Italy rewards the curious. From the marble bones of the Colosseum to sunlit Chianti vineyards and the fiery legacy of Vesuvius, this country invites you to taste, climb, sip, and linger. Over 20 days you’ll explore Rome’s ancient heart, Florence’s Renaissance masterpieces and Tuscan wine country, and Naples’ kinetic streets with day trips to Pompeii and the Amalfi Coast.

Rome’s emperors engineered spectacles, Florence’s Medici funded genius, and Naples fueled an irresistible food culture—pizza, espresso, and slow-simmered ragù. You’ll weave between world-class museums and fresh-air adventures: bike the Appian Way, cook pasta with unlimited wine, and ferry to pastel-hued coastal towns.

Practical notes: Trains are fast and affordable; book in advance for the best fares. Dress modestly for churches (shoulders and knees covered), keep an eye out for pickpockets in crowded areas, and reserve popular restaurants and museum entries ahead. Coffee culture is quick—order at the bar, pay, and savor standing with locals.

Rome

The Eternal City layers millennia of history: pagan temples reborn as churches, Renaissance palaces, and trattorie that feel like family living rooms. Between ruins and river sunsets, chase an adventurous rhythm—catacombs, cobbles, and bold street food.

Base yourself in Trastevere, Monti, or the historic center for walkable sightseeing and great coffee. Don’t miss the Capitoline Museums, the Borghese’s baroque jewels, and an evening passeggiata along the Tiber.

Days 1–7: Ancient wonders, Vatican art, food neighborhoods, and offbeat Rome

• Sightseeing hit list: Colosseum, Roman Forum, Palatine Hill, Pantheon, Trevi Fountain, Spanish Steps, Piazza Navona, and the Capitoline Hill outlook. Time the Trevi and Pantheon early morning for fewer crowds.
• Vatican and art: Book skip-the-line access to the Vatican Museums and Sistine Chapel, then step into St. Peter’s Basilica. Consider climbing the dome for 360° views.
• Adventurous Rome: Rent bikes on the ancient Appian Way to coast past aqueducts and tombs; explore the Catacombs of San Sebastiano or San Callisto; join a small-group golf cart tour to stitch the city’s highlights together in one breezy ride.
• Neighborhood grazing: In Trastevere, wander ivy-draped lanes and trattorie. In Monti, browse indie boutiques, sip natural wine, and snack on supplì (fried rice balls) and Roman-style pizza al taglio.

Recommended tours (aligning with your interests):

Skip-the-Line Group Tour of the Vatican, Sistine Chapel & St. Peter's Basilica

Rome: Colosseum, Roman Forum, and Palatine Hill Guided Tour

Rome Highlights City Tour by Golf Cart with Gelato

Winner 2025 Rome Twilight Trastevere Food Tour by Eating Europe

Optional adventurous day from Rome: If you prefer a guided dash south before changing cities, this small-group tour bundles Pompeii, the Amalfi Coast, and Positano into one day: Pompeii, Amalfi Coast and Positano Day Trip from Rome.

Coffee & breakfast: Sant’Eustachio Il Caffè (legendary wood-roasted espresso near the Pantheon), Tazza d’Oro (try the granita di caffè), and Pasticceria Regoli (cream-filled maritozzi since 1916).

Lunch ideas: Pizzarium Bonci (inventive pizza al taglio by the Vatican), Trapizzino (pocket bread stuffed with Roman classics), and Mercato Testaccio (market stalls for pasta, panini, and Sicilian sweets).

Dinner picks: Da Enzo al 29 (carbonara and amatriciana in Trastevere), Roscioli Salumeria con Cucina (cacio e pepe and a superb wine list), and Cesare al Casaletto (Roman comfort dishes and natural wines). For cocktails, try Drink Kong or the speakeasy-style Jerry Thomas Project (book ahead).

Where to stay (mid-range friendly):

• Hotels in Rome (Hotels.com) | Apartments in Rome (VRBO)
• Specific picks: Hotel Eden, Dorchester Collection (splurge), Hotel Santa Maria (Trastevere charmer), The Beehive (stylish budget).

Getting to Rome: Search flights to Italy on Omio (Flights). For multi-city planning from non-European hubs, compare on Kiwi.com.

Travel to Florence (morning of Day 8): High-speed train Rome→Florence takes ~1h30–1h40; advance fares often €25–€60. Book on Omio (Trains). Buses take 3.5–4.5 hours and can be cheaper on Omio (Buses).

Florence

Florence is a Renaissance open-air museum where Brunelleschi’s dome crowns a compact city of ateliers, chapels, and wine bars. Cross the Arno to the artisan Oltrarno, then climb to Piazzale Michelangelo for that postcard skyline at golden hour.

Balance Uffizi and Accademia masterpieces with Tuscan countryside days—cypresses, castles, and Chianti Classico. Adventurous souls can go off-road on a “wine safari” or cycle the rolling lanes between hill towns.

