THE ORIGINAL SMALL GROUP TOUR OF ITALY

Italy's Great Cities (12 Day)

Story-Driven, Thoughtfully Paced 11-Day Journey Through Italy
Boutique 4+ to 5-Star Hotels | Seasons: Apr-June, Sep-Oct
Balanced – no rushing • Small Group Touring → 8 to 12 Guests (Max 16)

 

Italy's Great Cities: 12-Day Story of Italy —

Italy’s Great Cities is a 12-day small group tour of Italy created for travelers who want more than a highlight reel. This thoughtfully paced, story-driven journey through Venice, Florence, Tuscany, Rome, and the Amalfi Coast allows time to linger, absorb, and truly connect with each destination. Led by expert Now Journey Tour Captains, the experience unfolds like a well-told story — each place a chapter, each day designed to build context, meaning, and emotional connection. Blending iconic cultural landmarks with regional cuisine, boutique hotels, and immersive moments, the journey flows naturally, with fewer rushed transitions and space for reflection. It’s Italy experienced with warmth, rhythm, and perspective — where the story stays with you long after you return home.

Our Tours Are Designed to Feel Different
The Italy’s Great Cities journey is shaped around presence, not pace. With an average of 8 to 12 guests (maximum 16) and a dedicated Tour Captain hosting throughout, the rhythm of travel slows — allowing connection, conversation, and the joy of simply being there.


Discovery Walk Planning Travel for 2026? Explore the Trip Tabs below — when it feels right, we’ll prepare a Complimentary Tour Proposal.

📩 Send Me the Details | 💬 Ask a Question | 📞 Call & Chat



Discover the Best Tour to Italy. Take it from our guests:



See Full ItineraryRead our 5-Star TripAdvisor Reviews


Designed for Connection.
Not Crowds.

• Many companies call 24 guests a small group — we believe something else.
• We believe intimacy changes everything — how you dine, explore, and connect.
• That's why 16 guests is our limit, and a Tour Captain is always at the heart of the journey.

Because the most meaningful moments in travel aren't on a checklist.

Discovery WalkGet Started: Receive your Free Tour Proposal — then decide if it feels right.

See Full ItineraryTimeless Moments in Italy's Great Cities.

We're different from mainstream tour operators. Our Italy small group tours are intentionally limited in size, allowing for a more personal and flexible experience. We favor off-the-path restaurants and thoughtfully chosen experiences, and our expert Tour Captains focus on guiding and storytelling — not upselling — so you can simply enjoy a world-class, see-it-all Italy journey without distractions.
★ Your Italian Story begins here. Step into the Journey, one Chapter at a time.
Chapter 1: Venice
Gondolas glide as Venice whispers its Secrets
Chapter 2: Florence
David's city, Florence of the Renaissance
Chapter 3: Under the Tuscan Sun
Vine-covered hills in the heart of Tuscany

Chapter 4: Rome
A Thousand Roads Lead Always to Rome
Chapter 5: Pompeii, Sorrento & the Amalfi Coast
The Costa Amalfitana is the perfect finalé

Leave the details to us – We handle everything: Travel, simplified.
  • All-inclusive special-access sightseeing with admissions included — no hidden fees.
  • Expert local guides & dedicated Tour Captain for a seamless, insider-led experience.
  • Your Now Journey Tour Captain (a professional tour director and storyteller) travels with the group throughout the journey, providing continuity, care, and insight at every stage.
  • Balanced itinerary with immersive touring and ample leisure time.
  • Hand-Picked, Heart of City Hotels feature Classic: 3-Star + and Deluxe: 4 to 5-Star properties.
  • Skip-the-long-line access at major sites — no waiting in long lines, no flags, no big buses.
  • Exclusive Tuscan Wine Experience & paired luncheon in a stunning vineyard setting.
  • Signature moments — rooftop prosecco toasts, hidden gems, and even complimentary laundry*.
  • No annoying Upsell while on Tour — just a beautifully curated, immersive journey.
  • Small Group Touring – 8 to 12 Guests (Max 16)

  • Read real Reviews from Our Guests | Read Reviews on TripAdvisor


    Our Popular 12-Day Adventure: Venice to the Amalfi Coast: Italy isn’t meant to be rushed — So We Designed a Journey That Isn't.

    ★ "Every day, every place, every meal, every experience was amazing! I can't say enough good things about our entire Journey. Thank you and Now Journey for being such a major part in making our whole European adventure such a success!" — Edward K.

    "I can't say enough about our recent trip to Italy. It was perfection from beginning to end. We never had any worries from our transportation, to our luggage handling, to our guides who navigated us through museums and ancient ruins. Our hotel accommodations were all perfect. NowJourney did an exceptional job planning and we even got surprises along the way that were so much appreciated. Our tour guide Gina was knowledgeable, friendly, and truly tried to make this a special experience for the entire group." —  Tammy A.

    Are you considering Tauck? Discover a more intimate Italy with Now Journey. Our Journeys are intentionally small up to 16 like-minded guests.

See Full ItineraryElegance: Perfect-pace. Uniquely Italian.

Just like a great novel, Italy's Great Cities begins in Venice on San Marco Island, where your story-driven, guided Italy tour unfolds at an unhurried pace. Designed as a luxury small group Italy experience, the journey moves thoughtfully through each chapter. And like the perfect finale to a great story, the Enchanted Amalfi Coast Adventure brings your Italian journey to a breathtaking close.

