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AI-LewisClark
02 Dec 2025
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Rome Florence Venice & Wine Country Highlights

Rome, Florence, Venice & Italian Wine Country — Highlights Itinerary

Experience Italy’s greatest hits in a well-rounded journey: explore Rome’s ancient marvels and Baroque piazzas, immerse yourself in Florence’s unparalleled Renaissance art and architecture, drift along Venice’s canals and ornate basilicas, then unwind among the vineyards of Tuscany and northeastern Italy. This itinerary balances world-class museums and historic monuments with scenic escapes and memorable wine tastings — ideal for travelers who appreciate culture, cuisine and picturesque landscapes. Expect a mix of guided tours and independent time for wandering, food and wine experiences, and plenty of photo-worthy moments.

Recommended Activities

  • Trip Point Pin1

    Colosseum

    Iconic symbol of Ancient Rome where gladiatorial games and public spectacles were held; visiting offers a vivid sense of Roman engineering, architecture and social life, with accessible archaeological remains, underground passages and panoramic views of the Forum and Palatine Hill.
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  • Trip Point Pin2

    Vatican Museums & Sistine Chapel

    Home to one of the world’s greatest art collections, the Museums chronicle millennia of artistic achievement culminating in Michelangelo’s Sistine Chapel ceiling and Last Judgment—an unparalleled experience of Renaissance masterpieces, ornate galleries and sacred history within the independent Vatican City.
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  • Trip Point Pin3

    Pantheon

    Exceptionally well-preserved Roman temple-turned-church featuring a striking oculus and harmonious classical architecture; the Pantheon conveys the engineering mastery and aesthetic ideals of ancient Rome and remains a living monument used for ceremonies and national commemorations.
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  • Trip Point Pin4

    Uffizi Gallery

    Houses one of the world’s most important collections of Renaissance art, including masterpieces by Botticelli, Leonardo da Vinci, Michelangelo and Raphael; visiting offers deep insight into the artistic, cultural and political flowering of Florence and Italy.
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  • Trip Point Pin5

    Cathedral of Santa Maria del Fiore (Duomo)

    A monumental centerpiece of Florence combining Gothic and Renaissance design, famed for Brunelleschi’s innovative dome, Giotto’s bell tower and intricate façade; climbing the dome rewards visitors with panoramic views of the city and appreciation of extraordinary engineering and artistry.
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  • Trip Point Pin6

    Galleria dell'Accademia (David)

    Home of Michelangelo’s iconic statue of David—one of the pinnacles of Renaissance sculpture—plus other notable works in painting and sculpture; seeing David in person offers a powerful encounter with artistic skill, proportion and the humanist ideals of the period.
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  • Trip Point Pin7

    St. Mark's Basilica (Basilica di San Marco)

    A masterpiece of Italo-Byzantine architecture richly decorated with mosaics, gold and marble; visiting reveals Venice’s religious and political history, spectacular interiors, the Pala d’Oro altarpiece, and views from the terrace over Piazza San Marco.
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  • Trip Point Pin8

    Doge's Palace (Palazzo Ducale)

    Once the political heart of the Venetian Republic, the palace showcases opulent Gothic architecture, grand state rooms, and artworks by Titian and Tintoretto; touring the palace and its prisons (via the Bridge of Sighs) immerses you in Venice’s civic power, justice system and art patronage.
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  • Trip Point Pin9

    Grand Canal (Canal Grande)

    Venice’s main waterway lined with palaces and churches spanning centuries of architectural styles; traveling the Grand Canal by vaporetto or private boat provides a sweeping, photogenic perspective on the city’s urban fabric, daily life on the water and historic landmarks from the Rialto to Santa Lucia.
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  • Trip Point Pin10

    Piazza San Marco (St. Mark's Square)

    Venice’s principal public square and social heart, framed by historic landmarks like St. Mark’s Basilica and the Doge’s Palace; its open expanse, cafés, clock tower and frequent musical performances make it ideal for people-watching and appreciating the city’s layered history and atmosphere.
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  • Trip Point Pin11

    Ponte Vecchio

    A medieval stone bridge spanning the Arno known for its charming shops (historically goldsmiths) and picturesque views; strolling across at sunrise or sunset offers intimate views of Florence’s riverside architecture and a tangible sense of the city’s commercial and artistic heritage.
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  • Trip Point Pin12

