Italy rewards the curious. In Florence, the Renaissance still glows in the light on Brunelleschi’s dome and Botticelli’s brushstrokes at the Uffizi. Siena’s brick lanes pour you into Il Campo like a medieval amphitheater, while the surrounding Tuscan hills shift with olive groves and Sangiovese vines.

Then there’s Rome—its layers stacked like millefoglie: gladiators and emperors, Baroque fountains, family-run trattorie serving carbonara just the way nonna insists. With swift trains and compact historic centers, you’ll see a lot without rushing—time for museum mornings, vineyard-flavored afternoons, and golden-hour passeggiate.

Practical notes: reserve major museums (Uffizi, Accademia), the Colosseum, and Vatican well ahead—prime slots sell out. Carry small cash for cafes, dress modestly for churches, and plan for cobblestones (comfortable shoes). Coffee is quick at the bar; aperitivo is an art. Trains are the easiest way between cities—details and booking links are included below.

Florence

Birthplace of the Renaissance, Florence packs galleries, palaces, and artisan workshops into a walkable old town. Peer up at the Duomo’s marble stripes, cross the Ponte Vecchio to the Oltrarno, and watch sunset from Piazzale Michelangelo as the Arno blushes.

• Top sights: Duomo complex (Cathedral, Dome, Baptistery, Campanile), Uffizi Gallery, Accademia (Michelangelo’s David), Palazzo Vecchio, Santa Croce, Boboli Gardens.
• Eat & drink: espresso at Ditta Artigianale; schiacciata sandwiches at All’Antico Vinaio; bistecca alla fiorentina at Trattoria Sabatino or All’Antico Ristoro di Cambi; natural wines at Le Volpi e l’Uva; gelato at Gelateria dei Neri or La Carraia.
• Insider tip: the Negroni was invented here—order one at Caffè Gilli or Rivoire and toast Count Negroni’s 1919 experiment.

Where to stay (central and Oltrarno are ideal): Browse apartments and boutique stays on VRBO Florence or compare hotels on Hotels.com Florence.

Getting there: Fly into Florence (FLR) or Pisa (PSA). For flights within or to Europe, check Omio Flights. Arriving from outside Europe, compare fares on Trip.com Flights. From FLR, the T2 tram reaches the center in ~20 minutes (~€1.70).

Siena (Tuscany)

Gothic Siena orbits its shell-shaped Piazza del Campo, where the Palio horse race blurs past medieval palazzi twice each summer. The striped Duomo stuns inside and out, and the surrounding hills invite day trips to San Gimignano or the Chianti Classico vineyards.

• Top sights: Piazza del Campo, Torre del Mangia, Duomo & Piccolomini Library, Santa Maria della Scala, San Gimignano’s towers (easy bus ride).
• Eat & drink: pici pasta with cacio e pepe at Antica Trattoria Papei; local pecorino and cured meats at Osteria Le Logge; classic Sienese sweets—ricciarelli and panforte—from Pasticceria Bini.

Where to stay: Sleep inside the walls near Il Campo for night strolls. See VRBO Siena or Hotels.com Siena.

Getting around: Florence–Siena is ~1h15 by bus or ~1h30 by train (via Empoli). Compare and book on Omio Trains and Omio Buses. For San Gimignano, buses run ~1h15 from Siena (change at Poggibonsi).

Rome

Rome’s timeline is visible at every corner—from the Colosseum’s arches to Bernini’s fountains and Trastevere’s cobbles. It’s also a food city: supplì, Roman pizza al taglio, and trattorie where the cacio e pepe is black-pepper assertive and perfect.

• Top sights: Colosseum, Roman Forum, Palatine Hill, Vatican Museums & Sistine Chapel, St. Peter’s Basilica, Pantheon, Trevi Fountain, Spanish Steps, Piazza Navona, Castel Sant’Angelo.
• Eat & drink: breakfast cornetti at Roscioli Caffè; lunch at Pizzarium Bonci; trattorie like Armando al Pantheon, Da Enzo al 29, Felice a Testaccio; gelato at Gelateria del Teatro or Fatamorgana; cocktails at Drink Kong.