How Your Journey Is Designed:

  • A Dedicated Tour Captain — beginning to end
    A constant, friendly presence who knows your name, your rhythm, and how to make every moment feel effortless — from the first Ciao to the farewell toast.
  • True Small Group Experience
    Travel with just 8 to 12 guests (Max 16), creating space for connection, flexibility, and a more personal journey.
  • Privately Guided Touring with Fast-Track Access
    Skip the long lines and step straight into Italy’s most iconic sites with expert local guides.
  • Exceptional Local Guides
    Warm, English-speaking storytellers who don’t recite history — they bring it to life.
  • Signature Discovery Walks
    Led by your Tour Captain, designed to help you truly know each city beyond the highlights.
  • Seamless Arrival in Venice
    Included meet-and-greet airport transfer from Venice Marco Polo Airport (VCE).
  • Signature Venetian Welcome
    A rooftop reception in Venice with a prosecco toast — the perfect opening chapter.
  • Luggage Handling Throughout
    Your bags are taken care of, so you can travel light and free.
  • No Surprise Up-Sells — Ever
    What’s included is included. No pressure. No awkward moments.
  • Effortless Transportation
    Premium fast trains and micro-concept transportation — never large tour buses.
  • Mid-Journey Laundry Service
    Complimentary service* mid-way through your Journey up to €25/person.
  • Hand-Picked, Heart-of-the-City Hotels
    Carefully selected 4+ to 5-star properties chosen for character, warmth, and location.
  • Transparent Pricing
    No hidden fees, no city taxes at checkout. Gratuities included — except for your Tour Captain.

★ A Dining Experience Unique in the Industry

19 Meals Included with Unlimited Premium Beverages
— 11 full hot buffet breakfasts
— 7 Now Journey-style hosted dinners
— 1 luncheon with wine tasting and thoughtfully paired morsels
— 2 Italian Apericeni
— More surprises along the way


Italy’s Great Cities Tour — Quick Answers

•  What’s included in the tour?
Boutique hotels, expert guides, Tour Captain, breakfast, industry-leading select dinners, skip-the-line sightseeing & unique experiences like a gondola ride, rooftop surprises and our Tuscan vineyard wine-tasting lunch.

• How many guests on the tour?
Small groups of 8–12 travelers (Max 16).

•  Best time to go to Italy?
Spring (Apr–Jun) and fall (Sep–Oct) for great weather, lighter crowds, and seasonal charm.


Frances Mayes in "Under the Tuscan Sun" once said that "...most trips have an underlying quest. We're looking for something. What? Fun, escape, adventure--but then what?"

Everyone travels for different reasons, but my question for you would be what are you looking for?

See Full ItineraryHere's Everything: Venice to the Amalfi Coast

Each day of Italy's Great Cities builds naturally on the one before it, allowing guests to experience Italy's iconic destinations while also discovering quieter moments, local traditions, and unexpected stories along the way.
One of Now Journey's most popular small group adventures begins upon arrival at Venice Marco Polo International Airport (VCE Airport Code) and finalés on the Amalfi Coast (NAP Airport code).

Italy's Great Cities is offered in three thoughtfully designed formats (12 Day - our Original Small Group Italy Tour: Venice to the Amalfi Coast, 14 Day: Lake Como to Amalfi Coast and our 10 Day Venice to Rome) — allowing you to choose the rhythm that best fits the way you want to experience Italy.


Chapter 1: Venice

La Serenissima: The Most Serene —
2 Days, 2 Nights


DAY 1: WELCOME TO BEAUTIFUL VENICE

Begin your Journey in signature Now Journey style: a seamless airport arrival complete with a warm welcome and included private water taxi to our hotel in the very heart of San Marco Island. Check in, refresh, and get ready for your first taste of Venice.

Discovery WalkDiscovery Walk
Later today, you will meet your Tour Captain and begin our Discovery Walk — a signature Now Journey touch: a short orientation with your Tour Captain through Venice's highlights, including Piazza San Marco, the Campanile, the Grand Canal, and more. It's the perfect warm-up before tomorrow's immersive guided tour.

Journey Dinners IconOur Venetian Opening Night: An Evening Together

Later this evening, we'll gather at one of our favorite Venetian restaurants for an Italian dinner inspired by the regions of Italy, thoughtfully paired with excellent wines and premium beverages — all included of course.

Journey Hotels IconWhere We Stay in Venice, 2 Nights with breakfast

Deluxe Hotels Collection —
Hotel Saturnia & International, Hotel Monaco & Grand Canal or Similar

Our Deluxe Collection features thoughtfully selected 4- and 5-star hotels, including upgraded rooms at 4-star properties and refined entry-level rooms at 5-star stays. Guests may inquire with their Trip Specialist about larger rooms or higher-category accommodations with specific views, where available.

Classic Hotels Collection
Our Classic Collection offers well-located 3-star-plus hotels featuring private bathrooms, air conditioning, continental breakfast, and heart-of-the-city locations.

DAY 2: VENICE: The Story Begins

Sightseeing IconToday's Adventure: The Story of Venice – Her Secrets & Treasures

Discover Venice’s hidden corners and layered history with our local guide as you explore St. Mark’s Basilica, the Doge’s Palace, the Old Prison, and the Bridge of Sighs — along with the story of Casanova.Venice Canal

Discover Venice's hidden corners and layered history alongside our local guide as today's story unfolds.

