8-Day Family-Friendly Italy Itinerary: Rome, Venice, and Milan from Chicago

Day 1: Arrival in Rome

Rome, Italy

2:00PM

Arrival in Rome

Arrive at Fiumicino Airport and take the Leonardo Express train to Termini station, where your Italian adventure begins.

EUR14, 1 hour

3:30PM

Check into Hotel

Settle into your family-friendly hotel in the heart of Rome, providing a perfect base for exploration.

EUR150, 30 mins

5:00PM

Visit the Colosseum

Explore the iconic Colosseum, where ancient Roman gladiators once fought, engaging your children with fascinating stories of history.

EUR18 family ticket, 2 hours

7:30PM

Dinner at Trattoria Al Forno

Enjoy authentic Italian dishes, such as pizza and pasta, at this cozy family-run restaurant nearby.

EUR80, 1 hour

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Day 2: Explore Rome

Rome, Italy

8:00AM

Breakfast at Pasticceria Regoli

Start your day with fresh pastries and cappuccinos at this local favorite bakery that kids will love.

EUR20, 1 hour

9:30AM

Visit Vatican Museums

Discover the stunning art collection in the Vatican Museums, with highlights such as the Sistine Chapel.

EUR42 family ticket, 2.5 hours

12:00PM

Lunch at Pizzeria La Montecarlo

Enjoy delicious Roman-style pizza at this family-friendly pizzeria known for its vibrant atmosphere.

EUR60, 1 hour

1:30PM

Stroll at St. Peter's Square

Take the family for a tour of magnificent St. Peter's Basilica and enjoy the artistic treasures around the square.

EUR0, 1 hour

3:00PM

Explore the Pantheon

Visit the Pantheon, a 2,000-year-old temple that will fascinate kids with its grand architecture.

EUR0, 1 hour

5:00PM

Gelato at Giolitti

Cool off with world-famous gelato at Giolitti, a perfect treat for kids of all ages.

EUR15, 30 mins

6:00PM

Dinner at Osteria da Fortunata

Enjoy dinner at this traditional Roman trattoria featuring homemade pasta that kids can watch being made.

EUR70, 1 hour

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Day 3: Rome to Venice

Rome, Italy to Venice, Italy

8:00AM

Breakfast at Cafe Giolitti

Start your day with rich coffee and delicious breakfast pastries at this popular café.

EUR25, 1 hour

9:00AM

Travel to Venice

Board the high-speed Trenitalia train to Venice, taking in glimpses of the beautiful Italian countryside on your way.

EUR40 family ticket, 3.5 hours

12:30PM

Check into Hotel in Venice

Arrive in Venice and check into a charming hotel, ready for exploration in the canals.

EUR150, 1 hour

1:30PM

Lunch at Trattoria al Gatto Nero

Treat your family to a typical Venetian meal at this hidden gem that offers local seafood.

EUR90, 1.5 hours

3:00PM

Explore Burano Island

Stroll through the picturesque streets of Burano, known for its colorful houses and lace shops.

EUR0, 2 hours

5:00PM

Gondola Ride

Take a classic gondola ride through Venice’s tranquil canals, leaving lasting memories with your family.

EUR80, 30 mins

6:00PM

Dinner at Ristorante Da Ivo

Conclude your day with dinner at this renowned restaurant frequented by celebrities.

EUR120, 1 hour

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Day 4: Explore Venice

Venice, Italy

8:00AM

Breakfast at Caffe Florian

Savor a delicious Italian breakfast at this historic café in St. Mark's Square.

EUR35, 1 hour

9:30AM

Visit St. Mark's Basilica

Marvel at the stunning mosaics and architecture of St. Mark's Basilica, a highlight of Venice.

EUR0, 1.5 hours

11:00AM

Doge's Palace

Explore the impressive Doge's Palace and its rich history, offering an exciting glimpse into Venice’s past.

EUR40 family ticket, 2 hours

1:00PM

Lunch at Osteria alle Testiere

Enjoy seafood lunch at this tiny yet popular local spot that is well-loved by tourists and locals alike.

EUR60, 1 hour

2:30PM

Explore the Rialto Market

Wander through the bustling market, sampling local foods and soaking in the vibrant Venetian atmosphere.

