TWO WAYS THROUGH ITALY
Italy Itineraries
Eight days for two. Ten days with the family.
Two routes we actually took, including the reservations that shaped the trip, the days we loved, and the places we would handle differently next time.
TRIP OVERVIEW
Route overview
We have traveled through Italy two very different ways: an eight-day couples trip and a ten-day family trip. Both left enough room for the meals, walks, and unexpected stops we remember most.
Couples route · 8 days
Florence → Cinque Terre → Rome
Family route · 10 days
Milan → Venice → Rome → Herculaneum → Florence → Pisa
Couples route · 8 days · Days 1–2
Florence
The Duomo, the Accademia, leather markets, Florentine steak, gelato, and enough open time to walk instead of racing between museums.
Duomo
Accademia
Piazzale Michelangelo
Ponte Vecchio
Couples route · 8 days · Days 3–4
Cinque Terre
Two slower coastal days with regional trains, steep village streets, meals near the water, and sunset as the evening plan.
Monterosso
Vernazza
Coastal trains
Sunset
Couples route · 8 days · Days 5–8
Rome
Ancient Rome, the Vatican, churches, fountains, long walks, outdoor dinners, and one major reservation at a time.
Colosseum
Vatican
Pantheon
Piazza Navona
Family route · 10 days · Days 1–2
Milan
The Duomo, The Last Supper, excellent food, and an easy rail connection into the rest of northern Italy.
Milan Duomo
The Last Supper
Galleria
Aperitivo
Family route · 10 days · Days 2–4
Venice
St. Mark's, the Doge's Palace, vaporetti, bridges, and time to get a little lost without dragging the whole trip behind us.
St. Mark's
Doge's Palace
Vaporetto
Canals
Family route · 10 days · Days 4–6
Rome
Ancient Rome, the Vatican, churches, fountains, long walks, outdoor dinners, and one major reservation at a time.
Colosseum
Vatican
Pantheon
Piazza Navona
Family route · 10 days · Day 7
Herculaneum
A focused day trip from Rome through a Roman city that felt easier for our family to understand and manage than a much larger ruins day.
Ancient streets
Homes
Baths
Roman history
Family route · 10 days · Days 8 and 10
Florence
The Duomo, the Accademia, leather markets, Florentine steak, gelato, and enough open time to walk instead of racing between museums.
Duomo
Accademia
Piazzale Michelangelo
Ponte Vecchio
Family route · 10 days · Day 9
Pisa
An easy half-day for the Leaning Tower, Piazza dei Miracoli, goofy family pictures, and a return to Florence.
Leaning Tower
Piazza dei Miracoli
Half-day train trip
Couples: Days 1–2 · Family: Days 8 and 10
Florence
The Duomo, the Accademia, leather markets, Florentine steak, gelato, and enough open time to walk instead of racing between museums.
Couples route
DAYS 1-2
Florence
We spent May 25 and 26 in Florence, and the city worked because we did not turn it into a race.
Start near the Duomo, cross the Arno, and leave the middle of the day loose enough for side streets, small shops, and La Carraia gelato.
Choose one museum or climb that genuinely matters. We would rather remember David, the skyline, and a good dinner than rush through three timed entries.
Take the bus up to Piazzale Michelangelo if it saves the energy you want for the walk down. Planning a Florentine-steak dinner was a better use of our evening than squeezing in one more attraction.
Stay: Florence.
Eat: Gelateria La Carraia and a Florentine-steak dinner.
Reserve: Accademia Gallery or the official Duomo climb you care about; not every major sight at once.
Family route
DAY 8
Florence
Take the morning train to Florence.
Walk to the Ponte Vecchio, Piazza della Signoria, and the Duomo. Florence is compact enough that the city itself becomes the itinerary.
Leave room to wander. The side streets, small churches, leather shops, and one more gelato stop are not filler.
Stay: La Casa di Greta
Eat: Trattoria dall'Oste for the Florentine dinner we booked; Gelateria La Carraia for gelato.
Reserve: Accademia Gallery, the Accademia and Uffizi combination, or a pasta-making class; reserve Trattoria dall'Oste for a preferred dinner time.
