16 GUESTS OR FEWER
Small enough to feel the difference.
Smaller groups create access to more personal hotels, local tables, flexible moments and conversations that larger tours simply miss.
Why Small Groups →
FeaturedThe Beauty of Small-Group Travel
Now Journey Signature Italy
The Original 12-Day Small Group Italy Journey.
Venice → Florence → Tuscany → Rome → Sorrento & Amalfi Coast
Venice · Florence · Tuscany · Rome · Sorrento & Amalfi Coast
THE ORIGINAL 12-DAY ITALY’S GREAT CITIES
Arrive in Venice by private water taxi. Stand before Michelangelo’s David. Share a winery lunch in Tuscany, discover the treasures of Rome, and unwind in Sorrento overlooking the Bay of Naples and the Amalfi Coast.
I’m Mark Story, owner and managing director of Now Journey. My team and I have thoughtfully crafted this journey around something we believe makes all the difference in travel: experiencing remarkable places without feeling rushed, crowded, or caught up in the ordinary tourist experience.
You’ll enjoy wonderful heart-of-city hotels, the company of a very small group of like-minded travelers, and the personal attention of your Now Journey Tour Captain. Our expert local guides bring Italy’s stories to life, while we’ve made sure there’s plenty of time for your own discoveries — a neighborhood café, an afternoon of shopping, or a long lunch with new friends.
Every detail considered. Every day brings something more.
Journey at a Glance
Venice → Florence → Cortona/Tuscany → Rome → Sorrento
Scroll through citiesSwipe through cities
Why Now Journey
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.
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.
No one-night hotel stops. Guided discoveries are balanced with time to explore independently, enjoy a long lunch, or savor the magic of Tuscany and the Amalfi Coast.
Well-located hotels, coordinated transportation, and local guide and driver gratuities included. No on-tour upselling—just more time to enjoy the journey.
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
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 upselling while you’re on tour.
Read Our TripAdvisor Reviews12 Days from Venice to Sorrento
See exactly how each day unfolds—from your arrival by private water taxi in Venice to the final days overlooking the Bay of Naples.
Chapter One
Days 1–2
Private water-taxi arrival, guided San Marco visits and a gondola experience with live musicians.
Day 1
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.
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.
Day 2
Discover Venice’s hidden corners and layered history with our incredible local guide as you explore St. Mark’s Basilica, the Doge’s Palace, the historic prisons and the Bridge of Sighs—along with the story of Casanova. Venice emerges not as a postcard, but as a republic shaped by power, intrigue, faith and extraordinary beauty.
Included Admissions and Expert Guiding: Explore St. Mark’s Basilica and the Doge’s Palace with the admission arrangements published for this Journey. Standard security procedures and attraction access requirements still apply.
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.
Chapter Two
Days 3–4
High-speed rail, the Accademia and Renaissance streets; independent time on the afternoon of Day 4.
Day 3
A private boat transfer brings you to Venezia Santa Lucia, where you board a comfortable high-speed train bound for Florence—a seamless transition from lagoon light to Renaissance stone.
Discovery Walk: Florence. Upon arrival, your Tour Captain introduces the historic center through Giotto’s Campanile, the Baptistery and Florence Cathedral—the Duomo—before continuing past Orsanmichele, the storied lanes near Santa Margherita dei Cerchi and the Ponte Vecchio. This welcoming orientation places the city’s streets, landmarks and cultural rhythms in context before tomorrow’s expert-guided sightseeing.
Day 4
Following our included 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 architecture and stories of Santa Maria del Fiore, Giotto’s Bell Tower, the Baptistery and the Gates of Paradise, then continue through Piazza della Signoria and Piazza della Repubblica. Interior admission to these cathedral-complex monuments is not part of today’s guided visit.
The afternoon is intentionally open: time to wander, shop, linger over lunch, visit Santa Croce, choose another gallery or simply look up. Later, gather for sunset views from Piazzale Michelangelo.
This evening, your Tour Captain will invite you to join the group for an optional dinner, or the evening is entirely yours.
