Italy rewards slow travel. In three weeks you can trace 2,000 years of history from the Colosseum to the Vatican, wander Renaissance streets where Brunelleschi and Michelangelo changed art forever, and sail past lemon terraces toward Capri’s Blue Grotto. You’ll taste regional cuisines that transform with every train you take—Roman carbonara, Florentine bistecca, Neapolitan pizza, and Amalfi’s seafood and lemons.

Expect lively piazzas, morning espresso rituals, and museums that house half the world’s masterpieces. Italy is safe and welcoming; pickpocketing can occur in crowded areas, so carry valuables with care. Churches enforce modest dress (shoulders and knees covered), and many restaurants prefer reservations at dinner, especially on weekends.

Getting around is easy by high-speed rail. Book European flights and trains with Omio flights and Omio trains; travelers flying from outside Europe can compare fares on Trip.com flights or Kiwi.com. Trains are usually punctual; strikes are announced in advance. Visit in spring or fall for milder weather, fewer crowds, and great value.

Rome

Rome is a living palimpsest: emperors and popes, Baroque fountains and buzzing trattorias, cats sunning on marble ruins. Let yourself time-travel between forums and frescoes by day, then linger over pasta in Trastevere as street musicians tune the evening.

Arrive via Omio flights if you’re already in Europe (often $90–$250 one-way intra-Europe) or price round-trips from North America ($550–$1,100 in shoulder season) on Trip.com or Kiwi.com. From FCO, the Leonardo Express to Termini takes 32 minutes.

Days 1–3: Ancient Rome, the Centro Storico, and iconic first tastes

Start with the Colosseum, Roman Forum, and Palatine Hill to orient the city’s ancient spine. Stroll to the Pantheon at golden hour, then watch Trevi Fountain gleam before a gelato nightcap near Piazza di Spagna.

• Coffee & breakfast: Sant’Eustachio Il Caffè (wood-roasted espresso from an ancient aqueduct supply) and Pasticceria Regoli for maritozzi (cream-filled brioche).
• Lunch: Roscioli Salumeria con Cucina (cacio e pepe, Roman cured meats) or Bonci Pizzarium near the Vatican for creative pizza al taglio.
• Dinner: Da Enzo al 29 (Trastevere, classic amatriciana), Cesare al Casaletto (Roman trattoria with an epic wine list), or Trapizzino for pocket pizzas stuffed with Roman stews.

Recommended tour to bring the forums to life:

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

Days 4–5: The Vatican, St. Peter’s, and Baroque Rome

Dedicate a morning to the Vatican Museums and the Sistine Chapel, then step into St. Peter’s Basilica and, if you wish, climb the dome for a citywide panorama. Later, trace Bernini and Borromini’s Baroque rivalry across Piazza Navona and Sant’Agnese in Agone.

Book a skip-the-line Vatican experience to maximize your time:

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

Skip the line: Vatican Museums, Sistine Chapel & St Peters Tour

• Snack breaks: Gelateria dei Gracchi (classic pistachio), and espresso at Tazza d’Oro.
• Dinner nearby: Armando al Pantheon (since 1961; book ahead) or Salumeria Roscioli Rimessa for Roman classics paired with Italian natural wines.

Days 6–7: Neighborhoods, food culture, and easy day trips

Wander Trastevere’s cobbles in the late afternoon—peek into Santa Maria in Trastevere’s mosaics—then join a guided food walk for suppli, porchetta, and gelato with context. Alternatively, ride the ancient Appian Way by bike and step into the cool hush of the catacombs.

Two immersive options:

Winner 2025 Rome Twilight Trastevere Food Tour by Eating Europe

Rome Highlights City Tour by Golf Cart with Gelato

• Day trip choice: Ostia Antica (Rome’s “mini Pompeii,” 30–40 minutes by train) for frescoed taverns and mosaicked baths without big-city crowds.
• Casual eats: Marigold (Ostiense; seasonal bakery-brunch) and Pizzarium for a final square of potato–rosemary pizza.

