Italy, remembered properly.

The Italy story started before the full group ever reached Rome. Colin and Leslie had their own opening act in Lake Como: quieter, northern, and wrapped around the kind of scenery that makes every ordinary errand look staged for a movie.

That first chapter belongs mostly to them. The important date was Thursday, June 11, when Colin proposed to Leslie. By the time the rest of the group caught up in Rome, the trip was no longer just a vacation. It had become an engagement celebration, with every dinner and piazza walk carrying a little extra charge.

The Lake Como photos sit here as the prologue: Colin and Leslie’s private beginning before the Roman heat, the food tours, the museums, the missed turns, and the long family story that followed.

The group left for Rome the way many good trips begin: too early at the airport, comfortably fed in the Delta Lounge, and with a sleep strategy that worked almost too well. Richard took trazodone and melatonin early enough that boarding became its own small adventure. Once seated, he disappeared almost immediately, sleeping through the tarmac delay and most of the nine-hour flight.

Rome announced itself with chaos. Passport control was crowded and badly managed, the pickup was not waiting exactly where expected, and the first minutes in Italy were more scramble than postcard. Eventually the Mercedes van appeared, the ride smoothed out, and the trip found its footing.

By afternoon, Rome was already doing what Rome does. There were excellent sandwiches near the hotel, eaten in a piazza, and then Colin and Leslie arrived with the glow of people who had just gotten engaged two days earlier. The first dinner was at Tartufi & Friends — more touristy than treasured — but the night still worked: truffles, piazzas, gelato, and the feeling of having finally made it.

Sunday began with the breakfast rhythm that would become familiar: pastry and cappuccino near the hotel, with Caitie making it very clear when she had been left out of the first breakfast run. From there the group walked across the old center toward the food tour, eventually finding the guide and stepping into the day’s real agenda.

The tour moved through the Campo de’ Fiori area and the ancient layers around the Theatre of Pompey: pesto, truffles, balsamic vinegar, cured meats, cheeses, wine, pasta, pizza, tiramisu, espresso, and gelato. Rome was not presenting itself as a museum only; it was presenting itself as a place where history and lunch keep interrupting each other.

There was also a brief phone panic at the gelato stop — because no family trip is complete without at least one missing-device emergency — but the day recovered. Dinner at Bottega Tredici near the Jewish Ghetto became one of the clear wins of the entire trip. Afterward came ruins, the synagogue, Largo di Torre Argentina, pastries on the walk back, and a late return that everyone would feel the next morning.

Monday was the heavy history day. It started gently enough with the now-standard pistachio pastry and cappuccino, then moved to the Pantheon, where the scale finally made sense only from inside the room. The dome, the oculus, the original marble floor, and the impossible age of the building all did what they were supposed to do: they stopped everyone for a minute.

The middle of the day was more uneven. Bathrooms were hard to find, churches were under construction or closed, the catacombs plan fell apart when cabs would not cooperate, and the group ended up walking too far toward the Colosseum in too much heat.

Then Dennis arrived. The private tour through the Forum, Palatine Hill, and the Colosseum gave the day its shape. The Via Sacra, the imperial hill, the Farnese Gardens, the view back across Rome, and finally the Colosseum itself made the ancient city feel less like scattered ruins and more like a working world. By dinner, everyone was cooked, but Campo de’ Fiori and a big charcuterie board at Giordi brought the day safely home.

Tuesday began with the kind of logistical problem that kept repeating all week: finding a cab for five people in Rome. The solution, at the last minute, was the metro. The metro was fine. The train station was not.

The track assignment looked like “1–10,” which Richard interpreted as level one, track ten. At 9:08 for a 9:10 train, that interpretation collapsed. Panic arrived immediately. A calm American woman pointed out that the train was delayed by ten minutes, and that grace period saved the day.

The train to Florence was fast, clean, and surprisingly easy once everyone was on board. In Florence, Dennis turned into exactly the guide the day needed: informed, multilingual, and sharply opinionated about authentic Florence versus TikTok-tourist Florence. There were hot beef sandwiches, the Duomo, Uffizi-area fountains, Ponte Vecchio, Papini leather, Lambrusco, gelato, belts, and a quick museum run for Richard and Colin. Back in Rome, dinner at Sistina 52 delivered one of the best steaks of the trip.

Wednesday began early, with the group heading from Spagna toward the Vatican and Richard catching up after nearly being left behind. The papal audience was better than expected: surprisingly good seats, the Pope passing in the Popemobile, and the unmistakable sense of being inside a global ritual.