Chapter Three
Days 5–6
San Gimignano, a winery visit and lunch; a full independent day in Cortona on Day 6.
Day 5
The landscape shifts as rolling hills and cypress trees guide you into the Tuscan countryside. Begin in San Gimignano, famed for its medieval skyline and artisan streets, with a toast of Vernaccia, the town’s signature white wine.
Settle into a family-run Tuscan estate for a guided cellar visit, curated wine tasting and leisurely included luncheon. Later, a scenic journey carries us to Cortona, where your Tour Captain handles check-in at our charming Cortona hotel before leading a gentle Discovery Walk into the historic center.
Day 6
Enjoy a full day at leisure in Cortona. The day can be as quiet or active as you wish: a long piazza morning, a countryside walk or time exploring Cortona’s upper streets and Etruscan layers.
Your Tour Captain can help shape the day around your style, and the evening remains open for an unhurried night in one of Tuscany’s loveliest hill towns.
Read Why We Spend Two Nights in Cortona to see how the full independent Tuscany day adds a different rhythm to Signature Italy.
This evening, your Tour Captain will invite you to join the group for an optional dinner, or the evening is entirely yours.
Chapter Four
Days 7–9
Vatican and Imperial Rome visits, three nights in the historic heart and an independent afternoon on Day 8.
Day 7
The Journey leaves Tuscany and continues south toward the Eternal City. After checking into our centrally located hotels, we join our Tour Captain for a Discovery Walk through the very heart of Old Rome.
Our exploration begins with a curious elephant—Bernini’s beloved sculpture near Piazza della Minerva—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, Campo de’ Fiori and Largo di Torre Argentina, where Julius Caesar’s final chapter and modern Roman life meet. Along the way, we may even spot some of Rome’s famous resident cats.
Day 8
Begin with an expert-guided morning in Vatican City, where the Vatican Museums reveal centuries of collecting, patronage and artistic achievement. Your guide prepares us before we enter the Sistine Chapel, and when visitor operations and access permit, the experience continues to St. Peter’s Basilica and Square.
Special Sightseeing Includes
Included Admission · Expert Local Guiding
Included admission and expert-guided touring through remarkable galleries of sculpture, painting, tapestries and historic collections.
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.
Discover the history, architecture and extraordinary artwork of St. Peter’s Basilica and Square when Vatican operations and access permit.
The afternoon and evening are intentionally open for independent discovery, with suggestions from your Tour Captain.
This evening, your Tour Captain will invite you to join the group for an optional dinner, or the evening is entirely yours.
Day 9
Walk among the Curia, temples and triumphal arches that shaped ancient political and religious life, with perspectives toward Palatine Hill, the imperial palace complexes and Capitoline Hill. Ancient ruins and modern Rome remain side by side throughout the experience.
As evening falls, one final Roman celebration awaits before the Journey turns south toward the coast.
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.
Explore the Flavian Amphitheatre with included admission and expert guiding as the stories of gladiators, emperors and public spectacles come into focus.
Explore the center of ancient civic, political and religious life, with the Curia, temples, the House of the Vestals and monumental triumphal arches placing Rome’s public history in context.
Discover how imperial residences, public monuments and Rome’s seven hills shaped the city’s extraordinary urban story.
See and discuss nearby historic landmarks encountered along the guided route, with access and site order governed by official operations.
Final Chapter
Days 10–12
Expert-guided Pompeii, two nights in Sorrento and a full independent day on Day 11.
Day 10
Leave Rome as the Journey turns south toward Pompeii, the remarkable Roman city preserved beneath volcanic ash for nearly 1,700 years. On our included expert-guided archaeological visit, walk its ancient streets and enter the human story revealed through homes, shops, public spaces and the everyday details of a city interrupted in time.
After Pompeii, continue to Sorrento on the beautiful Sorrento Peninsula. Following hotel check-in and time to refresh, your Tour Captain leads a Discovery Walk through the heart of town as a new coastal atmosphere settles over the Journey beside the Bay of Naples.
