Ultimate Italy Itinerary: Florence, Bologna, Milan, Lake Como & Venice in 8 Days

Day 1: Arrival & Historic Florence

Florence, Italy on June 28, 2025

9:00am

Arrival via Train

Arrive in Florence by high-speed train from Rome or Milan. The train takes about 1.5 hours from Rome and 2 hours from Milan, providing a scenic introduction to Tuscany.
EUR25, 1h30m

11:00am

Check-in at Hotel Spadai

Settle into your 4-star Hotel Spadai, located near the Duomo with stunning rooftop views of Florence’s skyline.
Included, 1h

12:00pm

Coffee at Caffè Gilli

Enjoy your first Florentine coffee at Caffè Gilli, the city’s oldest café with elegant interiors and rich barista tradition.
EUR5, 45m

1:00pm

Lunch Near Duomo

Grab a light Tuscan lunch at a nearby trattoria offering paninis or pasta to prepare for an afternoon of exploring.
EUR15, 1h

3:00pm

Stroll Ponte Vecchio

Wander along the iconic Ponte Vecchio, admiring the jewellery shop windows and historic charm of this medieval bridge.
Free, 1h

6:00pm

Sunset at Piazzale Michelangelo

Enjoy the spectacular free sunset views over Florence from Piazzale Michelangelo, an ideal spot for photos of the Duomo and Arno river.
Free, 1h

8:00pm

Dinner at Trattoria Mario

Dine authentically at Trattoria Mario, famous for rustic Tuscan classics like ribollita and bistecca alla Fiorentina.
EUR30, 1h30m
View Hotels

Day 2: Art & Hidden Gems

Florence, Italy on June 29, 2025

8:30am

Breakfast at Hotel Spadai

Begin your day with a sumptuous breakfast at the hotel, featuring fresh pastries and Italian coffee.
Included, 1h

9:30am

Accademia Gallery

Visit the Accademia Gallery early to view Michelangelo’s David and Renaissance masterpieces. Pre-book tickets to avoid long queues. Open 8:15am–6:50pm.
EUR16, 2h

12:00pm

Coffee Break at La Menagère

Relax in the artsy La Menagère café, which doubles as a flower shop, offering creative coffee blends and a chic atmosphere.
EUR6, 45m

1:00pm

Lunch Nearby

Enjoy a light lunch of fresh panini or salads at a café close to La Menagère to remain nearby for afternoon activities.
EUR15, 1h

2:30pm

Bargello Museum

Explore the lesser-visited Bargello Museum, home to stunning Renaissance sculptures by Donatello and others. Open 8:15am–1:50pm and 2pm–7:50pm.
EUR8, 2h

7:00pm

Aperitivo at Locale

Unwind with upscale cocktails and chic ambiance at Locale, a stylish bar renowned for its creative drinks and vibrant atmosphere.
EUR12, 1h30m

9:00pm

Dinner Near Hotel

Choose a nearby trattoria for a light dinner or small plates to complement your cocktail experience.
EUR25, 1h
View Hotels

Day 3: Chianti Wine Tour

Florence & Chianti, Italy on June 30, 2025

8:00am

Breakfast at Hotel

Fuel up with breakfast at Hotel Spadai before your day trip to Chianti.
Included, 1h

9:00am

Half-Day Chianti Wine Tour

Join a half-day guided tour exploring Chianti vineyards. The tour includes tastings of regional wines and snacks amid stunning Tuscan views. Costs €50-70 and runs typically 4-5 hours.
EUR60, 5h

3:00pm

Return to Florence & Rest

Return to Florence and relax on the hotel rooftop bar, soaking in the city views and reflecting on your wine experience.
Drinks extra, 2h

7:30pm

Dinner Nearby

Opt for a light Tuscan dinner at a nearby trattoria or sample gelato as a final treat in Florence.
EUR20, 1h
View Hotels

Day 4: Foodie Bologna

Bologna, Italy on July 1, 2025

8:00am

Train to Bologna

Take an early morning train from Florence to Bologna, a quick 35-minute journey costing about €20.
EUR20, 35m

9:00am

Coffee at Café Terzi

Upon arrival, enjoy an artisan espresso at Café Terzi, celebrated for its rich coffee culture and expertly prepared drinks.
EUR4, 30m

12:00pm

Lunch at Osteria dell’Orsa

Savour traditional Bolognese dishes such as tortellini in brodo at Osteria dell’Orsa, a local favourite known for authentic flavours.
EUR25, 1h

2:00pm

Climb Asinelli Tower

Climb the 498 steps to the top of Asinelli Tower for panoramic views over the red rooftops of Bologna. Open 9:00am–7:00pm.
EUR5, 1h

5:30pm

Leisurely Stroll

Explore Bologna’s historic centre at a relaxed pace, stopping at markets or piazzas with gelato or espresso breaks.
Free to wander, 1h30m

7:30pm

Dinner at Trattoria Anna Maria

Enjoy classic Bolognese cuisine such as tagliatelle al ragù at Trattoria Anna Maria, a family-run institution.
EUR30, 1h30m

9:30pm

Train to Milan

Catch an evening train from Bologna to Milan, approximately 1 hour and €25.
EUR25, 1h
View Hotels