From the glittering mosaics of St. Mark’s Basilica to the seat of Venetian power inside the Doge’s Palace, you’ll step into a world of intrigue, ambition, and beauty. Cross the haunting Bridge of Sighs, explore the historic prisons, and hear tales of justice, secrecy, and the legendary Casanova — all woven together as Venice reveals her secrets and treasures.

Today’s highlights include:

    • 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

Gondola IconVenetian Gondola Experience

Later today, just before sunset, enjoy an included gondola ride through Venice’s storied canals, accompanied by live musicians.
In the event of inclement weather, this experience may be replaced with a thoughtfully selected alternative later in the journey.

Enjoy the balance of the afternoon and evening at your leisure.

May We Suggest?
• We think simply soaking up Venice this afternoon is a great plan, but if you'd like to fill it up a bit more, consider:

— Isle of Murano Glass Blowing Demonstration: A free visit can be arranged, just ask your Now Journey specialist.

Your Tour Captain will invite you to an optional dinner after the Gondola ride, and they can also help you with dining reservations if you choose to explore lovely Venice on your own.

BACK TO TOP      Got a question? CHAT HERE.



Chapter 2: Florence

Birthplace of the Renaissance –
2 Days, 2 Nights


DAY 3: ONWARD TO FLORENCE

This morning, Venice gently fades behind us as we journey toward the artistic heart of Italy in belle Florence. After a relaxed breakfast, transfer by private boat to Venezia Santa Lucia, where you’ll board a comfortable high-speed train bound for Florence — a seamless and scenic transition from lagoon to Renaissance splendor.

Orientation Walk IconDiscovery Walk: Florence

Upon arrival to Florence we will begin our Discovery Walk and explore the heart of the city. We'll see the impressive Giotto's Campanile, the Baptistery, the Duomo, the historic Ponte Vecchio and end at our hotel.

Journey Dinners IconWelcome to Florence Dinner: Tuscany's Regional Specialties

Your Tour Captain hosts a warm welcome dinner at a hidden restaurant that features authentic Tuscan cuisine, premium beverages, and generous pours of local wines from Tuscany and Chianti.

Journey Hotels IconWhere We Stay in the Heart of Florence, 2 Nights with breakfast

Deluxe Hotels Collection —
Grand Hotel Cavour, Hotel Bernini Palace or Similar

Our Deluxe Collection features thoughtfully selected 4- and 5-star hotels, including upgraded rooms at 4-star properties and refined entry-level rooms at 5-star stays. Guests may inquire with their Trip Specialist about larger rooms or higher-category accommodations with specific views, where available.

Classic Hotels Collection
Our Classic Collection offers well-located 3-star-plus hotels featuring private bathrooms, air conditioning, continental breakfast, and heart-of-the-city locations.

BACK TO TOP      Got a question? CHAT HERE.


DAY 4: FLORENCE – Birthplace of the Renaissance

Sightseeing IconToday's Adventure: Florence Secrets & Treasures

Florence greets you with elegance, artistry, and timeless beauty.
Walk in the footsteps of masters as today’s exploration brings the city’s artistic soul to life — where stone, canvas, and history combine to shape one of the most influential cities in the world.

Florence Journeyers enjoying the afternoon sun.

Today's highlights include:

  • 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

Following our Secrets & Treasures experience, the remainder of the day is yours to enjoy — wander, linger, or simply savor Florence at your own pace.

May we suggest some optional activities to fill up your afternoon?

Exploring More of Florence

May We Suggest?
• We think simply soaking up Florence this afternoon is a great plan, but if you'd like to fill it up a bit more, consider:

— Interested in checking out the leather market?
— What about a climb of the Duomo? We can arrange visits, admissions and more for you in advance.
— Consider a visit to the Basilica di Santa Croce (Basilica of the Holy Cross) is the principal Franciscan church in Florence and a minor Basilica of the Catholic Church. Many illustrious Italians are buried there including Michelangelo, Galileo, Rossini, Marconi, Machiavelli. Thus it is known as the Temple of the Italian Glories.

Optional Guided Experiences for your afternoon:
We usually schedule most of these at around 3PM if possible.

• Uffizi Gallery: Private Tour with Guide: $339 per person (3 Hours).
Guided our licensed guide with a PHD in Art History, as well as a published art books author, you will discover the unique artistic and cultural richness as the cradle of the Renaissance. The Uffizi Gallery is one of the most incredible art collections in the world of Italian and European Paintings. During the tour the guide will tell you the incredible stories of such masterpieces including those made by Giotto, Piero della Francesca, Filippo Lippi, Botticelli, Michelangelo, Raphael, Titian, Leonardo da Vinci and Caravaggio.

Uffizi Gallery: Small Group Guided Tour: $179 per person.
Enjoy the Gallery in a small group: The art history expert will guide you through the Uffizi Gallery and to the masterpieces contained within. During your tour, the guide will accompany you from hall to hall, taking you on a journey into art and its history as he or she illustrates the most beautiful works of art in the museum. Not only will you learn about the importance of each painting, but also the context in the times when they were made.

Uffizi Gallery: Admission Ticket Only: $49 per person.
Enjoy an admission ticket to the Gallery.

Climb the Duomo Ticket: $59 per person.
Enjoy a climb to the top of the cupola by climbing its 463 steps to get an extraordinary view of Florence.

