Your itinerary
Day 1
Day 1: Lively Milan
Meet your Travel Director at Milan Malpensa Airport and join your group for a welcome dinner with wine at a traditional restaurant.
Meals: Dinner
Day 2
Day 2: Travel from Milan to Venice
Drive from Milan across the Veneto plain to Venice, check into your hotel and optionally spend the evening in St. Mark’s Square at an alfresco café with live music.
Meals: Breakfast
Day 3
Day 3: Venice Highlights: Canals and Crafts
Travel by private boat to St. Mark’s Square; see the Doge’s Palace and Bridge of Sighs; enjoy a gondola ride and a glassblowing demonstration; optional excursion to Burano with dinner.
Meals: Breakfast
Day 4
Day 4: Visit Pisa and Dine in Tuscany
Visit Pisa to see the Leaning Tower, then continue to Florence; optional traditional Tuscan dinner in the evening.
Meals: Breakfast
Day 5
Day 5: Renaissance Florence: Art and San Gimignano
In Florence, choose the Accademia Gallery to see Michelangelo’s David or enjoy a local café treat; with a Local Specialist visit Piazza del Duomo, Giotto’s bell tower and the Baptistery doors, and Piazza della Signoria; watch gold and leather craftsmanship; afternoon at leisure or optional visit to San Gimignano.
Meals: Breakfast,Dinner
Day 6
Day 6: Orvieto to Rome: Piazzas and Pantheon
Stop in Orvieto to see Piazza del Duomo and its cathedral, then continue to Rome; optional evening passeggiata to piazzas, fountains and the Pantheon, with a coin toss at the Trevi Fountain.
Meals: Breakfast
Day 7
Day 7: Explore Rome's Art and Vatican Icons
Skip-the-line visit to the Vatican Museums and Sistine Chapel with a Local Specialist; view St. Peter’s Basilica exterior; free time; dinner featuring regional cuisine in Rome. If Vatican access is limited, visit the Capitoline Museums instead.
Meals: Breakfast,Dinner
Day 8
Day 8: Farewell To Italy's Cities And Chapels
Farewell and departure from Rome.
Meals: Breakfast
What’s included
What’s not included
Additional information
Dining Summary
- 3 Dinner (D)
- 7 Breakfast (B)
How You'll Travel
- Business class coach with extended leg room
- Top-rated dining, from farm-to-table to local restaurants
- 4 & 5-star stays
Authentic Dining
- Milan: Get to know your fellow travelers over a special dinner with wine.
- Rome: Savor regional flavors and embrace Rome’s rich culinary heritage as you toast to the Eternal City over your Roman dinner.
Trafalgar Choice
- Florence: Stand beside Michelangelo’s monumental statue, ‘David’, in the Accademia Gallery, and admire the exquisite technique and absorbing history behind the world’s most famous sculpture.
- Florence: Join your Travel Director on a short walk to a local spot loved by residents. Sample a classic Italian treat and hear how it became a staple of the area. It’s a chance to experience the flavors locals grow up with and return to time and again.
Premium Experience
- Vatican City: Visit the Vatican Museums and witness the genius of Michelangelo in the Sistine Chapel.
Venice Orientation Cruise: Giudecca Canal to St Mark’s Square
Cruise the Venetian lagoon by private boat along the Giudecca Canal, gliding past Gothic and Renaissance palazzi as your Travel Director sets the scene for La Serenissima. Step ashore by the Doge’s Palace to take in the drama of St Mark’s Square, where stone arcades frame the shimmering basilica.
Feel the light salt breeze and hear the soft slap of water against the hull while stories of Venice’s maritime republic bring facades to life. This waterborne introduction captures the city’s perspective best seen from the canals.
Venice Gondola Glide through the Canals
Glide on a gondola along quiet backwater canals, slipping under stone bridges and past centuries-old palaces. Your gondolier sets an unhurried rhythm, oar whispering through the water as balconies, laundry lines, and church campanili reveal the city’s intimate side.
Learn how these hand-crafted black-lacquered boats and their pilots became icons of Venice. The gentle sway and echoing footsteps along the fondamenta create a mood of palace-lined canals and hushed waterways seen at eye level.
Venetian Glassblowing Demonstration
Witness a glassblowing demonstration as masters coax molten glass from the furnace heat, shaping vases and filigreed forms in a choreography of breath and motion. Stand close enough to sense the glow as color and clarity emerge by practiced hand.
Hear how the Murano tradition guarded techniques for centuries, fueling Venice’s reputation for luxury craft. From ornate goblets to sculptural pieces, each creation celebrates precision, patience, and the city’s legacy of delicate artistry.
Pisa’s Leaning Tower & Piazza dei Miracoli Orientation
See the Leaning Tower of Pisa on an orientation that explores the Piazza dei Miracoli—a harmonious ensemble of Romanesque cathedral and baptistery set on a lawn of startling green. Trace the tower’s famous tilt from marble base to belfry as arcades and columns climb at a graceful slant.
Hear the tales of medieval Pisa and the science legend of Galileo as you pause for photos and reflection among white marble carvings and geometries that glow softly in Tuscan light.
Florence Walking Tour & Leather and Gold Workshop
Join a guided walking tour across Piazza del Duomo to admire the cathedral’s marble patterns, Giotto’s bell tower, and the baptistery’s gilded “Gates of Paradise”. In Piazza della Signoria, sculptures and the fortress-like Palazzo Vecchio reveal Florence’s civic heart.