DAY 10
Farewell Italy
Have one last cappuccino and pastry, take a final walk, and head to the airport.
This route covers a lot without asking every day to prove how productive the vacation was.
The usual question on the way home is not whether we saw enough. It is: When can we come back?
Stay: Departure day in Florence.
Eat: One last cappuccino and gelato.
Reserve: Airport or station transfer if the timing is tight.
FLORENCE FAQ
Good to know before you go.
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Two full days is our minimum. That leaves room for David, the Duomo area, a long meal, shopping, and one evening view without turning the city into a museum sprint.
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Reserve the Accademia, Uffizi, and any Duomo climb that matters to you. Leave the markets, churches, meals, and neighborhood walks flexible.
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We walked almost everywhere. The bus to Piazzale Michelangelo saves the uphill climb, and taking it up before walking down worked well for us.
Couples: Days 3–4
Cinque Terre
Two slower coastal days with regional trains, steep village streets, meals near the water, and sunset as the evening plan.
Couples route
DAYS 3-4
Cinque Terre
We were in Cinque Terre May 27 and 28. It is as beautiful as people say, and also more crowded, hilly, and stair-heavy than the postcard suggests.
Use the train, start early, and pick fewer villages. Monterosso, Vernazza, and Riomaggiore each gave us something different, but the day improved when we stopped trying to collect all five.
Pesto focaccia at Il Massimo della Focaccia in Monterosso and Batti Batti in Vernazza fit this route better than forcing a formal lunch between train stops.
Leave room for a drink, gelato, or ten quiet minutes with the view. Moving through a village is easy. Feeling like you were actually there takes more time.
Stay: Choose one Cinque Terre base.
Eat: Il Massimo della Focaccia and Batti Batti.
Reserve: Official Cinque Terre trail and card information and the Florence-to-Liguria train. Reserve a specific dinner only if the view or table matters to you.
CINQUE TERRE FAQ
Good to know before you go.
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Two nights gave us a real break between Florence and Rome. A day trip is possible, but it adds more train pressure and less time to enjoy the coast.
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No. Choose the villages that interest you and protect time for the stairs, platforms, meals, and views. Treating all five like a checklist makes the day harder than it needs to be.
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Bring the smallest bag you can comfortably manage. Stations, stairs, hills, and lodging without easy access make large roller bags especially annoying here.
Couples: Days 5–8 · Family: Days 4–6
Rome
Ancient Rome, the Vatican, churches, fountains, long walks, outdoor dinners, and one major reservation at a time.
Couples route
DAY 5
Rome: Choose One Big Anchor
Travel to Rome and make the Colosseum or Forum the only major timed commitment of the day.
Rome is walkable in sections, not as one giant checklist. Give the anchor enough time, then stay in the surrounding neighborhood for churches, food, and the parts of the city you notice between landmarks.
Do not add the Vatican just because it fits on a spreadsheet. Heat, crowds, and distance make a short transfer day feel longer than it looks.
Stay: Rome.
Eat: Keep dinner in the neighborhood around the day's anchor.
Reserve: Official Colosseum tickets and the Liguria-to-Rome train.
DAYS 6-7
Rome: Central Streets, Churches, and One Theme
Keep central Rome on foot: the Pantheon, Piazza Navona, a church walk, gelato, and dinner nearby made the city feel personal instead of procedural.
Use the next day for one theme. Choose the Vatican and St. Peter's, the Appian Way and basilicas, or a slower food-and-neighborhood day.
The Pantheon area after dinner was one of our favorite Rome moments. The temperature dropped, the pace changed, and After dinner, the cooler streets around the Pantheon were enough.
We stopped for gelato often. Fatamorgana, La Romana, and Venchi are all easy options around central Rome.
Stay: Use the same Rome base. Avoid another hotel change.
Eat: Fatamorgana, La Romana, or Venchi.
Reserve: Vatican Museums only if that is the theme you choose; leave the other day flexible.
DAY 8
A Final Rome Morning
Use the final morning for the church, square, cafe, or gelato stop you kept talking about after you left it.