Day 11
Today is intentionally open for the coast. Follow your Tour Captain’s recommendations through Sorrento’s historic streets, settle into a seaside café, browse local shops, linger over a long lunch or simply enjoy the atmosphere of your hotel and the Sorrento Peninsula at your own pace.
Our Big Recommend: Add our Private Boat Excursion to the Isle of Capri!
Join your Tour Captain and cross the Bay of Naples for a full day combining Capri and Anacapri, open-air island transportation and an opportunity to ride the scenic chairlift to Monte Solaro. When sea conditions permit, we then return to the water for coastal views, selected grottoes and optional swimming to become a member of the Roman Legionnaire’s Swim Club! See optional details below.
Day 12
As the Journey closes, your Tour Captain or the Now Journey team can assist with practical departure guidance.
An optional transfer to Naples Airport may be requested separately and is not included in the base Journey. If you would like more time in Southern Italy, ask about extending your stay when appropriate and subject to availability.
From Venice’s canals and Florence’s Renaissance treasures to Tuscany’s vineyards, Rome’s ancient layers, Pompeii’s human stories and the beauty of the Sorrento Peninsula, the Journey ends with wonderful memories and new friendships to carry home.
Hotel Collections
Choose among three thoughtfully curated Hotel Collections. The itinerary, Tour Captain services, sightseeing, transportation and included dining remain exactly the same.
Signature Collection
Hand-selected 4+ to 5-star properties emphasizing location, service, comfort, and thoughtful room selection.
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.
Lotus Hotel Collection
The Lotus Hotel Collection brings an elevated level of comfort and distinction to your Italian Journey.
Thoughtfully selected premium accommodations, spacious rooms, Junior Suites, Suites, and preferred views or terraces where available. You can also choose to upgrade just one or two hotels — or all of them. Simply inquire about the available options.
Classic Hotel Collection
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.

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

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

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

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

Coastal Deluxe stays such as Grand Hotel Capodimonte, Bellevue Syrene, Hilton Sorrento Palace or similar.
Dates & prices
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: 11 breakfasts, 6 hosted dinners, 1 Italian apericena and 1 Tuscan winery lunch with tasting.
A selection of spring 2027 departures.
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 $3,790, and the Lotus Hotel Collection supplement is $6,900. Classic solo pricing will be confirmed in your personalized proposal.
One of the best times to be in Italy: moderate temperatures, fewer crowds, and spring atmosphere.
Near-perfect weather, flowers, sunshine, and la dolce vita.
A classic Italy window with warm days and high-demand departures.
Fresh, hot Italian summer days and long golden evenings.
September brings Tuscany's harvest, late-summer warmth, and some of the year's most requested weeks.
Autumn atmosphere, softer crowds, and warm days that often linger into the month.
Traveling solo? The published Deluxe Collection supplement is $3,790, and the Lotus Hotel Collection supplement is $6,900. Classic solo pricing will be confirmed in your personalized proposal.
One of the best times to be in Italy: moderate temperatures, fewer crowds, and spring atmosphere.
Near-perfect weather, flowers, sunshine, and la dolce vita.
A classic Italy window with warm days and high-demand departures.
Fresh, hot Italian summer days and long golden evenings.
September brings Tuscany's harvest, late-summer warmth, and some of the year's most requested weeks.
Autumn atmosphere, softer crowds, and warm days that often linger into the month.
Traveling solo? The published Deluxe Collection supplement is $3,790, and the Lotus Hotel Collection supplement is $6,900. Classic solo pricing will be confirmed in your personalized proposal.
Explore the complete Journey before requesting your proposal, or tell us your preferred season, travel style, and hotel collection. We will help you compare dates without pressure.
YOUR NEXT STEP
A thoughtful next step, with no booking commitment.
You’ve explored the Journey. Now let us help you make it yours. Requesting a proposal starts a personal conversation—not a booking commitment.
Choose a departure and Hotel Collection, or simply tell us when you’d like to travel. We’ll carry your selections into your request so you don’t have to start over.
A Now Journey specialist reviews your travel preferences, checks current availability and prepares a personalized proposal with the options that fit your plans.
