around the Journey’s departure framework.

Ready to return?

Perhaps the first Journey never really ended.

Italy has a way of calling us back—not to repeat what came before, but to discover what the next chapter holds. Tell us when you would like to travel, whether Lake Como belongs at the beginning and which hotel collection feels right for you.

Request a Journey ProposalAsk Us Anything