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13-Day Italy Route: Milan to the Dolomites, Florence, Naples & Amalfi, Ending in Rome

Viewed by 140 travelers

Day 1: Milan Highlights

Milan, Italy on August 19, 2025

8:00am

Breakfast at Pasticceria Marchesi

Classic Milanese pastry shop near the Duomo — perfect for a cappuccino and cornetto to start; opens around 7:30am so it's great for an early start.
EUR8, 0h30m

9:00am

Duomo di Milano & Rooftop

Explore the cathedral interior and take the rooftop terraces for panoramic city and Gothic detail views; rooftop access roughly 9:00am–7:00pm (hours vary seasonally) and advance tickets or city pass recommended.
EUR20, 1h30m

11:00am

Galleria Vittorio Emanuele II & Piazza del Duomo

Stroll the historic shopping arcade and surrounding square — great for photos and window-shopping; open all day, most shops open by 10:00am.
EUR0, 0h45m

12:30pm

Lunch at Luini (panzerotti)

Legendary spot for panzerotti and a fast, delicious lunch right off the Duomo; typically open 10:00am–8:00pm but lines can form at midday.
EUR7, 0h30m

2:00pm

Santa Maria delle Grazie — Last Supper (book in advance)

See Leonardo da Vinci's Last Supper mural; entry is strictly timed (usually slots between 8:15am–7:30pm), so reserve weeks ahead — otherwise admire the exterior and nearby neighborhoods.
EUR15, 0h30m

3:00pm

Sforza Castle & Parco Sempione

Walk the castle courtyards and the adjacent park for a relaxed afternoon; museum hours commonly 9:00am–5:30pm for interior visits (check specific museum times).
EUR10, 1h30m

7:30pm

Dinner at Trattoria Milanese

Traditional Milanese cuisine (ossobuco, risotto alla Milanese) in a cozy, reliable trattoria; typical dinner service from 7:00pm–11:00pm and reservations recommended.
EUR35, 1h30m

Day 2: To the Dolomites

Cortina d'Ampezzo (Dolomites), Italy on August 20, 2025

7:00am

Breakfast at hotel or local bar

Quick coffee and pastry before departure; local bars open from 6:30–7:30am in many towns.
EUR6, 0h20m

8:00am

Travel Milan → Cortina (train + bus)

Take an early train Milan to Calalzo di Cadore (approx 3.5–4h with change in Venice/Mestre) then regional bus to Cortina (~1h); total travel 4.5–6h depending on connections.
EUR50, 5h0m

1:30pm

Lunch in Cortina — Rifugio/Local osteria

Simple mountain cuisine and polenta in town — many eateries open 12:00pm–3:00pm and again for dinner.
EUR20, 1h0m

3:00pm

Faloria cable car & easy walks

Ride the Faloria cable car for sweeping Dolomite views and short alpine walks; cable car usually operates 9:00am–5:30pm (seasonal), check local schedule for last rides.
EUR15, 2h0m

6:30pm

Dolomites sunset viewpoint

Find a sunset viewpoint near Cortina for golden-hour photography; sunset times vary — dress in layers as it cools quickly.
EUR0, 0h45m

8:00pm

Dinner at Trattoria Alle Alpi or local rifugio

Hearty mountain dishes and local wines; most restaurants serve dinner from 7:00pm–10:00pm, reservation recommended in summer.
EUR30, 1h30m

Day 3: Dolomites Hike

Dolomites (Tre Cime/Monte Piana area), Italy on August 21, 2025

7:30am

Breakfast at hotel

Carb-up breakfast before a full day hiking; most hotels open buffet around 7:00–8:00am.
EUR8, 0h30m

8:30am

Transfer to trailhead (Tre Cime di Lavaredo or Seceda)

Take local bus or drive to the trailhead (buses run seasonally; check times); the iconic Tre Cime hikes are accessible by bus from Cortina or nearby towns and offer incredible scenery.
EUR10, 1h0m

9:45am

Hike: Tre Cime loop or Seceda ridge

Moderate full-morning hike with rock towers and panoramic ridgelines; plan 3–5 hours depending on route and weather — mountain trails are open year-round but cable lifts and buses are seasonal.
EUR0, 4h0m

2:00pm

Lunch at rifugio on-route

Mountain hut meal with local specialties and views; rifugi usually serve lunch until roughly 3:00–4:00pm.
EUR18, 1h0m

4:00pm

Return to Cortina & rest

Relax and stroll Cortina’s pedestrian center, visit boutiques and alpine stores; many shops close by 7:00–8:00pm.
EUR0, 1h30m

8:00pm

Dinner at a local gourmet mountain restaurant

Try local game, speck, dumplings, and alpine desserts; dinner service typically 7:00pm–10:00pm.
EUR35, 1h30m

