Italy rewards unhurried travel. Over 21 days you’ll trace the arc of Western civilization—from the Colosseum and Vatican to the workshops of Florence and the palazzi of Venice—while savoring everyday rituals: an early cappuccino, a late-afternoon spritz, a moonlit stroll.

Rome introduces the ancient empire and the seat of the Catholic world; Florence delivers Renaissance genius and Tuscan countryside; Venice gives you the lagoon’s mercantile past, Byzantine sparkle, and island rhythms. Trains make it easy, food ties it together, and every piazza becomes your living room.

Practical notes: book major sights in advance (Vatican, Colosseum, Uffizi), travel light for train days, and embrace regional cuisine—carbonara in Rome, bistecca in Florence, lagoon seafood in Venice. Spring and fall are ideal; summer is busier and hotter.

Getting to Italy and between cities: Fly into Rome and out of Venice (open-jaw). For flights to/from Europe and for intra-Europe options, compare on Omio. For Italy’s high-speed and regional trains, book seats and times on Omio Trains (Italy/Europe). Buses and ferries are also on Omio Buses and Omio Ferries.

Rome

Rome is a layered time capsule: emperors’ forums, baroque churches, and neighborhood trattorias where recipes don’t change for decades. Mornings are for ruins and Raphael; evenings are for strolls across cobbles and gelato on the Tiber.

Arriving: Fly into FCO or CIA and head into the center by train, bus, or taxi. If flying from within Europe, check Omio Flights. For trains anywhere in Italy during this trip, use Omio.

Days 1–2: Ancient Rome & the Historic Center

• Colosseum, Roman Forum, Palatine Hill—start with the big story. Consider a guided visit for context and easier access:
  Rome: Colosseum, Roman Forum, and Palatine Hill Guided Tour

  

• Pantheon, Piazza Navona, Trevi Fountain, Spanish Steps—link them on foot. Step into the Pantheon’s perfect dome, then people-watch over espresso at a nearby bar.

Days 3–4: The Vatican, Art, and Views

• Vatican Museums, Sistine Chapel, St. Peter’s Basilica—book skip-the-line access to maximize time with the Raphael Rooms and Michelangelo’s ceiling:
  Skip the line: Vatican Museums, Sistine Chapel & St Peters Tour

  

• Castel Sant’Angelo to Trastevere—walk across Ponte Sant’Angelo’s angels to the cobbled lanes of Trastevere for a golden-hour aperitivo.

Day 5: Trastevere Flavors & Local Life

• Explore markets and beloved eateries on a small-group tasting stroll:
  Winner 2025 Rome Twilight Trastevere Food Tour by Eating Europe

  

Day 6: Hidden Rome by Golf Cart

• Cover quiet hills, keyhole views, and tucked-away fountains without the miles:
  Rome by Golf Cart Private Tour: Beyond the Landmarks

  

• Later, stroll the Appian Way or relax in Villa Borghese gardens for sunset.

Day 7: Optional Day Trip—Pompeii & the Amalfi Coast

• Ambitious but unforgettable small-group excursion, round-trip from Rome:
  Pompeii, Amalfi Coast and Positano Day Trip from Rome

  

Where to eat & drink (curated)

• Breakfast/coffee: Roscioli Caffè (supplì and maritozzi), Sant’Eustachio Il Caffè (classic Roman espresso), Panificio Bonci (Roman pizza by the slice).
• Lunch: Mordi & Vai in Mercato Testaccio (iconic panini with braised beef), Pizzarium Bonci near the Vatican (creative toppings, crisp al taglio crust), Armando al Pantheon (book ahead for cacio e pepe).
• Dinner: Da Enzo al 29 (Trastevere trattoria; artichokes and amatriciana), Taverna Trilussa (pasta served in pans), Cesare al Casaletto (Roman comfort food, great wine list).
• Sweet & sips: Gelateria del Teatro (seasonal flavors), Fatamorgana (inventive gelato), Jerry Thomas Speakeasy (reservations; Roman cocktail history).

Where to stay

• Search apartments and villas: VRBO Rome
• Browse hotels: Hotels.com Rome
• Top picks: Hotel Eden, Dorchester Collection (refined hilltop views), Hotel de Russie (secret garden near Piazza del Popolo), Rome Cavalieri, A Waldorf Astoria Hotel (spa and art collection), Hotel Santa Maria (Trastevere courtyard calm), The Beehive (stylish budget near Termini), Hotel Mascagni (solid mid-range near Repubblica).

Next stop: On Day 8, depart Rome around 9:00 AM for Florence. High-speed Frecciarossa trains take ~1h 30m, typical fares €25–€60 in advance. Book seats on Omio Trains.

Florence

Florence is the workshop of the Renaissance: Brunelleschi’s dome, Botticelli’s Primavera, Michelangelo’s David, and artisans hammering gold on the Ponte Vecchio. Beyond the galleries lie trattorie that define Tuscan soul food and vineyards rolling to the horizon.

Days 8–9: Renaissance Core—Duomo, Uffizi, Accademia

• Duomo Complex—cathedral, Baptistery doors, and if you’re up for it, climb the Cupola for citywide views.
• Uffizi—Botticelli, Leonardo, Raphael; reserve timed entry. Stroll to Piazza della Signoria and the Arno afterward.
• Accademia—meet Michelangelo’s David and the unfinished Prigioni that reveal his process.

Day 10: Oltrarno, Boboli & Artisans

• Cross the Ponte Vecchio to the Oltrarno for workshops (wood marquetry, bookbinding), Pitti Palace courtyards, and the Boboli Gardens’ Renaissance landscaping.
• Sunset at Piazzale Michelangelo with a gelato from San Niccolò.

