Ultimate 23-Day Italy Itinerary: From Milan to Palermo with Scenic Trains & Hiking

Day 1: Milan Introduction

Milan, Italy on May 1, 2026

9:00am

Breakfast at Pavé

Start your morning with artisanal pastries and excellent cappuccinos at Pavé, a trendy Milan cafe known for fresh baked goods.
EUR10, 1h

10:30am

Visit the Duomo di Milano

Explore Milan's iconic cathedral, including rooftop access for panoramic city views. Open 9am-7pm.
EUR15, 1h30m

12:15pm

Lunch at Luini

Try the famous panzerotti, a delicious Italian stuffed pastry, at this popular take-away spot near the Duomo.
EUR7, 45m

2:00pm

Sforza Castle and Park

Wander through this historic fortress housing museums and the lush Parco Sempione right behind it—perfect for a light hike experience.
EUR10, 2h

5:00pm

Aperitivo at Nottingham Forest

Enjoy inventive cocktails with small plates in this award-winning bar popular among locals. Opens from 6pm.
EUR20, 1h

7:30pm

Dinner at Trattoria Milanese

Finish your day with traditional Milanese dishes like risotto alla Milanese in a cozy, authentic setting.
EUR35, 1h30m
View Hotels

Day 2: Milan Modern & Transit

Milan, Italy on May 2, 2026

8:00am

Breakfast at Marchesi 1824

Indulge in a historic Milanese café renowned for elegant pastries and coffee in a sophisticated setting.
EUR12, 1h

9:30am

Visit Pinacoteca di Brera

Explore one of Milan’s premier art galleries featuring Renaissance and Baroque art. Open 8:30am-7:15pm.
EUR15, 2h

12:00pm

Lunch at Eataly Smeraldo

Enjoy diverse Italian cuisine in this sprawling food marketplace offering quality regional dishes.
EUR25, 1h

2:00pm

Train to Venice

Take a 2.5-hour high-speed train from Milan Centrale to Venice Santa Lucia station, relaxing and enjoying scenic views.
EUR40, 2h30m

5:00pm

Check-in and explore Venice surroundings

Check into your hotel and enjoy a gentle exploratory walk along canals near your lodging, soaking in Venetian charm.
Free, 1h

7:00pm

Dinner at Antiche Carampane

Savor fresh seafood dishes in this classic Venetian trattoria beloved for authentic flavors off the tourist beaten path.
EUR40, 1h30m
View Hotels

Day 3: Venice City Tour

Venice, Italy on May 3, 2026

8:00am

Breakfast at Pasticceria Tonolo

Enjoy traditional Venetian pastries, such as bussolai and frittelle, paired with espresso to fuel your day.
EUR8, 45m

9:00am

Doge's Palace Tour

Explore the lavish Venetian Gothic palace and prison with audio guide; open 9am-7pm.
EUR25, 2h

11:30am

St. Mark's Basilica

Visit the stunning basilica famed for its gold mosaics, open 9:30am-5pm; climb the terrace for views.
Free (terrace EUR5), 1h30m

1:00pm

Lunch at Osteria Al Portego

Sample cicchetti and Venetian small plates paired with local wine in a cozy setting near the Rialto Market.
EUR20, 1h

2:30pm

Gondola Ride & Canal Walks

Take a classic gondola ride to fully experience Venice’s waterways, followed by a scenic stroll to discover hidden alleys.
EUR80, 1h

4:00pm

Visit Murano Island

Hop on a vaporetto to Murano (30 mins), famous for glassmaking workshops; open daily, visit small museums and galleries.
EUR20 round trip, 3h

7:30pm

Dinner at Trattoria alla Madonna

Enjoy fresh Adriatic seafood and Venetian classics in a lively, traditional atmosphere near the Rialto Bridge.
EUR40, 1h30m
View Hotels

Day 4: Venice Hiking & Islands

Venice, Italy on May 4, 2026

7:30am

Breakfast at Farini

Grab a quick breakfast with artisan bread and fresh coffee to energize you for a day of hiking and island touring.
EUR8, 30m

8:30am

Hike the Lido to Malamocco

Walk 7 km along Venice’s sandy Lido island, enjoying sea views and peaceful beaches on this easy, scenic hike.
Free, 3h