Rome got better when we stopped trying to finish it. Leave one street unexplored and one restaurant for next time, then head to the airport without turning departure day into another endurance test.
Stay: Rome departure day.
Eat: One final cappuccino, pastry, or gelato is enough of a plan.
Reserve: Prearrange the airport transfer if the flight is early or luggage makes the train impractical.
Family route
DAY 4
Venice to Rome
Take the high-speed train to Rome.
Once you are checked in, keep the first afternoon simple. Walk through Piazza Navona, visit the Pantheon, and throw a coin into the Trevi Fountain.
Do not rush this part. Rome is at its best when the walk between the famous places has enough room for a church, a bakery, or an unexpected square.
Finish with dinner outside.
Stay: Largo Arenula Suites by Hili
Eat: Quel che c'e or Fatamorgana Gelato
Reserve: The Venice-to-Rome train. Dinner can stay flexible.
DAY 5
Ancient Rome
Book the earliest practical entry for the Colosseum, then continue through the Roman Forum and Palatine Hill.
This is a full history day. Give it time, carry water, and do not stack another major reservation immediately afterward.
Spend the evening in Trastevere, where dinner and a slower neighborhood walk are enough.
Stay: Largo Arenula Suites by Hili
Eat: Quel che c'e or Fatamorgana Gelato
Reserve: Colosseum, Forum, and Palatine Hill
DAY 6
Vatican City
Start at St. Peter's Basilica. If you plan to climb the dome, do it early.
Continue to the Vatican Museums and the Sistine Chapel with timed tickets already booked.
The museums are enormous. Decide what matters most before you go, especially with children, and let the rest of the day stay slow.
Stay: Largo Arenula Suites by Hili
Eat: Quel che c'e or Fatamorgana Gelato
Reserve: Vatican, Sistine Chapel, and St. Peter's tour
ROME FAQ
Good to know before you go.
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Four or five days is ideal for us. Three can work if you choose priorities, but Rome becomes much better when every neighborhood is not squeezed into one route.
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Book the Colosseum and Roman Forum, Vatican Museums, and any special-access tour you would be disappointed to miss. Keep the fountains, churches, squares, and meals flexible.
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Rome is walkable in sections, not as one giant loop. Group sights by neighborhood, use a taxi or transit when it protects everyone's feet, and wear shoes that already work on cobblestones.
Family: Days 1–2
Milan
The Duomo, The Last Supper, excellent food, and an easy rail connection into the rest of northern Italy.
Family route
DAY 1
Arrive in Milan
Land in Milan and take the train into the city.
Once you are settled, make your way to the Milan Duomo. Go inside if you have time, but do not skip the rooftop. Standing among the spires and looking across the city is one of the best introductions to Italy.
Walk through the Galleria Vittorio Emanuele II, grab pizza or risotto, and let everyone go to bed early.
Highlights: Milan Duomo, rooftop terraces, Galleria Vittorio Emanuele II.
Stay: Milan.
Eat: Risotto or cotoletta near the Duomo. Reserve only a dinner that matters to you.
Reserve: Milan hop-on hop-off bus for a low-effort first overview; book The Last Supper for Day 2.
DAY 2
The Last Supper & Venice
Start the day with The Last Supper. Book this months ahead. Tickets are limited and this is not something you can count on buying after you arrive.
Seeing the painting in person was far more emotional than we expected.
After lunch, take the high-speed train to Venice. The ride is about two and a half hours, and arriving by train is part of the fun. You step outside and suddenly the street is water.
Check in, then spend the evening wandering with no major agenda.
Highlights: The Last Supper, high-speed train, first evening in Venice.
Stay: Venice.
Eat: Choose cicchetti and a simple dinner near the evening walk.
Reserve: The Last Supper and Duomo tour and the Milan-to-Venice train.
MILAN FAQ
Good to know before you go.
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Start looking two or three months ahead. Entry is tightly limited, and this is not a stop we would leave to same-day availability.
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Yes. Two days gave us time for the Duomo, The Last Supper, excellent food, and a little wandering. That was the right amount for us.