    Piazza Navona

    Built on the site of an ancient Roman stadium, this Baroque square impresses with grand fountains (notably Bernini’s Fountain of the Four Rivers), ornate churches and lively street life; it’s a cultural focal point for art, performance, outdoor dining and the enduring blend of Rome’s ancient and Baroque identities.
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  • Trip Point Pin13

    Spanish Steps (Scalinata di Trinità dei Monti)

    A monumental staircase connecting Piazza di Spagna and the Trinità dei Monti church, famed for its elegant Baroque design and sweeping views; it’s a popular social and cultural meeting point ideal for photography, people-watching and enjoying the surrounding boutiques and cafés.
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  • Trip Point Pin14

    Trevi Fountain (Fontana di Trevi)

    An iconic Baroque fountain celebrated for its dramatic sculpture, ornate façade and the tradition of tossing a coin to ensure a return to Rome; visiting reveals impressive craftsmanship and lively street atmosphere, especially evocative illuminated at night.
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  • Trip Point Pin15

    Isola Bella (Lake Garda)

    A small, elegantly landscaped island renowned for its terraced Italian gardens and the lavish Borromeo Palace; accessible by boat, it offers scenic views, historic interiors, and a peaceful contrast to city sightseeing—perfect for garden lovers, photography and lakeside relaxation.
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  • Trip Point Pin16

    Valpolicella Wine Region (Amarone producers near Verona)

    Renowned for robust Amarone and other distinctive reds made from partially dried grapes; visiting offers cellar tours and tastings at family-run estates, insight into the appassimento drying method, scenic vineyard landscapes near Verona and opportunities to pair wines with local cuisine.
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  • Trip Point Pin17

    Chianti Classico Wine Region (Tuscany)

    Heart of Tuscany’s wine tradition producing Sangiovese-based Chianti Classico with elegant structure and food-friendly balance; exploring the region provides picturesque hilltop villages, historic wineries and cellars, guided tastings of diverse producers, and combined cultural experiences of art, cuisine and countryside views.
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  • Trip Point Pin18

    Montalcino (Brunello wine region)

    Home to Brunello di Montalcino, one of Italy’s most prestigious and age-worthy red wines produced from 100% Sangiovese; visiting allows tastings at acclaimed cantinas, visits to medieval Montalcino village and fortress, and immersive experiences in slow-food dining and panoramic Tuscan landscapes that shaped the wine’s character.
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  • Trip Point Pin19

    Bolgheri (Super Tuscan wine area)

    Famous for Super Tuscans—innovative, high-quality blends that transformed modern Italian winemaking; visiting Bolgheri offers visits to prestigious estates and cellars, tastings of robust and complex wines, elegant Mediterranean scenery along the coast, and the opportunity to combine wine with refined seaside dining and historic villages.
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  • Trip Point Pin20

    Prosecco Road (Conegliano-Valdobbiadene)

    The birthplace of Prosecco with rolling, vine-covered hills recognized as a UNESCO World Heritage landscape; touring the Prosecco Road includes sparkling wine tastings at family-run wineries, scenic drives or bike rides through vineyards, cellar visits to learn traditional and Charmat-method production, and tasting fresh, lively bubbles paired with local cuisine.
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Restaurants

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    Roscioli (Rome)

    4.3
    $$$$

    Roscioli (Rome)

    A celebrated deli-restaurant offering refined Roman classics and an exceptional wine list; known for its carbonara, cured meats and artisanal pantry goods—ideal for a gourmet taste of Rome.
    4.3
    $$$$
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    La Pergola (Rome)

    4.6
    $$$$

    La Pergola (Rome)

    Three-Michelin-starred fine dining with panoramic views and an inventive degustation menu; perfect for special-occasion haute cuisine and an extensive Italian wine cellar.
    4.6
    $$$$
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    Osteria Francescana (Modena — recommended for food lovers en route from Florence)

    4.5
    $$$$

    Osteria Francescana (Modena — recommended for food lovers en route from Florence)

    Chef Massimo Bottura’s world-renowned restaurant blending tradition and avant-garde creativity; a must-visit for ambitious gourmets seeking a transformative tasting experience (reservations essential).
    4.5
    $$$$
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    Osteria All’Antico Vinaio (Florence)

    4.5
    $$$$

    Osteria All’Antico Vinaio (Florence)

    Famous for generously filled schiacciata sandwiches and casual Tuscan flavors—excellent for quick, authentic and celebrated street-style eating in the historic center.
    4.5
    $$$$
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    Trattoria da Fiore (Venice)

    4.3
    $$$$

    Trattoria da Fiore (Venice)

