Ultimate 24-Day Italy Tour: Milan to Palermo with History, Hiking, and Culinary Delights

Day 1: Milan Arrival & Orientation

Milan, Italy on May 1, 2026

9:00am

Breakfast at Panificio Pattini

Start your first morning in Milan with freshly baked pastries and Italian coffee at this popular local bakery that opens early to fuel your day.
EUR5, 0h45m

10:00am

Duomo di Milano Visit

Explore Milan’s iconic Gothic cathedral with rooftop access providing panoramic city views. Opens 9am-7pm.
EUR15, 2h0m

12:30pm

Lunch at Luini Panzerotti

Famous for their panzerotti, traditional fried stuffed bread - perfect quick Italian street food near the Duomo.
EUR10, 1h0m

2:00pm

Visit Sforza Castle

Wander through the historical castle grounds and museums showcasing Renaissance art and history. Open 9:00am-5:30pm.
EUR10, 2h0m

5:00pm

Aperitivo at Navigli District

Enjoy Milan’s vibrant aperitivo culture along the canals with local drinks and complimentary snacks before dinner.
EUR15, 2h0m

7:30pm

Dinner at Trattoria Madonnina

Cozy traditional Milanese cuisine focusing on risotto and ossobuco, perfect for a hearty first-night meal.
EUR30, 1h30m
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Day 2: Milan Art & Culture

Milan, Italy on May 2, 2026

8:30am

Breakfast at Pavé

Enjoy artisan pastries and fresh coffee at this trendy café that opens early and is beloved by locals.
EUR8, 1h0m

9:30am

Visit Pinacoteca di Brera

Tour one of Milan’s top art galleries with stunning Renaissance and Baroque collections. Opens 8:30am-7:15pm.
EUR12, 2h0m

12:00pm

Lunch at Eataly Smeraldo

Sample diverse Italian dishes in this bustling food emporium focusing on fresh, regional ingredients.
EUR25, 1h0m

1:30pm

Leonardo da Vinci's The Last Supper

Pre-book a timed ticket to see the iconic mural in the Convent of Santa Maria delle Grazie. Tour lasts about 15 minutes; museum and church open 8:15am-7pm.
EUR20, 1h0m

3:00pm

Stroll through Brera District & Botanical Garden

Wander the artistic streets of Brera and visit the peaceful Botanical Garden, ideal for a relaxed afternoon walk.
Free, 2h0m

6:00pm

Dinner at Ratanà

Enjoy contemporary Milanese cuisine in a stylish setting focusing on local and seasonal ingredients.
EUR35, 1h30m
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Day 3: Day Trip Hiking & Departure to Venice

Milan, Italy to Venice, Italy on May 3, 2026

7:30am

Breakfast at Marchesi 1824

Start your day with elegant pastries and espresso at one of Milan’s oldest pastry shops.
EUR10, 0h45m

8:30am

Train to Lake Como Hiking - Varenna Trail

Take the early train (1.5 hours) to Varenna for a beautiful hike along the lake (approx. 2-3 hours). Hike offers spectacular views and quaint villages.
EUR12 train + Free hiking, 5h0m

2:00pm

Lunch in Varenna – Ristorante La Vista

Enjoy lakefront dining with traditional Lombardy dishes, perfect for refueling after hiking.
EUR25, 1h0m

4:00pm

Return train to Milan then high-speed train to Venice

Travel back to Milan then catch a 2.5 hour high-speed train to Venice, arriving in the evening.
EUR70, 3h30m

8:30pm

Dinner at Osteria Al Bacco, Venice

Casual Venetian seafood trattoria near the train station, serving cicchetti and fresh dishes.
EUR30, 1h30m
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Day 4: Exploring Venice Canals & History

Venice, Italy on May 4, 2026

8:00am

Breakfast at Rosa Salva

Start with Venetian pastries and an espresso at this renowned historic cafe since 1819.
EUR10, 0h45m