A private tour of the Pitti Palace in Florence Ticket: $339 per person (2 hours, 2 guest minimum for this privately guided tour.
Italy, provides a personalized journey through this Renaissance marvel, led by an expert guide. Beginning with an introduction to the palace's rich history and Medici legacy, visitors delve into its opulent interior, admiring frescoes, stuccowork, and masterpieces by artists like Raphael and Caravaggio. The tour navigates grand halls, sumptuous apartments, and private chambers, culminating in exploration of the world-class art collections housed within. Following this, a leisurely stroll through the Boboli Gardens offers panoramic vistas and insights into Renaissance landscape architecture. With flexibility for customization, the experience caters to individual interests, ensuring an enriching encounter with Florence's cultural heritage amidst the palace's splendor.

• Admission only to Pitti Palace and/or Gardens.
Option 1: Pitti Palace only (not including gardens) - admission only (no guide): $32 per person
Option 2: Pitti Palace Gardens (Boboli Gardens) only (not including Palace) - admission only (no guide): $23 per person
Option 3: Pitti Palace & Boboli gardens combo; admission only (no guide): $45 per person

Your Tour Captain will invite you to an optional dinner tonight or you can explore Florence at leisure.

 

Chapter 3: Tuscany

Tuscany's Countryside —
2 Days, 2 Nights


Under the Tuscan Sun

DAY 5: TUSCANY – A DAY OF FLAVOR & TRADITION

Sightseeing IconToday's Adventure: Fruits of the Tuscan Sun

The landscape shifts as rolling hills and cypress trees guide us into the Tuscan countryside.
Today is a celebration of slower rhythms — charming villages, vineyard views, and the simple pleasures that define life beyond the city walls.

Our journey begins in San Gimignano, famed for its medieval skyline rising above the Elsa Valley. Once an important stop along the historic Via Francigena, this hilltop town invites you to wander its stone streets and browse its artisan shops at a relaxed pace. We toast our arrival in Tuscany with a glass of Vernaccia, San Gimignano’s signature white wine.

Now Journey Exclusive: Tuscan Winery Experience

Settle into the heart of the countryside at a family-run Tuscan estate. Enjoy a guided cellar visit, a curated wine tasting, and a leisurely farm-to-table lunch featuring regional specialties — perfectly paired with Chianti and Super Tuscan wines.

Today’s highlights include:

  • Time to explore San Gimignano, Tuscany’s iconic hill town of towers
  • An exclusive winery visit with tasting and lunch at a countryside estate
  • A scenic journey along Tuscany’s wine road, winding through vineyards, rolling hills, and storybook villages

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

Discovery Walk IconDiscovery Walk: Cortona
Stroll through Cortona’s historic heart as your Tour Captain welcomes you to Tuscany, weaving together Etruscan, Roman, and modern stories. Wander from Via Nazionale to Piazza Garibaldi and Piazza della Repubblica before settling into a relaxed Tuscan evening beneath the warm afternoon sun.

Journey Dinners IconNow Journey Exclusive: Apericena in Cortona

This evening, gather with your Tour Captain for a Now Journey–exclusive Apericena — a modern Italian tradition that blends aperitivo and dinner.
Designed as a light, flavorful finale to a day of Tuscan discovery, this relaxed evening showcases regional tastes, local wine, and the inviting ambiance of Cortona’s historic streets.

Afterward, enjoy the rest of the evening at your leisure, soaking in the quiet magic of this hill town under the Tuscan sky.

Journey Hotels IconWhere We Stay in Cortona, 2 Nights with breakfast

Deluxe Hotels Collection —
Villa Marsili, Hotel San Michele, Monastero di Cortona Hotel & Spa or Similar

Our Deluxe Collection features thoughtfully selected 4- and 5-star hotels, including upgraded rooms at 4-star properties and refined entry-level rooms at 5-star stays. Guests may inquire with their Trip Specialist about larger rooms or higher-category accommodations with specific views, where available.

Classic Hotels Collection
Our Classic Collection offers well-located 3-star-plus hotels featuring private bathrooms, air conditioning, continental breakfast, and heart-of-the-city locations.



DAY 6: CORTONA – SLOW MOMENTS & SIMPLE PLEASURESCortona in Tuscany, Italy

Enjoy a full free day at your leisure in beautiful Cortona.

Many options are available from Cooking Classes to a day trip to Siena and more. Today, enjoy Tuscany at your leisure - perhaps it's a thorough exploration of delightful Cortona, a cooking class, horse-back riding, Vespa rental and much more.

May we suggest some optional activites for your day (and night) in Cortona:

Cortona to Explore

Options for Today
Might we suggest:

Cooking Class from Cortona
— Just outside of Cortona, in the company of an expert chef, participants learn how to make several courses including a dessert. It is a different experience where the participants learn to prepare a multiple-course meal and then partake in the sampling of the prepared dishes while enjoying the olive oils and wines of the region! -Duration 3-5 hours. $280 per person.

Horseback Riding Adventure
— Commences at 9:30/10:00am or 2:00/3:00pm. $99 per person for first 2 hours, $37 per hour for each additional hour. Front desk of hotel will arrange round-trip taxi for you at guest expense. Options available for beginner or experienced riders.

