September 2026 Grand Italy Tour: Sicily to Udine Itinerary

Palermo · Tuesday, September 1, 2026

Arrival in Palermo and Historic Markets

Morning:

Your Grand Italy Tour begins with a warm welcome at Falcone Borsellino Airport before bypassing the rush to reach the historic heart of Sicily's capital. Marvel at the intricate architectural layers of the Palermo Cathedral and wander toward the grand Quattro Canti, where the four historic quarters of the city meet in a display of Baroque splendor.

Afternoon:

Delve into the chaotic charm of the Ballarò Market, navigating through stalls of fresh produce and sizzling street food while soaking in the city's spirited atmosphere. Later, find a moment of architectural awe at the Teatro Massimo, Italy's largest opera house, before wandering the palm-lined paths of the Villa Bonanno gardens.

Evening:

As dusk settles over the city, admire the fountain's intricate sculptures at Piazza Pretoria before indulging in a seafood dinner in the historic Kalsa District. Conclude your first evening with a digestif at a waterfront bar in La Cala, watching the moon rise over the ancient harbor.

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Palermo · Wednesday, September 2, 2026

Baroque Architecture and Monreale Cathedral

Morning:

Begin your second day at the Palazzo dei Normanni, the seat of the Kings of Sicily, where you will marvel at the glittering Byzantine mosaics within the hidden Cappella Palatina. Afterward, transition from the city center to the surrounding hills to explore the breathtaking Monreale Cathedral, a UNESCO World Heritage site renowned for its stunning gold leaf interior and the intricate sculptures of its Benedictine Cloister.

Afternoon:

After descending from the hills, delve into the macabre history of the Catacombe dei Cappuccini, where a vast collection of mummified remains provides a hauntingly unique glimpse into Palermo's past. Conclude the afternoon by admiring the iconic red domes of San Giovanni degli Eremiti before exploring the narrow, spice-scented alleys of the Mercato del Capo for a taste of local life.

Evening:

As night falls, enjoy a sophisticated passeggiata along the vibrant Via Maqueda, making your way to the historic Piazza Bellini to see the illuminated facade of the Church of Santa Maria dell'Ammiraglio. Conclude your stay in the capital with a gourmet Sicilian dinner in the trendy Piazza Marina, surrounded by the shadows of majestic banyan trees and historic palazzi.

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Agrigento · Thursday, September 3, 2026

Ancient Ruins of the Valley of the Temples

Morning:

Departing Palermo, travel south through the rugged Sicilian interior to reach the spectacular Valley of the Temples, where you will begin your morning exploration at the exceptionally preserved Temple of Concordia. Walk along the ancient Sacred Way to admire the towering columns of the Temple of Juno, perched high on a ridge overlooking the Mediterranean Sea. Complete your morning journey through antiquity at the Temple of Heracles, the oldest structure in the park, as you soak in the golden hues of the Doric architecture against the azure sky.

Afternoon:

Continue your archaeological odyssey at the colossal ruins of the Temple of Olympian Zeus, where you can stand beside the replica of a massive Atlas (Telamon) stone giant. Find a refreshing escape within the lush greenery of the Kolymbethra Garden, an ancient citrus grove and orchard nestled between the sandstone cliffs. Afterward, deepen your historical understanding at the Pietro Griffo Archaeological Museum, which houses an extensive collection of artifacts recovered from the surrounding archaeological site.

Evening:

As the sun sets, retreat to the historic hilltop center of Agrigento to join the evening crowds along the vibrant Via Atenea, the city's primary social thoroughfare. Take in sweeping views of the illuminated archaeological park from the Belvedere di Agrigento before enjoying a refined Sicilian dinner near the architectural facade of Piazza Pirandello as the day's heat fades.

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Syracuse · Friday, September 4, 2026

Ortigia Island and Greek Heritage

Morning:

Begin your exploration of ancient Syracuse at the Neapolis Archaeological Park, where the massive Greek Theatre remains one of the most impressive structures of the Hellenic world. Step inside the towering limestone walls of the Latomia del Paradiso to experience the legendary acoustics of the Ear of Dionysius and witness the ruined majesty of the Altar of Hiero II nearby. Conclude your morning journey through time at the nearby Roman Amphitheatre, imagining the gladiator spectacles that once captivated the city's ancient residents.