9:00am

St Mark’s Basilica & Square Visit

Tour the breathtaking gold mosaics and architecture of the basilica; must-see Venetian landmark. Opens 9am-5pm.
EUR3 donation, 2h0m

11:30am

Doge’s Palace Tour

Explore the palace interior, prison, and Bridge of Sighs for a deep dive into Venetian history. Opens 9am-7pm.
EUR25, 2h0m

1:30pm

Lunch at Trattoria Alla Madonna

Enjoy classic Venetian dishes with fresh seafood in a welcoming atmosphere near the Rialto Bridge.
EUR30, 1h0m

3:00pm

Gondola Ride on the Canals

Relax on a 30-minute gondola trip navigating picturesque canals for unique city views.
EUR90 (per gondola), 0h30m

4:00pm

Walk and shop in Rialto Market

Explore the iconic fish and produce market and nearby shops for local crafts and food items.
Free, 1h0m

7:00pm

Dinner at Osteria alle Testiere

Highly rated for Venetian seafood specialties with a local wine list in an intimate setting; reserve ahead.
EUR45, 1h30m
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Day 5: Murano & Burano Island Visit

Venice, Italy on May 5, 2026

7:30am

Breakfast at Hotel or nearby cafe

Light breakfast in Venice to energize for island day trip.
EUR8, 0h30m

8:00am

Vaporetto to Murano Island

Famous for glassmaking, visit Murano museums and watch glassblowing artisans at work. Museums open 10am-5pm.
EUR20 vaporetto ticket, 3h0m

11:00am

Travel to Burano Island

Colorful fishing village known for lace making, quaint streets, and photo-worthy houses. Walk and explore at leisure.
Included in vaporetto ticket, 2h0m

1:30pm

Lunch at Trattoria al Gatto Nero, Burano

Local favorite serving fresh seafood and Venetian classics in vibrant surroundings.
EUR30, 1h0m

3:00pm

Return to Venice Main Island

Leisurely vaporetto ride back to Venice center for afternoon relaxation.
Included in vaporetto ticket, 1h0m

4:00pm

Visit Peggy Guggenheim Collection

Modern art museum featuring Picasso, Pollock, and Dali in Peggy’s former home on the Grand Canal; open 10am-6pm.
EUR15, 1h30m

7:00pm

Dinner at Antiche Carampane

Hidden gem serving fresh Venetian seafood, away from the tourist crowds; reservation recommended.
EUR40, 1h30m
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Day 6: Venice to Florence Travel & Intro

Venice to Florence, Italy on May 6, 2026

8:00am

Breakfast at Farini Bakery, Venice

Delicious and fresh pastries with espresso to start your travel day.
EUR8, 0h45m

9:00am

Train Venice to Florence

High-speed train approximately 2 hours, arriving before noon to maximize your day in Florence.
EUR50, 2h0m

11:30am

Check-in and lunch at Mercato Centrale

Explore Florence’s famous food market, enjoy a variety of Tuscan specialties for lunch in casual stalls.
EUR20, 1h0m

1:00pm

Florence Cathedral & Baptistery Tour

Visit the Duomo, climb the dome for city views and see the famous Baptistery inside the Piazza del Duomo. Open 10am-5pm.
EUR18, 2h0m

3:30pm

Walk Ponte Vecchio & Explore Oltrarno

Stroll the historic bridge and artisan district known for crafts and quieter cafes.
Free, 2h0m

7:30pm

Dinner at Trattoria 4 Leoni

Traditional Tuscan dishes with homemade pasta in a charming setting in Oltrarno.
EUR30, 1h30m
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Day 7: Florence Art Exploration

Florence, Italy on May 7, 2026

8:00am

Breakfast at Ditta Artigianale

Specialty coffee and light breakfast to fuel your art-filled day.
EUR10, 0h45m

9:00am

Uffizi Gallery Visit

One of the most famous art museums in the world, home to works by Botticelli, Leonardo da Vinci, and Michelangelo; open 8:15am-6:50pm.
EUR25, 3h0m