12:00pm

Lunch at Gran Viale, Lido

Dine on Venetian seafood specialties served fresh by the beach in a laid-back Lido eatery.
EUR25, 1h

2:00pm

Visit Burano Island

Travel by vaporetto (30 mins) to colorful Burano, famous for lace making and vibrant houses, great for wandering and photos.
EUR20 round trip, 3h

6:00pm

Return to Venice

Relax on the boat trip back to Venice; catch sunset views of the lagoon and city skyline.
Included, 45m

7:30pm

Dinner at Osteria alle Testiere

Reserve ahead for exquisite seafood dishes at this small, highly regarded Venice osteria with a great wine list.
EUR50, 1h30m
View Hotels

Day 5: Venice to Amalfi

Venice to Amalfi Coast, Italy on May 5, 2026

7:00am

Breakfast at your hotel

Enjoy a quick breakfast before departure to maximize travel time.
Included, 30m

8:00am

Train Venice to Naples

Board a high-speed train to Naples (approx. 5h30m), prepare snacks and water for the journey.
EUR45, 5h30m

2:00pm

Bus transfer to Amalfi Coast

Take a bus from Naples to Amalfi (approx. 1h30m) with beautiful coastal views along the way.
EUR10, 1h30m

3:45pm

Check-in and relax

Check into your accommodation and unwind from the journey with a stroll around Amalfi town.
Free, 1h

6:30pm

Dinner at Trattoria da Gemma

Enjoy authentic regional cuisine with spectacular views of the sea and lemon groves.
EUR40, 1h30m
View Hotels

Day 6: Amalfi Hiking & Exploring

Amalfi Coast, Italy on May 6, 2026

7:30am

Breakfast at Pasticceria Pansa

Taste classic Neapolitan pastries and coffee at this historic Amalfi bakery.
EUR8, 45m

8:30am

Path of the Gods Hike

Hike the iconic Sentiero degli Dei from Bomerano to Nocelle, offering breathtaking views of the Amalfi Coast (approx. 3-4 hours).
Free, 4h

1:00pm

Lunch in Nocelle

Enjoy local dishes at a small trattoria after the hike, refuel with fresh pasta and seafood.
EUR25, 1h

3:00pm

Bus back to Amalfi

Take a short bus ride back to Amalfi town to rest and explore leisurely.
EUR5, 30m

5:00pm

Visit Amalfi Cathedral

Tour the impressive cathedral with its striking Arab-Norman architecture, open until 7pm.
EUR3, 1h

7:00pm

Dinner at Eolo

Dine on refined Mediterranean dishes with sea views at this Michelin recommended restaurant.
EUR50, 1h30m
View Hotels

Day 7: Amalfi Beaches & Boat

Amalfi Coast, Italy on May 7, 2026

8:00am

Breakfast at hotel

Start your day with a leisurely breakfast featuring fresh local produce.
Included, 45m

9:00am

Boat tour along Amalfi Coast

Enjoy a private or group boat tour visiting picturesque towns like Positano and Ravello from the sea, best to book in advance.
EUR60, 3h

1:00pm

Lunch at Da Adolfo, Positano

Dine alfresco on fresh fish dishes on the beach in Positano, accessible by boat.
EUR45, 1h30m

3:00pm

Relax on Marina Grande Beach

Spend a relaxing afternoon swimming or sunbathing on this iconic beach surrounded by cliffs and colorful houses.
EUR10 (loungers), 3h

7:30pm

Dinner in Amalfi at La Caravella

Enjoy exquisite cuisine in the oldest restaurant of Amalfi, blending tradition with modern flair.
EUR55, 1h30m
View Hotels

Day 8: Amalfi to Cinque Terre

Amalfi to Cinque Terre, Italy on May 8, 2026

7:00am

Breakfast at hotel

Light breakfast before departure, preparing for a travel day with transfers.
Included, 30m

8:00am

Bus to Naples then train to La Spezia

Travel by bus to Naples then take a train (~5h total) to La Spezia, the gateway to Cinque Terre.
EUR55, 5h30m

