Italy rewards the curious. Ancient forums double as open-air classrooms; Renaissance domes pierce the skyline; and coastal roads twist toward vertiginous sea views. In five days, we’ll focus on two icons—Rome and Florence—linked by a quick high-speed train, with one big adventure to Pompeii and the Amalfi Coast and a Tuscan vineyard morning to toast it all.

Rome’s story spans emperors, popes, and revolutionaries. You’ll stand on the Colosseum’s gladiator routes, follow Caesar’s footsteps in the Forum, and taste Rome through cucina romana—carbonara, amatriciana, and fried artichokes. Florence offers cathedral domes, artisan workshops, and trattorie where recipes are older than the furniture.

Practical notes: Buy timed-entry tickets for major sights when you can; metro and walking cover most city centers. Expect a modest tourist tax at hotels. For a mid-range budget (50/100), pick central 3–4 star stays, mix sit-down trattorie with street food, and book a couple of guided tours to save time in line.

Rome

Rome is a layered palimpsest—Etruscan foundations, imperial grandeur, Baroque theatricality, and a modern food scene that’s both inventive and fiercely local. The best way to meet it? On foot, with detours for espresso, ruins, and piazzas.

• Top sights: Colosseum, Roman Forum, Palatine Hill, Pantheon, Trevi Fountain, Spanish Steps, Trastevere lanes, Capitoline Hill.
• Local flavor: Roman pizza al taglio (try potato and rosemary), supplì (fried rice balls), and offal-inspired quinto quarto in Testaccio.
• Getting in: Compare flights to Rome (FCO/CIA) on Omio. Coming from outside Europe? See long-haul options on Trip.com or flexible multi-city fares via Kiwi.com.

Where to stay (mid-range picks plus value options):

• Atmospheric Trastevere: Hotel Santa Maria (cloistered courtyards, walkable to trattorie).
• Central and calm: Hotel Mascagni (near Repubblica; great for metro access).
• Budget-friendly, social: The Beehive (eco-minded, handy for Termini).
• Browse more apartments and stays: VRBO Rome or Hotels.com Rome.

Day 1: Arrival, Centro Storico wander, and Trastevere bites

Afternoon (arrival): Check in, then shake off the flight with a loop through the Pantheon (2,000 years of engineering), Piazza Navona’s Bernini sculptures, and Trevi Fountain—toss a coin over your left shoulder. Espresso at Sant’Eustachio Il Caffè for a classic Roman roast; gelato at Gelateria del Teatro (seasonal fruit, Sicilian pistachio).

Evening: Eat your way through medieval Trastevere on this award-winning food walk: Winner 2025 Rome Twilight Trastevere Food Tour by Eating Europe. Expect Roman salumi, suppli, cacio e pepe, and a sweet finale—great intro to the neighborhood and its stories.

Nightcap: Cross the Tiber for cocktails at Drink Kong (neo-Tokyo vibes) or a simple amaro at Freni e Frizioni. If you prefer a sit-down dinner, Taverna Trilussa serves generous Roman pastas in a lively courtyard.

Day 2: Gladiators, emperors, and hidden hills

Morning: Beat the crowds with a guided deep dive: Rome: Colosseum, Roman Forum, and Palatine Hill Guided Tour. Some departures include special arena access—ask when booking. You’ll trace the city’s origin on Palatine Hill and read the politics of empire among the Forum’s arches.

Afternoon: Lunch in Monti: La Taverna dei Fori Imperiali for silky carbonara or Trattoria al 19 for Roman comfort plates. Explore Monti’s vintage shops on Via del Boschetto, then climb the Capitoline Hill for a postcard overlook across the Forum.

Evening: Head to Testaccio, the old slaughterhouse district turned culinary lab. Try Felice a Testaccio (tonnarelli cacio e pepe tossed tableside) or SantoPalato (chef-driven, nose-to-tail). On the way back, grab a late-night Trapizzino—triangular pockets filled with classics like pollo alla cacciatora.

Day 3: Big adventure—Pompeii, Amalfi Coast, and Positano (full day)

Early start for a blockbuster day trip: Pompeii, Amalfi Coast and Positano Day Trip from Rome. Walk ancient streets with an expert, then ride the cliffside Amalfi Drive to seaside Positano for lunch and a swim (weather permitting). Expect 12–13 hours; wear comfy shoes and bring a light layer.

Tip: Pack a bakery breakfast (Pasticceria Regoli near Termini) and cash for coastal cafés. Back in Rome, a simple late dinner near your hotel—pizza al taglio at Pizzarium or a plate of amatriciana—will hit the spot.