Where to stay: Base in Monti (walk to the Forum), Centro Storico (by the Trevi/Pantheon), Trastevere (nightlife), or Prati (near Vatican). Browse VRBO Rome and Hotels.com Rome.

Getting there/away: Siena–Rome by train via Florence takes ~3–3.5h (€25–€45); direct buses are ~3h (€15–€25). Book on Omio Trains or Omio Buses. From Rome FCO Airport, the Leonardo Express reaches Termini in ~32 minutes (~€14), or taxis have a fixed city-center rate.

Day 1: Arrive in Florence (afternoon/evening)

Afternoon: Arrive and check in. Shake off the flight with a gentle loop: Piazza del Duomo to admire the Cathedral, Baptistery doors, and Giotto’s Campanile; then stroll Via dei Calzaiuoli to Piazza della Signoria and the copy of David outside Palazzo Vecchio.

Evening: Aperitivo at La Terrazza (Arno views). Dinner nearby at Trattoria Sabatino (old-school Tuscan classics) or Trattoria Mario (no-frills bistecca; go early). Gelato at La Carraia, then an Arno-side passeggiata across the Ponte Vecchio.

Day 2: Florence—Uffizi, Oltrarno artisans, and sunset views

Morning: Espresso and a buttery sfoglia at Caffè Concerto Paszkowski, then the Uffizi (book the first slot; hit Botticelli’s Primavera and Birth of Venus, Raphael’s Madonna of the Goldfinch, and the Tribune). Cross to Santa Croce if you love tombs (Michelangelo, Galileo).

Afternoon: Quick schiacciata at All’Antico Vinaio (worth the buzz, go off-peak). See Michelangelo’s David at the Accademia (time-slot essential). Wander to the Oltrarno: peek into artisan botteghe on Via Maggio and Borgo San Frediano; wine flight at Le Volpi e l’Uva.

Evening: Golden hour at Piazzale Michelangelo and the quieter San Miniato al Monte above it (Gregorian chant at vespers is a gift). Dinner in Santo Spirito at Trattoria La Casalinga or All’Antico Ristoro di Cambi (order peposo). Nightcap Negroni at Rivoire.

Day 3: Morning to Siena (Tuscany) + Siena highlights

Morning (travel): Depart Florence for Siena. Fastest is the express bus (~1h15, ~€10). Trains via Empoli take ~1h30. Compare departures on Omio Buses or Omio Trains. Drop bags inside the walls.

Afternoon: Lunch at Antica Trattoria Papei (pici with ragù, outdoor tables off Il Campo). Explore the Duomo complex—don’t miss the inlaid marble floors (seasonal openings) and the jewel-box Piccolomini Library. Climb Torre del Mangia for a terracotta panorama.

Evening: Espresso at Torrefazione Fiorella; drift the contrade lanes to learn their animal symbols. Dinner at Osteria Le Logge (refined Tuscan) or La Taverna di San Giuseppe (vaulted, romantic). Taste vinsanto with cantucci to finish.

Day 4: San Gimignano (optional) and on to Rome

Morning: Optional half-day to San Gimignano by bus (~1h15, ~€8 each way; check schedules on Omio Buses). Climb Torre Grossa, sip crisp Vernaccia, and try saffron-inflected dishes at Trattoria Chiribiri. Alternatively, linger in Siena’s Santa Maria della Scala museum beneath the Duomo.

Afternoon (travel): Head to Rome. Easiest: bus back to Florence, then high-speed Frecciarossa to Roma Termini (Siena–Florence ~1h30 + Florence–Rome ~1h30; €25–€45 total). Or direct bus ~3h. Book via Omio Trains/Omio Buses. Check in and refresh.

Evening: Intro to Rome on a gentle loop: Trevi Fountain to toss a coin, Spanish Steps for twilight. Dinner at Roscioli Salumeria con Cucina (reserve; carbonara royalty) or Osteria da Fortunata (hand-rolled tonnarelli). Gelato at Giolitti.

Day 5: Ancient Rome—Colosseum, Forum & Palatine

Morning: Cappuccino and maritozzo at Roscioli Caffè, then join a guided experience that includes Arena access for context and skip-the-line entry: Rome: Colosseum with Arena, Roman Forum and Palatine Guided Tour.