    A classic Venetian trattoria praised for fresh seafood, cicchetti and seasonal dishes in a welcoming atmosphere—great for experiencing local Venetian flavors off the main tourist routes.
    4.3
    $$$$
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Hotels

  • Hotel Icon

    Hotel Artemide (Rome)

    4.8

    Hotel Artemide (Rome)

    Elegant 4-star hotel on Via Nazionale with spacious rooms, rooftop terrace and excellent service—ideal base for visiting the Colosseum, Pantheon and Trevi Fountain.
    4.8
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    Portrait Firenze (Florence)

    4.8

    Portrait Firenze (Florence)

    Luxury boutique hotel by the Lungarno collection overlooking the Arno and Ponte Vecchio; offers suites with river views, personalized service and prime access to the Uffizi and Duomo.
    4.8
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    Hotel Brunelleschi (Florence)

    4.7

    Hotel Brunelleschi (Florence)

    Historic hotel located in a medieval tower steps from the Cathedral of Santa Maria del Fiore; blends period character with refined amenities—great for exploring Florence’s art and architecture.
    4.7
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    Belmond Hotel Cipriani (Venice)

    4.7

    Belmond Hotel Cipriani (Venice)

    Iconic luxury hotel on Giudecca Island offering lavish rooms, waterfront gardens and a short boat transfer to Piazza San Marco—perfect for a serene, high-end Venetian stay.
    4.7
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  • Hotel Icon

    Castello di Casole, A Belmond Hotel (Tuscany)

    4.8

    Castello di Casole, A Belmond Hotel (Tuscany)

    Restored Tuscan estate in the countryside ideal for exploring Chianti and Montalcino; features farm-to-table cuisine, winery experiences and expansive views of rolling vineyards.
    4.8
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Local Events & Happenings

  • Event Icon

    Mannarino | Acieloaperto

    Mannarino | Acieloaperto

    The event will take place at Parco fluviale Santa Sofia in Santa Sofia (Forlì-Cesena).
    Map IconParco fluviale Santa Sofia in Santa Sofia (Forlì-Cesena) (13.29 mi)
    Calendar Icon2 Aug 2026
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Travel Gems from Reddit

  • Reddit Icon

    13 votes, 48 comments. Ok, this amazing group has helped me figure out that these 3 are the way to go for a trip at the end of October! Now I need

    Venice, Rome, Florence

    13 votes, 48 comments. Ok, this amazing group has helped me figure out that these 3 are the way to go for a trip at the end of October! Now I need

    /r/ItalyTravel
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  • Reddit Icon

    I recently finished a 10 day trip covering Venice, Florence, and Rome, and had a great time! This was from the end of September to the beginning of October. We spent 2 nights ...

    10 day trip report/advice (Venice, Florence, Rome)

    I recently finished a 10 day trip covering Venice, Florence, and Rome, and had a great time! This was from the end of September to the beginning of October. We spent 2 nights ...

    /r/ItalyTravel
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  • Reddit Icon

    11 votes, 34 comments. Our semi-finalized itinerary. First time going so please let me know if Ive over-filled it or left something out. I tried to

    Venice, Florence, Rome 10 day Itinerary- suggestions welcome

    11 votes, 34 comments. Our semi-finalized itinerary. First time going so please let me know if Ive over-filled it or left something out. I tried to

    /r/ItalyTravel
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  • Reddit Icon

    Whether you take a morning or afternoon train would depend on what you want to see in Florence and Rome. I would plan on staying in Florence the 18th to the morning of the 22n...

    Itinerary Advice for Rome, Florence, Tuscany, Cinque Terre, Venice ...

    Whether you take a morning or afternoon train would depend on what you want to see in Florence and Rome. I would plan on staying in Florence the 18th to the morning of the 22n...

    /r/ItalyTravel
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  • Reddit Icon

    If you already have Rome and Venice air travel booked than stick with them and skip Florence. Just be sure you visit Florence on your next visit to Italy. ... Vatican City, an...

    6 days in Rome, Florence and Venice

    If you already have Rome and Venice air travel booked than stick with them and skip Florence. Just be sure you visit Florence on your next visit to Italy. ... Vatican City, an...

    /r/ItalyTravel
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  • Reddit Icon

    Me and my partner are looking at doing a 10-day trip to Italy next April - we want to do Rome for 3 nights, Florence for 3 nights, and then spend some time in Tuscany for 4 ni...