Florence

Florence is compact, walkable, and dense with masterpieces. Beyond the Big Three—Duomo, Uffizi, Accademia—there’s a living city of artisans pounding leather, goldsmiths on the Ponte Vecchio, and osterie serving bistecca and hearty ribollita.

• Top sights: Duomo and Brunelleschi’s dome, Piazza della Signoria, Ponte Vecchio, Oltrarno workshops, San Lorenzo Market, Santa Croce.
• Vibe: Renaissance grandeur by day, aperitivo culture by sunset, and trattorie buzzing late into the night.
• Getting there from Rome: Frecciarossa train, ~1 hr 30 min, €25–€70—book on Omio (Trains Europe). Morning departures are frequent; aim for Roma Termini → Firenze S. M. Novella.

Where to stay (walkable and wallet-wise):

• Steps to Ponte Vecchio: Hotel Della Signoria (classic rooms, unbeatable location).
• Value in Santa Croce: Hotel Santa Croce (friendly, simple, central).
• Budget gem near the Duomo: Hotel Dali (clean, characterful, great rates).
• Browse more stays: VRBO Florence or Hotels.com Florence.

Day 4: Rome → Florence, Duomo quarter, and Oltrarno sunset

Morning: Depart Rome on a Frecciarossa to Florence (reserve on Omio). Drop bags, then circle the Duomo complex. If you want the dome climb, pre-book a timed slot; otherwise visit the Baptistery’s shimmering mosaics and the Opera del Duomo museum for Ghiberti’s doors up close.

Afternoon: Lunch at the San Lorenzo Market’s downstairs stalls—try Da Nerbone for lampredotto (Tuscan-style tripe sandwich) or a bowl of ribollita. Stroll to Piazza della Signoria to greet Michelangelo’s David replica and the Loggia dei Lanzi’s open-air sculptures, then cross the Ponte Vecchio into the artisan Oltrarno.

Evening: Aperitivo with a view at La Terrazza (Hotel Continentale) or the riverside Locale Bistrò. Dinner options: Trattoria Mario (bistecca fiorentina, convivial), Osteria del Cinghiale Bianco (hand-rolled pappardelle al cinghiale), or La Giostra (Tuscan classics, candlelit). Gelato finale at Gelateria dei Neri.

Day 5: Tuscan wines by morning, departure by afternoon

Morning tour: Sip and swirl on a time-efficient countryside escape: Small-Group Wine Tasting Experience in the Tuscan Countryside. It’s a half-day with two wineries, cellar walks, and olive oil tastings—great if you’re catching an afternoon train or flight.

Lunch + last stroll: Back in town, grab schiacciata sandwiches at All’Antico Vinaio (prosciutto, pecorino, truffle cream) or a sit-down plate at Trattoria da Burde (old-school Tuscan fare). If time allows, pop into the historic Officina Profumo-Farmaceutica di Santa Maria Novella for herbal elixirs and perfumes.

Departure: For onward travel, check Omio for trains to Rome or Milan airports, or find flights from Florence/Pisa on Omio (Flights). Those continuing beyond Europe can compare fares on Kiwi.com.

Optional swap: Vatican morning (if you prefer art to coast)

If you’d rather trade Day 3’s coastal adventure for the Vatican, book a small-group skip-the-line tour to maximize time and context: Skip-the-Line Group Tour of the Vatican, Sistine Chapel & St. Peter's Basilica.

Budget-savvy tips for a mid-range (50/100) trip:

• Trains between cities beat flying on time and cost—book advance Frecciarossa fares on Omio.
• Alternate trattorie and street food: pizza al taglio, panini, and market stalls keep costs down without sacrificing flavor.
• Reserve two paid tours (Colosseum + a day trip) and self-guide the rest with piazza time and museum selectivity.

At-a-glance intercity logistics:

• Rome → Florence: 1 hr 30 min on high-speed trains, €25–€70 (standard to business class) via Omio; plan a ~9:00 a.m. departure on Day 4.
• Airport transfers: FCO/Rome Termini by Leonardo Express (32 min) or regional; Florence SMN to FLR by taxi (~20–30 min).

With ancient stadiums, cliffside roads, and vineyard lanes, this five-day adventure balances headline sights and local flavor without rushing. You’ll leave with pasta techniques you tasted, panoramas you earned on foot, and a train-car window’s worth of Tuscan green etched into memory.