Continue into the Santa Croce quarter to watch artisans at work during a leather and gold demonstration. Smell fine hides, see precise tooling, and learn how Florentine craftsmanship has defined elegance from Renaissance workshops to today.
Florence Choice: Accademia Gallery & Michelangelo’s David
Stand before Michelangelo’s David at the Accademia Gallery, contemplating sinew, veins, and the focused gaze carved from a single block of Carrara marble. Your Local Specialist illuminates the sculpture’s role in Renaissance Florence and its audacious scale and symbolism.
Witness the chisel’s legacy in Michelangelo’s unfinished “Prisoners” and appreciate the city’s devotion to art as civic pride. This is an included Trafalgar Choice experience—select it in place of the tasting walk.
Florence Choice: Local Treat Tasting Walk
Sample a classic Italian treat on a short neighborhood stroll with your Travel Director to a spot beloved by Florentines. Sip, bite, and savor as you hear local food lore and how small rituals—morning espresso, afternoon sweets—anchor daily life.
This relaxed tasting reveals the city’s flavor traditions beyond the museums, inviting you to slow down and connect with a favorite address locals return to again and again. This is an included Trafalgar Choice experience—select it in place of the Accademia visit.
Orvieto Hilltown Orientation & Duomo Facade
Explore hilltop Orvieto, poised on tufa cliffs above Umbrian vineyards. In Piazza del Duomo, gaze at the Cathedral of Orvieto, its mosaic-studded facade alive with gilded scenes, bas-reliefs, and slender pinnacles that catch the changing light.
Hear how Etruscan roots and medieval devotion shaped this serene town. From artisan shops to panoramic glimpses of the countryside, it’s a moment to pause for photos and reflection in a place where time moves gently.
Ancient Rome Orientation: Circus Maximus, Arch of Constantine & Palatine Hill
Explore Rome’s storied past as you view the sweep of Circus Maximus, the triumphal Arch of Constantine, and the mythical slopes of Palatine Hill. Your Travel Director frames each landmark within the city’s epic narrative of emperors, victories, and daily spectacle.
Imagine chariots thundering past packed stands and processions passing beneath victory arches. With vistas toward the Colosseum and Forum, this orientation gathers the essential threads of Rome’s ancient heart.
Vatican Museums, Sistine Chapel & St Peter’s Square
Benefit from fast-tracked entry to the Vatican Museums with a Local Specialist, culminating in the hush of the Sistine Chapel. Tilt your gaze to Michelangelo’s frescoes—the Creation of Adam, prophets and sibyls—alive with movement and color.
Step into the embrace of St Peter’s Square, where Bernini’s colonnades arc like welcoming arms. On rare occasions when Vatican access is restricted, a curated visit to the Capitoline Museums showcases Rome’s classical masterpieces instead.
Roman Dinner: Flavors of the Eternal City
Savor Roman cuisine at a local restaurant, where simple, time-honored recipes shine—think pecorino-rich pasta and seasonal produce. Relax over conversation and sample regional wines that pair naturally with the city’s bold, elemental flavors.
Hear how cucina romana reflects frugality and flair, from market stalls to trattorie. This shared table is a warm, unpretentious celebration, inviting you to toast the Eternal City and its enduring appetite for la dolce vita.
Venice Lagoon Cruise to Burano with Dinner
Cruise the Venetian lagoon to Burano’s candy-colored houses, where fishermen’s cottages and a leaning bell tower create postcard-perfect scenes. Stroll quiet lanes and watch lace-makers keep a delicate tradition alive.
Settle in for a seafood-forward dinner that reflects the islands’ briny pantry and convivial spirit. This is an optional experience at additional cost, bookable on tour with your Travel Director.
Tuscan Countryside Dinner with Chianti
Venture into the rolling hills for a traditional Tuscan dinner in a rustic countryside setting. Expect olive oil-fragrant dishes, garden herbs, and hearty meats complemented by sample regional wines from nearby vineyards.
Between candlelit tables and stone walls, stories of the land and its vintners flow easily. This is an optional experience at additional cost, bookable on tour for an evening steeped in Tuscan warmth.
San Gimignano: Towers and Medieval Lanes
Walk medieval streets in UNESCO-listed San Gimignano, where a striking skyline of towers rises over vineyards and olive groves. Wander stone lanes to Piazza della Cisterna, framed by noble houses and artisan shops.
Hear how rival families built skyward for prestige and protection, shaping the town’s distinctive profile. Enjoy time to pause for photos and reflection. This is an optional experience at additional cost, bookable on tour.
Rome Evening Passeggiata: Pantheon, Piazzas & Trevi Fountain
Join an evening passeggiata with a Local Specialist through baroque squares and lively alleys to the Pantheon, Piazza Navona’s Bernini fountains, and the luminous Trevi Fountain. The city’s stones seem to glow as twilight settles.
Unpack tales of emperors, popes, and artists while streets fill with musicians and café chatter. Toss a coin and make a wish—an atmospheric close to Rome by night. This is an optional experience at additional cost, bookable on tour.
Operated By
Insight Vacations
Milan Welcome Dinner with Wine
Savor a convivial welcome dinner in Milan and meet your Travel Director and fellow travelers. In a classic local setting, sample regional wines alongside Northern Italian flavors—silky risotto, aged cheeses, and seasonal produce—setting a generous first impression of Lombardy’s table and its modern, stylish capital.
Hear how Milan’s aperitivo traditions shape social life and pick up tips on dining like a local. This relaxed introduction celebrates shared plates and warm conversation, inviting you to toast the journey ahead in Italy’s design-driven city.