Day 4: Travel to Florence

Florence, Italy on August 22, 2025

7:00am

Early breakfast and checkout

Light breakfast and prepare for the long travel south; check bus and train connections the evening before to confirm times.
EUR8, 0h30m

8:00am

Travel Cortina → Florence (train via Venice/Mestre)

Depart by bus to Calalzo or Venice then high-speed train from Venice/Mestre to Florence Santa Maria Novella; expect total travel time about 4.5–6h depending on connections.
EUR60, 5h0m

2:00pm

Lunch near Santa Maria Novella — Trattoria nearby

Florentine simple lunch of panini or pappa al pomodoro; many central restaurants open 12:00–3:00pm.
EUR15, 1h0m

3:30pm

Cathedral of Santa Maria del Fiore (Duomo) & Baptistery

Visit the Duomo complex — interior, Baptistery, and consider climbing Brunelleschi's Dome (advance booking required); galleries and dome generally open 10:00am–5:00pm but times vary by season.
EUR25, 2h0m

6:00pm

Walk to Ponte Vecchio & sunset views

Stroll across the famous medieval bridge and explore the Oltrarno neighborhood; shops commonly close by 7:00pm but the view at dusk is memorable.
EUR0, 0h45m

8:00pm

Dinner at Trattoria ZaZa

Popular Florentine spot for bistecca and Tuscan classics; open for dinner roughly 7:00pm–11:00pm, reservations strongly recommended.
EUR40, 1h30m

Day 5: Florence Museums

Florence, Italy on August 23, 2025

8:00am

Breakfast at Caffè Gilli

Historic café in the heart of Florence — great pastries and coffee; opens early around 7:00–8:00am.
EUR10, 0h30m

9:00am

Uffizi Gallery (book timed entry)

World-class Renaissance collection with Botticelli and Leonardo highlights; Uffizi usually opens 8:15/9:00am–6:50pm (closed Mondays), book timed entry in advance.
EUR25, 2h0m

12:30pm

Lunch at Mercato Centrale

Bustling market food hall with many stalls offering fresh pasta, pizza, and Tuscan specialties; open 10:00am–midnight in summer, ideal for casual lunches.
EUR15, 1h0m

2:00pm

Galleria dell'Accademia (Michelangelo's David)

See Michelangelo's David and other Renaissance sculptures; typically open 8:15am–7:30pm but book ahead for timed entry as slots fill up.
EUR12, 1h0m

3:30pm

Boboli Gardens & Palazzo Pitti

Large gardens with sculptures and great views over Florence; gardens usually open 8:15am–7:30pm though closing times vary seasonally.
EUR10, 1h30m

8:00pm

Dinner at La Giostra

Romantic trattoria known for high-quality Tuscan cooking and warm service; dinner service typically 7:00pm–11:00pm — reserve in advance.
EUR45, 1h30m

Day 6: Chianti Day

Chianti Region (from Florence), Italy on August 24, 2025

7:30am

Breakfast and pickup for Chianti wine tour

Light breakfast and meet your small-group or private tour (many tours depart around 8:00–9:00am) for winery visits and scenic drives.
EUR8, 0h30m

9:00am

Drive into Chianti — vineyard visits

Visit 2–3 wineries, learn about Sangiovese and Chianti production with tastings; many wineries welcome visitors 10:00am–5:00pm but require bookings for tastings and lunch.
EUR60, 4h0m

1:00pm

Lunch at winery (traditional Tuscan menu)

Long, leisurely lunch with local produce and wines — typically served 12:30–2:30pm at agriturismos or winery restaurants.
EUR35, 1h30m

3:00pm

Explore hilltop towns (Greve, Castellina, Radda)

Short visits to picturesque medieval villages for walking, olive oil tastings, and shops; most local shops open until early evening, closing around 6:30–7:30pm.
EUR0, 2h0m

6:30pm

Return to Florence

Drive back and relax before dinner; travel time about 1h depending on traffic.
EUR0, 1h0m

8:00pm

Dinner near Santo Spirito — Osteria or trattoria

Evening in the artisan Oltrarno quarter with relaxed Florentine dining; many spots serve dinner 7:00pm–11:00pm.
EUR30, 1h30m

Day 7: Florence → Naples & Pompeii

Naples & Pompeii, Italy on August 25, 2025

7:00am

Early breakfast and check-out

Quick breakfast and head to Florence Santa Maria Novella station for high-speed train to Naples Centrale; trains often depart early and journey is ~2h45–3h.
EUR8, 0h30m

8:00am

Train Florence → Naples (Frecciarossa/Italo)

High-speed train to Naples Centrale takes about 2.5–3 hours; book tickets in advance for best fares.
EUR45, 3h0m