Where to stay in Rome

• Iconic: Hotel Eden, Dorchester Collection (views above the Spanish Steps).
• Boutique: Hotel Santa Maria (Trastevere courtyard haven).
• Value: The Beehive (stylish budget near Termini).
• Browse more: Hotels.com Rome or VRBO Rome apartments.

Transfer: Rome to Florence (morning of Day 8)

Take a Frecciarossa from Roma Termini to Firenze S. M. Novella: 1h30–1h40 direct, typically €25–€60 if booked in advance on Omio trains. Sit on the left side for countryside views as Lazio blurs into Tuscany.

Florence & Tuscany

Florence is the cradle of the Renaissance, a city of domes, marble façades, and goldsmith workshops along the Arno. It’s also intimate—walkable lanes and markets where you can taste lampredotto, sip Chianti Classico, and watch artisans hand-tool leather.

Days 8–9: Renaissance essentials—Duomo, Uffizi, and Oltrarno sunset

Climb Brunelleschi’s Dome early, then tour the Uffizi for Botticelli and Caravaggio. Cross Ponte Vecchio to the Oltrarno for artisans and a golden sunset from Piazzale Michelangelo.

• Coffee & breakfast: Ditta Artigianale (specialty roasts) or Pasticceria Nencioni for cornetti.
• Lunch: Mercato Centrale—try Da Nerbone’s bollito sandwich or fresh pasta from the upper floor stands.
• Dinner: Trattoria Sostanza (butter chicken; a Florentine classic), Trattoria Mario (market-fresh Tuscan plates, lunch only), or Buca Lapi for bistecca alla fiorentina.

Days 10–11: Accademia, artisans, and Tuscan wine

Meet Michelangelo’s David at the Accademia, then wander the leather workshops and silversmiths of Santo Spirito. Reserve one afternoon for a guided tasting in the Chianti hills—vines, stone farmhouses, and Sangiovese in your glass.

Small-Group Wine Tasting Experience in the Tuscan Countryside

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

Day 12: Grand Tuscan loop—Siena, San Gimignano, Pisa with winery lunch

Cover a lot in one expertly organized day: medieval Siena’s Campo, San Gimignano’s towers, Pisa’s Campo dei Miracoli, and a long-table lunch at a winery. It’s a sweeping snapshot of Tuscany’s landscapes and hilltowns.

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

Days 13–14: Cooking, markets, and slow-living Florence

Take a market-to-table cooking class, master fresh pasta shapes, then enjoy what you made with a Tuscan pour. Leave time to stroll the Boboli Gardens or the quiet cloisters of San Marco.

Florence: Pasta Cooking Class with Unlimited Wine

• Wine bar: Le Volpi e l’Uva (tiny, curated Tuscan list and crostini).
• Sweet tooth: Gelateria La Carraia (creamy pistachio) or Vivoli (founded 1930).

Where to stay in Florence

• Classic luxury: Four Seasons Hotel Firenze (private gardens) or The St. Regis Florence (Arno-side elegance).
• Boutique: Hotel Brunelleschi (medieval tower setting) or Grand Hotel Minerva (rooftop pool).
• Value gems: Hotel Dali or Hotel Santa Croce.
• Browse more: Hotels.com Florence or VRBO Florence apartments.

Transfer: Florence to Naples (morning of Day 15)

High-speed train from Firenze S.M.N. to Napoli Centrale: 2h50–3h10 direct, usually €29–€75 on Omio trains. Grab a panino at the station and enjoy hill country giving way to volcanic Campania.

Naples & the Amalfi Coast

Naples is exuberant—UNESCO-listed lanes, Caravaggio in dim chapels, and the world’s most storied pizza. It’s your springboard to Pompeii, the Amalfi Coast’s cliff towns, and Capri’s cobalt coves.

Day 15: Historic Naples—art, alleys, and pizza night

Walk Spaccanapoli’s knife-straight lane past nativity workshops and marble churches. See the Veiled Christ at Sansevero (reserve ahead), then feast on pizza where it was born.