1:30pm

Lunch near La Spezia station

Grab a quick lunch at Osteria Riva del Sole with Ligurian specialties.
EUR20, 1h

3:00pm

Check-in and explore Riomaggiore

Short train from La Spezia to Riomaggiore; check in and stroll this picturesque fishing village.
EUR7 (train), 1h30m

6:30pm

Dinner at Trattoria La Grotta

Enjoy fresh seafood and local pesto dishes in Riomaggiore’s charming setting.
EUR35, 1h30m
View Hotels

Day 9: Cinque Terre Hiking & Views

Cinque Terre, Italy on May 9, 2026

7:30am

Breakfast at bakery in Riomaggiore

Quick local pastries and coffee to prepare for hiking the scenic trails.
EUR5, 30m

8:00am

Hike from Riomaggiore to Manarola

Walk the famous Via dell'Amore coastal trail if open; otherwise, alternative trails offer stunning sea views.
EUR7 (Cinque Terre Card), 1h

9:30am

Continue hike to Corniglia

Ascend the terraced hills for breathtaking panoramas then explore Corniglia village.
Included in Cinque Terre Card, 2h

12:00pm

Lunch at Nessun Dorma, Corniglia

Enjoy bruschetta and local wines with spectacular views of the rugged coastline.
EUR22, 1h

2:00pm

Train to Vernazza

Short scenic train ride to explore Vernazza, one of the most picturesque villages in Cinque Terre.
EUR7, 15m

2:30pm

Explore Vernazza and hike to Monterosso

Explore colorful Vernazza, then take the trail to Monterosso al Mare (approx. 2h), the largest village with beaches.
Included in Cinque Terre Card, 2h

6:00pm

Dinner at Ristorante Miky, Monterosso

Dine on award-winning Ligurian seafood dishes in a modern ambiance.
EUR45, 1h30m
View Hotels

Day 10: Cinque Terre Leisure & Transit

Cinque Terre, Italy on May 10, 2026

8:00am

Breakfast at cafe in Monterosso

Light breakfast before a relaxing day by the beach.
EUR8, 45m

9:00am

Beach day at Monterosso

Enjoy sunbathing and swimming on Monterosso's sandy beaches, perfect to relax after hiking.
EUR12 (beach chair rental), 3h

12:30pm

Lunch at Ristorante Belvedere

Savor casual Ligurian fare with great views of the sea and town.
EUR25, 1h

2:00pm

Train to Florence

Board an afternoon train from La Spezia to Florence (~2h30m), enjoying rolling Tuscan landscapes.
EUR30, 2h30m

5:00pm

Check-in and light city walk

Explore Florence’s historic center near your hotel with gelato stops and views of the Arno River.
Free, 1h30m

7:30pm

Dinner at Trattoria Mario

Experience hearty Tuscan cuisine in this lively, traditional Florence spot near the Mercato Centrale.
EUR30, 1h30m
View Hotels

Day 11: Florence Art & History

Florence, Italy on May 11, 2026

7:30am

Breakfast at Ditta Artigianale

Enjoy specialty coffee and fresh pastries in a modern Florentine café.
EUR10, 45m

8:30am

Visit Uffizi Gallery

Explore one of the world's greatest art museums with masterpieces by Botticelli and Michelangelo. Book timed entry in advance. Open 8:15am-6:50pm.
EUR20, 3h

12:00pm

Lunch at La Prosciutteria

Casual stop for delicious sandwiches filled with Tuscan meats and cheeses.
EUR15, 1h

1:30pm

Climb the Duomo

Climb Brunelleschi's Dome for stunning views of Florence. Open 8:30am-7pm.
EUR25, 1h30m

3:30pm

Walk to Piazzale Michelangelo

Hike or take a bus up to this iconic viewpoint overlooking Florence for sunset.
EUR1.50 (bus), 1h30m

7:00pm

Dinner at Osteria Vini e Vecchi Sapori

Enjoy authentic Tuscan home cooking in an intimate atmosphere, renowned for traditional flavors.
EUR40, 1h30m
View Hotels

Day 12: Florence to Rome

Florence to Rome, Italy on May 12, 2026

7:00am

Breakfast at hotel

Enjoy a relaxing breakfast before departing Florence.
Included, 30m

8:00am

Train to Rome

Take a high-speed train from Florence to Rome (~1h30m) arriving mid-morning.
EUR35, 1h30m

