21 Days Exploring Italy's Finest Itinerary

Travel from the Dolomites to Milan (approximately 3 hours). Start your Milan adventure with a visit to Milan Duomo, one of Italy's most iconic cathedrals. Take an elevator ride to the rooftop terraces for panoramic views of the city. Follow this up with Milan: Last Supper 1-Hour Skip-the-Line Guided Tour to see Leonardo da Vinci's masterpiece.

Head over to Galleria Vittorio Emanuele II, one of the world's oldest shopping malls, where you can enjoy some high-end shopping or simply marvel at its stunning architecture. For lunch, dine at Luini, famous for its delicious panzerotti.

In the evening, visit Sforza Castle (Castello Sforzesco), which houses several museums and art collections. End your day with dinner at Trattoria Milanese, known for its traditional Milanese dishes like risotto alla milanese.

Travel from Milan to Florence (approximately 2 hours). Begin your exploration of Florence with a visit to Florence Duomo (Cattedrale di Santa Maria dei Fiori). Climb up Brunelleschi's Dome for breathtaking views over Florence. Follow this up with Florence: Michelangelo's David Priority Ticket & Audio App at Galleria dell'Accademia.

Stroll through Piazza della Signoria and admire statues like Neptune’s Fountain and Perseus holding Medusa’s head. For lunch, stop by All’Antico Vinaio for their famous sandwiches filled with local Tuscan ingredients.

Spend your evening exploring Ponte Vecchio, Florence’s oldest bridge lined with jewelry shops. Conclude your day with dinner at Trattoria ZaZa, renowned for its Tuscan cuisine and lively atmosphere.

Start your day with a visit to Lucca Cathedral (Duomo di Lucca). This stunning cathedral is a masterpiece of Romanesque architecture and offers beautiful frescoes and intricate carvings. After exploring the cathedral, take a leisurely stroll along the ancient city walls of Lucca, which provide panoramic views of the city and surrounding countryside.

In the afternoon, join Lucca: Guided Small Group Highlights Walking Tour to delve deeper into the history and culture of this charming town. The tour will take you through key landmarks such as Piazza dell'Anfiteatro and Via Fillungo. For lunch, enjoy some traditional Tuscan cuisine at Osteria Baralla, known for its delicious local dishes.

Conclude your day with a short drive to Pisa (approximately 30 minutes) to visit the iconic Leaning Tower. Enjoy a guided tour with Pisa: Guided Walking Tour with Optional Leaning Tower Ticket, which includes access to the cathedral and baptistery as well. For dinner, head back to Lucca and dine at Ristorante Giglio, offering an elegant setting and exquisite Italian cuisine.

From Florence: Chianti Hills Half-Day Tour with Wine Tasting is an excellent way to start your day in the Tuscan countryside. This tour will take you through picturesque vineyards and rolling hills, offering wine tastings at renowned wineries in the Chianti region.

From Florence: Tuscany Day Trip with Lunch at Chianti winery continues your exploration of Tuscany's culinary delights. Enjoy a traditional Tuscan lunch paired with local wines while soaking in the beautiful landscape. After lunch, visit some charming villages like Greve in Chianti or Castellina in Chianti for a taste of local life.

Osteria di Passignano is an ideal spot for dinner, located within an ancient abbey in Badia a Passignano. The restaurant offers gourmet Tuscan cuisine made from locally sourced ingredients. End your evening with a relaxing walk through the vineyards under the starlit sky.

Cooking class of Spoleto recipes, with Chef Stefano offers an immersive experience into Umbrian cuisine. Learn how to prepare traditional dishes using fresh local ingredients under the guidance of Chef Stefano.

Spoleto: Market Tour and Home-Cooked Meal takes you on a guided tour through Spoleto's vibrant markets where you can sample regional specialties and purchase fresh produce. Afterward, enjoy a home-cooked meal featuring ingredients from your market visit.

Ristorante Apollinare in Spoleto is perfect for dinner, known for its refined Italian dishes served in a cozy atmosphere. After dinner, take an evening stroll around Spoleto's historic center to admire its medieval architecture illuminated by night lights.

Begin your day with a visit to Church of San Giorgio (Chiesa di San Giorgio). This charming church offers stunning views over the harbor and the Ligurian Sea. Afterward, embark on Portofino Stand Up Paddleboard Experience for a unique perspective of the coastline. Paddleboarding in the clear waters around Portofino is both exhilarating and serene.

For lunch, dine at Ristorante Puny, known for its fresh seafood and picturesque setting by the harbor. After lunch, take a leisurely walk through Portofino's quaint streets, exploring its boutique shops and cafes. In the afternoon, join Portofino: Coasteering Tour, an adventurous tour that involves climbing, swimming, and jumping along the rugged coastline.

Conclude your day with dinner at Da U Batti, famous for its delicious lobster dishes. After dinner, enjoy a drink at Bar Morena, where you can relax and take in the beautiful evening views of Portofino's harbor.

From Naples or Sorrento: Amalfi Coast Full-Day Trip is an excellent way to start your day in Positano. This tour will take you along the stunning Amalfi Coast, offering breathtaking views of cliffs, beaches, and charming villages.