Review your proposal, ask questions and explore the details without pressure. A proposal request does not reserve space or require a payment.
Now Journey guest reviews
Now Journey guests consistently mention the same things: thoughtful planning, seamless logistics, special surprises, beautiful hotels, and the feeling of being genuinely cared for.
"I can't say enough about our recent trip to Italy. It was perfection from beginning to end."Esther P., Now Journey guest
"We all were made to feel special, almost like royalty, with skip-the-line access, personal service by fabulous chefs, and seamless check-ins at our gorgeous hotels."
Teresa C."Our hotel accommodations were all perfect. Now Journey did an exceptional job planning and we even got surprises along the way."
Tammy A.Plan & prepare
Expect moderate walking in historic centers, including cobblestones and stairs, alongside guided visits, independent time and travel between destinations.
Included: 11 hotel nights, daily breakfast, 6 dinners, a wine-estate luncheon, 1 apericena experience, itinerary-listed guided visits and admissions, the Venice arrival water taxi and planned tour transportation. Not included: international airfare, optional experiences and the Naples Airport departure transfer.
Our journeys are thoughtfully paced, but exploring Italy’s historic centers means walking on cobblestones, uneven pavement, stairs and occasionally uphill streets. The guidance below is provided to help you plan comfortably.
Canal-side routes and historic lanes include bridges, cobblestones and stairs. The orientation walk, welcome dinner and guided sightseeing require periods of walking and standing.
Historic-center walking includes stone streets, museum visits and extended standing during guided sightseeing. Activity during the independent afternoon varies by guest.
Expect hill-town streets, inclines and steps during the included visits. Day 6 is independent, so its activity level depends on your plans.
Old Rome, Vatican City and Imperial Rome involve substantial historic-center walking, cobblestones, stairs, inclines and extended standing at major sites.
Pompeii has uneven ancient stone surfaces and requires walking and standing during the expert-guided visit. The day also includes a Tour Captain-led orientation in Sorrento.
Day 11 activity varies with your independent or optional plans. Day 12 has no scheduled guided walking activity.
Guided tours may require extended standing. Guests should be comfortable walking independently through historic centers. Travelers with mobility concerns should speak with Now Journey before requesting a booking so we can discuss the itinerary’s practical demands.
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 add additional walking.
The day-by-day “Included Today” lists show the included visits and services. Eleven breakfasts are included; departure-morning breakfast depends on flight timing. Dining includes 6 dinners, 1 wine-estate luncheon and 1 apericena experience—a relaxed evening combining aperitivo and dinner. Other meals and optional experiences are extra. Included admissions do not eliminate security procedures or every queue.
Planned tour-day transportation uses appropriately sized private vehicles or luxury micro-coaches, with Italian rail on selected segments. Ask the team about luggage arrangements and limits for your departure before booking.
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.
Prices are per person, double occupancy. The supplements for a double room for solo use are $3,790 for DELUXE and $6,900 for the Lotus Hotel Collection. Request a Journey Proposal for your selected departure and room preference; Classic solo pricing is confirmed by proposal.
The private water-taxi arrival transfer from Venice Marco Polo Airport is included. The Naples Airport departure transfer is optional, requested separately and not included in the base journey.
Independent afternoons are planned for Florence on Day 4 and Rome on Day 8, with full independent days in Cortona on Day 6 and Sorrento on Day 11. Amalfi Coast and Capri visits are optional and cost extra; they are not an included coast excursion. See the optional-experience choices below.
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.
Yes. Compare the 10-, 12- and 14-day journeys in the Journey Selector near the top of this page.
Make the Journey Your Own
Explore experiences to make the journey your own, or enjoy your time at leisure. Optional experiences are available at an additional cost.
Your Journey Begins Here
Tell us your preferred departure, hotel collection and travel party. Our team will confirm availability and prepare your personalized proposal.
No obligation. No pressure. Just a thoughtful conversation about your Italy.