    Italy Itinerary Advice - Rome, Florence, & Tuscany

    Me and my partner are looking at doing a 10-day trip to Italy next April - we want to do Rome for 3 nights, Florence for 3 nights, and then spend some time in Tuscany for 4 ni...

    /r/travel
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  • Reddit Icon

    Day 2: Rome Day 3: Rome Day 4: Rome Day 5: Leave Rome early/mid-morning and head to Naples. Spend day in Naples Day 6: Day trip from Naples to Pompeii Day 7: Hang around in Na...

    Itinerary Help - Rome, Naples, Florence, Venice

    Day 2: Rome Day 3: Rome Day 4: Rome Day 5: Leave Rome early/mid-morning and head to Naples. Spend day in Naples Day 6: Day trip from Naples to Pompeii Day 7: Hang around in Na...

    /r/ItalyTravel
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  • Reddit Icon

    We will be renting a car and spending time in Rome, Tuscany wine region, and Florence. Our high-level itinerary is below. I would love advice on whether to begin the trip with...

    Florence/Tuscany/Rome itinerary

    We will be renting a car and spending time in Rome, Tuscany wine region, and Florence. Our high-level itinerary is below. I would love advice on whether to begin the trip with...

    /r/ItalyTravel
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    Here's our current itinerary: Day 1: Arrive in Venice in the morning Day 2: Venice Day 3: Milan Day 4: Florence Day 5: Florence Day 6: Rome Day 7: Rome Day 8: Rome Day 9: Fly ...

    8-9 Day Itinerary: Venice - Milan - Florence - Rome

    Here's our current itinerary: Day 1: Arrive in Venice in the morning Day 2: Venice Day 3: Milan Day 4: Florence Day 5: Florence Day 6: Rome Day 7: Rome Day 8: Rome Day 9: Fly ...

    /r/ItalyTravel
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  • Reddit Icon

    Or you could potentially do the ... days in Tuscany back by a day. It adds more travel, but it looks like it's less than 2 hours by train from San Miniato to Bologna so n...

    Itinerary advice (Venice/Tuscany/Florence/Rome)

    Or you could potentially do the ... days in Tuscany back by a day. It adds more travel, but it looks like it's less than 2 hours by train from San Miniato to Bologna so n...

    /r/ItalyTravel
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  • Reddit Icon

    If you have 10 days, I would do 5 and 5. There is so much to do in Rome, and Florence is amazing, but this also gives you some time to do ... I agree with the 5 and 5 plus som...

    Rome and Florence in one trip.

    If you have 10 days, I would do 5 and 5. There is so much to do in Rome, and Florence is amazing, but this also gives you some time to do ... I agree with the 5 and 5 plus som...

    /r/ItalyTravel
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  • Reddit Icon

    75 votes, 41 comments. So I just got back from a two-week trip to Italy visiting Rome, Florence, Venice, and Milan. I wanted to share some places I'd

    The Newbie Guide to Italy - Rome, Florence, Venice, and Milan

    75 votes, 41 comments. So I just got back from a two-week trip to Italy visiting Rome, Florence, Venice, and Milan. I wanted to share some places I'd

    /r/ItalyTravel
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  • Reddit Icon

    Hello everyone! I'm planning a trip to Italy with my mom in 5th of September and would appreciate your feedback on our 8 days itinerary. Day 1

    Seeking Feedback on 8 Days Itinerary for Rome and Florence Trip in September

    Hello everyone! I'm planning a trip to Italy with my mom in 5th of September and would appreciate your feedback on our 8 days itinerary. Day 1

    /r/travel
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    We're in the early stages of planning our honeymoon to Italy & Slovenia for late September (getting married in August), but since we plan to register

    Help with Honeymoon Itinerary (Rome, Florence, Venice, and Slovenia!)

    We're in the early stages of planning our honeymoon to Italy & Slovenia for late September (getting married in August), but since we plan to register

    /r/ItalyTravel
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    I'd do 3 days Rome, 2 Florence, 2 Venice. Arrive in Rome and depart in Venice. People usually pick one hotel for their stay in each city. It's rare you need to switch hotel in...

    Best way to stay for Rome, Florence, and Venice?

    I'd do 3 days Rome, 2 Florence, 2 Venice. Arrive in Rome and depart in Venice. People usually pick one hotel for their stay in each city. It's rare you need to switch hotel in...

    /r/ItalyTravel
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  • Reddit Icon

    Hi all, we are a couple with a 2 year old kid from Melbourne, booked the tickets for our mid September travel to Italy , Paris and London. Our main

    Rome, Florence & Venice in 12 Days.