The rest of the day was harder. The heat was punishing, lunch was forgettable, the guide’s English was difficult, and the headsets were bad. As a tour, it struggled. As a place, the Vatican still overwhelmed.

The museums brought ancient Roman pieces, bath mosaics, enormous basins, costly blues, and rooms that felt almost too dense to absorb. The Sistine Chapel still landed. St. Peter’s was almost beyond scale, with Bernini’s bronze baldacchino anchoring the impossible space and Michelangelo’s Pietà reminding everyone that some works are famous for a reason. The day ended with a failed rooftop idea, a strong dinner at Mimì E Cocò, and the usual gelato-and-pastry drift back through Rome.

After three hard days, Thursday was intentionally slower. Everyone slept in, returned to the breakfast spot for cappuccinos and pistachio croissants, and then took a cab to Trastevere.

Giuseppe, the guide, had immediate character: about thirty-five, two linguistics degrees, a Sisters of Mercy T-shirt, and the energy of someone who could talk food, language, and punk records with equal conviction. The tour was excellent from the first stop: burrata, tomatoes, bread, olive oil, wine, then Spirito DiVino with its excavated basement and slow-roasted pork, supplì, local Peroni, porchetta-style pork on focaccia, Peppo al Cosimato, pasta, pizza, and finally Fatamorgana gelato.

This was the day Rome felt easiest. Trastevere had the neighborhood feel the group wanted, and by the end the future-trip lesson was clear: come back in the fall, and strongly consider staying near Trastevere or the Jewish Ghetto. Dinner returned to Bottega Tredici, which only strengthened its claim as the favorite restaurant of the trip.

Friday was the big day south. The driver met the group at 7:00 a.m., and the ride out of Rome included what Colin accurately named Italian Buc-ee’s: a highway stop with the worst cappuccino of the trip and a pastry that did its best.

The Amalfi Coast was beautiful, but Positano was also crowded, chaotic, and hard to navigate. Traffic was bad, the driver had to change plans because of an emergency near the usual parking area, cell coverage was weak, and the group split up almost immediately. The girls enjoyed the shopping and photos, Richard spent part of the stop hunting for a restroom and trying to reconnect, and lunch was forgettable. It was gorgeous. It was also enough.

Pompeii was brutally hot and the guide was weak, but the site itself carried the afternoon: the forum, shopfronts, thermopolia, rich-house floors and frescoes, the fish market, and the plaster casts that make the eruption feel suddenly personal. Back in Rome, showers and another Bottega Tredici dinner were not just nice; they were necessary.

Saturday started with the familiar breakfast and then a cab to the Appia Antica area for e-bikes: Richard, Tara, and Caitie taking on one of the oldest roads in Rome. The ride was bumpy in patches but quickly became one of the best side trips of the week. There is something hard to beat about moving along a road that has carried people for more than two thousand years.

The roadside tombs made the Roman idea of memory feel concrete: families placing monuments where travelers would keep passing their names. Then came the less solemn part of the ride, where tour guide Ricky P missed the turnoff not once but twice and heard about it, especially from Caitie. The accidental detour still produced a dog-petting stop and one of those views — fields, ruins, distance — that a camera cannot quite hold.

The aqueduct park was enormous and humbling. So was the heat. By the time the bikes returned, the shaded cafe at the rental place felt like rescue: prosciutto and mozzarella sandwiches, tomatoes, focaccia, olive oil, balsamic, and a cold IPA. Richard later split off for the San Callisto catacombs, where the underground air was blessedly cool. The final night brought Villa Borghese, Pincian Hill, the Spanish Steps, a phenomenal dinner at La Nonna in Trastevere, gelato, and the clearest lesson of the trip: next time, stay closer to the parts of Rome that felt alive at night.

The trip left a strong return list. Come back when Rome is cooler. Build the days around food, neighborhoods, and one major sight at a time. Stay closer to Trastevere or the Jewish Ghetto, where evenings feel easier and the restaurants that mattered most are within reach.

Bottega Tredici earned favorite-restaurant status. Trastevere earned a longer stay. The Appian Way earned its place as the surprise hit. Positano, at least in peak crowd conditions, probably does not need a repeat. Florence deserves more than a day. And every future plan should remember the most practical lesson of the week: Rome rewards patience, shade, water fountains, and fewer assumptions about cabs.