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14-Day Family Adventure in Italy: Exploring the Best of the Boot

Viewed by 142 travelers

Day 1: Arrival in Rome

Rome, Italy

10:00AM

Check-In

Arrive in Rome, settle into your hotel and refresh after your flight.
Hotel near the city center for easy access.
EUR150, 2 hours

12:30PM

Lunch at Da Enzo al 29

Enjoy authentic Roman cuisine with the family in a cozy trattoria.
Located in the Trastevere district, it's a short walk from most central hotels.
EUR70, 1.5 hours

2:00PM

Explore Trastevere

Stroll through the picturesque streets of Trastevere and visit Santa Maria in Trastevere.
Walking tour through narrow cobblestone streets.
Free, 2 hours

4:30PM

Visit the Colosseum

Incredible ancient history awaits! Take a guided tour through Rome's iconic landmark.
Brief bus ride or a manageable walk from Trastevere.
EUR100, 2 hours

7:00PM

Dinner at Osteria da Fortunata

Delight in handmade pasta at this family-friendly spot known for its ambiance.
Located close to Piazza Navona, very accessible.
EUR80, 1.5 hours
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Day 2: Explore Rome

Rome, Italy

8:00AM

Breakfast at Pasticceria Regoli

Try some Italian pastries and cappuccinos to start the day right.
Short walk from your hotel.
EUR30, 1 hour

9:30AM

Visit the Vatican City

Explore the Vatican Museums and marvel at the Sistine Chapel.
Take the Metro or a taxi from your hotel.
EUR120, 3 hours

1:00PM

Lunch at Pizzarium

Indulge in delicious Roman-style pizza by the slice for lunch.
Close to the Vatican, easily reachable on foot.
EUR50, 1 hour

2:30PM

Explore Roman Forum

Take a walk through ancient ruins and learn about Roman history.
Short walk from the Vatican area.
EUR70, 2 hours

5:00PM

Gelato Break at Giolitti

Treat the family to some of the finest gelato in Rome.
A lovely stroll through the historic centre will take you there.
EUR20, 30 minutes

6:00PM

Walk around the Trevi Fountain

Don't forget to toss a coin to return to Rome!
Take a leisurely walk from Giolitti to the fountain.
Free, 1 hour

7:30PM

Dinner at Trattoria Al Moro

Enjoy traditional Roman dishes in a family-friendly setting.
Located near the Trevi Fountain.
EUR90, 2 hours
Find Hotels in Rome

Day 3: Travel to Florence

Florence, Italy

8:00AM

Breakfast at Hotel

Fuel up with a hearty breakfast before the train ride to Florence.
Enjoy breakfast at your hotel.
Included in stay, 1 hour

9:00AM

Train to Florence

Enjoy a scenic train ride through the Italian countryside.
Catch the train from Roma Termini to Firenze Santa Maria Novella.
EUR80, 1.5 hours

11:00AM

Check-In at Florence Hotel

Drop off luggage, freshen up and get ready to explore.
Choose a hotel in the heart of the city.
EUR140, 30 minutes

12:00PM

Lunch at All’ Antico Vinaio

Try the best panini in Florence at this bustling eatery.
Located near the Uffizi Gallery.
EUR40, 1 hour

1:30PM

Visit the Uffizi Gallery

Home to masterpieces from Italian artists, great for art lovers.
A short walk from lunch.
EUR100, 2.5 hours

4:00PM

Visit Ponte Vecchio

Stroll across the famous bridge and enjoy the jewelry shops.
Just a short walk from the Uffizi Gallery.
Free, 1 hour

5:30PM

Gelato at Gelateria dei Neri

Indulge in delicious gelato to recharge for dinner.
Close to the Ponte Vecchio.
EUR15, 30 minutes

7:00PM

Dinner at La Giostra

Experience Tuscan cuisine in a charming atmosphere.
Just a short taxi ride away.
EUR100, 2 hours
Find Hotels in Florence

Day 4: Explore Florence

Florence, Italy

8:00AM

Breakfast at Caffè Gilli

Start your day with pastries and a cup of coffee at this historic café.
Located in Piazza della Repubblica.
EUR25, 1 hour

9:00AM

Visit the Accademia Gallery

Get a glimpse of Michelangelo's David and other renowned works.
Short walk from the café.
EUR80, 1.5 hours

10:30AM

Explore the Duomo

Climb to the top for stunning views of Florence.
Located right by the Accademia Gallery.
EUR20, 2 hours

12:30PM

Lunch at Mercato Centrale

Enjoy a variety of local foods at this vibrant food market.
Short walk to the market.
EUR50, 1.5 hours