10:00am

Check-in and visit Spanish Steps

Check into your Rome accommodation then visit the Spanish Steps and nearby Via Condotti shopping street.
Free, 1h30m

12:30pm

Lunch at Hostaria Romana

Enjoy classic Roman dishes such as cacio e pepe in a cozy local favorite spot.
EUR25, 1h

2:00pm

Visit Pantheon and Piazza Navona

Tour the majestic Pantheon (open 9am-7pm, EUR3 entry) and relax at the lively Piazza Navona.
EUR3, 2h

5:00pm

Coffee break at Sant'Eustachio Il Caffè

Taste one of Rome’s best espressos at this historic cafe near the Pantheon.
EUR5, 30m

7:30pm

Dinner at Roscioli

Delight in refined Roman cuisine with an extensive wine selection in a gourmet deli-restaurant.
EUR50, 1h30m
View Hotels

Day 13: Ancient Rome Tour

Rome, Italy on May 13, 2026

7:30am

Breakfast at Panella - L'Arte del Pane

Start your day with artisan breads, pastries and specialty coffee in this historic bakery.
EUR10, 45m

8:30am

Colosseum & Roman Forum

Tour two of Rome's most famous ancient sites; pre-book tickets with the Forum and Palatine included. Open 8:30am-7:15pm.
EUR18, 3h

12:00pm

Lunch at Aroma Restaurant

Enjoy lunch with a spectacular view of the Colosseum featuring Michelin-starred cuisine.
EUR60, 1h30m

2:00pm

Visit Capitoline Museums

Explore Rome’s ancient art and archaeological treasures in Renaissance palazzos. Open 9:30am-7pm.
EUR15, 2h

5:00pm

Walk along Via dei Fori Imperiali

Stroll this historic avenue lined with ruins, perfect for photographs around dusk.
Free, 1h

7:30pm

Dinner at Da Enzo al 29

Dine on classic Roman cuisine in a cozy Trastevere neighborhood trattoria.
EUR35, 1h30m
View Hotels

Day 14: Vatican & Gardens

Rome, Italy on May 14, 2026

7:30am

Breakfast at Roscioli Caffè

Enjoy a refined breakfast in this high-end cafe with pastries and espresso.
EUR10, 45m

8:30am

Vatican Museums & Sistine Chapel

Visit the world-renowned art collections and Michelangelo's Sistine Chapel ceiling (book early). Open 9am-6pm.
EUR30, 3h

12:00pm

Lunch at Borgo Pio

Eat at a casual trattoria nearby Vatican with Roman specialties.
EUR25, 1h

2:00pm

St. Peter’s Basilica

Explore this monumental basilica and climb to the dome for panoramic city views. Open 7am-7pm.
Free (dome climb EUR10), 1h30m

4:00pm

Walk and relax in Vatican Gardens

Book a guided tour of the serene gardens if you prefer a lush peaceful break.
EUR32, 1h30m

7:00pm

Dinner at Il Margutta RistorArte

Vegetarian gourmet option offering artful dishes near Piazza del Popolo.
EUR45, 1h30m
View Hotels

Day 15: Rome Leisure Day

Rome, Italy on May 15, 2026

8:00am

Breakfast at Pasticceria Regoli

Enjoy fresh pastries and coffee at this classic Roman bakery.
EUR8, 45m

9:00am

Trastevere Walking Tour

Wander through the charming streets of Trastevere, visiting Santa Maria in Trastevere church and lively piazzas.
Free, 3h

12:30pm

Lunch at Pizzeria Ai Marmi

Enjoy traditional Roman-style pizza in a lively, no-frills atmosphere.
EUR15, 1h

2:00pm

Villa Borghese Gardens & Gallery

Relax and visit the Borghese Gallery featuring Bernini sculptures and Caravaggio paintings (book in advance).
EUR20, 2h

5:00pm

Coffee and gelato near Piazza di Spagna

Unwind at a café with people-watching opportunities near the Spanish Steps.
EUR10, 1h

7:30pm

Dinner at Armando al Pantheon

Classic Roman cuisine restaurant steps from the Pantheon with a warm, traditional vibe.
EUR40, 1h30m
View Hotels