Afternoon: Continue through the Forum’s Via Sacra and up Palatine Hill’s pine-framed overlooks. For lunch, grab pizza al taglio at Li Rioni or trapizzino (saucy pocket sandwich) in Monti. Espresso at Tazza d’Oro by the Pantheon (note: Pantheon now uses timed entry; secure a slot if you want to go inside).

Evening: Aperitivo in Monti at Ai Tre Scalini (natural wines, Roman snacks). Dinner at La Carbonara (since 1906; hearty Roman pastas). Gelato at Fatamorgana Monti—creative but balanced flavors.

Day 6: Vatican Masterpieces + Trastevere flavors

Morning: Beat the crowds with early access: Early Morning Vatican, Sistine, St. Peter's Semi or Private Tour. You’ll traverse the Vatican Museums (Raphael Rooms, maps gallery), the Sistine Chapel under softer light, and St. Peter’s.

Afternoon: Climb St. Peter’s dome for a citywide marble-and-cupola view. Walk the Passetto side to Castel Sant’Angelo’s bridge angels. Lunch at Pizzarium Bonci (inventive toppings; stand-up only) or Pastasciutta (fast, fresh pasta) in Prati. Coffee at Pergamino Caffè (specialty roasts).

Evening: Explore Rome through its cuisine on the award-winning Winner 2025 Rome Twilight Trastevere Food Tour by Eating Europe—from supplì to porchetta and gelato while learning neighborhood lore.

Day 7: Baroque Rome + Hidden Gems by Golf Cart

Morning: Forno Campo de’ Fiori for warm pizza bianca, then meander to Piazza Navona (Bernini’s Fountain of the Four Rivers) and the Pantheon’s perfect dome (reserve entry time if going inside). Sip one of Rome’s most storied espressos at Sant’Eustachio Il Caffè.

Afternoon: Cover more ground and discover quiet corners with a private, customizable spin: Rome by Golf Cart Private Tour: Beyond the Landmarks. Ask to include Aventine Keyhole, Orange Garden, and views over the Forum.

Evening: Dinner in Testaccio—Felice a Testaccio (cacio e pepe tossed at the table) or Flavio al Velavevodetto (terrace under Monte dei Cocci). Nightcap along the Tiber or a reservation-only cocktail at Drink Kong.

Day 8: Last sips of Rome and departure

Morning: Choose one: Borghese Gallery (Caravaggio, Bernini; timed tickets) followed by a bike or stroll in Villa Borghese, or the Appian Way with ancient tombs and aqueduct views (bike hires near Porta San Sebastiano).

Afternoon (departure): Pick up picnic panini from Forno Roscioli and head to the airport or station. For trains within Italy, check Omio Trains; for airport transfers, consider Leonardo Express or authorized taxis from central stands.

Handy Transport Snapshot

• Florence Airport (FLR) to center: T2 tram ~20 min (~€1.70).
• Florence → Siena: bus ~1h15 (~€10); train via Empoli ~1h30. Book on Omio Buses / Omio Trains.
• Siena → Rome: train via Florence ~3–3.5h (€25–€45) or bus ~3h (€15–€25). Book on Omio Trains / Omio Buses.
• International flights to Italy: compare on Omio Flights (within/to Europe) or Trip.com Flights (from outside Europe).

Optional Add-Ons (if you extend)

• Chianti wine day with a driver—taste Classico among cypress-lined roads and stone hamlets.
• Pompeii & Amalfi Coast from Rome—long but unforgettable; go with a guided small group for context and coast views to Positano.

Bookable Rome Activities Featured Above (for quick access and skip-the-line convenience):

• Colosseum with Arena, Forum & Palatine Guided Tour
• Early Morning Vatican, Sistine & St. Peter’s (Small Group)
• Twilight Trastevere Food Tour
• Rome by Golf Cart Private Tour

This 8-day Florence–Tuscany–Rome itinerary pairs masterpieces and medieval lanes with unforgettable plates and piazza sunsets. With reserved entrances, walkable days, and easy train links, you’ll savor Italy’s art, countryside, and capital at just the right pace.