12:30pm

Lunch at All’Antico Vinaio

Famous sandwich shop near Uffizi serving delicious Tuscan sandwiches, perfect quick lunch.
EUR12, 1h0m

2:00pm

Accademia Gallery

See Michelangelo’s David and other Renaissance masterpieces; opens 8:15am-6:50pm.
EUR20, 2h0m

4:30pm

Walk or Taxi up to Piazzale Michelangelo

Enjoy amazing panoramic views over Florence, perfect for sunset photographs.
Free, 1h30m

7:00pm

Dinner at Cibrèo

Refined Tuscan cuisine with traditional recipes in an elegant atmosphere.
EUR50, 1h30m
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Day 8: Florence to Cinque Terre

Florence to Cinque Terre, Italy on May 8, 2026

7:30am

Breakfast at hotel or local café

Light breakfast to prepare for scenic train travel to Cinque Terre.
EUR8, 0h30m

8:30am

Train Florence to La Spezia then Cinque Terre village

Board train to La Spezia (2h), then transfer to regional train into Cinque Terre villages (30m). Arrive by late morning.
EUR30, 3h0m

11:30am

Lunch at Nessun Dorma, Manarola

Famous spot overlooking the sea with delicious paninis and bruschetta; ideal lunch with views.
EUR20, 1h0m

1:00pm

Hike from Manarola to Corniglia

Enjoy the scenic coastal trail (approx. 1.5h), a stunning path with cliffs and sea views. Check trail conditions before hiking.
Free, 2h0m

4:00pm

Explore Corniglia village

Wander narrow streets, shops, and enjoy gelato or coffee in this peaceful village.
Free, 1h0m

6:00pm

Dinner at La Posada, Corniglia

Traditional Ligurian dishes focusing on seafood pasta and pesto specialties.
EUR35, 1h30m
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Day 9: Cinque Terre Hiking & Beach

Cinque Terre, Italy on May 9, 2026

7:30am

Breakfast at bakery in village

Start fresh with Italian pastries and coffee before hiking.
EUR8, 0h30m

8:00am

Hike Vernazza to Monterosso

Traverse the most famous and scenic segment of the Cinque Terre trail; 2-3 hours with expansive views of the Mediterranean.
EUR7 trail pass, 3h0m

12:00pm

Lunch at Ristorante Miky, Monterosso

Highly rated seafood restaurant in Monterosso, perfect to enjoy lunch after your hike.
EUR40, 1h30m

2:00pm

Beach time at Monterosso

Relax on the sandy beaches of Monterosso and swim in crystal clear waters.
Free, 3h0m

5:30pm

Return to accommodation

Freshen up and rest after an active day.
Free, 1h0m

7:30pm

Dinner at Belforte, Vernazza

Amazing terrace dining overlooking the sea with local Ligurian cuisine and wine.
EUR50, 1h30m
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Day 10: Cinque Terre Villages & Departure

Cinque Terre to Amalfi Coast, Italy on May 10, 2026

8:00am

Breakfast at hotel or café

Light breakfast before departure.
EUR8, 0h30m

9:00am

Morning walk in Riomaggiore

Visit the southernmost village, browse shops and enjoy a stroll along the harbor.
Free, 1h0m

10:30am

Train to Naples then Amalfi Coast by bus

Long travel day: Train La Spezia to Naples (approx. 5h), then transfer to SITA bus or private shuttle (1.5h) to Amalfi Coast area (Positano or Amalfi town).
EUR60 train + EUR10 bus, 7h0m

6:00pm

Check-in and Light dinner at Hotel

Rest from travel and enjoy a casual dinner at your hotel or nearby eatery in Amalfi Coast.
EUR25, 1h0m
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Day 11: Explore Amalfi & Hiking