12:30pm

Lunch in Naples — L'Antica Pizzeria Da Michele

Iconic Neapolitan pizza spot; note queues and limited opening hours (commonly 11:00am–3:00pm and 6:00pm–11:00pm), but it's worth the wait.
EUR12, 1h0m

2:00pm

Afternoon: Pompeii Archaeological Park

Visit the remarkably preserved Roman city — open generally 9:00am–7:30pm in summer (closing times change seasonally), allow at least 2–3 hours for the site.
EUR16, 3h0m

6:00pm

Return to Naples & stroll Spaccanapoli

Walk the narrow historic street, try sfogliatella and espresso, and view lively street life; bakeries open early and into the evening.
EUR0, 1h0m

8:30pm

Dinner at a Naples trattoria

Seafood or more Neapolitan specialties — aim for a well-reviewed local place, many open 7:00pm–11:00pm.
EUR30, 1h30m

Day 8: To the Amalfi Coast

Positano (Amalfi Coast), Italy on August 26, 2025

7:30am

Breakfast and depart for Amalfi Coast

Light breakfast and take Circumvesuviana/train to Sorrento then ferry or bus to Positano; total travel from Naples ~1.5–2.5 hours depending on chosen route.
EUR10, 2h0m

10:30am

Arrival & settle in Positano

Check into hotel and enjoy the cliffside village ambiance; shops and beaches are open by mid-morning.
EUR0, 0h45m

12:30pm

Lunch at Chez Black on the beachfront

Classic beachfront dining with seafood and pizza, open 12:00pm–11:00pm in high season; great people-watching spot.
EUR25, 1h0m

2:00pm

Relax on Fornillo or Spiaggia Grande

Beach time or rent a lounger; beach vendors typically operate 9:00am–6:00pm, and water temperature is pleasant in August.
EUR20, 2h0m

5:30pm

Sunset walk up to viewpoints / shopping

Wander the narrow streets for ceramic and linen boutiques and catch the sunset views over the sea; shops often remain open until 8:30pm in high season.
EUR0, 1h0m

8:00pm

Dinner at La Tagliata (or local family-run restaurant)

Rustic, family-style dinners with terrace views — typically open for dinner 7:00pm–10:30pm and reservations are essential for peak season.
EUR40, 1h30m

Day 9: Capri Day Trip

Capri (from Positano), Italy on August 27, 2025

7:30am

Breakfast & ferry to Capri

Early breakfast then catch the morning ferry from Positano to Capri (ferries typically run 8:00am–6:00pm in season, schedule varies), booking in advance is recommended.
EUR30, 1h0m

9:30am

Blue Grotto or coastal boat tour

Boat trips circle the island and visit sea caves; Blue Grotto visits depend on sea conditions and are operated 9:00am–5:00pm in best weather, expect small-boat transfers and additional fees.
EUR20, 1h30m

11:30am

Anacapri & chairlift to Monte Solaro

Short bus up to Anacapri and take the chairlift to Monte Solaro for the island's highest views; chairlift open roughly 9:00am–5:30pm (seasonal).
EUR14, 1h15m

1:00pm

Lunch in Capri town (La Piazzetta or local trattoria)

Enjoy Capri specialties and limoncello sweets; lunches commonly served 12:30–3:00pm.
EUR30, 1h15m

3:00pm

Explore Gardens of Augustus & Via Krupp

Beautiful gardens and famous coastal viewpoint (check cliff access; Via Krupp access can be restricted on windy days); gardens often open 9:00am–7:00pm in high season.
EUR1, 1h0m

6:00pm

Return ferry to Positano & dinner

Ferry back in the early evening and dine seaside — many restaurants remain open late into the summer months.
EUR30, 1h30m

Day 10: Amalfi & Ravello

Amalfi Coast (Amalfi & Ravello), Italy on August 28, 2025

8:00am

Breakfast and short ferry/bus to Amalfi

Breakfast then take the scenic coastal route to Amalfi town (ferries and SITA buses run frequently in high season), travel time ~30–60 minutes.
EUR8, 1h0m

9:30am

Amalfi Cathedral (Duomo di Sant'Andrea)

Visit the striking exterior and interior; cathedral and cloister hours are generally 9:30am–7:00pm but may vary for services.
EUR3, 0h45m

11:00am

Ferry or bus up to Ravello — Villa Rufolo & Villa Cimbrone

Short trip up to Ravello to see the historic villas and sweeping gardens with incredible Amalfi Coast vistas; villas typically open 10:00am–7:00pm (check seasonal hours).
EUR10, 2h0m

1:30pm

Lunch at a Ravello trattoria (Rossellinis or local osteria)

Elegant lunch option with panoramic terrace choices; Rossellinis is fine-dining and requires reservation — many Ravello restaurants operate 12:30–3:00pm for lunch.
EUR50, 1h30m