2:00PM

Leisurely Walk in Boboli Gardens

Relax in the beautiful gardens and enjoy some fresh air.
Takes about 15 minutes to walk from the market.
EUR15, 2 hours

4:30PM

Visit Pitti Palace

Discover the former residence of the Grand Dukes and its art collections.
Just a short walk from the gardens.
EUR30, 1.5 hours

6:00PM

Dinner at Ristorante da Bule

Savour delicious Italian dishes in a family-friendly atmosphere.
Located in the Oltrarno district, accessible by foot.
EUR90, 2 hours
Find Hotels in Florence

Day 5: Day Trip to Pisa

Pisa, Italy

8:00AM

Breakfast at Hotel

Enjoy a leisurely breakfast before the trip to Pisa.
Breakfast at the hotel.
Included in stay, 1 hour

9:00AM

Train to Pisa

Experience the Italian countryside on your way to Pisa.
Catch a regional train from Florence to Pisa.
EUR40, 1 hour

10:00AM

Visit the Leaning Tower of Pisa

Climb this world-famous monument with your family.
Short walk from the train station.
EUR60, 1.5 hours

12:00PM

Lunch at Ristorante da Mario

Enjoy authentic local cuisine in this charming restaurant.
Walking distance from the Leaning Tower.
EUR50, 1.5 hours

1:30PM

Visit the Cathedral of Pisa

Explore the beautiful architecture and history.
Next to the Leaning Tower.
EUR10, 1 hour

3:00PM

Gelato at Gelateria De'Coltelli

Recharge with some refreshing gelato in Pisa.
Close to the Cathedral.
EUR10, 30 minutes

4:00PM

Return to Florence

Head back to Florence to relax and enjoy the evening.
Catch a train from Pisa back to Florence.
EUR40, 1 hour

6:00PM

Dinner at Trattoria I’Tuscani

Dine on Tuscan delicacies right in the heart of Florence.
Near your hotel, easily walkable.
EUR80, 2 hours
Find Hotels in Pisa

Day 6: Travel to Venice

Venice, Italy

8:00AM

Breakfast at Hotel

Start the day with breakfast before the journey to Venice.
Breakfast at the hotel.
Included in stay, 1 hour

9:15AM

Train to Venice

A scenic train ride across the northern Italian landscape.
Departure from Florence's main train station.
EUR60, 2 hours

11:15AM

Check-In at Venice Hotel

Get settled and get ready for exploring.
Choose a centrally-located hotel for convenience.
EUR150, 30 minutes

12:00PM

Lunch at Osteria alle Testiere

Taste fresh and local seafood in this intimate restaurant.
Located a stroll away from your hotel.
EUR90, 1.5 hours

1:30PM

Explore St. Mark's Square

Visit the iconic square and enjoy the Venetian atmosphere.
Walk to the square from lunch.
Free, 1 hour

2:30PM

Visit Doge's Palace

Explore the historic seat of Venetian power and its beautiful architecture.
Just a short walk from St. Mark's Square.
EUR70, 2 hours

4:30PM

Gondola Ride

A classic Venetian experience perfect for the whole family.
Gondola dock located near St. Mark's.
EUR100, 30 minutes

6:00PM

Dinner at Trattoria Al Gatto Nero

Famous for seafood pasta and local Venetian dishes.
Located in Burano, accessible by vaporetto.
EUR120, 2 hours
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Day 7: Discover Venice

Venice, Italy

8:00AM

Breakfast at Hotel

Enjoy breakfast at the hotel to energize yourself for the day.
Hotel breakfast.
Included in stay, 1 hour

9:00AM

Visit Rialto Market

Experience the local market and dazzling array of fresh goods.
Walk to the market from your hotel.
Free, 1.5 hours

10:30AM

Explore the Peggy Guggenheim Collection

Delve into modern art while enjoying a family-friendly atmosphere.
A pleasant walk along the Grand Canal.
EUR24, 2 hours

12:30PM

Lunch at Osteria Da Fiore

Savor exquisite Venetian dishes in this Michelin-starred restaurant.
Conveniently located near the gallery.
EUR100, 1.5 hours

2:00PM

Visit the Murano Glass Factory

Learn about the art of glass-making and perhaps buy a souvenir.
Take a vaporetto to Murano Island.
EUR25, 2 hours

4:30PM

Return to Venice and relax

Take a leisurely afternoon to rest and recharge.
Travel back on the vaporetto.
EUR15, 1 hour

6:00PM

Dinner at Antiche Carampane

Enjoy the region's rich flavors in this cozy restaurant.
Easily reachable from your hotel.
EUR120, 2 hours
Find Hotels in Venice

