Ten days is the goldilocks number for an Italian honeymoon. Enough to see four destinations without rushing, enough to actually relax, and enough to have at least two days where you do absolutely nothing except eat well and hold hands. I've been planning Italian trips professionally for years. This is the itinerary I'd hand to my best friend.
Get a personalized version →Rome (2.5 days) → Amalfi Coast (3 days) → Tuscany countryside (2 days) → Florence (1.5 days) → Venice (1 day). Yes, Venice gets only one full day. I know. But one day done right — arriving by water, wandering without a map, dinner on a quiet canal — is more romantic than three days fighting crowds at San Marco.
Day 1: Colosseum (8:30am, arena floor access €24), Roman Forum, Palatine Hill morning. Lunch in Monti at La Taverna dei Fori Imperiali. Afternoon wander through Monti's vintage shops. Evening passeggiata: Trevi Fountain → Spanish Steps → dinner at Roscioli (book ahead, ~€55/person).
Day 2: Vatican Museums (8am entry, book online), Sistine Chapel, St. Peter's dome climb. Lunch at Pizzarium Bonci in Prati. Afternoon: Castel Sant'Angelo rooftop. Evening: cross to Trastevere for dinner at Da Enzo al 29 (cash only, expect a wait, the cacio e pepe is perfect). After dinner, walk along the Tiber — the bridges lit up at night are impossibly romantic.
Day 3 morning: Galleria Borghese (9am slot, book 2 months ahead, €15). Bernini's sculptures make marble look like flesh. Then Villa Borghese gardens — rent a rowboat on the lake (€3/20min). Grab lunch at Pastificio Guerra (fresh pasta, €5, eaten standing). Afternoon train south.
Day 3 afternoon: Arrive Positano by ferry from Naples. Check in, walk to the beach, first Aperol Spritz overlooking the sea. Dinner at Da Vincenzo — fish caught that morning, terrace with view, ~€40/person.
Day 4: Morning bus to Ravello. Villa Cimbrone Terrace of Infinity (€10) — the most romantic viewpoint in southern Italy, no exaggeration. Lunch in Amalfi town at Trattoria Da Gemma. Afternoon: swim at Fornillo Beach (Positano's quieter beach, turn left at the bottom).
Day 5: Private boat day. A gozzo boat from Positano (€350-600, 4-6 hours) to Li Galli islands, hidden coves, swimming in impossible blue water. Captain brings prosecco. This is the single best money you'll spend on the entire trip. Book through your hotel.
Day 6: Train to Florence, pick up rental car (€40-60/day from Firefly or Sicily by Car at SMN station). Drive 1.5 hours to Val d'Orcia. Check into an agriturismo — Podere Il Casale near Pienza (from €120/night, pool, vineyard views) or La Bandita Townhouse in Pienza (from €200/night, design hotel). Walk Pienza's streets, buy pecorino directly from a producer.
Day 7: Morning: Montalcino for Brunello wine tasting. Fattoria dei Barbi does excellent tastings (€15-25 for 3-4 wines plus local salumi). Afternoon: drive the iconic cypress-lined roads, stop at Bagno Vignoni (a medieval village built around a thermal pool). Evening: dinner at your agriturismo or at Trattoria Latte di Luna in Pienza (pici cacio e pepe, ~€25/person).
Day 8: Return car. Uffizi (8:15am slot, €25). Ponte Vecchio. Lunch at Mercato Centrale food hall (lampredotto sandwich at Nerbone, €5 — trust me). Afternoon: Oltrarno artisan workshops — watch leather craftsmen, paper marbling, goldsmiths. Aperitivo at Volume in Piazza Santo Spirito. Dinner at Il Latini — shared tables, hanging prosciutti, bistecca, pure Florentine chaos.
Day 9 morning: Accademia (Michelangelo's David, €16, book online). Then Piazzale Michelangelo for the panorama. Afternoon train to Venice (2h, €19-50).
Morning: Skip San Marco until afternoon. Start in Dorsoduro — the most beautiful sestiere. Peggy Guggenheim Collection (€16) if you love modern art. Walk to Punta della Dogana for the view across to San Giorgio Maggiore.
11am — Get lost. Seriously. Put the phone away and walk. Venice without a map is Venice at its best. Cross bridges, follow cats, find a campo with no tourists and sit.
1pm — Cicchetti lunch. Venice's version of tapas. All'Arco near Rialto (best cicchetti in the city, €1.50-3 each) or Cantina Do Spade. Glass of prosecco, three cicchetti, stand at the bar — total €10-12.
4pm — San Marco. The crowds thin after 4. The basilica is free (skip the line for €3 online). The mosaics inside are gold — literally. Then: gondola at sunset. Yes, it's €80-100 for 30 minutes. Yes, it's touristy. Yes, on your honeymoon, you do it anyway. Request the quieter canals away from the Grand Canal — the gondolier knows which ones.
8pm — Dinner at Osteria alle Testiere (Calle del Mondo Novo 5801). Tiny, 9 tables, seafood only, changes daily. Book 2 weeks ahead minimum. ~€55/person with wine. The best restaurant meal in Venice.
Boutique hotels and agriturismi, trains in standard, trattorias and osterias, one private boat, one Michelin-adjacent dinner. This is how I'd do it.
5-star hotels, first-class trains, private transfers, Le Sirenuse, gondola at sunset, tasting menus. Gorgeous but not 2x better than mid-range.
I list multiple partners so you can compare. I earn a small commission, but I'd never recommend something I wouldn't use myself.
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