Afternoon:

Cross the bridge into the ancient heart of Ortigia Island to witness the remains of the Temple of Apollo, the oldest Doric temple in Sicily. Wander the labyrinthine streets to reach the stunning Piazza del Duomo, where you can admire the unique facade of the Syracuse Cathedral, famously built around the columns of an ancient Greek temple. Conclude your afternoon walk by the freshwater springs of the Fonte Aretusa, observing the wild papyrus plants while taking in views across the Great Harbor.

Evening:

As the sun dips below the horizon, make your way to the southern tip of the island to admire the formidable medieval architecture of Castello Maniace against the darkening waves. Afterward, join the locals for a vibrant stroll along the Lungomare Alfeo, stopping for a glass of Sicilian wine in the historic Giudecca District. Conclude your evening with a refined dinner near the fountain of Piazza Archimede, reflecting on the layered history of this ancient port city.

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Taormina · Saturday, September 5, 2026

Mount Etna Exploration and Taormina Views

Morning:

Rise early to ascend the slopes of Mount Etna, Europe's highest active volcano, to explore the dramatic lunar landscape surrounding the Silvestri Craters. From the base at Rifugio Sapienza, enjoy a guided trek or a cable car ascent toward the summit craters to witness breathtaking views of the Ionian Sea stretching toward the horizon.

Afternoon:

Descend the volcano to reach the hilltop gem of Taormina, where you will explore the remarkably preserved Teatro Antico di Taormina for breathtaking vistas of the coastline and the smoking summit you just visited. Wander the shop-lined Corso Umberto until you emerge onto the panoramic Piazza IX Aprile, a lively square perfect for spotting the tiny islet of Isola Bella from above. End your afternoon in the shade of the Villa Comunale gardens, marveling at the unique architectural 'follies' and vibrant Mediterranean flora.

Evening:

As twilight glimmers, enter the city's western gate at Porta Catania to admire the fortress-like Duomo di Taormina and the baroque Fontana di piazza Duomo illuminated by the streetlamps. Finish your evening with a candlelit dinner in a cobblestone alleyway within the historic Borgo Medievale, pairing Sicilian specialties with a glass of local Malvasia as the Mediterranean breeze drifts through the town.

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Tropea · Sunday, September 6, 2026

Cross the Strait of Messina and Calabria Coast

Morning:

Begin your journey toward the mainland by visiting the Messina Cathedral to witness its famous astronomical clock before boarding a scenic ferry to traverse the historic Strait of Messina. As you reach the Italian peninsula at Villa San Giovanni, enjoy the transition to the rugged Calabrian landscape while following the coastal roads north toward the Tyrrhenian Sea.

Afternoon:

After driving along the stunning 'Coast of the Gods,' arrive in Tropea to explore the iconic Santa Maria dell'Isola Sanctuary, a medieval monastery perched dramatically on a rocky promontory. Continue your afternoon by wandering through the narrow, sun-drenched alleys of the Centro Storico before reaching the Affaccio del Corso balcony for a breathtaking panoramic view of the turquoise Tyrrhenian Sea.

Evening:

As the sun begins its descent, head to Piazza del Cannone for a spectacular sunset view before settling into a café in Piazza Ercole to sample the famous local Cipolla Rossa di Tropea during a relaxed aperitivo. Afterward, descend toward the Marina di Tropea for a sophisticated seafood dinner where you can watch the lights of the harbor twinkle against the dark silhouette of the cliffs. End your evening with a moonlit walk along the Lungomare to experience the town's peaceful coastal magic and refreshing sea breeze.

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Naples · Monday, September 7, 2026

Scenic Drive through Campania and Naples Halt

Morning:

Bid farewell to Calabria as you journey north through the scenic heart of the Cilento and Vallo di Diano National Park, enjoying the shifting vistas of the rugged Italian landscape as you approach the Neapolitan border. Upon arriving in the bustling city of Naples, begin your immersion into the capital of Campania with a visit to the grand Piazza del Plebiscito to admire the neoclassical facade of the Basilica of San Francesco di Paola.