EUR0, 1.5 hours

4:00PM

Visit the Peggy Guggenheim Collection

Engage your family with modern art at this collection located in a beautiful canal-side palace.

EUR30 family ticket, 2 hours

6:30PM

Dinner at Ristorante da Raffaele

Dine on delicious pasta dishes against a backdrop of Venetian charm, perfect for families.

EUR70, 1 hour

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Day 5: Venice to Milan

Venice, Italy to Milan, Italy

8:00AM

Breakfast at Hotel

Enjoy a convenient breakfast at your hotel to fuel up for the day ahead.

EUR30, 1 hour

9:00AM

Travel to Milan

Board a high-speed train back to Milan, relaxing and enjoying the scenic views of northern Italy.

EUR30 family ticket, 2.5 hours

11:30AM

Check into Hotel in Milan

Arrive in Milan and check into your centrally-located hotel, ready for urban discovery.

EUR150, 1 hour

12:30PM

Lunch at Luini Panzerotti

Try the famous Panzerotti, a delicious stuffed pastry, at this popular lunch spot loved by locals.

EUR40, 1 hour

2:00PM

Visit the Duomo di Milano

Delve into Milan’s centerpiece, the majestic Duomo, and enjoy breathtaking views from the rooftop.

EUR28 family ticket, 2 hours

4:00PM

Explore Galleria Vittorio Emanuele II

Visit this stunning shopping arcade, where you can wander amongst luxury shops and enjoy gelato.

EUR0, 1 hour

5:30PM

Dinner at Ristorante Pizzeria Bacco

Indulge in authentic Milanese pizza while enjoying a family-friendly atmosphere.

EUR80, 1 hour

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Day 6: Explore Milan

Milan, Italy

8:30AM

Breakfast at Pavé

Enjoy excellent coffee and pastries at this chic café known for local breakfast delights.

EUR30, 1 hour

10:00AM

Visit the Castello Sforzesco

Explore the historic Sforza Castle, including its beautiful grounds and museums that are enchanting for children.

EUR20 family ticket, 2 hours

12:30PM

Lunch in Sempione Park

Have a relaxed picnic in the picturesque Sempione Park, nearby the castle, enjoy sandwiches.

EUR30 for picnic supplies, 1.5 hours

2:00PM

Visit Museo del Risorgimento

Engage with Italian history at the museum located in a fascinating palace, perfect for curious children.

EUR10 family ticket, 2 hours

4:30PM

Explore the Navigli District

Stroll through the vibrant Navigli district, known for its canals, shops, and art galleries.

EUR0, 1.5 hours

6:00PM

Dinner at Ristorante Al Giordano

End the day with delicious Italian cuisine in a cozy setting, special kids' menu available.

EUR70, 1 hour

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Day 7: Return to Chicago

Milan, Italy

8:00AM

Breakfast at Hotel

Enjoy a final Italian breakfast in your hotel before bidding farewell to Milan.

EUR30, 1 hour

9:00AM

Travel to Malpensa Airport

Head to Milan Malpensa Airport for your return journey to Chicago, reminiscing about your memorable family trip.

EUR20 family ticket, 1 hour

11:00AM

Check-in for Flight

Arrive at the airport with ample time for check-in and security.

EUR0, 2 hours

1:00PM

Flight to Chicago

Board your flight back home, taking unforgettable memories of Italy with you.

check airline fare, N/A

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Step 1 Outline Preview:

8-Day Family-Friendly Italy Itinerary: Rome, Venice, and Milan from Chicago

Day 1: Arrival in Rome

2:00PM

3:30PM

5:00PM

7:30PM

Day 2: Explore Rome

8:00AM

9:30AM

12:00PM

1:30PM

3:00PM

5:00PM

6:00PM

Day 3: Rome to Venice

8:00AM

9:00AM

12:30PM

1:30PM

3:00PM

5:00PM

6:00PM

Day 4: Explore Venice

8:00AM

9:30AM

11:00AM

1:00PM

2:30PM

4:00PM

6:30PM

Day 5: Venice to Milan

8:00AM

9:00AM

11:30AM

12:30PM

2:00PM

4:00PM

5:30PM

Day 6: Explore Milan

8:30AM

10:00AM

12:30PM

2:00PM

4:30PM

6:00PM

Day 7: Return to Chicago

8:00AM

9:00AM

11:00AM

1:00PM