Tour of Siena
— Departs around 9:30am. $465 per person. The tour includes round-trip transfer from Cortona to Siena with a walking tour of Siena in the morning and some free time in the afternoon. Today's tour will walk you through the old Ghetto, the Tower District (Contrada della Torre), and through little alleys, and on to the Basilica dei Servi, from which point you can enjoy an amazing view of the old town. We will take in Orto dei Pecci; a pleasant and easily accessible garden, located just behind the main square: The serenity and tranquility of this green oasis, together with the view of the incredible Torre del Mangia will mesmerize you.

Morning Tour of Siena with Cooking Class in Afternoon
— Departs around 9:30am. $599 per person. Enjoy the morning tour (see description above) and then a special cooking class in the afternoon. Our driver then whisks you to a nearby villa where you will enjoy a tour of the vines, immersion in all things Wine, Balsamic, and Olive Oil followed by a cooking lesson. And, yes, you then enjoy the fruits of your labor. Our chef is capable and entertaining as you enjoy learning more about Tuscan cooking. We then return to the hotel in Cortona for a free evening.

Cortona and the Franciscan Monastery Le Celle
— $190 per person. A classic private walking tour of Cortona comprises the Garibaldi Square with its magnificent panoramic view over the Valdichiana, the Church of St. Dominic built for the Dominicans with its medieval architecture and paintings by Luca Signorelli e Lorenzo di Niccolò, via Nazionale, the Republic Square with the Town Hall, the Church of St. Francis with its collection of objects owned to St. Francis of Assisi, Piazza Signorelli with Palazzo Casali and the Duomo. Then the tour continues by car outside the city walls of Cortona to the Franciscan Monastery of Le Celle, immersed in a forest and a place of an extraordinary beauty, calm and Franciscan spirituality.

• Cortona Ancient Walls, Fortresses, Convents and Churches
— $190 per person. This is a walking tour on steep slopes in the oldest part of Cortona leading up to the very top of the hill. For this reason is suitable for guests who enjoy walking (hiking) on slopes. The prize at the end is a fantastic view of Cortona and the valley below and the beauty of this less frequented and untouched part of the town. Above the center, half-way up to the hill of Cortona, are the Church San Francesco and beyond a cypress-lined courtyard, is the 15th century Chiesa di San Niccolò. The 15th-century church has a small porch with slender columns and the interior houses paintings by Luca Signorelli: the two-sided panel-painting, Descent from the Cross and Madonna Enthroned, and a fresco, Madonna with Saints. Passing by the little church San Cristoforo and Porta Montanina we will stop on the top to visit the Sanctuary of Santa Margherita, the town's patron saint. Finally walking down through the old part of town through the narrow alleyways of the quarter called Poggio San Marco you will admire also the beautiful 12 Via Crucis Stations with mosaics by the Futurist artist Gino Severin, a native of Cortona.

• Assisi Privately Guided Tour with round-trip transportation
— $279 per person. Enjoy this special visit to the hometown of Saint Francis, peacefully set on the slopes of the Subasio Mountain. The Basilica of Saint Francis is one of Europe's most important church buildings and undoubtedly the cultural highlight of the entire region. Our guide will show you the most important monuments, the Roman remains, the charming intact medieval town, stunning views of the landscape and the town's hidden treasures. During this guided tour you will see the Basilica of St. Francis*, Piazza del Comune (central square), Minerva temple and other sites.

About Cortona
Cortona is a small but fascinating hill town in the province of Arezzo, Tuscany. It is situated on a commanding hill that overlooks Lake Trasimeno, known for the infamous rout of the Romans by Hannibal and the Carthaginians. Its cyclopean walls, still preserved in great part, are said to be 3000 years old. It was one of the twelve cities of Etruria.

Soak in the morning: enjoy a walk through the vineyards, or a hike up to the castle or a leisurely stroll through the piazza and streets.

Your Journey Tour Captain will invite you to an optional dinner tonight or choose to enjoy your last night in Cortona at your leisure.

 

 

Chapter 4: Rome - Heart of the Empire

Where All Roads Lead —
3 Days, 3 Nights


 

DAY 7: THE ROAD TO ROME

Today, the journey continues south toward the Eternal City.
Travel comfortably as the story of Italy unfolds chapter by chapter, culminating in Rome — a city where ancient history and modern life exist side by side.

There Once was a Dream that Was Rome. Pantheon in Rome, Italy

Today, we enter Rome, where history stands still. As the city's energy rises around us, a skyline of domes, ruins, and ancient landmarks unfolds. Soon, we’ll walk among the remnants of an empire — cobblestones, columns, and arches whispering stories of emperors and philosophers. Welcome to the Eternal City.

Orientation Walk IconDiscovery Walk: Rome

We arrive at our hotels and check in. The locations of our hotels in Rome are within a minute or so walk of the incredible Pantheon. Conitnue with the Now Journey Tour Captain for a walk through the very heart of Old Rome.

We begin our exploration of Rome beginning with an elephant and continue to immerse ourselves in over 2000 years of history of the 'Empire. We enter the amazing Pantheon and learn of its interesting history and continue our walk to soak up Piazza Navona, once a site where mock naval battles were held. We continue with our Discovery Walk as we pass through Campo de Fiore (field of flowers) - do you know the name of the figure whose likeness is crafted in the statue in this amazing campo? We walk by Largo di Torre Argentina and learn of Julius Caesar's fate. We will also see a village of modern Roman felines.

