FLORENCE - CINQUE TERRE - ROME - MILAN - VENICE
Italy
We have been back more than once because Italy rewards both the famous reservations and the unplanned walk after dinner.
QUICK LINKS / TL;DR
The useful details first.
Itineraries: 8-day couples route or 10-day family route
Where we stayed: Our exact properties varied by trip. Compare walkable bases before booking: Rome stays · Florence stays
What we packed: Our useful Italy basics: Teva platform sandals · Compact umbrella · Universal plug adapter · Secure fanny pack
What we ate: Places from our Italy notes: La Buchetta · Gelateria La Carraia · Quel che c'e · Fatamorgana Gelato
Book ahead: Reserve the limited-entry stops first: Colosseum, Forum & Palatine Hill tour · Vatican, Sistine Chapel & St. Peter's tour · Accademia & Uffizi tour · Last Supper & Duomo tour
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OUR TRIP, BY PLACE
Choose a stop from our route.
Open a location for the part of the trip we remember, the practical details that mattered, and the changes we would make next time.
3 VISITS · IDEAL STAY: 4–5 DAYS
Rome keeps giving us reasons to come back.
We have visited Rome three times, and it has never felt finished. The major sights still matter, but the city became more enjoyable when we stopped trying to fit all of them into the same day.
We book the things that can ruin a day if they sell out: the Colosseum, Roman Forum, and Palatine Hill, the Vatican Museums and Sistine Chapel, and any special access that matters to us. A Pantheon visit is an easier single anchor when the day needs more room. Then we leave time to walk.
What our Rome days looked like
We wandered from the Trevi Fountain to Piazza Navona, stepped into churches because the doors were open, ate outside, and let Google Maps point out small places nearby. Rome rewards the hours between reservations just as much as the reservations themselves.
The architecture still stops us. Ancient stone, Baroque churches, apartment streets, ruins, fountains, and ordinary neighborhood life all sit together without asking permission.
What we would keep
Four or five days instead of a two-day sprint
Two comfortable pairs of shoes for the cobblestones
Timed entry for the major sights, with open space around them
What we would change
We would avoid the hottest part of summer when possible, group sights by neighborhood, and never schedule the Vatican and the Colosseum as if they are quick stops. Rome is better when dinner is not the first moment anyone gets to sit down.
Our take: Rome is a 12/10 for us. We return for the history and food, but the streets between the landmarks are why we keep thinking about another trip.
2 VISITS · IDEAL STAY: 2–3 DAYS
Florence feels personal, even when it is busy.
The first time I walked up to the Duomo, I cried. I had seen the photographs. They did not explain the scale, the marble, or what it feels like when the cathedral suddenly fills the end of a street.
We reserve the museums before the trip. If David and the Uffizi are priorities, the combined Accademia and Uffizi visit keeps the day clear without turning the whole visit into a string of ticket times.
The Florence days we loved
We could see a museum in the morning, eat a long lunch, shop for leather, stop for gelato, and still end at Piazzale Michelangelo. A pasta-making class is the kind of hands-on reservation we would choose when the family needs a break from another formal interior.
Florentine steak was worth the price. Traditional saltless Tuscan bread was not. I understand the history and remain personally offended.
Next time, we would pack lighter and read every lodging review for stairs. Roller luggage over cobblestones and an elevator-free building can turn arrival into the least charming part of Florence.
Our take: We have been twice and would go back again. Florence gives us world-class art without making the whole day feel like museum homework.
COUPLES ROUTE · 2 NIGHTS
Cinque Terre was the pause between city days.
We used Cinque Terre as the slower middle of our couples route between Florence and Rome. The change of pace mattered as much as the coastline: trains replaced long museum lists, and the view became the main appointment.
The villages are close on a map, but stairs, heat, crowded platforms, and luggage make them feel farther apart. We were happier choosing a few places well than treating all five villages as a scorecard.
What we did
We rode the regional train, walked the streets that interested us, ate near the water, and let sunset be enough of an evening plan. The route worked because we had already decided not to move hotels every night.
What we would keep
Two nights instead of a rushed day trip
Small luggage that can handle stairs
A weather-aware plan rather than a rigid village checklist
What we would change
We would verify trail conditions and ferry schedules immediately before the trip and protect more margin around train transfers. Cinque Terre is easy to enjoy and easy to make stressful if every connection is timed too tightly.
Our take: This was the right contrast to Florence and Rome. We would return for the coast, but we would keep the schedule even lighter.
OUR VERDICT: 8/10 · IDEAL STAY: 2–3 DAYS
Milan surprised us, especially at the table.
We expected fashion, business, and a more modern version of Italy. We did not expect the food to be one of the strongest parts of the stop.
The Duomo is unlike any other church we have visited, and Leonardo's Last Supper is one of the reservations we would build the day around. The Last Supper and Duomo tour is useful when both are priorities and tickets are limited.
What stayed with us
We found the Basilica of Sant'Ambrogio while wandering. Outside it, a Roman column has two holes that local legend blames on the devil's horns. That strange story became one of the memories we still repeat, and we would have missed it with an hour-by-hour schedule.
Milan also worked as a base for a day trip into Switzerland. That made the city more useful than a checklist of Milan landmarks alone.
It was not my favorite Italian city because I prefer the older atmosphere of Rome and Florence. I would still keep two or three Milan days for the Duomo, The Last Supper, the food, and an easy northern-Italy connection.
Our take: Milan was worth the stop, even though it was not the place that pulled us back most strongly.
FAMILY ROUTE · 2 NIGHTS
Arriving by train made Venice feel impossible in the best way.
You step out of the station and the street is water. That first view did more than any careful introduction could have done.
We treated St. Mark's Basilica and the Doge's Palace as the fixed part of the stay. The St. Mark's and Doge's Palace tour is the kind of ticket we would book before filling in the rest of the day.
What we did
We walked bridges, followed narrow streets, crossed the city by vaporetto, and let getting slightly lost be part of the plan. Venice is not efficient in the usual sense, which is exactly why rushing it feels wrong.
What we would keep
Two nights so the city is not only a day-trip crowd
A light bag for bridges and stairs
One major reservation, then time to wander
What we would change
We would arrive with the exact walking route to the hotel saved offline and avoid dragging more luggage than we can comfortably lift over a bridge.
Our take: Venice is inconvenient, beautiful, and unlike anywhere else. The inconvenience is manageable when the stay is not overpacked.
WHAT WORKED
We would keep these parts.
Two honest routes: The couples trip and family trip solve different problems instead of pretending one pace fits everyone.
Train-connected bases: We used the rail route to move between cities, then relied on walking once we arrived.
One day-shaping reservation: A major museum or archaeological site gave the day structure without filling every hour.
Lodging by the next morning: Location, stairs, room setup, and the first stop mattered more than the most impressive redemption.
WHAT WE WOULD CHANGE
A better version of the same trip.
Label compressed stops honestly: A route can include one Milan or Florence day without making that the ideal standalone visit.
Reduce one-night moves: We would remove a stop before turning every morning into luggage and checkout.
Add day trips as real days: Herculaneum and Pisa need their own travel margin; they should not disappear inside a Rome or Florence day count.
Choose the art: The Accademia, Uffizi, and a Duomo climb do not all need to happen simply because they can.