Afternoon:

Stroll through the glass-domed grandeur of the Galleria Umberto I before exploring the opulent state apartments of the Royal Palace of Naples. Afterward, lose yourself in the vibrant energy of the Spanish Quarters, pausing to discover the labyrinthine history hidden beneath the city streets at Naples Underground.

Evening:

As the sun sets over the Tyrrhenian Sea, enjoy a relaxing walk along the Lungomare Caracciolo to admire the ancient stone walls of Castel dell'Ovo illuminated against the darkening waves. Retreat to the charming harbor of Borgo Marinari for a traditional seafood dinner, and conclude your Neapolitan experience with a craft cocktail in the lively Piazza Bellini, soaking in the city's intellectual and bohemian atmosphere.

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Rome · Tuesday, September 8, 2026

Central Italian Heartland and Eternal City Transit

Morning:

Bid farewell to Campania as you journey north through the scenic Lazio countryside, entering the capital along the remnants of the ancient Appian Way. Your Roman introduction begins at the magnificent Archbasilica of Saint John Lateran, where you can marvel at the towering statues of the Apostles and climb the sacred steps of the nearby Scala Sancta.

Afternoon:

Continue your Roman journey toward the city's ancient core to stand in the shadow of the colossal Colosseum and wander through the sun-bleached ruins of the Roman Forum. From there, make your way to the bustling Piazza Venezia to admire the towering white marble of the Altare della Patria and the historic facade of Palazzo Venezia.

Evening:

Spend your first Roman night wandering toward the Baroque heart of the city to witness the illuminated majesty of the Trevi Fountain before standing in awe beneath the ancient portico of the Pantheon. Afterward, stroll through the vibrant Piazza Navona to admire Bernini's Fountain of the Four Rivers before settling in for a classic Roman dinner near the lively, historic square of Campo de' Fiori.

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Florence · Wednesday, September 9, 2026

Tuscan Countryside and Renaissance Art

Morning:

Leave the Eternal City behind to journey through the golden, rolling hills of the Tuscan Countryside, pausing in the medieval jewel of Siena to walk across the historic, shell-shaped Piazza del Campo. Upon arriving in Florence, your Renaissance exploration begins at the Piazza del Duomo, where you can marvel at the intricate marble patterns of the Florence Cathedral and the soaring height of Giotto's Bell Tower.

Afternoon:

Step into the heart of the Renaissance at the Uffizi Gallery, where you will encounter world-renowned works by Botticelli and Michelangelo within a stunning architectural setting. Afterward, take a scenic stroll toward the Arno River to cross the legendary, shop-lined Ponte Vecchio, and conclude your afternoon by marveling at the colossal statues on display in Piazza della Signoria.

Evening:

As the sun begins to set, make your way up to Piazzale Michelangelo for an unparalleled panoramic view of Florence's skyline as it glows in the golden hour light. Afterward, cross back over the river to the artisan Oltrarno district to enjoy an authentic dinner in a cozy trattoria near the Basilica di Santo Spirito. Complete your evening with a vibrant walk through Piazza della Repubblica, where the illuminated carousel and street musicians create a magical atmosphere under the Tuscan stars.

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Venice · Thursday, September 10, 2026

Venetian Canals and Bridge of Sighs

Morning:

Depart the rolling hills of Tuscany for the floating city, arriving at the Venezia Santa Lucia railway station where the shimmering Grand Canal immediately greets you. Begin your Venetian adventure with a visit to the iconic Piazza San Marco to admire the golden mosaics of St. Mark's Basilica and the majestic heights of the St. Mark's Campanile.

Afternoon:

Step into the opulent chambers of the Doge's Palace to admire the Venetian Gothic architecture before walking through the haunting passage of the Bridge of Sighs. Afterward, navigate the bustling labyrinth of streets to reach the iconic Rialto Bridge, where you can browse the vibrant market stalls and watch the gondolas glide along the busy waters.

