Romantic 6-Day Italy Itinerary: Rome, Florence & Venice with Dining & Train Tips

Day 1: Discover Rome

Rome, Italy on June 14, 2025

8:00am

Arrive in Rome and Check-in

Arrive at Rome Fiumicino Airport; transfer via taxi or Leonardo Express train to city center and check into your hotel.
EUR30, 1h

9:30am

Breakfast at Roscioli Caffè

Enjoy traditional Italian pastries and robust coffee in this popular Roman cafe to start your day.
EUR15, 1h

10:30am

Visit the Colosseum and Roman Forum

Explore Rome’s iconic ancient amphitheater and the ruins of the Roman Forum, rich with history and breathtaking architecture. Open 8:30am-7:00pm.
EUR18, 3h

1:30pm

Lunch at Trattoria Vecchia Roma

Savor authentic Roman dishes like carbonara in a traditional setting close to your sightseeing areas.
EUR25, 1.5h

3:00pm

Explore the Pantheon and Piazza Navona

Visit the stunning Pantheon and relax at the lively Piazza Navona with its famous fountains and street artists.
Free, 1.5h

5:00pm

Trevi Fountain and Spanish Steps

End your afternoon by tossing a coin in Trevi Fountain, then climb the iconic Spanish Steps for great city views.
Free, 1h

7:00pm

Dinner at La Pergola

Dine at Rome’s Michelin 3-star restaurant offering exquisite cuisine and breathtaking views. Reservation recommended.
EUR150, 2h
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Day 2: Vatican & Historic Sights

Rome, Italy on June 15, 2025

8:00am

Breakfast at Pasticceria Regoli

Start your day with delicious cornetti and cappuccino at this historic Roman bakery.
EUR10, 1h

9:00am

Vatican Museums and Sistine Chapel Tour

Discover priceless art and the stunning Sistine Chapel with early entry tickets to avoid crowds. Open 9:00am-6:00pm, closed Sundays except last Sunday of month.
EUR25, 3h

12:30pm

Lunch at Borgo Pio 91

Enjoy fresh seafood and Italian specialties conveniently located near the Vatican.
EUR30, 1.5h

2:00pm

St. Peter’s Basilica and Dome Climb

Visit the world-famous basilica and, if energy allows, climb to the dome top for panoramic views. Open 7:00am-7:00pm.
Free admission, EUR10 for dome climb, 2h

5:00pm

Relax at Villa Borghese Gardens

Stroll or rent a bike to enjoy the beautiful park and fountains.
Free, 1.5h

7:30pm

Dinner at Osteria der Belli

Taste Sardinian seafood delicacies in a charming Roman osteria.
EUR40, 2h
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Day 3: Train to Florence & Sightseeing

Rome to Florence, Italy on June 16, 2025

7:30am

Breakfast at hotel

Enjoy a quick breakfast at your accommodation before departure.
Included, 0.5h

8:30am

Train to Florence

Take the high-speed Frecciarossa train from Rome Termini to Florence Santa Maria Novella station. Journey takes about 1.5 hours.
EUR45 per person, 1.5h

10:30am

Check-in & Light Coffee

Check into your Florence hotel and recharge with an espresso at a nearby café.
EUR5, 1h

11:30am

Explore Florence Duomo and Baptistery

Marvel at Florence’s iconic cathedral complex; climbing the dome offers spectacular views. Open 10:00am-5:00pm.
EUR20 combo ticket, 2h

1:30pm

Lunch at Trattoria Mario

Experience home-style Tuscan food at this lively and authentic trattoria near the Mercato Centrale.
EUR25, 1.5h

3:00pm

Uffizi Gallery Visit

See world-famous Renaissance artworks by Botticelli and Michelangelo. Open 8:15am-6:30pm, closed Mondays.
EUR20, 2h

5:30pm

Walk on Ponte Vecchio and View Sunset

Stroll the historic bridge lined with jewelry shops and enjoy sunset from nearby Piazzale Michelangelo.
Free, 1.5h

7:30pm

Dinner at La Giostra

Cozy restaurant serving romantic ambiance and traditional Tuscan specialties, perfect for couples.
EUR50, 2h
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Day 4: Florence Art & Culture

Florence, Italy on June 17, 2025

8:00am

Breakfast at Caffè Gilli

Enjoy a chic start to the day with pastries and excellent coffee at this historic Florentine café.
EUR15, 1h

9:00am

Accademia Gallery Tour

Home of Michelangelo’s David, this museum offers masterpieces of Renaissance sculpture. Opens 8:15am-6:50pm.
EUR16, 2h

11:30am

Visit San Lorenzo Market

Browse the vibrant market known for leather goods, food stalls, and souvenirs.
Free, 1h

12:30pm

Lunch at Mercato Centrale

Taste a variety of fresh, local food options at this modern food hall.
EUR20, 1.5h

2:30pm

Boboli Gardens Walk

Explore these remarkable Renaissance gardens with sculptures and stunning views.
EUR10, 2h

5:00pm

Relax at Hotel or Piazza della Signoria

Enjoy leisure time or watch street performances at Florence’s historic square.
Free, 1.5h

7:30pm

Dinner at Il Latini

Dine family-style with robust Tuscan flavors in a lively traditional setting.
EUR45, 2h
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Day 5: Venice Arrival & Exploration

Florence to Venice, Italy on June 18, 2025

7:30am

Breakfast at hotel

Enjoy a quick breakfast before your train departure.
Included, 0.5h

8:30am

Train to Venice

Take the high-speed Frecciarossa or Italo train from Florence Santa Maria Novella to Venice Santa Lucia station. Trip time about 2 hours.
EUR45 per person, 2h

10:30am

Check-in & Coffee

Check into your Venice accommodation and enjoy a quick coffee nearby.
EUR5, 1h

11:30am

St. Mark’s Basilica and Square

Visit Venice’s dazzling cathedral with its ornate mosaics and explore the lively piazza. Basilica open 9:30am-5:00pm.
Free entry, EUR3 for museum, 2h

1:30pm

Lunch at Osteria alle Testiere

Highly rated intimate seafood restaurant serving Venetian specialties, reserve in advance.
EUR50, 1.5h

3:00pm

Explore Doge’s Palace

Tour the historic palace and Bridge of Sighs with rich art and architecture. Open 8:30am-7:00pm.
EUR25, 2h

5:30pm

Gondola Ride

Experience a romantic gondola ride through Venice's canals, typically lasting 30-40 minutes.
EUR80 per gondola, 0.75h

7:30pm

Dinner at Antiche Carampane

Enjoy traditional Venetian dishes including fresh catch-of-the-day in an off-the-beaten-path setting.
EUR45, 2h
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Day 6: Departure Day

Venice, Italy on June 19, 2025

7:30am

Breakfast at Pasticceria Tonolo

Treat yourselves to Venetian pastries and coffee at this beloved bakery before leaving.
EUR10, 1h

9:00am

Last Stroll in Venice

Enjoy a peaceful morning walk along the canals or visit any last-minute shops or sights.
Free, 2h

11:30am

Transfer to Venice Marco Polo Airport

Take a taxi or water taxi to the airport for your flight back to Chicago.
EUR40, 1h

2:30pm

Flight Departure

Board your return flight, concluding a memorable Italian trip with your girlfriend.
Included, N/A
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