Day 16: Rome to Palermo Travel

Rome to Palermo, Italy on May 16, 2026

7:00am

Breakfast at hotel

Quick breakfast before check-out and transit.
Included, 30m

8:00am

Flight Rome to Palermo

Take a direct flight (approx. 1h15m) to Palermo for the final segment of your Italian journey.
EUR60, 1h15m

10:30am

Check-in and orientation walk

Familiarize yourself with Palermo's historic center including Quattro Canti and Piazza Pretoria.
Free, 2h

1:00pm

Lunch at Antica Focacceria San Francesco

Taste traditional Sicilian street food such as arancini and panelle at this century-old eatery.
EUR20, 1h

3:00pm

Visit Palermo Cathedral

Explore this architectural gem blending Norman, Arabic, and Baroque styles. Open 7am-7pm, entry free with some areas paid.
EUR5, 1h

5:00pm

Visit Palazzo dei Normanni and Cappella Palatina

Tour the Norman Palace and its stunning Byzantine mosaics within the chapel. Open 8:15am-5:40pm.
EUR12, 2h

7:30pm

Dinner at Osteria dei Vespri

Savor contemporary Sicilian cuisine with fresh local ingredients in a stylish setting.
EUR50, 1h30m
View Hotels

Day 17: Palermo Markets & Hiking

Palermo, Italy on May 17, 2026

8:00am

Breakfast at Pasticceria Costa

Enjoy famous Sicilian cannoli and coffee to start your day.
EUR8, 45m

9:00am

Visit Mercato di Ballarò

Experience Palermo’s bustling street market with fresh produce and street food amidst lively locals.
Free, 2h

11:30am

Hike Monte Pellegrino

Take a scenic hike up Monte Pellegrino for spectacular views of Palermo and the sea (approx. 4h round trip).
Free, 4h

4:00pm

Rest and refresh at hotel

Relax after the hike before dinner.
Free, 1h

7:30pm

Dinner at FUD Bottega Sicula

Casual dining focusing on Sicilian street food and craft beer selections.
EUR30, 1h30m
View Hotels

Day 18: Day Trip to Cefalù

Palermo, Italy on May 18, 2026

7:30am

Breakfast at hotel

Early breakfast before day trip.
Included, 30m

8:30am

Train to Cefalù

Board a train to the beautiful coastal town of Cefalù (~1h15m).
EUR6, 1h15m

10:00am

Explore Cefalù Old Town & Cathedral

Visit the stunning Norman cathedral and wander medieval streets and beautiful beaches.
Free (cathedral donation EUR3), 3h

1:00pm

Lunch at Ristorante La Brace

Taste fresh catch-of-the-day seafood beside Cefalù’s harbor.
EUR35, 1h30m

2:30pm

Hike La Rocca

Hike to the summit of La Rocca for panoramic views of the town and Tyrrhenian Sea (approx. 1.5h).
Free, 2h

5:00pm

Train back to Palermo

Return to Palermo by train for a relaxed evening.
EUR6, 1h15m

7:30pm

Dinner at Trattoria ai Cascinari

Enjoy traditional Sicilian dishes in an informal setting in Palermo.
EUR30, 1h30m
View Hotels

Day 19: Palermo Culture & Farewell

Palermo, Italy on May 19, 2026

8:30am

Breakfast at Pasticceria Madonna

Fuel up with sweet Sicilian treats and coffee before your last day.
EUR8, 45m

9:30am

Visit Teatro Massimo

Tour Italy’s largest opera house and learn about its history (guided tours from 9:30am).
EUR8, 1h30m

11:30am

Relax in Foro Italico

Enjoy a peaceful walk along the waterfront park, great for photos and nature.
Free, 1h

1:00pm

Lunch at Bisso Bistrot

Contemporary Sicilian cuisine focused on fresh local ingredients in a modern setting.
EUR30, 1h

3:00pm

Shopping in local markets

Explore artisanal shops or markets like Mercato del Capo for souvenirs and final experiences.
Free, 2h

7:00pm

Farewell Dinner at Bye Bye Blues

Treat yourself to a memorable fine dining experience blending Sicilian flavors with creative cuisine
EUR60, 2h
View Hotels