Journey Dinners IconWelcome to Rome Dinner: Flavors of Lazio

This evening, gather with your Journey Tour Captain for a warm welcome to Rome.
Enjoy a thoughtfully curated regional dinner paired with premium beverages and wines from Lazio and neighboring regions — a relaxed and convivial beginning to your time in the Eternal City.

Journey Hotels IconWhere We Stay in Rome, 3 Nights with breakfast

Deluxe Hotels Collection — 
Palazzo Navona, Antico Albergo del Sole al Pantheon, Iconic Pantheon Rome Hotel, L'Orologio or Similar

Our Deluxe Collection features thoughtfully selected 4- and 5-star hotels, including upgraded rooms at 4-star properties and refined entry-level rooms at 5-star stays. Guests may inquire with their Trip Specialist about larger rooms or higher-category accommodations with specific views, where available.

Classic Hotels Collection
Our Classic Collection offers well-located 3-star-plus hotels featuring private bathrooms, air conditioning, continental breakfast, and heart-of-the-city locations.




DAY 8: EXPLORING THE VATICANVatican City, Rome, Italy

Sightseeing IconToday's Adventure: Vatican City Privileged Access

Today’s discoveries reveal Rome beyond the postcards.
From sacred spaces to tucked-away neighborhoods, experience the city through a deeper lens — where stories, rituals, and daily life intersect.

With Privileged Entry, explore the Vatican Museums, marvel at the Sistine Chapel, and stand in awe of St. Peter’s Basilica and Square. As we exit into St. Peter’s Square, spot the Swiss Guard in their colorful uniforms. When ready, Now Journey transports await to return us to our hotels.

Today's highlights include:
  • St. Peter's Basilica and Square: Admission and Guided Tour to St. Peter's Basilica. Enjoy Skip-the-Long-Line special access with Priviledged Access Admission Included.
  • Sistine Chapel: Admission and Guided Tour of the Sistine Chapel: You will find inside the chapel The Last Judgment painting by Michelangelo, which he painted during the years 1535 to 1541. The work, designed on a grand scale, spans the entire wall behind the Sistine Chapel altar.
  • Vatican Museums: Admission and Guided Tour of the Vatican City Museums: The Museums boast some of the most impressive tapestries and other works of art and sculpture found in the world.

Enjoy the balance of the afternoon and evening at your leisure.

Your Tour Captain will invite you to an optional dinner tonight or you can explore Rome at your leisure.

This afternoon may we suggest an optional activity:

May We Suggest?
• We think simply soaking up Rome this afternoon is a great plan, but if you'd like to fill it up a bit more, consider:

Consider experiencing the Baths of Caracalla while in Rome. Includes privately guided tour, admissions and roundtrip taxi transfer from hotel. Also includes standard gratuities. $250 per person, minimum 2 guests

—  Visit Ostia Antica

Just ask us and we can help you!

 



DAY 9: Rome: Eternal city, history's living canvasRoman Forum, Italy

Sightseeing IconToday'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 still shapes Roman life today.

We make our way to the Colosseum and Roman Forum, the town center of the Roman Empire, for our special access, in-depth touring experience, complete with admissions. 

Special Sightseeing Includes:

  • Colosseo: Flavian's amphitheater known popularly as the Colosseum. Admission and Guided Tour of the Colosseum: Heart of The Empire. Enjoy Skip-the-Long-Line entrance.
  • Foro Romano: Admission and Guided Tour of the Roman Forum ~ We walk through the archaeological dig for unique perspectives of the Old Town Center of Rome, Palatine Hill, Capitoline Hill, Caesar's Palace, Curia or the Senate House, Temple of the Vestal Virgins, and the Triumphal Arches.
  • Capitoline Hill: We ascend this amazingly sculptured and architecturally inspirational locale.
  • Walking Delights: Views of Trajan's Market, Palatine Hill, Caesar's Palace, Curia known as the Senate Building, the Vittorio Emanuele II National Monument, the Jewish Ghetto, and other historic landmarks. 

Journey Dinners IconNow Journey Exclusive: A Very Special Evening

Tonight join your Tour Captain for our included 'Farewell to Rome' dinner at a very exclusive location. Our days have been filled with new sights, tastes and discoveries - tonight enjoy reflecting on the incredible journey we've had together. It has been a Journey of Adventure and Discovery, along with making new friends!

Tomorrow we will say, 'Arrivederci Roma!' but tonight we sing and make melody in the very heart of Rome. 


Chapter 5: Sorrento

Sorrento and the Amalfi Coast —
2 Days, 2 Nights


Amalfi Coast & Sorrento Peninsula

Day 10: NAPLES, POMPEII, THE SORRENTO PENINSULA & AMALFI COAST

Say goodbye to Rome as we make our way to the amazing Amalfi Coast and Sorrento Peninsula. Upon arrival to Naples and the modern city of Pompei is where we enjoy an expertly guided tour of Pompeii (note the two i's), which is the ancient Roman city we will visit with our tour this morning.

Amazing Amalfi. Pompeii, Sorrento.

Sightseeing IconToday's Adventure: Pompeii Ancient Site
On our tour of the World Heritage Site of Pompeii we find out the city was lost for nearly 1700 years before its rediscovery in 1748. Enjoy the commentary of our Local Guide as you learn of its colorful history and tragic end.