Evening:

As twilight falls, escape the crowds for a traditional cicchetti crawl through the atmospheric Cannaregio district, stopping at historic wine bars nestled along the vibrant Fondamenta della Misericordia. Conclude your Venetian night with a moonlit stroll past the illuminated facade of Teatro La Fenice before pausing at the wooden Ponte dell'Accademia to admire the city lights reflecting off the water toward the distant dome of Santa Maria della Salute.

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Udine · Friday, September 11, 2026

Friulian Foothills and Udine Castle Peaks

Morning:

Bid farewell to the lagoons of Venice as you journey northeast into the Friuli-Venezia Giulia region, arriving in the elegant center of Udine at the spectacular Piazza Libertà. Marvel at the Venetian Gothic influence of the Loggia del Lionello and the nearby Torre dell'Orologio before ascending the hill to the Castello di Udine, where sprawling views of the city and the distant Friulian Prealps stretch toward the horizon.

Afternoon:

Descend from the castle hill to explore the Udine Cathedral, where the baroque interior gives way to the stunning Oratorio della Purità and its celestial Tiepolo frescoes. Continue your cultural immersion at Casa Cavazzini, the city's museum of modern art, before settling into a cafe in the bustling, portico-lined Piazza Matteotti to soak in the local Friulian atmosphere.

Evening:

As the shadows lengthen, join the locals for the classic tajut ritual along the charming Via Mercatovecchio, perhaps stopping at the rustic Osteria alla Ghiacciaia to sip wine beside an ancient canal. End your first evening in Udine with a sumptuous Friulian dinner near the historic Porta Aquileia, savoring local flavors while reflecting on the journey from Sicily to the northern reaches of Italy.

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Udine · Saturday, September 12, 2026

Star-shaped City of Palmanova and Local Markets

Morning:

Start the final day of your grand tour by traveling a short distance from Udine to the extraordinary star-shaped fortress city of Palmanova, a UNESCO World Heritage site renowned for its radial symmetry. Stand in the center of the massive, hexagonal Piazza Grande to admire the statues representing the city's military history and the elegant facade of the Dogal Cathedral. Before departing, explore the defensive earthworks and the monumental Porta Udine, one of the three historic gates that have guarded this Venetian masterpiece for centuries.

Afternoon:

Upon returning to the provincial capital, immerse yourself in the local lifestyle at the bustling Mercato di Via Zanon, where you can browse stalls of regional delicacies and artisanal Friulian handicrafts. Conclude your final afternoon with a peaceful stroll through the verdant pathways of Parco del Cormor or by admiring the historic storefronts along the elegant Via Gemona as your grand tour draws to a close.

Evening:

Celebrate the conclusion of your Italian odyssey with a final celebratory feast in the historic Borgo Grazzano district, savoring traditional Friulian flavors and world-class regional wines. Conclude your grand tour with a reflective moonlit stroll along the ancient stone banks of the Roggia di Udine canal, cherishing the memories of a journey that spanned the entire length of the beautiful peninsula.

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Estimated Costs (per person)

Place / ActivityCost
Palermo Cathedral (Monumental Area)€15
Quattro CantiFree
Ballarò MarketFree
Teatro Massimo Guided Tour€12
Street Food in Kalsa District€15
Palazzo dei Normanni & Cappella Palatina€19
Monreale Cathedral (Cloister)€8
Catacombe dei Cappuccini€5
Valley of the Temples€17
Kolymbethra Garden€7
Pietro Griffo Archaeological Museum€10
Dinner near Piazza Pirandello€35
Neapolis Archaeological Park€13
Syracuse Cathedral€2
Castello Maniace€4
Mount Etna Tour 3000 (Cable Car & 4x4)€80
Teatro Antico di Taormina€14
Santa Maria dell'Isola (Garden Access)€2
Ferry Strait of Messina (Foot Passenger)€5
Royal Palace of Naples€15
Naples Underground (Napoli Sotterranea)€15
Colosseum & Roman Forum€18
Pantheon€5
Uffizi Gallery€29
Giotto's Bell Tower (Giotto Pass)€20
Doge's Palace€30
St. Mark's Basilica & Campanile€25
Castello di Udine Museums€10
Casa Cavazzini€7
Tajut Ritual in Udine€10
Palmanova Dogal CathedralFree
Estimated Total (per person)€464
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