Amalfi Coast, Italy on May 11, 2026

7:30am

Breakfast at Pasticceria Pansa, Amalfi

Famous pastry shop serving lemon treats, perfect to start your day on the coast.
EUR10, 0h45m

8:30am

Hike the Path of the Gods

Take this famous hiking trail from Bomerano (Agerola) to Nocelle, offering breathtaking views over the Amalfi Coast. Trail access is free, best to start early to avoid heat.
Free, 4h0m

1:00pm

Lunch at Il Ritrovo, Nocelle

Cozy hillside restaurant serving local specialties, ideal for rested hikers.
EUR30, 1h0m

3:00pm

Relax at Hotel or Beach

Enjoy some leisure time swimming or relaxing after the strenuous hike.
Free, 3h0m

7:30pm

Dinner at Ristorante Eolo, Amalfi

Upscale dining with stunning views and refined Campania cuisine.
EUR50, 1h30m
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Day 12: Capri Day Trip

Amalfi Coast, Italy on May 12, 2026

7:00am

Early breakfast at Hotel

Light breakfast before boat trip to Capri.
EUR8, 0h30m

7:30am

Boat to Capri

Ferry from Amalfi to Capri (approx. 1h), scenic travel with sea views.
EUR25 round trip, 2h0m

9:30am

Blue Grotto Visit

Famous sea cave known for glowing blue waters; opens from 9am with boats entering in small groups. Arrive early to avoid crowds.
EUR15, 1h0m

11:00am

Anacapri Village and Chairlift to Monte Solaro

Explore the charming town and take the chairlift for spectacular panoramic views (opens 9am-5pm).
EUR14 chairlift, 2h0m

1:30pm

Lunch at Da Gelsomina

Rustic restaurant with breathtaking views and traditional Capri cuisine.
EUR40, 1h30m

3:30pm

Walk the Gardens of Augustus and Via Krupp

Botanical gardens with extraordinary floral displays and the famous winding path to the sea; open 9am-7pm.
EUR1.5, 1h0m

5:00pm

Return ferry to Amalfi

Relaxing boat ride back to Amalfi for evening rest.
Included in round trip ticket, 1h0m

7:30pm

Dinner at Ristorante Marina Grande

Seafood restaurant on Amalfi’s harbor with fresh catches and local wines.
EUR45, 1h30m
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Day 13: Amalfi Coast Leisure Day & Travel to Rome

Amalfi Coast to Rome, Italy on May 13, 2026

8:00am

Breakfast at Hotel

Leisurely breakfast to enjoy your last moments on the coast.
EUR10, 0h45m

9:00am

Morning Beach or Explore Amalfi Town

Optional stroll through Amalfi center and its cathedral or relax on the beach.
Free, 2h0m

11:00am

Bus to Naples Train Station

Transfer by bus (1.5h) to Naples for high-speed train to Rome.
EUR10 bus, 1h30m

1:00pm

Train Naples to Rome

High-speed train (1.5h) to Rome, arriving mid-afternoon.
EUR30, 1h30m

3:00pm

Check-in and late lunch at Mercato Centrale Roma

Diverse Italian fare in a vibrant market atmosphere perfect for a quick bite.
EUR20, 1h0m

5:00pm

Walk along the Tiber River & Trastevere

Enjoy the charm of Rome’s riverside paths and bohemian Trastevere district for lively evening ambience.
Free, 2h0m

7:30pm

Dinner at Osteria da Zi’ Umberto

Traditional Roman trattoria in Trastevere serving classic dishes such as Cacio e Pepe.
EUR35, 1h30m
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Day 14: Ancient Rome & History

Rome, Italy on May 14, 2026

8:00am

Breakfast at Roscioli Caffè

Start the day with excellent coffee and pastries near Campo de’ Fiori.
EUR10, 0h45m