Days 8–13: Renaissance Florence and Tuscan wine country

• Art and architecture: Book timed entry for the Uffizi and Accademia (Michelangelo’s David). Climb Giotto’s Bell Tower or Brunelleschi’s Dome for sweeping views. Don’t miss Santa Croce’s frescoes and artisan leather workshops nearby.
• Tuscany day trips: Siena’s scallop-shaped Piazza del Campo, San Gimignano’s medieval towers, and Pisa’s Leaning Tower are classic. Wine lovers can dedicate a day to Chianti estates and small-production tastings.
• Unique hands-on: Join a pasta-making class with bottomless wine, or head into vineyards by 4x4 to taste among the vines.

Recommended tours (wine tasting + unique activities):

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Small-Group Wine Tasting Experience in the Tuscan Countryside

SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

Florence: Pasta Cooking Class with Unlimited Wine

Coffee & breakfast: Ditta Artigianale (specialty roaster; try the flat white with a cornetto), Caffè Gilli (since 1733 on Piazza della Repubblica), and Forno Pugi (schiacciata alla fiorentina and savory focacce).

Lunch ideas: Trattoria Mario (hearty ribollita and bistecca alla fiorentina; lunch only), All’Antico Vinaio (overflowing schiacciata panini—go early), and Mercato Centrale (upstairs food hall for quick, tasty options).

Dinner picks: Trattoria Sostanza (butter chicken and artichoke omelet; book well ahead), Trattoria da Burde (old-school Tuscan fare), and Le Volpi e L’Uva (intimate wine bar with small plates—perfect pre-dinner).

Where to stay (great for a mid-range budget):

• Hotels in Florence (Hotels.com) | Apartments in Florence (VRBO)
• Specific picks: Hotel Brunelleschi (historic tower setting), Hotel Santa Croce (excellent location and value), Grand Hotel Minerva (rooftop pool near Santa Maria Novella).

Travel to Naples (morning of Day 14): High-speed train Florence→Naples takes ~2h50–3h10; advance fares often €30–€70. Book on Omio (Trains). Budget buses (5.5–7 hours) on Omio (Buses).

Naples

Naples brims with life: scooters and church bells, laundry lines and baristas pulling short, intense shots. It’s a launchpad for Pompeii and the Amalfi Coast, but its own treasures—Roman ruins beneath the streets, exquisite chapels, and the world’s best pizza—demand time.

Spend your days between the historic center, the seafront promenade, and hilltop viewpoints. For museums, the National Archaeological Museum (MANN) holds the finest Pompeii mosaics; Capodimonte showcases Renaissance and Baroque masterpieces.

Days 14–20: Naples, Pompeii, and the Amalfi Coast

• Pompeii with an expert: Ride the Circumvesuviana to Pompei Scavi or take a guided tour with skip-the-line access for deep context (recommended below). If you have extra time, add Herculaneum—smaller, but astonishingly preserved.
• Amalfi Coast adventure: Day trip via train to Sorrento, then ferry to Positano/Amalfi (book on Omio (Ferries)). Hikers can tackle the Path of the Gods from Bomerano to Nocelle (start early, bring water, moderate difficulty, spectacular sea views).
• Underground Naples: Explore tunnels, cisterns, and war shelters beneath the city, then visit the Sansevero Chapel to marvel at the Veiled Christ (reserve timed slots).
• Evening by the water: Stroll the Lungomare from Castel dell’Ovo at sunset and sip a spritz overlooking the bay.

Recommended tour:

Pompeii Small Group Tour with an Archaeologist

Coffee & breakfast: Gran Caffè Gambrinus (liberty-style icon; try a sfogliatella), Caffè Mexico (neon-orange cups; classic Neapolitan roast), and Pasticceria Attanasio (warm sfogliatelle near the station).

Lunch ideas: L’Antica Pizzeria da Michele (the pilgrimage—Margherita or Marinara), 50 Kalò (elegant pies with precise dough), and Pignasecca Market (street-food crawl: fried anchovies, cuoppo, and taralli).

Dinner picks: Starita a Materdei (montanara fritta and classic pies), Tandem (slow-cooked ragù napoletano over pasta), and Osteria della Mattonella (majolica tiles, homestyle seafood).

Where to stay (great bases in Chiaia, Centro Storico, or along the seafront):

• Hotels in Naples (Hotels.com) | Apartments in Naples (VRBO)
• Specific picks: Grand Hotel Vesuvio (Bay views by Castel dell’Ovo), Hotel Piazza Bellini (boutique in the historic center), Hotel Royal Continental (seafront strolls).

Departing Italy: Consider flying out of Naples or a fast train back to Rome (~1h10 on the Frecciarossa; book via Omio (Trains)). For flights home, compare on Omio (Flights).

Budget & timing tips for a 50/100 spend

• Prioritize a few key paid tours (Vatican, Colosseum, Pompeii, one wine day) and mix in free highlights (piazzas, churches, viewpoints). Reserve skip-the-line options to maximize time.
• Trains booked 2–4 weeks ahead are often half the last-minute price. In cities, walk or use metro/buses; taxis are pricier and slower in traffic.
• Eat like a local: stand at the bar for cheaper coffee; choose house wine at trattorie; markets make excellent picnic lunches between museum visits.

Summary: In three vibrant bases—Rome, Florence, and Naples—you’ll trace the arc of Italian history from empire to Renaissance to the modern South. Expect museum mornings, espresso interludes, vineyard afternoons, and coastal sunsets, all stitched together by fast trains and unforgettable plates of pasta.