Venice was not created merely as a beautiful refuge on the lagoon. It grew into an independent maritime republic whose merchants, diplomats and ships connected Europe with the eastern Mediterranean and beyond. That exchange brought wealth, rare materials and ideas into a city where trade, government and faith were deliberately staged together.
Seen with that story in mind, St. Mark’s is more than an ornate church and the Doge’s Palace more than a graceful façade. They expressed the confidence of a trading power whose political life unfolded within sight of the water that made it possible. Venice’s beauty was also its public language.
A detail worth noticingLook for the winged lion of St. Mark. It appears across the city as an emblem of Venice and its former republic.
Renaissance Florence was not simply fortunate enough to contain great artists. It created an unusually concentrated world in which merchants, bankers, civic leaders, religious institutions, workshops and ambitious patrons all competed to shape the city. Art and architecture became expressions of faith, status, public pride and new ways of understanding the human figure and the natural world.
That is why Florence can feel so coherent when you walk it. The cathedral, baptistery, palaces, sculpture and streets are not isolated masterpieces; they are parts of an ongoing civic conversation. Knowing this changes the experience from checking off famous works to seeing how creative energy was woven into everyday urban life.
Look forThe way major works address public space: doors face piazzas, sculpture meets the street and Brunelleschi’s dome organizes the skyline.
In Tuscany, food and wine make the landscape legible. Regional cooking grew from what the land, season and household could provide: olive oil, bread, beans, garden vegetables, herbs, cured meats and wines shaped by particular hills and soils. The result is not elaborate for its own sake. Its character comes from restraint, good ingredients and a close relationship between place and table.
A Tuscan meal also follows a different social clock. Conversation matters; courses arrive with room between them; wine is understood alongside food rather than apart from it. That is why this winery visit and lunch are allowed to breathe. The unhurried pace is not empty time around the experience—it is part of the experience.
A detail worth noticingListen for how the hosts describe the estate, the vintage and the meal together. Here, provenance is a family story as much as a label.
Rome rarely presents its history in a neat sequence. An ancient column may be built into a later wall; a Renaissance palace may face a Baroque fountain; a modern street may cross the footprint of an imperial complex. Christian Rome reused, preserved and sometimes transformed the fabric of the ancient city, while later generations added their own ambitions above and beside it.
This is why Rome is best understood as a palimpsest rather than a timeline. The Vatican, the Forum, neighborhood churches and everyday piazzas belong to different eras, yet they remain physically and visually in conversation. As you move through the city, history does not stay behind glass. It keeps interrupting the present.
Look forChanges in street level, reused stone and fragments embedded in later buildings—small clues that another Rome often survives directly beneath or within the one you see.
It is easy to arrive thinking of Pompeii as a field of ruins. The site becomes far more affecting when you picture it as a working city: homes opening onto interior courtyards, shops facing busy streets, public baths, places to eat, workshops, painted walls and messages scratched by ordinary people. These details reveal routines that are unexpectedly recognizable.
The eruption of Vesuvius in AD 79 was catastrophic, but the city’s burial also preserved an extraordinary amount of evidence about daily Roman life. Pompeii’s power comes from that tension. The streets are ancient, yet the human impulses visible in them—commerce, humor, hospitality, display and domestic comfort—feel close. The tragedy matters precisely because the people who lived here stop feeling abstract.
A detail worth noticingWatch for stepping stones across the streets, worn thresholds and traces of painted shop signs. They help turn an archaeological plan back into a lived neighborhood.
Sorrento is a natural finale because it changes both the view and the tempo. The town looks across the Bay of Naples toward Vesuvius, while its terraces, citrus gardens and evening streets hold the coast close without requiring every hour to be scheduled. After the scale of Rome and the intensity of Pompeii, that openness feels earned.
The local passeggiata—the evening ritual of walking, greeting and lingering—captures the rhythm beautifully. You can stay near town, follow the peninsula, look toward the islands or simply let the day remain spacious. Ending here gives the Journey room to become personal again: not one last list of sights, but a final stretch shaped by sea air, conversation and choice.
Look forThe changing relationship between the town and the bay as evening arrives. The water becomes less a backdrop than the quiet center of the finale.