From Sorrento/Nerano: Amalfi and Positano Boat Tour continues your exploration of this beautiful region from a different perspective. Enjoy a boat ride along the coast with stops for swimming and snorkeling in crystal-clear waters. For lunch, dine at La Tagliata, known for its farm-to-table Italian cuisine and panoramic views over Positano.

Ristorante Bruno is perfect for dinner, offering traditional Italian dishes with a modern twist. After dinner, take an evening stroll through Positano's narrow streets lined with colorful buildings and artisan shops.

Salerno Cathedral (Duomo di Salerno) is a must-visit to start your day in Salerno. This historic cathedral features stunning architecture and beautiful mosaics. Follow this up with Maiori: Amalfi Coast Path of Lemons Day Trip with Tastings, which offers scenic walks through lemon groves along the Amalfi Coast.

Trattoria Da Nando is ideal for lunch, known for its delicious seafood dishes made from fresh local ingredients. After lunch, join From Salerno: Sightseeing Day Cruise to Amalfi Coast, which provides breathtaking views of coastal cliffs and charming villages from the sea.

Ristorante Cicirinella is perfect for dinner in Salerno’s historic center. End your evening with a relaxing walk along Lungomare Trieste promenade while enjoying gelato from one of Salerno’s famous gelaterias like Gelateria Nettuno.

Start your day with a visit to Li Galli (Sirenuse). This group of small islands is steeped in mythology and offers stunning views of the surrounding sea. Afterward, join From Sorrento: Capri Boat Tour with Blue Grotto Visit for an unforgettable experience exploring the island of Capri and its famous Blue Grotto.

For lunch, dine at Ristorante La Caravella, one of the oldest restaurants on the Amalfi Coast, known for its exquisite seafood dishes. After lunch, take a leisurely stroll through the charming town of Amalfi, visiting landmarks such as the Amalfi Cathedral and the Paper Museum.

Ristorante Eolo is perfect for dinner, offering a romantic setting with panoramic views over the sea. End your evening with a relaxing walk along the Amalfi promenade while enjoying a gelato from Gelateria Artigianale Marco Polo.

ATV Ride and Secret Caves Tour from Playa del Carmen is an adventurous way to start your day in Punta Campanella. This tour takes you through rugged terrain and secret caves, offering an exhilarating experience.

Ristorante Quattro Passi is ideal for lunch, known for its gourmet Italian cuisine and stunning views over the coastline. After lunch, join Cancún: Chichén Itzá Tour with Hubikú Cenote and Valladolid, which provides a fascinating exploration of ancient Mayan ruins and natural cenotes.

Ristorante Il Cantuccio is perfect for dinner, offering traditional Italian dishes made from fresh local ingredients. End your evening with a relaxing walk along Punta Campanella's scenic coastal paths.

Polignano a Mare: Street Food Tour with Tastings and Wine is an excellent way to start your day in Polignano a Mare. This tour takes you through the charming streets of Polignano while sampling delicious local street food and wines.

Osteria dei Mulini is ideal for lunch, known for its fresh seafood dishes and picturesque setting by the sea. After lunch, join Polignano: Guided Coastline & Caves Cruise with Swim Break, which offers breathtaking views of coastal cliffs and hidden caves.

Ristorante Grotta Palazzese is perfect for dinner, offering an unforgettable dining experience inside a cave overlooking the sea. End your evening with a relaxing walk along Polignano's scenic coastal paths while enjoying gelato from one of Polignano’s famous gelaterias like Gelateria Caruso.

Begin your day with a visit to Naples National Archaeological Museum (Museo Archeologico Nazionale). This museum houses one of the most extensive collections of Greco-Roman antiquities in the world, including artifacts from Pompeii and Herculaneum. Afterward, join Naples: The Holy Mile 3-Hour Guided Tour to explore the city's rich history and culture.

For lunch, dine at Pizzeria da Michele, famous for its traditional Neapolitan pizza. After lunch, take a leisurely stroll through the historic center of Naples, visiting landmarks such as Piazza del Plebiscito and Galleria Umberto I.

Ristorante La Cantina dei Mille is perfect for dinner, offering delicious Italian cuisine in a cozy setting. End your evening with a relaxing walk along the Naples waterfront while enjoying gelato from Gelateria della Scimmia.

Start your day with From Sorrento: Capri Boat Tour with Blue Grotto Visit. This tour offers an unforgettable experience exploring the island of Capri and its famous Blue Grotto. Enjoy the stunning coastal views and crystal-clear waters.

For lunch, dine at Da Paolino, known for its lemon grove setting and delicious Italian dishes. After lunch, take a leisurely stroll through Capri's charming streets, visiting landmarks such as Marina Grande and the Gardens of Augustus.

Ristorante Il Geranio is perfect for dinner, offering gourmet Italian cuisine with panoramic views over the sea. End your evening with a relaxing walk along Capri's scenic coastal paths while enjoying gelato from Gelateria Buonocore.