3:30pm

Leisurely return to Positano, beach or shopping

Afternoon at leisure to shop ceramics, relax on the beach or sip aperitivo with sea views; shops open until early evening in summer.
EUR0, 2h0m

8:00pm

Dinner in Positano — sunset dining

Enjoy a farewell Amalfi Coast dinner with seasonal seafood and local wine; many cliffside restaurants require reservations and open 7:00pm onwards.
EUR45, 1h30m

Day 11: To Rome & Ancient Sites

Rome, Italy on August 29, 2025

7:30am

Breakfast & depart Positano → Rome

Early transfer by ferry/bus to Naples then high-speed train to Rome Termini; expect 3.5–4.5 hours total travel depending on connections.
EUR40, 4h0m

12:30pm

Lunch near Colosseum — pizzeria or trattoria

Quick Italian lunch close to the ancient center; many central restaurants open 12:00–3:00pm and again for dinner.
EUR18, 1h0m

2:00pm

Colosseum & Roman Forum (prebooked timed entry)

Explore Rome’s iconic amphitheatre and the adjacent Forum/Palatine Hill; Colosseum timed entries start in morning and run through evening in summer — book ahead to skip long lines.
EUR16, 2h30m

5:00pm

Stroll Capitoline Hill & Piazza Venezia

Walk the central monumental area for cityscapes and history; public spaces open all day though museums have fixed hours.
EUR0, 0h45m

8:00pm

Dinner in Trastevere — Da Enzo al 29

Classic Roman trattoria in lively Trastevere with traditional dishes (carbonara, cacio e pepe); open evenings 7:00pm–11:00pm and reservations are recommended.
EUR35, 1h30m

Day 12: Vatican & Historic Rome

Rome (Vatican City & Centro Storico), Italy on August 30, 2025

7:00am

Breakfast near Vatican — Pizzarium or café

Grab coffee and an Italian-style breakfast — places near the Vatican often open by 7:00am which helps beat larger crowds.
EUR8, 0h30m

8:30am

Vatican Museums & Sistine Chapel (timed entry)

Prebook earliest timed entry possible to avoid crowds — museums commonly open 9:00am–6:00pm (closed Sundays except last Sunday of month), allow 2–3 hours.
EUR17, 2h30m

11:30am

St. Peter's Basilica & Dome climb

Visit St. Peter's (opens very early, around 7:00am) and climb the dome for sweeping views (dome hours roughly 8:00am–6:00pm, elevator part-way available for a fee).
EUR10, 1h30m

1:30pm

Lunch at Pizzarium or nearby trattoria

Excellent al taglio pizza options and street-friendly meals near the Vatican; open midday 11:00–15:00 typically.
EUR12, 0h45m

3:00pm

Pantheon, Piazza Navona & Trevi Fountain

Walk through central Rome to see the Pantheon (open 9:00am–7:00pm, donations requested), ornate Piazza Navona, and toss a coin at Trevi Fountain; public spaces available all day.
EUR0, 2h0m

8:00pm

Dinner at Osteria del Pegno or Armando al Pantheon

Classic Roman cuisine near the Pantheon for a memorable last-night meal; these spots are popular and often require reservations for dinner service starting around 7:00pm.
EUR40, 1h30m

Day 13: Rome: Borghese & Departure

Rome, Italy on August 31, 2025

8:00am

Breakfast at Roscioli Caffè

A refined start with pastries and excellent coffee; opens early in central Rome and perfect before a museum visit.
EUR10, 0h30m

9:30am

Galleria Borghese (prebook 2-hour slot)

Reserve a timed 2-hour slot to see Bernini and Caravaggio masterpieces in an intimate villa setting; entry is strictly timed (commonly slots at 9:00/11:00/1:00/3:00).
EUR20, 2h0m

12:00pm

Walk Villa Borghese park / rent a bike or rowboat

Enjoy the green lungs of Rome with panoramic views over the city; rental services open mid-morning to late afternoon.
EUR10, 1h0m

1:30pm

Lunch and last-minute shopping near Piazza di Spagna

Final Italian meal and chance to pick up gifts — many cafés and shops open throughout the afternoon (shops usually open 10:00am–7:30pm).
EUR20, 1h0m

3:00pm

Pack, checkout and transfer to airport or train station

Allow ample time for airport transfer (Rome Fiumicino ~45–60 minutes from center) or train departures; confirm departure time and allow buffer for city traffic.
EUR30, 2h0m

6:00pm

Final aperitivo or early dinner (if time allows)

If your schedule permits, enjoy an aperitivo to toast the trip at a local enoteca near your departure area; many spots offer evening service until 10:00pm.
EUR15, 1h0m
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