Day 5: Milan Highlights

Milan, Italy on July 2, 2025

8:30am

Check-in at NYX Milan

Arrive and check into NYX Milan, a design hotel near Central Station offering modern and stylish accommodation.
Included, 1h

9:30am

Breakfast at Pasticceria Marchesi

Indulge in a luxurious breakfast at Pasticceria Marchesi, a historic café owned by Prada, known for its exquisite pastries and coffee.
EUR10, 1h

11:00am

Duomo di Milano & Rooftop

Explore the iconic Duomo di Milano and pay extra for rooftop access to enjoy striking views of Milan’s skyline and Gothic spires. Open 9:00am–7:00pm.
EUR20, 2h

1:00pm

Lunch Nearby Galleria

Grab lunch at a café inside or near Galleria Vittorio Emanuele II, Milan’s luxury shopping arcade.
EUR20, 1h

2:30pm

Explore Galleria Vittorio Emanuele II

Wander the elegant arcs of Galleria Vittorio Emanuele II, browsing luxury boutiques and enjoying the grand architecture.
Free, 1h30m

6:00pm

Aperitivo at N’Ombra de Vin

Experience Milan’s famed aperitivo culture at N’Ombra de Vin, a historic wine bar offering refined cocktails and small plates.
EUR15, 2h

8:30pm

Dinner in Milan

Choose a nearby restaurant for dinner or enjoy a light meal from aperitivo offerings.
EUR25, 1h30m
View Hotels

Day 6: Lake Como Day Trip

Milan & Lake Como, Italy on July 3, 2025

7:30am

Train to Varenna

Early train from Milan to Varenna, a charming town on Lake Como, takes about 1 hour and costs €10.
EUR10, 1h

8:45am

Ferry to Bellagio

Take the short ferry ride across Lake Como to Bellagio, known as the “Pearl of the Lake,” offering stunning views.
EUR5, 30m

12:30pm

Lunch at Bar Il Molo

Have lunch lakeside at Bar Il Molo, famous for excellent espresso and delicious Italian panini with lake views.
EUR20, 1h

2:00pm

Villa Melzi Gardens

Visit Villa Melzi Gardens with its beautifully landscaped grounds and sculptures. Entry costs €6. Open approx. 9:00am–7:00pm.
EUR6, 1h30m

4:00pm

Explore Bellagio Town

Wander through Bellagio’s charming streets, browse local shops, or enjoy a gelato before returning to Milan.
Free, 1h

6:00pm

Return to Milan

Take the ferry and train back to Milan, arriving by early evening.
EUR15, 1h30m

8:00pm

Dinner in Milan

Enjoy dinner near your hotel or try a Milanese speciality like risotto alla Milanese.
EUR30, 1h30m
View Hotels

Day 7: Classic Venice

Venice, Italy on July 4, 2025

8:00am

Train from Milan to Venice

Travel by train from Milan to Venice in about 2.5 hours, fare around €30.
EUR30, 2h30m

11:00am

Check-in at Hotel Antiche Figure

Check into your hotel by the Grand Canal, offering charming Venetian views and easy access to main attractions.
Included, 1h

12:00pm

Coffee at Caffè Florian

Experience a splurge moment at Caffè Florian, the historic coffeehouse on St. Mark’s Square, with elegant surroundings. Coffee costs about €15.
EUR15, 1h

1:30pm

Lunch Nearby

Have a light lunch close to St. Mark’s area, sampling Venetian cicchetti or fresh seafood.
EUR20, 1h

3:00pm

St. Mark’s Basilica

Visit St. Mark’s Basilica early to avoid crowds; the basilica offers free entry and magnificent Byzantine mosaics. Open from 9:30am to 5:00pm.
Free, 1h

4:30pm

Rialto Market

Explore the vibrant Rialto Market, perfect for tasting local seafood and browsing prosecco bars nearby.
Free, 1h

8:00pm

Dinner at Osteria alle Testiere

Dine at Osteria alle Testiere, a cosy seafood restaurant known for fresh and authentic Venetian dishes. Reservation recommended.
EUR40, 1h30m
View Hotels

Day 8: Hidden Venice

Venice, Italy on July 5, 2025

8:30am

Peggy Guggenheim Collection

Visit the Peggy Guggenheim Collection in Dorsoduro to admire an exceptional modern art collection in a beautiful palazzo. Open 10:00am–6:00pm.
EUR15, 2h

11:00am

Coffee at Torrefazione Marchi

Pause for coffee at Torrefazione Marchi, a historic Venetian roastery well loved for its espresso.
EUR5, 30m

11:45am

Free Time in Dorsoduro

Wander the artistic Dorsoduro district, enjoying bacari wine bars and small eateries, soaking up the less touristy side of Venice.
Free, 3h

6:30pm

Gondola Ride at Dusk

Take a leisurely gondola ride at dusk, which is generally cheaper and more atmospheric than daytime rides, gliding through Venice’s canals in a romantic setting.
EUR80 (can be shared), 30m

8:00pm

Dinner Nearby

Enjoy your last Italian dinner at a nearby osteria offering Venetian specialties, reflecting on your wonderful Italian adventure.
EUR35, 1h30m
View Hotels