Begin your exploration of Rome with a visit to Colosseum (Colosseo). Join Rome: Colosseum Underground, Arena & Forum Tour to delve into the history of this iconic landmark. Explore the underground chambers where gladiators once prepared for battle.

For lunch, dine at Taverna dei Fori Imperiali, known for its traditional Roman dishes. After lunch, head to Vatican City to visit St. Peter's Basilica and join Rome: Vatican Museums, Sistine Chapel Tour & Basilica Entry for an in-depth exploration of these world-renowned sites.

Trattoria Da Enzo al 29 is perfect for dinner, offering authentic Roman cuisine in a cozy setting. End your evening with a relaxing walk through Rome's historic center while enjoying gelato from one of Rome’s famous gelaterias like Gelateria del Teatro.

Start your day with a visit to Sassi di Matera. This ancient cave dwelling complex is a UNESCO World Heritage site and offers a fascinating glimpse into the history of human habitation. After exploring the Sassi, join Sassi di Matera Walking Tour to delve deeper into the history and culture of this unique city.

For lunch, dine at Trattoria Lucana, known for its traditional Lucanian cuisine. After lunch, take a leisurely stroll through Matera's historic center, visiting landmarks such as the Matera Cathedral and the Palombaro Lungo.

Ristorante Francesca is perfect for dinner, offering delicious Italian cuisine in a cozy setting. End your evening with a relaxing walk through Matera's illuminated streets while enjoying gelato from Gelateria I Vizi degli Angeli.

Bari: Self-Guided Highlights Scavenger Hunt & Walking Tour is an excellent way to start your day in Puglia. This tour takes you through the charming streets of Bari while exploring its historical landmarks and hidden gems.

Ristorante La Cecchina is ideal for lunch, known for its fresh seafood dishes and picturesque setting by the sea. After lunch, join Polignano: Guided Coastline & Caves Cruise with Swim Break, which offers breathtaking views of coastal cliffs and hidden caves.

Ristorante Grotta Palazzese is perfect for dinner, offering an unforgettable dining experience inside a cave overlooking the sea. End your evening with a relaxing walk along Polignano's scenic coastal paths while enjoying gelato from one of Polignano’s famous gelaterias like Gelateria Caruso.

Lake Como: Bellano Gorge Entry Ticket with an Aperitif is an excellent way to start your day in Lake Como. This tour takes you through the stunning Bellano Gorge while enjoying an aperitif at the end.

Ristorante Bilacus is ideal for lunch, known for its delicious Italian dishes and picturesque setting by the lake. After lunch, join Lake Como: Golden Hour Guided Kayak Tour, which offers breathtaking views of Lake Como during sunset.

Ristorante Silvio is perfect for dinner, offering gourmet Italian cuisine with panoramic views over the lake. End your evening with a relaxing walk along Lake Como's scenic paths while enjoying gelato from one of Lake Como’s famous gelaterias like Gelateria Lariana.

Start your day with a visit to Villa Melzi Gardens (Giardini di Villa Melzi). These beautiful gardens are a perfect place to enjoy the serene beauty of Lake Como. Afterward, join BELLAGIO: Lake Como Shared Boat Tour for a scenic boat ride around the lake, offering stunning views of the surrounding mountains and villas.

For lunch, dine at Ristorante Bilacus, known for its delicious Italian dishes and picturesque setting by the lake. After lunch, take a leisurely stroll through Bellagio's charming streets, visiting boutique shops and cafes.

Ristorante Silvio is perfect for dinner, offering gourmet Italian cuisine with panoramic views over the lake. End your evening with a relaxing walk along Bellagio's scenic paths while enjoying gelato from one of Bellagio’s famous gelaterias like Gelateria del Borgo.

Sirmione: Scenic Afternoon Boat Cruise with Prosecco & Snack is an excellent way to start your day in Lake Garda. This tour takes you through the stunning waters of Lake Garda while enjoying prosecco and snacks on board.

Ristorante La Speranzina is ideal for lunch, known for its gourmet Italian cuisine and picturesque setting by the lake. After lunch, join Lake Garda: Historic Castle Cruise with Wine Tasting, which offers breathtaking views of historic castles along the lake.

Ristorante Al Gondoliere is perfect for dinner, offering traditional Italian dishes made from fresh local ingredients. End your evening with a relaxing walk along Lake Garda's scenic paths while enjoying gelato from one of Lake Garda’s famous gelaterias like Gelateria Artigianale Cavour.

Verona Arena Skip-the-Line Guided Tour is an excellent way to start your day in Verona. This tour takes you through the iconic Verona Arena while learning about its rich history and significance.

Ristorante Maffei is ideal for lunch, known for its delicious Italian dishes and picturesque setting in Piazza delle Erbe. After lunch, join Verona: Food Tasting and Walking Tour with Cable Car, which offers breathtaking views of Verona from above while sampling local delicacies.

Ristorante Il Desco is perfect for dinner, offering gourmet Italian cuisine in an elegant setting. End your evening with a relaxing walk through Verona's historic center while enjoying gelato from one of Verona’s famous gelaterias like Gelateria Savoia.