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.
Leonardo Express train from FCO to Termini, 32 mins.
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.
Walking distance from Termini.
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.
Take Metro Line B from Termini to Colosseo.
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.
Walking distance from Colosseum.
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.
Walking distance from hotel.
EUR20, 1 hour

9:30AM

Visit Vatican Museums

Discover the stunning art collection in the Vatican Museums, with highlights such as the Sistine Chapel.
Metro Line A from Termini to Ottaviano.
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.
Walking distance from Vatican.
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.
Walking distance from lunch spot.
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.
Take a bus or walk from St. Peter's.
EUR0, 1 hour

5:00PM

Gelato at Giolitti

Cool off with world-famous gelato at Giolitti, a perfect treat for kids of all ages.
Walking distance from the Pantheon.
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.
Walking distance.
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.
Walking distance from hotel.
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.
From Termini to Santa Lucia train station.
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.
Walking distance from Santa Lucia station.
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.
Take Vaporetto to Burano.
EUR90, 1.5 hours

3:00PM

Explore Burano Island

Stroll through the picturesque streets of Burano, known for its colorful houses and lace shops.
Walking on Burano.
EUR0, 2 hours

5:00PM

Gondola Ride

Take a classic gondola ride through Venice’s tranquil canals, leaving lasting memories with your family.
Starting point near St. Mark’s Square.
EUR80, 30 mins

6:00PM

Dinner at Ristorante Da Ivo

Conclude your day with dinner at this renowned restaurant frequented by celebrities.
Walking distance from Gondola dock.
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.
Walking distance from hotel.
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.
Walking distance from breakfast location.
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.
Next to St. Mark's Basilica.
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.
Walking distance.
EUR60, 1 hour

2:30PM

Explore the Rialto Market

Wander through the bustling market, sampling local foods and soaking in the vibrant Venetian atmosphere.
Walk to the Rialto Bridge.
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.
Walking distance.
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.
Walking distance from Peggy Guggenheim.
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.
At hotel.
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.
From Santa Lucia to Milano Centrale.
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.
Walking distance from the train station.
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.
Walking distance from hotel.
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.
Walking distance from lunch.
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.
Adjacent to the Duomo.
EUR0, 1 hour

5:30PM

Dinner at Ristorante Pizzeria Bacco

Indulge in authentic Milanese pizza while enjoying a family-friendly atmosphere.
Walking distance from Galleria.
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.
Walking distance from hotel.
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.
Walking distance.
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.
Walking distance.
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.
Walking distance from park.
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.
Take Metro Line 2.
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.
Walking distance from Navigli.
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.
At hotel.
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.
Take the Malpensa Express from Central Station.
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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