    Hi all, we are a couple with a 2 year old kid from Melbourne, booked the tickets for our mid September travel to Italy , Paris and London. Our main

    /r/ItalyTravel
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    Wife and I celebrating our 10th anniversary on a trip to Italy. Will be our first time visiting Europe. Rate (or roast) my itinerary- suggestions

    Rate my itinerary Venice/ Florence/ Rome

    Wife and I celebrating our 10th anniversary on a trip to Italy. Will be our first time visiting Europe. Rate (or roast) my itinerary- suggestions

    /r/ItalyTravel
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    I want to spend 3 nights in Rome before we depart but the rest of the itinerary is pretty much open. How long should we spend in Venice? Weve never been before. Is renting a c...

    Itinerary planning , Venice to Rome, advice requested

    I want to spend 3 nights in Rome before we depart but the rest of the itinerary is pretty much open. How long should we spend in Venice? Weve never been before. Is renting a c...

    /r/travel
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    Definitely Id do 4 nights Rome, 3 nights Florence, 2 nights somewhere in Tuscany (Siena or a small hill town like San Gimignano or Volterra), and 3-4 nights on the Amalfi Coas...

    2 weeks in Italy - Rome, Florence/Tuscany, Amalfi Coast possible?

    Definitely Id do 4 nights Rome, 3 nights Florence, 2 nights somewhere in Tuscany (Siena or a small hill town like San Gimignano or Volterra), and 3-4 nights on the Amalfi Coas...

    /r/ItalyTravel
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    182 votes, 51 comments. Recently did a 2 week, 2 person trip. I used this sub a lot before/during the trip, so I wanted to give back! We

    Trip Report - Rome/Florence/Venice in May

    182 votes, 51 comments. Recently did a 2 week, 2 person trip. I used this sub a lot before/during the trip, so I wanted to give back! We

    /r/ItalyTravel
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Music for Your Journey

  • Music Icon

    Andrea Bocelli - Con te partirò

    Andrea Bocelli - Con te partirò

    An evocative, yearning ballad that captures the romantic sweep of Italy’s landscapes and historic cities—perfect for train rides between Florence and Venice.
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    Luciano Pavarotti - O Sole Mio

    Luciano Pavarotti - O Sole Mio

    A timeless Neapolitan classic radiating warmth and sunshine, ideal for strolling piazzas and soaking up Italian street life.
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    Giuseppe Verdi - Rigoletto, Act III: La donna è mobile

    Giuseppe Verdi - Rigoletto, Act III: La donna è mobile

    A lively, dramatic aria from Verdi’s Rigoletto that complements the grandeur of opera houses, cathedrals and baroque theatres you’ll encounter.
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    Domenico Modugno - Nel blu dipinto di blu

    Domenico Modugno - Nel blu dipinto di blu

    An upbeat, iconic Italian pop standard that evokes joy and the sensation of soaring above scenic countryside and coastal views.
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    Dean Martin - Arrivederci Roma - Remastered 1998

    Dean Martin - Arrivederci Roma - Remastered 1998

    A nostalgic ode to Rome that matches reflective moments at monuments like the Colosseum and the Trevi Fountain.
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    Vic Sage - Estate

    Vic Sage - Estate

    A smooth, jazzy Italian standard whose mellow mood suits late-afternoon wine tastings and golden-hour walks through Tuscan hills.
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  • Music Icon

    Dean Martin - Mambo Italiano

    Dean Martin - Mambo Italiano

    A playful, energetic tune that adds fun and exuberance to market visits, gondola rides or lively evenings in piazzas.
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  • Music Icon

    Giacomo Puccini - Turandot, Act III: Nessun dorma!

    Giacomo Puccini - Turandot, Act III: Nessun dorma!

    A powerful operatic aria that heightens the sense of drama when visiting monumental sites and viewing historic masterpieces.
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  • Music Icon

    Renato Carosone - Tu Vuo Fa 'L'Americano - From "The American" Soundtrack

    Renato Carosone - Tu Vuo Fa 'L'Americano - From "The American" Soundtrack

    A cheeky, swing-infused Italian song blending cultures—great for upbeat moments, cafés and modern city nights.
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  • Music Icon

    Achille Togliani - La strada nel bosco

    Achille Togliani - La strada nel bosco

    An atmospheric instrumental piece that pairs well with scenic drives through wine regions and quiet, reflective walks in the countryside.
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