9:00am

Colosseum and Roman Forum Guided Tour

Visit Rome’s ancient amphitheater and forum with skip-the-line tickets, open 8:30am-7pm.
EUR35, 3h0m

12:30pm

Lunch at La Taverna dei Fori Imperiali

Authentic Roman dishes within walking distance of Colosseum.
EUR30, 1h0m

2:00pm

Capitoline Museums

Explore Rome’s oldest public museum, housing classical sculptures and Renaissance art; open 9:30am-7pm.
EUR15, 1h30m

4:00pm

Piazza Venezia and Vittoriano Monument

Visit this grand monument with panoramic city views from the terrace.
EUR7, 1h0m

7:00pm

Dinner at Trattoria Vecchia Roma

Traditional Roman trattoria famous for carbonara and amatriciana pasta dishes.
EUR35, 1h30m
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Day 15: Vatican City Tour

Rome, Italy on May 15, 2026

7:30am

Breakfast near Vatican

Light breakfast at a café close to Vatican Museums to start early.
EUR8, 0h30m

8:00am

Vatican Museums & Sistine Chapel

Pre-book timed entry and tour to avoid crowds; marvel at the Sistine Chapel ceiling and Vatican art collections. Opens 9am-6pm, early entry available.
EUR30, 3h0m

12:00pm

Lunch at Borgo Pio

Charming street with multiple trattorias offering Roman and Italian cuisine.
EUR25, 1h0m

1:30pm

St. Peter’s Basilica & Dome Climb

Explore the basilica’s interior and climb to the dome for breathtaking city views; dome open 7am-7pm.
Entry free, dome climb EUR10, 2h0m

4:00pm

Stroll Castel Sant’Angelo and Ponte Sant’Angelo

Visit the historic castle and cross the beautiful bridge lined with angel statues; castle open 9am-7:30pm.
EUR15, 1h30m

7:30pm

Dinner at Armando al Pantheon

Classic Roman dishes near the Pantheon; reservation recommended.
EUR40, 1h30m
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Day 16: Historic Squares & Food

Rome, Italy on May 16, 2026

8:00am

Breakfast at Panella

Popular bakery with wide selection of pastries and coffee.
EUR8, 0h45m

9:00am

Pantheon & Piazza Navona

Visit the architectural marvel of the Pantheon and stroll nearby Piazza Navona to admire fountains and street artists.
Free, 2h0m

11:00am

Campo de’ Fiori Market

Explore vibrant market with fresh produce and food stalls.
Free, 1h0m

12:00pm

Lunch at Roscioli Salumeria con Cucina

Famous deli and restaurant offering excellent Roman and Italian dishes.
EUR35, 1h0m

2:00pm

Walk to Spanish Steps & Trevi Fountain

Explore two iconic landmarks of Rome filled with history and atmosphere.
Free, 2h0m

5:00pm

Gelato at Gelateria La Romana

Enjoy artisan gelato near the Spanish Steps.
EUR5, 0h30m

7:30pm

Dinner at Da Enzo al 29

Popular local trattoria serving authentic Roman dishes in Trastevere.
EUR40, 1h30m
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Day 17: Rome to Palermo Flight & Intro

Rome to Palermo, Italy on May 17, 2026

6:30am

Breakfast at hotel

Early breakfast before airport transfer.
EUR8, 0h30m

7:30am

Transfer to Rome Airport

Travel to Rome Fiumicino Airport (approx. 1h by taxi or train).
EUR40, 1h0m

9:00am

Flight Rome to Palermo

Direct flight of approx. 1h 15m to Palermo.
EUR70, 2h0m

11:00am

Check-in and lunch at Antica Focacceria San Francesco

Iconic Sicilian eatery known for traditional street foods like arancini and panelle.
EUR20, 1h0m

12:30pm

Palermo Cathedral & Palazzo dei Normanni

Explore the impressive Norman cathedral and nearby royal palace with Cappella Palatina; open 7am-7pm.
EUR12, 2h0m