Day 11: The Best of Tuscany Day Trip

• See medieval Siena, towered San Gimignano, Pisa’s Leaning Tower, and enjoy a farmhouse lunch with Chianti wines—all in one curated day:
  Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

  

Day 12: Tuscan Wine Tasting (Small Group)

• Visit boutique estates, stroll vineyards, and learn the Sangiovese spectrum from Chianti Classico to Super Tuscans:
  Small-Group Wine Tasting Experience in the Tuscan Countryside

  

Days 13–14: Slow Florence—Markets, Gardens, and Churches

• Mercato Centrale & Sant’Ambrogio—browse produce stands and snack bars (try lampredotto, Florence’s street-food sandwich).
• Santa Croce & Santa Maria Novella—Giotto frescoes, cloisters, and perfumery heritage.
• Optional short train hops (30–90 minutes) to Lucca or Arezzo; book on Omio Trains.

Where to eat & drink (curated)

• Breakfast/coffee: Ditta Artigianale (specialty coffee), Caffè Gilli (since 1733, pastries and people-watching), Caffè Piansa (espresso purists).
• Lunch: Nerbone (Mercato Centrale; bollito sandwiches), Trattoria Mario (Tuscan staples; communal tables), All’Antico Vinaio (schiacciata panini; go early to avoid lines).
• Dinner: Trattoria Sostanza (butter chicken and bistecca; book early), Buca Lapi (historic cellar for steak), Il Santo Bevitore (modern Tuscan, great wine list).
• Sweet & aperitivi: Gelateria La Carraia and Gelateria dei Neri; aperitivo at Procacci (truffle bites) or La Ménagère (design-forward lounge).

Where to stay

• Search apartments and villas: VRBO Florence
• Browse hotels: Hotels.com Florence
• Top picks: Four Seasons Hotel Firenze (resort-like park), Hotel Brunelleschi (medieval tower setting steps from the Duomo), Grand Hotel Minerva (rooftop pool), Hotel Davanzati (warm, central), Hotel Santa Croce (value near the Basilica).

Next stop: On Day 15, depart Florence around 9:00 AM for Venice. High-speed trains take ~2h 05m, fares typically €20–€50 if booked ahead. Reserve on Omio Trains.

Venice

Venice is a maritime mosaic—Byzantine domes, Gothic tracery, and quiet canals that twist like calligraphy. Wander far from San Marco and you’ll find boatyards, neighborhood bàcari, and laundry strung like flags.

Days 15–16: San Marco, Rialto & the Grand Canal

• Piazza San Marco—Basilica’s gold mosaics and the Campanile’s views. Families can make it extra engaging with a kid-focused tour:
  Venice' St Mark Basilica Wonders Guided Tour for Kids & Families

  

• Rialto Market—arrive early for lagoon fish stalls, then ride the vaporetto down the Grand Canal to study palazzi facades.

Day 17: Dorsoduro & Galleries

• Gallerie dell’Accademia (Venetian masters) and the Peggy Guggenheim (20th-century hits) paired with a Zattere stroll for a late-afternoon gelato.

Day 18: Lagoon Islands—Murano, Burano, Torcello

• Glass furnaces in Murano, lace traditions in Burano (and those rainbow houses), Byzantine mosaics at Torcello’s cathedral. Use ACTV day passes; check ferries on Omio Ferries for regional options.

Day 19: Bacaro Crawl & Cannaregio

• Do as Venetians do: cicchetti (small bites) with ombra (house wine) at neighborhood bàcari. Thread canals and squares at an easy pace.

Day 20: Day Trip Option—Verona or Padua

• Verona’s Roman arena and Juliet lore or Padua’s Giotto frescoes at the Scrovegni Chapel. Trains are frequent (25–90 minutes). Book on Omio Trains.

Day 21: Slow Farewell

• Early gondola or a quiet walk through Castello’s gardens. Cappuccino, last cicchetti, then airport boat or train out.

Where to eat & drink (curated)

• Breakfast/coffee: Pasticceria Tonolo (beloved pastries), Rosa Salva (historic café), Torrefazione Cannaregio (artisanal roaster).
• Lunch: Osteria Alla Vedova (meatballs; sarde in saor), Al Timon (canal-side grills), Trattoria Anice Stellato (seasonal Venetian dishes).
• Dinner: Osteria alle Testiere (tiny seafood temple—book well ahead), Antiche Carampane (no-frills, serious fish), Da Fiore (classic lagoon flavors).
• Cicchetti & sweets: All’Arco and Cantina Do Spade for cicchetti; Gelatoteca Suso for gelato.

Where to stay

• Search apartments and villas: VRBO Venice
• Browse hotels: Hotels.com Venice
• Top picks: The Gritti Palace, a Luxury Collection Hotel (Grand Canal icon), Hotel Antiche Figure (canal-front, convenient to station), Hilton Molino Stucky Venice (Giudecca skyline views), Belmond Hotel Cipriani (resort feel on Giudecca), Aman Venice (palatial serenity).

Departing: Fly out of Venice (VCE). Compare fares on Omio Flights. For airport boats or regional trains to your next stop, search Omio.

Trip flow at a glance

• Days 1–7: Rome (ancient sites, Vatican, Trastevere food, optional Pompeii/Amalfi)
• Morning of Day 8: Train Rome→Florence (~1h 30m via Omio)
• Days 8–14: Florence (Renaissance highlights, Tuscany day trip, wine country)
• Morning of Day 15: Train Florence→Venice (~2h 05m via Omio)
• Days 15–21: Venice (San Marco, islands, cicchetti, day trip to Verona/Padua)

Three weeks in Italy lets you savor the country the way Italians hope you will—lingering over art and meals, trading speed for depth. With Rome’s grandeur, Florence’s craft, and Venice’s dreamlike light, this itinerary blends headline sights with local flavor, and leaves space for serendipity.