Day 8: Travel to Cinque Terre

Cinque Terre, Italy

7:00AM

Breakfast at Hotel

A full breakfast ensures you're ready for travel.
Breakfast at the hotel.
Included in stay, 1 hour

8:00AM

Train to Cinque Terre

Experience breathtaking views along the coast as you travel.
Combine trains from Venezia Santa Lucia to La Spezia, then switch.
EUR80, 3 hours

11:00AM

Check-In at Cinque Terre Hotel

Settle into your hotel and prepare for exploration.
Select a hotel in one of the five villages.
EUR150, 30 minutes

12:00PM

Lunch at Ristorante Da Billy

Savor fresh seafood and local favorites overlooking the sea.
Located in Manarola, a short walk from the hotel.
EUR80, 2 hours

2:00PM

Hike from Manarola to Riomaggiore

Enjoy breathtaking coastal views while hiking the Via dell'Amore.
Beautiful, well-marked walking paths connect the two villages.
Free, 1 hour

3:30PM

Explore Riomaggiore

Wander through the colorful streets and enjoy picturesque scenery.
Enjoy the leisurely pace here before returning.
Free, 1.5 hours

5:00PM

Gelato at Gelateria Cinque Terre

Cool off with some gelato as you take in the seaside views.
Located in the heart of Riomaggiore.
EUR10, 30 minutes

6:00PM

Dinner at Trattoria dal Billy

Experience delicious dishes crafted with a local twist and stunning sunsets.
Conveniently located in Manarola.
EUR80, 2 hours
Find Hotels in Cinque Terre

Day 9: Explore Cinque Terre

Cinque Terre, Italy

8:00AM

Breakfast at Hotel

Get started with breakfast, enjoying the sounds of the sea.
Breakfast at the hotel.
Included in stay, 1 hour

9:00AM

Boat Tour of Cinque Terre

Experience the stunning coastline from the water with a family-friendly boat tour.
Book a tour that departs from your village.
EUR150, 2.5 hours

11:30AM

Visit Monterosso al Mare

Spend leisure time on the beautiful beaches of Monterosso.
Arrive by boat from Manarola.
Free, 2 hours

1:30PM

Lunch at Ristorante Il Gabbiano

Feast on local specialties in a family-friendly environment.
Located right on the beach.
EUR70, 2 hours

3:30PM

Hike from Monterosso to Vernazza

A picturesque hike offering stunning views along the trail.
Signposted well and relatively easy.
Free, 1.5 hours

5:00PM

Explore Vernazza

Wander the charming streets and enjoy the views from the harbor.
Casual exploration before returning to your hotel.
Free, 1 hour

6:00PM

Dinner at Gambero Rosso

Indulge in fantastic seafood dishes with unforgettable seaside views.
Back in Manarola, easily walkable.
EUR90, 2 hours
Find Hotels in Cinque Terre

Day 10: Travel to Bologna

Bologna, Italy

8:00AM

Breakfast at Hotel

Enjoy breakfast to prep for your journey ahead.
Hotel breakfast.
Included in stay, 1 hour

9:00AM

Train to Bologna

Travel through the scenic landscape as you reach Bologna.
Catch a train from La Spezia to Bologna.
EUR50, 2 hours

11:00AM

Check-In at Bologna Hotel

Unpack and refresh before lunch.
Choose a hotel in the city center.
EUR120, 30 minutes

12:00PM

Lunch at Mercato delle Erbe

Taste various local delicacies at this vibrant market.
Located in the heart of Bologna.
EUR50, 1.5 hours

1:30PM

Walk to Piazza Maggiore

Explore Bologna’s main square and its impressive architecture.
A short stroll from the market.
Free, 1 hour

2:30PM

Visit the Tower of Bologna

Climb the Asinelli Tower for panoramic views over the city.
Located near Piazza Maggiore.
EUR10, 1 hour

3:30PM

Gelato at Gelateria Gianni

Recharge with high-quality gelato for the family.
Walk to the gelateria from the tower.
EUR15, 30 minutes

5:00PM

Explore the University of Bologna

Wander one of the oldest universities in the world.
Just a quick walk from gelato stop.
Free, 1 hour

6:30PM

Dinner at Trattoria da Me

Experience authentic regional dishes in a family-friendly atmosphere.
Located in the city center.
EUR80, 1.5 hours
Find Hotels in Bologna

Day 11: Day Trip to San Marino

San Marino, San Marino

7:30AM

Breakfast at Hotel

Breakfast before heading out for a day trip.
Breakfast at the hotel.
Included in stay, 1 hour