3:00pm

Stroll the Quattro Canti & Piazza Pretoria

Visit the famous Baroque intersection and beautiful fountain, perfect for photos.
Free, 1h0m

5:00pm

Visit Mercato di Ballarò

Lively open-air market great for exploring Sicilian street foods and culture.
Free, 1h30m

7:30pm

Dinner at Osteria Ballarò

Savor authentic Sicilian cuisine with local ingredients in a rustic setting near the market.
EUR35, 1h30m
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Day 18: Palermo Historical & Culinary Day

Palermo, Italy on May 18, 2026

8:00am

Breakfast at Bar Florio

Enjoy traditional Sicilian pastries and coffee to start your day.
EUR8, 0h45m

9:00am

Visit the Catacombs of the Capuchins

Unique and somewhat macabre display of mummified monks and citizens; opens 9am-1pm and 3pm-6pm.
EUR10, 1h30m

11:00am

Walk through Via Vittorio Emanuele

Historic street with architecture and shops, leading to Teatro Massimo.
Free, 1h0m

12:30pm

Lunch at Trattoria Ai Cascinari

Popular local spot offering traditional Sicilian pasta dishes like Pasta alla Norma.
EUR25, 1h0m

2:00pm

Visit Teatro Massimo and nearby Piazza Politeama

Tour the grand opera house (check guided tour availability; open 9am-6pm) and explore the lively square.
EUR8, 1h30m

4:00pm

Explore the Kalsa district

Historic neighborhood full of art galleries, piazzas, and street life.
Free, 1h30m

7:30pm

Dinner at Ferro di Cavallo

Well-loved eatery serving Sicilian specialties and great atmosphere.
EUR30, 1h30m
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Day 19: Day trip to Monreale & Beaches

Palermo, Italy on May 19, 2026

7:30am

Breakfast at Hotel

Quick breakfast before day trip.
EUR8, 0h30m

8:00am

Bus to Monreale

Short 30-minute bus ride to Monreale famous for its cathedral, a UNESCO World Heritage Site.
EUR5, 1h0m

9:00am

Visit Monreale Cathedral

Stunning Norman cathedral with remarkable golden mosaics; opens 7am-7pm.
Free, 1h0m

10:30am

Walk Monreale town and viewpoints

Enjoy views over Palermo and the surrounding plain, charming town streets.
Free, 1h30m

12:00pm

Return to Palermo and Lunch at Antico Cafe Spinnato

Historic Sicilian café offering classic dishes and pastries.
EUR25, 1h0m

2:00pm

Afternoon beach time at Mondello

Relax at Mondello beach with its turquoise water and sandy shore, just a short drive from Palermo.
Free, 3h0m

6:00pm

Return to Palermo

Head back to the city for dinner.
EUR10 taxi, 1h0m

7:30pm

Dinner at Osteria dei Vespri

Fine dining with creative Sicilian cuisine in a sophisticated ambiance.
EUR50, 1h30m
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Day 20: Explore Palermo Markets & Departure

Palermo, Italy to Fredericton NB on May 20, 2026

8:00am

Breakfast at nearby café

Light breakfast to enjoy your last day in Palermo.
EUR8, 0h30m

9:00am

Visit Mercato del Capo

Traditional market with fresh produce, fish, and street food; ideal for pickup of last-minute souvenirs.
Free, 1h30m

11:00am

Leisure walk and coffee

Enjoy Palermo’s street life and grab a relaxing coffee before heading to the airport.
EUR8, 1h0m

12:30pm

Transfer to Palermo Airport

Taxi to the airport for your departure flight.
EUR40, 0h45m

3:00pm

Flight Palermo to Rome

Flight approx. 1.5h to connect with international flight.
EUR70, 2h0m

6:30pm

Flight Rome to Fredericton NB (connecting flights)

Return journey home, connections as scheduled.
Included in initial booking, N/A
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