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Yes. The rooftop puts you among the stone spires and gives the cathedral a completely different scale than the view from the square.
Family: Days 2–4
Venice
St. Mark's, the Doge's Palace, vaporetti, bridges, and time to get a little lost without dragging the whole trip behind us.
Arrival from Milan
DAY 2 · EVENING
Arrive in Venice
After The Last Supper and lunch in Milan, take the high-speed train to Venice. The ride is about two and a half hours, and stepping outside the station to find water instead of a street is part of the fun.
Check in, then keep the first evening open for bridges, canals, cicchetti, and the first wrong turn that turns out better than the planned one.
Stay: Venice
Eat: Choose cicchetti and a simple dinner near the evening walk.
Reserve: The Milan-to-Venice train.
Full Venice day
DAY 3
Venice
Start early at St. Mark's Square before the biggest crowds arrive.
Visit St. Mark's Basilica and Doge's Palace, and climb the Campanile for the view if it is on your list.
After that, let Venice do what Venice does best. Cross the Rialto Bridge, follow the smaller streets, stop for food, and accept that getting a little lost is part of the day.
A gondola ride is optional. Cicchetti, seafood, and pasta are not.
Stay: Venice.
Eat: Cicchetti, seafood, and pasta. Casual counters are walk-in; reserve a special dinner.
Reserve: St. Mark's Basilica and Doge's Palace
Departure for Rome
DAY 4 · MORNING
One last Venice walk
Use the morning for coffee, one last canal walk, and anything you missed near the hotel. Then collect the luggage and take the high-speed train to Rome.
Stay: Largo Arenula Suites by Hili in Rome
Eat: Keep breakfast and lunch close to the train route.
Reserve: The Venice-to-Rome train.
VENICE FAQ
Good to know before you go.
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As little as possible. Bridges, steps, crowded paths, and a walk to the hotel make heavy luggage more work than it looks on a map.
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Book St. Mark's Basilica and the Doge's Palace if they are priorities. One firm reservation is enough for a day that is better when there is room to wander.
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We would. Two nights let us see Venice outside the busiest day-trip hours and made the city feel less like a crowded transfer stop.
Family: Day 7
Herculaneum
A focused day trip from Rome through a Roman city that felt easier for our family to understand and manage than a much larger ruins day.
Family route
DAY 7
Herculaneum Day Trip
Take an early train south for Herculaneum.
For families, we found Herculaneum easier to understand and manage than trying to conquer a much larger archaeological site. It is smaller, exceptionally preserved, and still gives you the feeling of walking through an ancient Roman town.
Add Mount Vesuvius only if the weather, timing, and everyone's energy make sense.
Return to Rome that evening.
Stay: Largo Arenula Suites by Hili
Eat: Pack breakfast and choose dinner near the hotel after the return train.
Reserve: Herculaneum entry and the southbound train.
HERCULANEUM FAQ
Good to know before you go.
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Herculaneum is smaller and extremely well preserved. For our family, that made the streets, homes, and daily life easier to understand in one day.
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Yes, but it is a long rail day with a change around Naples. Start early, keep the evening simple, and check the current train plan before leaving.
Family: Day 9
Pisa
An easy half-day for the Leaning Tower, Piazza dei Miracoli, goofy family pictures, and a return to Florence.
Family route
DAY 9
Pisa Half Day
Take an early train to Pisa.
See the Leaning Tower, take the goofy pictures, and spend time in the Piazza dei Miracoli before returning to Florence.
Use the rest of the afternoon for shopping, another museum, or Giotto's Bell Tower if everyone still has the legs for it.
Stay: La Casa di Greta
Eat: Gelateria La Carraia and La Buchetta
Reserve: The Pisa train does not need months of planning. If the afternoon stays in Florence, consider the Medici Chapel tour; otherwise keep the time open.
PISA FAQ
Good to know before you go.
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A half-day worked for us. Add more time only if you plan to climb the tower or visit several buildings in the complex.
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We would not for this route. Florence remained the better base, and the train made Pisa simple without another hotel change.