9:00AM

Drive to San Marino

A picturesque drive from Bologna to the tiny Republic.
Rent a vehicle for convenience.
EUR40, 1.5 hours

10:30AM

Explore Guaita Fortress

Explore the medieval fortress with stunning views.
Parking is available nearby.
EUR8, 1 hour

12:00PM

Lunch at Ristorante La Terrazza

Enjoy a meal with panoramic views over the landscape.
Short walk from the fortress.
EUR50, 1.5 hours

1:30PM

Visit the Basilica di San Marino

Marvel at the beautiful neoclassical architecture.
Located close to the restaurant.
Free, 45 minutes

2:30PM

Explore the Historic Centre

Visit shops and enjoy the charming atmosphere.
Meander through the streets at your leisure.
Free, 1.5 hours

4:00PM

Gelato at Gelateria di San Marino

Treat the family to some delicious gelato before returning.
Located in the city center.
EUR10, 30 minutes

5:00PM

Drive back to Bologna

Travel back to Bologna and unwind after the day.
Return by the same route.
EUR40, 1.5 hours

7:00PM

Dinner at Ristorante Da Cesari

Savor traditional Bolognese dishes in a friendly atmosphere.
Located near your hotel.
EUR80, 2 hours
Find Hotels in San Marino

Day 12: Travel to Milan

Milan, Italy

8:00AM

Breakfast at Hotel

Last breakfast in Bologna before leaving for Milan.
Breakfast at the hotel.
Included in stay, 1 hour

9:00AM

Train to Milan

Relish the comfortable ride as you reach Milan.
Depart from Bologna Centrale train station.
EUR30, 1 hour

10:00AM

Check-In at Milan Hotel

Settle in at your hotel and recharge.
Choose a family-friendly hotel in Milan.
EUR150, 30 minutes

11:00AM

Lunch at Luini

Try famous panzerotti in this street food gem.
Located close to the Duomo.
EUR30, 1 hour

12:30PM

Explore the Duomo di Milano

Visit the iconic cathedral and if you wish, climb to the rooftop.
Short walk from lunch.
EUR15, 2 hours

2:30PM

Visit the Galleria Vittorio Emanuele II

Experience this stunning shopping gallery right next to the Duomo.
Adjacent to the cathedral.
Free, 1 hour

3:30PM

Take a Walk in Sempione Park

Relax, play, and unwind in one of Milan's biggest and lush parks.
A walk from the Galleria.
Free, 1.5 hours

5:00PM

Dinner at Risoelat essence

Enjoy Milanese cuisine in a family-friendly environment.
Located in the city centre.
EUR80, 2 hours
Find Hotels in Milan

Day 13: Fashion and History in Milan

Milan, Italy

8:00AM

Breakfast at Hotel

Recharge with breakfast at your hotel.
Hotel breakfast.
Included in stay, 1 hour

9:00AM

Visit Castello Sforzesco

Explore this historic castle and its impressive grounds.
A short walk from the hotel.
Free, 2 hours

11:00AM

Visit the Pinacoteca di Brera

Discover one of Italy’s most important art collections.
Nearby the castle.
EUR10, 1.5 hours

12:30PM

Lunch at Da Giacomo

Savor traditional dishes in a chic eatery.
A brief walk from the gallery.
EUR100, 1.5 hours

2:00PM

Shopping on Via Montenapoleone

Stroll the glamorous shopping street of Milan.
Walk to the world-famous shopping district.
Free, 1.5 hours

3:30PM

Visit Santa Maria delle Grazie

See the Last Supper (make prior reservations).
Easily reachable via public transit.
EUR15, 1 hour

5:00PM

Gelato at Gelateria della Musica

Enjoy world-class gelato to end your sightseeing.
Located close to Santa Maria delle Grazie.
EUR15, 30 minutes

6:00PM

Dinner at Trattoria Milanese

Conclude the day with classic Milanese cuisine.
A short walk from the gelato shop.
EUR90, 2 hours
Find Hotels in Milan

Day 14: Departure from Milan

Milan, Italy

8:00AM

Breakfast at Hotel

Enjoy a final breakfast as you reminisce about the trip.
Breakfast at the hotel.
Included in stay, 1 hour

9:00AM

Last-Minute Shopping

Grab some souvenirs before you leave.
Head to local markets or nearby shops.
Varies, 1.5 hours

10:30AM

Check-Out of Hotel

Pack up and prepare for departure.
Make sure all luggage is ready.
Free, 30 minutes

11:00AM

Travel to Airport

Head to the airport for your return flight home.
Use public transport or shuttle service.
EUR20, 1 hour
Find Hotels in Milan
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