After our experience we make our way to Sorrento, our home to explore the amazing Amalfi Coast.

Orientation Walk IconDiscovery Walk: Sorrento
After our check in, and time to relax we will enjoy a Discovery Walk on the way into the heart of Sorrento. Nestled along the breathtaking Amalfi Coast, Sorrento captivates with its charming narrow streets adorned with vibrant bougainvillea and lemon trees. The town's picturesque cliffside location offers stunning panoramic views of the azure Tyrrhenian Sea, making every step of your discovery walk an enchanting journey through Mediterranean beauty.

Journey Dinners IconWelcome Dinner: Sorrento
Your Tour Captain hosts an amazing welcome dinner in Sorrento. The owner, Mario, and Chef Lina and their family welcome us to dinner tonight. Get ready for a wonderful evening of Sorrentina cuisine and hospitality.

Journey Hotels IconWhere We Stay in Sorrento, 2 Nights

Deluxe Hotels Collection — 
Grand Hotel Capodimonte with Sea View, Hotel Continental or Similar

Our Deluxe Collection features thoughtfully selected 4- and 5-star hotels, including upgraded rooms at 4-star properties and refined entry-level rooms at 5-star stays. Guests may inquire with their Trip Specialist about larger rooms or higher-category accommodations with specific views, where available.

Classic Hotels Collection
Our Classic Collection offers well-located 3-star-plus hotels featuring private bathrooms, air conditioning, continental breakfast, and heart-of-the-city locations.



DAY 11: EXPLORING THE AMALFI COAST AT LEISUREAmalfi Coast, Italy

You will have today completely at your leisure to explore Sorrento or consider one of our optional adventures.

Highly Recommended: Private Boat Tour to the Isle of Capri – $579/person
A premium experience well worth it! Set out on a stunning boat trip to the Isle of Capri, where you'll have free time to explore. Then, cruise around the island, enjoy a refreshing swim with towel service and onboard refreshments, and return to Sorrento in style.

Prosecco IconOur Special Journey Finalé

Upon our return to the hotel, enjoy some time at leisure before we meet to walk once more into the enchanting embrace of Sorrento. Amidst the ambience, we shall partake in the Passeggiata, savoring each step as we reminisce on our shared odyssey.

Our rendezvous culminates in a time-honored Traditional Farewell Apericena, a celebration of camaraderie and cherished memories at one of our favorite locales in Sorrento.

Thus concludes our Journey of Adventure and Discovery, enriched by the bonds of newfound friendship. Until we meet again on our next escapade — Arrivederci!

 

The Isle of Capri Awaits

Sightseeing IconToday's Optional Adventure: Isle of Capri, $579 per person
Your Journey Tour Captain will introduce Capri to you (and the other villa of Ana Capri). Occasionally, and when weather and seas permit, we are able to provide an experience that includes (in addition to round-trip service to and from Capri) time on the boat around the island with stops at various Grottos for viewing and swimming if you desire. We only "pass by" the Blue Grotto, we do not go inside the Blue Grotto as this usually takes the majority of the day.

Our Isle of Capri Adventure includes:

  • Seamless Transfers: Enjoy private hotel pick-up and drop-off for a stress-free journey.
  • Exclusive Island Transportation: Traverse the island in style with an open-air taxi service.
  • Charming Exploration: Discover the captivating towns of Capri and Anacapri.
  • Breathtaking Views: Ride the scenic chairlift to the summit of Monte Solaro for panoramic vistas.
  • Expert Guidance: Experience the island with your dedicated Tour Captain as your guide.
  • Onboard Luxury: Indulge in a luxurious towel service and refreshments, including prosecco, beer, soda, water, and snacks.
  • Private Boat* Experience: Cruise around Capri on a private boat equipped with a professional captain and onboard restroom facilities.

Please carefully note:

  • When weather permits, we are occasionally able to offer an enhanced experience: round-trip boat service from Sorrento to Capri, leisure time on the island, followed by a scenic cruise around Capri with stops at several beautiful grottos and optional swim time. Please note: we view the exterior of the Blue Grotto only, as entering typically requires most of the day and is not part of our itinerary.
  • *In some cases, our private boat may not be available. Final confirmation for the Isle of Capri Excursion will be made no later than 60 days prior to your trip departure. Should the excursion not be confirmed, you will be offered an alternative experience or receive a full refund of the amount paid.
  • In case of rough seas and/or inclement weather cancellation, there are no refunds should the excursion be cancelled. You will need to submit this as a claim to your travel insurance.

 

DAY 12: DEPAR


TURE DAY: Arrivederci Italy!

Breakfast is included this morning should you have time before your departure.

Are you wrapping up your Journey in Sorrento? May we recommend our Optional Departure Transfer to the Naples NAP Airport for $125 per person, minimum two guests. Departure Transfer optional and not included. Transfer from the Sorrento hotel to the Naples NAP airport #125 per person. (2 guest minimum. Price is per person, $250 for solo traveler.)

Be Our Guest! Add an extra night in Sorrento at a reduced rate with our promotion — inquire!

See Full ItineraryOur Hotels: We've Selected the Perfect Italian Palaces & Properties

Our Now Journey Hotels Collections feature Deluxe Collection properties with 4 to 5-Star hotels including entry-level room categories in 5-Star, and one category above entry-level in 4-Star. Elevate your stay with upgraded rooms - inquire. Our Classic Collection feature 3-Star + properties with bathrooms, air conditioning and continental breakfast also located in the hearts of the cities.