• Coffee & sfogliatella: Gran Caffè Gambrinus (belle époque café) or Sfogliatella Mary (Galleria Umberto).
• Lunch: Trattoria Da Nennella (hearty Neapolitan classics; lively), or a cuoppo (paper cone) of fried seafood on Via Toledo.
• Dinner: L’Antica Pizzeria Da Michele (ultra-traditional) or 50 Kalò (award-winning dough science) or Sorbillo (Via dei Tribunali).

Day 16: Pompeii with an archaeologist

Spend the day exploring frescoed villas and streets frozen by Vesuvius in 79 CE. A guided tour adds context to the forum, baths, and brothels’ infamous frescoes.

Pompeii Small Group Tour with an Archaeologist

• Getting there: Circumvesuviana train from Napoli Garibaldi to Pompei Scavi (35–40 min, ~€3–€5) via Omio trains.
• Alternative: Add Herculaneum (smaller but better-preserved wood and upper floors).

Days 17–18: Amalfi Coast—Positano, Amalfi, Ravello

Ride the ferry or bus to Positano’s pastel cascade, then continue to Amalfi’s cathedral and up to Ravello’s garden terraces. Expect coastal paths perfumed with lemons and views that swallow you whole.

• Transport: Naples to Amalfi/Positano by ferry in season (1h20–2h; check Omio ferries) or bus via Sorrento (2–3h; Omio buses).
• Lunch: Chez Black (Positano beachside spaghetti alle vongole) or simple lemon-scented salads at beach kiosks.
• Dinner: Ristorante Eolo (Amalfi; romantic terrace) or La Tagliata (Montepertuso; rustic family-style set menus).
• Optional overnight on the coast: Le Sirenuse, Positano, Hotel La Pergola, Amalfi Coast, or Hotel Marina Riviera, Amalfi.

Day 19: Capri day trip

Cruise to Capri for whitewashed lanes, sandal-makers, and views from Monte Solaro. If seas are calm, queue for the Blue Grotto or hire a small boat for grotto-hopping.

• Ferries: Naples or Sorrento to Capri (45–80 min, €25–€50 each way) via Omio ferries.
• Capri bites: Panino caprese from a deli near Piazzetta; gelato at Buonocore; lemon granita between hikes.

Days 20–21: Naples museums, Castel dell’Ovo, and departure

Tour the National Archaeological Museum’s Farnese marbles and Pompeian mosaics; walk the seafront to Castel dell’Ovo for a sunset over the bay. Depart from Naples Capodichino Airport or return to Rome by high-speed train (1h10–1h20) via Omio trains.

Where to stay in Naples

• Waterfront classic: Grand Hotel Vesuvio.
• Stylish value in the historic center: Hotel Piazza Bellini.
• Seafront views: Hotel Royal Continental.
• Browse more: Hotels.com Naples or VRBO Naples apartments.

Optional add-on from Rome (alternative to Ostia): Amalfi Coast & Pompeii in one day

If you prefer to keep Naples as a day-trip destination from Rome, this small-group tour checks three UNESCO sites in one long, memorable day:

Pompeii, Amalfi Coast and Positano Day Trip from Rome

Final notes on trains and tickets

• Book all intercity trains on Omio trains 2–6 weeks out for best fares; expect €25–€75 per leg for high-speed routes.
• Use Omio buses for budget intercity hops when schedules suit, and Omio ferries for coastal/Capri crossings.

Bonus Rome experiences (if you add a day)

Deep-dive into the Colosseum’s gladiator gate and arena, or go underground with special-access chambers:

Colosseum Arena Floor, Roman Forum and Palatine Hill Guided Tour

Colosseum Underground & Ancient Rome Guided Tour

This 21-day Italy itinerary blends blockbuster sights with local rituals—morning cappuccinos, market lunches, lazy passeggiate. With fast trains, a handful of smart tours, and these handpicked eateries and stays, you’ll experience Rome, Florence, and the Amalfi Coast like a seasoned traveler.