VENICE: 2 NIGHTS - AH! VENICE!




FLORENCE: 2 NIGHTS - BIRTHPLACE OF THE RENAISSANCE




CORTONA: 2 NIGHTS - UNDER THE TUSCAN SUN




ROME: 3 NIGHTS - WHERE ALL ROADS LEAD


SORRENTO: 2 NIGHTS - THE JET SETTER'S PARADISE


See Full ItineraryDepartures: The Very Best Times of the Year for Italy

We've curated the best times of the year to visit Italy's Great Cities. Solo Supplement: Enjoy a double occupancy room all to yourself for $3790.
Deluxe hotels feature 4+ to 5-Star properties. Classic hotels feature 3-Star + properties — everything else is the same.

2026 Italy's Great Cities • 12 Day
Small Group Tour Dates

TRIP DATES DELUXE
4+ to 5-Star
CLASSIC
3-Star +
Italy in the Spring
This is one of the best times to be in Italy: No crowds, moderate temps averaging in the 60s, and some showers to bring May flowers! Seasonal air conditioning is limited due to government regulations.
Apr 7-18
$10,849
$9,649
Apr 14-25
$10,849
$9,649
Apr 21-
May 2

$10,849
$9,649
Apr 28 -
May 9

$10,749
Limited Promotion
$9,549
Limited Promotion
May: Near Perfect
It's difficult to beat Italy in May. Early May can see some showers, but mid to late May is the time for moderate crowds, great temps in the 70s, sunshine and La Dolce Vita!
May 5-16
$10,549
Limited Availability
$9,349
Limited Availability
May 12-23
$10,549
Limited Availability
$9,349
Limited Availability
May 19-30 $10,549
Limited Availability
$9,349
Limited Availability
May 26 -
Jun 6
$10,549
Limited Availability
$9,349
Limited Availability
June: Graduate to More Perfection
The weather is near perfect in June, that's why the volume of travelers is high. It's a great time to celebrate our graduate as well!
Jun 2-13 $10,949
$9,749
Jun 9-20 $10,949
$9,749
Jun 23 -
Jul 4
$10,949
$9,749
July & August: It's Summer in Italy!
The reminds one of the fresh, hot days of summer from the states —  but it's still a great time to explore Italy.
Jun 30 -
Jul 11
$10,979
$9,749
Jul 14-25
$10,979
$9,749
Aug 11-22
$10,979
$9,749
September: Great Harvest
September is still considered high season these days and for good reason: The harvest in Tuscany and other areas is in swing and the weather is so very special. Highs in the 70s in mid to late September.
Sep 1-12
$10,549
Limited Availability
$9,349
Limited Availability
Sep 8-19 $10,549
Limited Availability
$9,349
Limited Availability
Sep 15-26

$10,549
Limited Availability
$9,349
Limited Availability
Sep 22 -
Oct 3
$10,549
Limited Availability
$9,349
Limited Availability
Italy in October
Though the hot summer temps are gone, October can still see some warm days. Highs in the 60s to low 70s.
Sep 29 -
Oct 10
$10,549
$9,349
Oct 6-17

$10,549
Limited Availability
$9,349
Limited Availability
Oct 13-24
$10,979
$9,749

2027 Italy's Great Cities • 12 Day
Small Group Tour Dates

TRIP DATES DELUXE
4+ to 5-Star
CLASSIC
3-Star +
Italy in the Spring
This is one of the best times to be in Italy: No crowds, moderate temps averaging in the 60s, and some showers to bring May flowers! Seasonal air conditioning is limited due to government regulations.
Mar 16-27
$10,979
$9,749
Apr 6-17 $10,979
$9,749
Apr 13-24 $10,979
$9,749
Apr 20-
May 1
$10,979
$9,749
May: Near Perfect
It's difficult to beat Italy in May. Early May can see some showers, but mid to late May is the time for moderate crowds, great temps in the 70s, sunshine and La Dolce Vita!
Apr 27-
May 8
$10,549 $9,349
May 4-15 $10,549 $9,349
May 11-22 $10,549 $9,349
May 18-29 $10,549 $9,349
June: Graduate to More Perfection
The weather is near perfect in June, that's why the volume of travelers is high. It's a great time to celebrate our graduate as well!
May 25-
Jun 5
$10,549 $9,349
Jun 22-
Jul 3
$10,549 $9,349
Jun 29-
Jul 10
$10,549 $9,349
July & August: It's Summer in Italy!
The reminds one of the fresh, hot days of summer from the states —  but it's still a great time to explore Italy.
Jul 13-24 $10,979
$9,749
Aug 10-21 $10,979
$9,749
Aug 31-
Sep 11
$10,979
$9,749
September: Great Harvest
September is still considered high season these days and for good reason: The harvest in Tuscany and other areas is in swing and the weather is so very special. Highs in the 70s in mid to late September.
Sep 7-18 $10,549 $9,349
Sep 14-25 $10,549 $9,349
Sep 21-
Oct 2
$10,549 $9,349
Sep 28-
Oct 9
$10,549 $9,349
Italy in October
Though the hot summer temps are gone, October can still see some warm days. Highs in the 60s to low 70s.
Oct 5-16 $10,549 $9,349
Oct 12-23 $10,549 $9,349